CS261250B2 - Method of 1-methylaminoquinolinecarboxyl acid's and its derivatives production - Google Patents

Method of 1-methylaminoquinolinecarboxyl acid's and its derivatives production Download PDF

Info

Publication number: CS261250B2
Authority: CS; Czechoslovakia
Prior art keywords: acid; formula; process according; general formula; iii
Prior art date: 1985-12-09

Application number

CS869090A

Other languages

Czech (cs)

English (en)

Other versions

CS909086A2 (en

Inventor

Istvan Hermecz

Geza Kereszturi

Lelle Vasvar

Agnes Horvath

Maria Balogh

Gabor Kovacs

Tamas Szuets

Peter Ritli

Judit Sipos

Aniko Pajor

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

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.)

1985-12-09

Filing date

1986-12-09

Publication date

1989-01-12

1986-12-09 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1988-05-16 Publication of CS909086A2 publication Critical patent/CS909086A2/cs

1989-01-12 Publication of CS261250B2 publication Critical patent/CS261250B2/cs

Links

238000000034 method Methods 0.000 title claims abstract description 16
239000002253 acid Substances 0.000 title claims description 19
238000004519 manufacturing process Methods 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 15
-1 4-methyl-piperazinyl Chemical group 0.000 claims abstract description 10
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 10
230000007062 hydrolysis Effects 0.000 claims abstract description 7
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 7
238000002360 preparation method Methods 0.000 claims abstract description 6
125000004193 piperazinyl group Chemical group 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims abstract 4
229910052736 halogen Inorganic materials 0.000 claims abstract 4
150000002367 halogens Chemical class 0.000 claims abstract 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
239000007864 aqueous solution Substances 0.000 claims description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
239000011230 binding agent Substances 0.000 claims description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
238000002955 isolation Methods 0.000 claims description 4
150000007530 organic bases Chemical class 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
150000001408 amides Chemical class 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
229910052796 boron Inorganic materials 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
150000003462 sulfoxides Chemical class 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 2
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 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
229910052760 oxygen Inorganic materials 0.000 claims 2
239000001301 oxygen Substances 0.000 claims 2
MHJYITZPUNCJFC-UHFFFAOYSA-N 1-(methylamino)-2h-quinoline-2-carboxylic acid Chemical class C1=CC=C2N(NC)C(C(O)=O)C=CC2=C1 MHJYITZPUNCJFC-UHFFFAOYSA-N 0.000 claims 1
XGCTUKUCGUNZDN-UHFFFAOYSA-N [B].O=O Chemical compound [B].O=O XGCTUKUCGUNZDN-UHFFFAOYSA-N 0.000 claims 1
150000007522 mineralic acids Chemical class 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 abstract description 6
230000035484 reaction time Effects 0.000 abstract description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
239000001257 hydrogen Substances 0.000 abstract description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
125000004423 acyloxy group Chemical group 0.000 abstract 2
125000001931 aliphatic group Chemical group 0.000 abstract 1
239000003242 anti bacterial agent Substances 0.000 abstract 1
125000003118 aryl group Chemical group 0.000 abstract 1
125000005843 halogen group Chemical group 0.000 abstract 1
230000003301 hydrolyzing effect Effects 0.000 abstract 1
239000011541 reaction mixture Substances 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000013078 crystal Substances 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
