FI70219C - Foerfarande foer framstaellning av en beta-laktamantibiotikumfoerening - Google Patents

Foerfarande foer framstaellning av en beta-laktamantibiotikumfoerening Download PDF

Info

Publication number: FI70219C
Authority: FI; Finland
Prior art keywords: oxo; mixture; added; formula; compound
Prior art date: 1978-04-12

Application number

FI791190A

Other languages

English (en)

Finnish (fi)

Other versions

FI70219B (fi

FI791190A7 (fi

Inventor

Hiroshi Ishikawa

Fujio Tabusa

Kazuyuki Nakagawa

Original Assignee

Otsuka Pharma Co Ltd

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.)

1978-04-12

Filing date

1979-04-11

Publication date

1986-09-15

1978-04-12 Priority claimed from JP53043624A external-priority patent/JPS6034957B2/ja

1978-09-07 Priority claimed from JP53110464A external-priority patent/JPS6037118B2/ja

1978-11-16 Priority claimed from JP53141785A external-priority patent/JPS6037119B2/ja

1978-11-24 Priority claimed from JP53145638A external-priority patent/JPS5951959B2/ja

1979-04-11 Application filed by Otsuka Pharma Co Ltd filed Critical Otsuka Pharma Co Ltd

1979-10-13 Publication of FI791190A7 publication Critical patent/FI791190A7/fi

1986-02-28 Application granted granted Critical

1986-02-28 Publication of FI70219B publication Critical patent/FI70219B/fi

1986-09-15 Publication of FI70219C publication Critical patent/FI70219C/fi

Links

238000000034 method Methods 0.000 title claims description 18
150000001875 compounds Chemical class 0.000 claims description 86
-1 nitro, amino, hydroxy, methyl Chemical group 0.000 claims description 70
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical class C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims description 21
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical class [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
150000005331 phenylglycines Chemical class 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
125000005948 methanesulfonyloxy group Chemical group 0.000 claims description 2
RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical class OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
239000007787 solid Substances 0.000 claims 1
239000000203 mixture Substances 0.000 description 128
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 118
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 105
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 95
239000013078 crystal Substances 0.000 description 92
238000006243 chemical reaction Methods 0.000 description 70
239000000243 solution Substances 0.000 description 70
238000001816 cooling Methods 0.000 description 65
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 59
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
239000011541 reaction mixture Substances 0.000 description 40
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
238000001914 filtration Methods 0.000 description 37
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
239000002904 solvent Substances 0.000 description 35
230000000052 comparative effect Effects 0.000 description 34
239000000706 filtrate Substances 0.000 description 33
235000011121 sodium hydroxide Nutrition 0.000 description 32
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 30
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
239000003921 oil Substances 0.000 description 24
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
239000000725 suspension Substances 0.000 description 21
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
NKBWMBRPILTCRD-UHFFFAOYSA-N 2-Methylheptanoic acid Chemical compound CCCCCC(C)C(O)=O NKBWMBRPILTCRD-UHFFFAOYSA-N 0.000 description 17
SKMGJUKSPNZRRK-UHFFFAOYSA-N 6H-benzo[b]quinolizine-2-carboxylic acid Chemical compound C1=C(C=CN2CC3=C(C=C12)C=CC=C3)C(=O)O SKMGJUKSPNZRRK-UHFFFAOYSA-N 0.000 description 17
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 17
239000002244 precipitate Substances 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
239000012456 homogeneous solution Substances 0.000 description 13
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
235000017557 sodium bicarbonate Nutrition 0.000 description 13
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 12
229960000723 ampicillin Drugs 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
238000001953 recrystallisation Methods 0.000 description 12
238000010992 reflux Methods 0.000 description 12
QOMCOKJKSCUOBB-UHFFFAOYSA-N 9h-carbazole-4-carboxylic acid Chemical compound N1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O QOMCOKJKSCUOBB-UHFFFAOYSA-N 0.000 description 11
229960000583 acetic acid Drugs 0.000 description 11
239000002253 acid Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 10
229920000137 polyphosphoric acid Polymers 0.000 description 10
239000000047 product Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
150000007514 bases Chemical class 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 7
229960003022 amoxicillin Drugs 0.000 description 7
LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
229910000147 aluminium phosphate Inorganic materials 0.000 description 6
230000000845 anti-microbial effect Effects 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
239000012362 glacial acetic acid Substances 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 5
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 5
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
235000017550 sodium carbonate Nutrition 0.000 description 5
239000007858 starting material Substances 0.000 description 5
ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 4
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
150000008065 acid anhydrides Chemical class 0.000 description 4
238000005119 centrifugation Methods 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000843 powder Substances 0.000 description 4
238000000746 purification Methods 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
241000894006 Bacteria Species 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
229940123973 Oxygen scavenger Drugs 0.000 description 3
230000007059 acute toxicity Effects 0.000 description 3
231100000403 acute toxicity Toxicity 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000000194 fatty acid Substances 0.000 description 3
229930195729 fatty acid Natural products 0.000 description 3
150000004665 fatty acids Chemical class 0.000 description 3
238000005755 formation reaction Methods 0.000 description 3
239000001530 fumaric acid Substances 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 3
ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
RAYMXZBXQCGRGX-UHFFFAOYSA-N quinoline-5-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=N1 RAYMXZBXQCGRGX-UHFFFAOYSA-N 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
XHWOXLCXKDATQS-UHFFFAOYSA-N (2-oxo-3,4-dihydro-1h-quinolin-5-yl) methanesulfonate Chemical compound N1C(=O)CCC2=C1C=CC=C2OS(=O)(=O)C XHWOXLCXKDATQS-UHFFFAOYSA-N 0.000 description 2
TXLWDZJPQCYYQY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinolin-5-yl methanesulfonate Chemical compound N1CCCC2=C1C=CC=C2OS(=O)(=O)C TXLWDZJPQCYYQY-UHFFFAOYSA-N 0.000 description 2
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
RBKMMJSQKNKNEV-UHFFFAOYSA-N 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound OC(=O)C1C(C)(C)SC2CC(=O)N21 RBKMMJSQKNKNEV-UHFFFAOYSA-N 0.000 description 2
BBHMZHDPVNXFMI-UHFFFAOYSA-N 4-chloro-2,3-dihydro-1h-indole Chemical compound ClC1=CC=CC2=C1CCN2 BBHMZHDPVNXFMI-UHFFFAOYSA-N 0.000 description 2
YOYCNNJAIOQWMD-UHFFFAOYSA-N 4-chloro-2-methyl-2,3-dihydro-1h-indole Chemical compound C1=CC=C(Cl)C2=C1NC(C)C2 YOYCNNJAIOQWMD-UHFFFAOYSA-N 0.000 description 2
IAKNLKLKKBPMHN-UHFFFAOYSA-N 4h-quinolizine-2-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CCN21 IAKNLKLKKBPMHN-UHFFFAOYSA-N 0.000 description 2
HSQOAURZPIFPOL-UHFFFAOYSA-N 6-fluoro-2,3,4,9-tetrahydro-1h-carbazole Chemical compound C1CCCC2=C1NC1=CC=C(F)C=C12 HSQOAURZPIFPOL-UHFFFAOYSA-N 0.000 description 2
NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 2
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
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 2
231100000111 LD50 Toxicity 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
238000003436 Schotten-Baumann reaction Methods 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