239000000203 mixture Substances 0.000 description 11
239000000243 solution Substances 0.000 description 11
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 7
RCNJBEXSAWUACU-UHFFFAOYSA-N 7-chloro-6-fluoro-1-(methylamino)-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C(Cl)C=C2N(NC)C=C(C(O)=O)C(=O)C2=C1 RCNJBEXSAWUACU-UHFFFAOYSA-N 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
238000009835 boiling Methods 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
ZRKFBTRXQQSIKC-UHFFFAOYSA-N difluoroboranyloxy(difluoro)borane Chemical compound FB(F)OB(F)F ZRKFBTRXQQSIKC-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical class C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
150000001642 boronic acid derivatives Chemical class 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 2
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
SPDVUMPQVJLXON-UHFFFAOYSA-N CNN1C=C(C(=O)C2=CC(=C(C=C21)Cl)F)C(=O)OC(=O)C3=CN(C4=CC(=C(C=C4C3=O)F)Cl)NC Chemical compound CNN1C=C(C(=O)C2=CC(=C(C=C21)Cl)F)C(=O)OC(=O)C3=CN(C4=CC(=C(C=C4C3=O)F)Cl)NC SPDVUMPQVJLXON-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
239000004327 boric acid Substances 0.000 description 2
150000001638 boron Chemical class 0.000 description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
239000000920 calcium hydroxide Substances 0.000 description 2
229910001861 calcium hydroxide Inorganic materials 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
150000007529 inorganic bases Chemical class 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
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
239000005968 1-Decanol Substances 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-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
KLIVFTBWBYWHNP-UHFFFAOYSA-N 6-fluoro-1-(methylamino)-4-oxoquinoline-3-carboxylic acid Chemical class FC1=CC=C2N(NC)C=C(C(O)=O)C(=O)C2=C1 KLIVFTBWBYWHNP-UHFFFAOYSA-N 0.000 description 1
HMZAPVPSPOQCTB-UHFFFAOYSA-N 7-chloro-1-(ethylamino)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C(Cl)C=C2N(NCC)C=C(C(O)=O)C(=O)C2=C1 HMZAPVPSPOQCTB-UHFFFAOYSA-N 0.000 description 1
QMGIOWTYWHZVEO-UHFFFAOYSA-N FOBOF Chemical compound FOBOF QMGIOWTYWHZVEO-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
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 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
235000011116 calcium hydroxide Nutrition 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
OKVJWADVFPXWQD-UHFFFAOYSA-N difluoroborinic acid Chemical compound OB(F)F OKVJWADVFPXWQD-UHFFFAOYSA-N 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
TYZJYJKPICJYCW-UHFFFAOYSA-N ethyl 7-chloro-6-fluoro-1-[formyl(methyl)amino]-4-oxoquinoline-3-carboxylate Chemical compound ClC1=C(F)C=C2C(=O)C(C(=O)OCC)=CN(N(C)C=O)C2=C1 TYZJYJKPICJYCW-UHFFFAOYSA-N 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
NGCRXXLKJAAUQQ-UHFFFAOYSA-N undec-5-ene Chemical compound CCCCCC=CCCCC NGCRXXLKJAAUQQ-UHFFFAOYSA-N 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Luminescent Compositions (AREA)
Peptides Or Proteins (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS869090A 1985-12-09 1986-12-09 Method of 1-methylaminoquinolinecarboxyl acid's and its derivatives production CS261250B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU854691A HU196782B (en)	1985-12-09	1985-12-09	Process for production of quinoline carbonic acid

Publications (2)

Publication Number	Publication Date
CS909086A2 CS909086A2 (en)	1988-05-16
CS261250B2 true CS261250B2 (en)	1989-01-12

Family

ID=10968683

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS869090A CS261250B2 (en)	1985-12-09	1986-12-09	Method of 1-methylaminoquinolinecarboxyl acid's and its derivatives production

Country Status (13)