239000004599 antimicrobial Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000012024 dehydrating agents‎ Substances 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
238000005187 foaming Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
229960003424 phenylacetic acid Drugs 0.000 description 2
239000003279 phenylacetic acid Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
229960003975 potassium Drugs 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000011736 potassium bicarbonate Substances 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
229940086066 potassium hydrogencarbonate Drugs 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
OMAFFHIGWTVZOH-UHFFFAOYSA-N 1-methyltetrazole Chemical compound CN1C=NN=N1 OMAFFHIGWTVZOH-UHFFFAOYSA-N 0.000 description 1
QEAAGGDOKYACRD-UHFFFAOYSA-N 1H-indol-4-yl hypochlorite Chemical compound ClOC1=CC=CC2=C1C=CN2 QEAAGGDOKYACRD-UHFFFAOYSA-N 0.000 description 1
YAUCGRHYMHRNPV-UHFFFAOYSA-N 2,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound OC(=O)C1(C)C(C)SC2CC(=O)N21 YAUCGRHYMHRNPV-UHFFFAOYSA-N 0.000 description 1
RBKMMJSQKNKNEV-UHFFFAOYSA-M 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound [O-]C(=O)C1C(C)(C)SC2CC(=O)N21 RBKMMJSQKNKNEV-UHFFFAOYSA-M 0.000 description 1
CGWOEOXQHIMZEQ-UHFFFAOYSA-N 3-[1-[[4-(2-phenylquinolin-3-yl)phenyl]methyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound OC1=NC2=CC=CC=C2N1C(CC1)CCN1CC(C=C1)=CC=C1C1=CC2=CC=CC=C2N=C1C1=CC=CC=C1 CGWOEOXQHIMZEQ-UHFFFAOYSA-N 0.000 description 1
YYFLDZZDOUDZQM-UHFFFAOYSA-N 3-[1-[[4-(3-phenylquinolin-2-yl)phenyl]methyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1C(CC1)CCN1CC(C=C1)=CC=C1C1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 YYFLDZZDOUDZQM-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
PAFKJCJIJXBWED-UHFFFAOYSA-N 4-chloro-2-methyl-1h-indole Chemical compound C1=CC=C2NC(C)=CC2=C1Cl PAFKJCJIJXBWED-UHFFFAOYSA-N 0.000 description 1
KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
PYHSWIJJWIWGKV-UHFFFAOYSA-N 4-oxo-1-azatetracyclo[7.6.1.05,16.010,15]hexadeca-2,5,7,9(16),10,12,14-heptaene-3-carboxylic acid Chemical compound O=C1C(=CN2C3=C1C=CC=C3C=1C=CC=CC2=1)C(=O)O PYHSWIJJWIWGKV-UHFFFAOYSA-N 0.000 description 1
YNSDWOHGYTZNDL-UHFFFAOYSA-N 4h-quinolizine-2-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CCN21 YNSDWOHGYTZNDL-UHFFFAOYSA-N 0.000 description 1
FQTGBHZZNVFFFM-UHFFFAOYSA-N 4h-quinolizine-2-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC=CC2=CC(C(=O)O)=CCN21 FQTGBHZZNVFFFM-UHFFFAOYSA-N 0.000 description 1
GLNUVOZWZUUKNT-UHFFFAOYSA-N 5,7-dichloro-1,2,3,4-tetrahydroquinoline Chemical compound C1CCNC2=CC(Cl)=CC(Cl)=C21 GLNUVOZWZUUKNT-UHFFFAOYSA-N 0.000 description 1
YMSHIIDMJGHMIX-UHFFFAOYSA-N 5-chloro-2,3,4,9-tetrahydro-1h-carbazole Chemical compound C1CCCC2=C1NC1=C2C(Cl)=CC=C1 YMSHIIDMJGHMIX-UHFFFAOYSA-N 0.000 description 1
UTTJAIFHRUAFED-UHFFFAOYSA-N 5-hydroxy-3,4-dihydro-2(1h)-quinolinone Chemical compound N1C(=O)CCC2=C1C=CC=C2O UTTJAIFHRUAFED-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
PASUADIMFGAUDB-UHFFFAOYSA-N 6-chloro-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(Cl)=CC=C21 PASUADIMFGAUDB-UHFFFAOYSA-N 0.000 description 1
RMOYSWDTCQZJGS-UHFFFAOYSA-N 6h-benzo[a]quinolizine Chemical compound C1=CC=CN2CC=C(C=CC=C3)C3=C21 RMOYSWDTCQZJGS-UHFFFAOYSA-N 0.000 description 1
NPISOEZDZIJCSD-UHFFFAOYSA-N 6h-benzo[b]quinolizine Chemical compound C1=CC=C2CN(C=CC=C3)C3=CC2=C1 NPISOEZDZIJCSD-UHFFFAOYSA-N 0.000 description 1
BKLZWTGHZHVWHD-UHFFFAOYSA-N 7-fluoro-4-oxo-1-azatetracyclo[7.6.1.05,16.010,15]hexadeca-2,5(16),6,8-tetraene-3-carboxylic acid Chemical compound C12CCCCC2C2=CC(F)=CC3=C2N1C=C(C(=O)O)C3=O BKLZWTGHZHVWHD-UHFFFAOYSA-N 0.000 description 1
LYIGMUYGOWBALS-UHFFFAOYSA-N 9-chloro-2-methyl-6-oxo-1,2-dihydro-6h-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid Chemical compound C1C(C)N2C=C(C(O)=O)C(=O)C3=C2C1=C(Cl)C=C3 LYIGMUYGOWBALS-UHFFFAOYSA-N 0.000 description 1
MBMRTJANBKFZPV-UHFFFAOYSA-N 9-chloro-6-oxo-1,2-dihydro-6h-pyrrolo-[3,2,1-ij]quinoline-5-carboxylic acid Chemical compound C1CC2=C(Cl)C=CC3=C2N1C=C(C(=O)O)C3=O MBMRTJANBKFZPV-UHFFFAOYSA-N 0.000 description 1
LDPRPCQCLNSMAO-UHFFFAOYSA-N 9h-carbazole-4-carboxamide Chemical compound N1C2=CC=CC=C2C2=C1C=CC=C2C(=O)N LDPRPCQCLNSMAO-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
FJHJDAXMUMKTKU-UHFFFAOYSA-N C1(CCCCC1)NC1CCCCC1.CC(=CCCCCC)C(=O)O Chemical compound C1(CCCCC1)NC1CCCCC1.CC(=CCCCCC)C(=O)O FJHJDAXMUMKTKU-UHFFFAOYSA-N 0.000 description 1
GESZXSULIBJIET-UHFFFAOYSA-N C1=CC=CC=2C=3C(=CC=CC3NC12)C(=O)NC(C(=O)N)C1=CC=CC=C1 Chemical compound C1=CC=CC=2C=3C(=CC=CC3NC12)C(=O)NC(C(=O)N)C1=CC=CC=C1 GESZXSULIBJIET-UHFFFAOYSA-N 0.000 description 1
VIKIHYLOIKVHNS-UHFFFAOYSA-N C1=CC=CC=2C=3C(=CC=CC3NC12)C(=O)NC(C(=O)O)C1=CC=CC=C1 Chemical compound C1=CC=CC=2C=3C(=CC=CC3NC12)C(=O)NC(C(=O)O)C1=CC=CC=C1 VIKIHYLOIKVHNS-UHFFFAOYSA-N 0.000 description 1
HJRJNYYSNGSXSH-UHFFFAOYSA-N C1=CC=CC=2C=3C(=CC=CC3NC12)C(=O)NC1(CC=CC=C1)CC(=O)O Chemical compound C1=CC=CC=2C=3C(=CC=CC3NC12)C(=O)NC1(CC=CC=C1)CC(=O)O HJRJNYYSNGSXSH-UHFFFAOYSA-N 0.000 description 1
QCZQDYLAWPMSAK-UHFFFAOYSA-N C=1C(=CCN2C=CC=CC12)C(=O)NC(C(=O)N)C1=CC=CC=C1 Chemical compound C=1C(=CCN2C=CC=CC12)C(=O)NC(C(=O)N)C1=CC=CC=C1 QCZQDYLAWPMSAK-UHFFFAOYSA-N 0.000 description 1
MNACKOKOGBBSML-UHFFFAOYSA-N C=1C(=CCN2C=CC=CC12)C(=O)NC(C(=O)O)C1=CC=CC=C1 Chemical compound C=1C(=CCN2C=CC=CC12)C(=O)NC(C(=O)O)C1=CC=CC=C1 MNACKOKOGBBSML-UHFFFAOYSA-N 0.000 description 1
CLZIPFZPCPIZHH-UHFFFAOYSA-N Cl.C1=C(C=CN2CC3=C(C=C12)C=CC=C3)C(=O)O Chemical compound Cl.C1=C(C=CN2CC3=C(C=C12)C=CC=C3)C(=O)O CLZIPFZPCPIZHH-UHFFFAOYSA-N 0.000 description 1
241000588914 Enterobacter Species 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241000588747 Klebsiella pneumoniae Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
241000085494 Pseudomonas aeruginosa E2 Species 0.000 description 1
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 description 1
241000607715 Serratia marcescens Species 0.000 description 1
241000607760 Shigella sonnei Species 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
241000194017 Streptococcus Species 0.000 description 1
241000193996 Streptococcus pyogenes Species 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
239000004098 Tetracycline Substances 0.000 description 1
241001080482 Urbanus proteus Species 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000008272 agar Substances 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
238000010640 amide synthesis reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
238000006664 bond formation reaction Methods 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 description 1
229960003669 carbenicillin Drugs 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
XCPXPFNKTCFWTA-UHFFFAOYSA-N ethyl carbonobromidate Chemical compound CCOC(Br)=O XCPXPFNKTCFWTA-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
XHGJOIDWPAJLHO-UHFFFAOYSA-N heptyl hydrogen carbonate Chemical compound CCCCCCCOC(O)=O XHGJOIDWPAJLHO-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052806 inorganic carbonate Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
QQHNGZNHRRLNKI-UHFFFAOYSA-N methyl carbonobromidate Chemical compound COC(Br)=O QQHNGZNHRRLNKI-UHFFFAOYSA-N 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
NHTXRWUMLXSOGJ-UHFFFAOYSA-N n-hexylformamide Chemical compound CCCCCCNC=O NHTXRWUMLXSOGJ-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
LZHJFZLHEGJWAU-UHFFFAOYSA-N quinoline-5-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=CC2=N1 LZHJFZLHEGJWAU-UHFFFAOYSA-N 0.000 description 1
RAYMXZBXQCGRGX-UHFFFAOYSA-M quinoline-5-carboxylate Chemical compound C1=CC=C2C(C(=O)[O-])=CC=CC2=N1 RAYMXZBXQCGRGX-UHFFFAOYSA-M 0.000 description 1
ZXVCNGYTKNZMMS-UHFFFAOYSA-N quinoline-5-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC=C2C(C(=O)O)=CC=CC2=N1 ZXVCNGYTKNZMMS-UHFFFAOYSA-N 0.000 description 1
150000003250 quinolizines Chemical class 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
229940115939 shigella sonnei Drugs 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
229960002180 tetracycline Drugs 0.000 description 1
229930101283 tetracycline Natural products 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003952 β-lactams Chemical class 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Hydrogenated Pyridines (AREA)
Cephalosporin Compounds (AREA)

FI791190A 1978-04-12 1979-04-11 Foerfarande foer framstaellning av en beta-laktamantibiotikumfoerening FI70219C (fi)

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date	Title
JP4362478		1978-04-12
JP53043624A JPS6034957B2 (ja)	1978-04-12	1978-04-12	ペニシラン酸誘導体
JP11046478		1978-09-07
JP53110464A JPS6037118B2 (ja)	1978-09-07	1978-09-07	ペニシラン酸誘導体
JP14178578		1978-11-16
JP53141785A JPS6037119B2 (ja)	1978-11-16	1978-11-16	ペニシラン酸誘導体
JP53145638A JPS5951959B2 (ja)	1978-11-24	1978-11-24	ペニシラン酸誘導体
JP14563878		1978-11-24

Publications (3)

Publication Number	Publication Date
FI791190A7 FI791190A7 (fi)	1979-10-13
FI70219B FI70219B (fi)	1986-02-28
FI70219C true FI70219C (fi)	1986-09-15

Family

ID=27461393

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI791190A FI70219C (fi)	1978-04-12	1979-04-11	Foerfarande foer framstaellning av en beta-laktamantibiotikumfoerening

Country Status (18)

Country	Link
US (1)	US4317820A (de)
AR (2)	AR227005A1 (de)
AT (1)	AT368159B (de)
AU (1)	AU524795B2 (de)
CA (1)	CA1133469A (de)
CH (1)	CH642081A5 (de)
DE (1)	DE2914218C2 (de)
DK (1)	DK149479A (de)
ES (2)	ES480281A1 (de)
FI (1)	FI70219C (de)
FR (1)	FR2422666A1 (de)
IT (1)	IT1162605B (de)
MX (1)	MX5704E (de)
NL (1)	NL180589C (de)
NO (2)	NO791223L (de)
PT (1)	PT69473A (de)
SE (1)	SE7903297L (de)
SU (1)	SU1151212A3 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5792774A (en) *	1996-02-21	1998-08-11	Chiroscience Limited	Quinolones and their therapeutic use
US6525049B2 (en)	2000-07-05	2003-02-25	Pharmacia & Upjohn Company	Pyrroloquinolones as antiviral agents
KR20080064173A (ko) *	2005-10-21	2008-07-08	글락소 그룹 리미티드	항균제로서 유용한 페리 축합 트리시클릭 화합물

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL175419C (nl) *	1971-10-23	1984-11-01	Bayer Ag	Werkwijze ter bereiding of vervaardiging van antibiotisch werkzame farmaceutische preparaten, alsmede werkwijze ter bereiding van antibiotisch werkzame alfa-gesubstitueerde 6-(alfa-(3-acylureido)acetylamino) penicillanzuurderivaten.
US3780034A (en) *	1971-11-29	1973-12-18	Merck & Co Inc	Process for preparing substituted cephalosporins
US3778432A (en) *	1971-12-13	1973-12-11	Merck & Co Inc	Isocyanates and carbamates of penicillins and 3-cephem-4-carboxylic acids
US3954731A (en) *	1972-07-03	1976-05-04	Eli Lilly And Company	Process for preparing 6-alkoxypenicillanic and 7-alkoxycephalosporin acids
US3917609A (en)	1973-06-27	1975-11-04	Minnesota Mining & Mfg	Pyrroloquinoline carboxylic acids and derivatives
US4062842A (en) *	1973-09-06	1977-12-13	E. R. Squibb & Sons, Inc.	Method for preparing 7-substituted cephalosporins and 6-substituted penicillins by replacement of sulfur-containing groups
DE2559932C2 (de)	1974-05-09	1983-04-21	Toyama Chemical Co. Ltd., Tokyo	Cephalosporine, Verfahren zur Herstellung derselben und Mittel mit einem Gehalt derselben
US3962214A (en) *	1974-07-11	1976-06-08	Eli Lilly And Company	Process for preparing amino substituted β-lactam antibiotics

1979
- 1979-04-09 DE DE2914218A patent/DE2914218C2/de not_active Expired
- 1979-04-10 DK DK149479A patent/DK149479A/da not_active Application Discontinuation
- 1979-04-10 IT IT48691/79A patent/IT1162605B/it active
- 1979-04-10 US US06/028,770 patent/US4317820A/en not_active Expired - Lifetime
- 1979-04-10 NO NO79791223A patent/NO791223L/no unknown
- 1979-04-11 AU AU46038/79A patent/AU524795B2/en not_active Ceased
- 1979-04-11 FI FI791190A patent/FI70219C/fi not_active IP Right Cessation
- 1979-04-11 AT AT0269079A patent/AT368159B/de not_active IP Right Cessation
- 1979-04-11 AR AR276166A patent/AR227005A1/es active
- 1979-04-11 ES ES480281A patent/ES480281A1/es not_active Expired
- 1979-04-11 PT PT69473A patent/PT69473A/pt unknown
- 1979-04-11 MX MX797868U patent/MX5704E/es unknown
- 1979-04-11 CA CA325,375A patent/CA1133469A/en not_active Expired
- 1979-04-11 SU SU792753360A patent/SU1151212A3/ru active
- 1979-04-11 CH CH343479A patent/CH642081A5/de not_active IP Right Cessation
- 1979-04-12 NL NLAANVRAGE7902906,A patent/NL180589C/xx not_active IP Right Cessation
- 1979-04-12 FR FR7909337A patent/FR2422666A1/fr active Granted
- 1979-04-12 SE SE7903297A patent/SE7903297L/xx unknown
1980
- 1980-01-30 ES ES488833A patent/ES488833A0/es active Granted
1981
- 1981-03-11 AR AR284582A patent/AR226883A1/es active
1984
- 1984-02-20 NO NO84840617A patent/NO840617L/no unknown

Also Published As

Publication number	Publication date
NO840617L (no)	1979-10-15
NL180589C (nl)	1987-03-16
SE7903297L (sv)	1979-12-21
NL7902906A (nl)	1979-10-16
AT368159B (de)	1982-09-27
IT7948691A0 (it)	1979-04-10
SU1151212A3 (ru)	1985-04-15
US4317820A (en)	1982-03-02
FI70219B (fi)	1986-02-28
DE2914218A1 (de)	1979-10-25
DK149479A (da)	1979-10-13
AU4603879A (en)	1979-10-18
FI791190A7 (fi)	1979-10-13
FR2422666A1 (fr)	1979-11-09
NL180589B (nl)	1986-10-16
AR226883A1 (es)	1982-08-31
CA1133469A (en)	1982-10-12
AR227005A1 (es)	1982-09-15
ES8200339A1 (es)	1981-11-16
PT69473A (en)	1979-05-01
DE2914218C2 (de)	1985-10-24
CH642081A5 (de)	1984-03-30
IT1162605B (it)	1987-04-01
NO791223L (no)	1979-10-15
AU524795B2 (en)	1982-10-07
ES480281A1 (es)	1980-08-16
ES488833A0 (es)	1981-11-16
FR2422666B1 (de)	1983-02-04
MX5704E (es)	1983-12-16
ATA269079A (de)	1982-01-15

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: OTSUKA PHARMACEUTICAL CO. LTD

Publication	Publication Date	Title
US4382892A (en)	1983-05-10	Benzoxazine derivatives
US5091384A (en)	1992-02-25	Anti-bacterial quinolone- and naphthyridone-carboxylic acid compounds
HU183218B (en)	1984-04-28	Process for producing new naphtridine derivatives
SE448542B (sv)	1987-03-02	Bensoheterocykliska foreningar, forfarande for deras framstellning och farmaceutisk komposition derav
EP0690862B1 (de)	2002-07-10	Chinolonderivate und verfahren zu deren herstellung
CS235502B2 (en)	1985-05-15	Method of 1-ethyl or vinyl-6-halogen-1-4-dihydro-4-oxo-7- (1-piperazinyl)-1,8-naphtyridin-3-carboxyl acid production
CS246065B2 (en)	1986-10-16	Method of new 7-substituted cyclic aminonaphthyridine-,quinoline-and benzoxazinecarboxylic acids production
HU199821B (en)	1990-03-28	Process for production of derivatives of in 8 position substituated quinoline carbonic acid and medical compositions containing them
IE54898B1 (en)	1990-03-14	New quinolone compounds and preparation thereof
EP0109284B1 (de)	1989-01-11	6,7-Dihydro-5,8-dimethyl-9-fluor-1-oxo-1H,5H-benzo(ij)chinolizin-2-carbonsäure und ihre Derivate
HU187356B (en)	1985-12-28	Process for producing quinoline-carboxylic acid derivatives
NO166130B (no)	1991-02-25	Analogifremgangsmaate for fremstilling av terapeutisk aktive 4-pyridonderivater.
FI70219C (fi)	1986-09-15	Foerfarande foer framstaellning av en beta-laktamantibiotikumfoerening
SE445917B (sv)	1986-07-28	Benso(ij)kinolizin-2-karboxylsyraderivat, framstellning derav och terapeutisk komposition
JPS6237628B2 (de)	1987-08-13
IE872444L (en)	1988-03-12	Pyrido-benzoxadiazine derivatives
HUT56366A (en)	1991-08-28	Process for producing diazobicycloamine derivatives
US4720495A (en)	1988-01-19	Benzo[ij]quinolizine-2-carboxylic acids useful for treating bacterial infection
NZ204900A (en)	1986-11-12	1,3-dioxolo(4,5-g)quinolines and pharmaceutical compositions containing such
KR900009024B1 (ko)	1990-12-17	퀴놀론카르복실산 화합물 및 이의 약학적 용도
US4497816A (en)	1985-02-05	7-(4-Pyridyl)-1,8-naphthyridine derivatives and their antibacterial compositions
US3313817A (en)	1967-04-11	4-alkyl (and alkenyl)-1-oxo-1, 4-dihydro-4, 7-phenanthroline-2-carboxylic acid derivatives
FI66612C (fi)	1984-11-12	Foerfarande foer framstaellning av nya saosom antimicrobica anaendbara piperazinylbensoheterocykliska foereningar
HU205114B (en)	1992-03-30	Process for producing 1,8-benzonaphthyridine derivatives
KR970001159B1 (ko)	1997-01-29	신규 1,8-나프티리딘 유도체 및 그의 제조방법