Country	Link
US (1)	US4871849A (no)
EP (1)	EP0248876B1 (no)
KR (1)	KR940008304B1 (no)
AT (1)	ATE119884T1 (no)
CA (1)	CA1294621C (no)
CS (1)	CS261250B2 (no)
DD (1)	DD252602A5 (no)
FI (1)	FI86420C (no)
HU (1)	HU196782B (no)
NO (1)	NO170153C (no)
SU (1)	SU1579459A3 (no)
WO (1)	WO1987003586A1 (no)
YU (1)	YU45392B (no)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU198709B (en) *	1987-04-08	1989-11-28	Chinoin Gyogyszer Es Vegyeszet	Process for producing quinoline-carboxylic acid derivatives
SI8810667A8 (en) *	1987-04-08	1996-04-30	Chinoin Gyogyszer Es Vegyeszet	Anhydride of quinoline carboxylic acid of boron acid and process for their production.
US5380845A (en) *	1987-06-24	1995-01-10	Chinoin Gyogyszer- Es Vegyeszeti Termekek Gyara Rt.	Process for the preparation of quinoline carboxylic acid derivatives
HU203746B (en) *	1988-12-22	1991-09-30	Chinoin Gyogyszer Es Vegyeszet	Process for producing quinoline-carboxylic acid derivatives
US20050161429A1 (en) *	2002-02-07	2005-07-28	Andrew Sauciunac	Non-symmetrical photo tooling and dual surface etching

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6011913B2 (ja) *	1977-12-27	1985-03-28	広栄化学工業株式会社	１，８−ナフチリジン誘導体ならびにその製造方法
DE3363711D1 (en) *	1982-03-31	1986-07-03	Sterling Drug Inc	New quinolone compounds and preparation thereof
JPS5980683A (ja) *	1982-10-30	1984-05-10	Koei Chem Co Ltd	６−フルオロ−１，８−ナフチリジン誘導体およびその製造法
AU553415B2 (en) *	1983-09-19	1986-07-17	Abbott Japan Co., Ltd.	6-fluoro-1-4-dihydro-4-oxo-7-substituted piperazinyl- quinoline-3-carboxylic acids

1985
- 1985-12-09 HU HU854691A patent/HU196782B/hu not_active IP Right Cessation
1986
- 1986-12-08 CA CA000524727A patent/CA1294621C/en not_active Expired - Lifetime
- 1986-12-09 WO PCT/HU1986/000067 patent/WO1987003586A1/en active IP Right Grant
- 1986-12-09 EP EP87900245A patent/EP0248876B1/en not_active Expired - Lifetime
- 1986-12-09 KR KR1019870700632A patent/KR940008304B1/ko not_active IP Right Cessation
- 1986-12-09 YU YU2105/86A patent/YU45392B/xx unknown
- 1986-12-09 CS CS869090A patent/CS261250B2/cs unknown
- 1986-12-09 US US07/105,299 patent/US4871849A/en not_active Expired - Fee Related
- 1986-12-09 DD DD86297302A patent/DD252602A5/de not_active IP Right Cessation
- 1986-12-09 AT AT87900245T patent/ATE119884T1/de active
1987
- 1987-07-13 FI FI873097A patent/FI86420C/fi not_active IP Right Cessation
- 1987-07-23 NO NO873097A patent/NO170153C/no unknown
- 1987-08-07 SU SU874203110A patent/SU1579459A3/ru active

Also Published As

Publication number	Publication date
EP0248876A1 (en)	1987-12-16
WO1987003586A1 (en)	1987-06-18
FI86420C (fi)	1992-08-25
FI873097A0 (fi)	1987-07-13
SU1579459A3 (ru)	1990-07-15
FI86420B (fi)	1992-05-15
NO873097D0 (no)	1987-07-23
KR880700792A (ko)	1988-04-12
NO170153B (no)	1992-06-09
YU45392B (en)	1992-05-28
HUT43840A (en)	1987-12-28
KR940008304B1 (ko)	1994-09-12
YU210586A (en)	1987-12-31
DD252602A5 (de)	1987-12-23
ATE119884T1 (de)	1995-04-15
EP0248876B1 (en)	1995-03-15
NO873097L (no)	1987-07-23
US4871849A (en)	1989-10-03
CS909086A2 (en)	1988-05-16
FI873097A (fi)	1987-07-13
HU196782B (en)	1989-01-30
CA1294621C (en)	1992-01-21
NO170153C (no)	1992-09-16

Publication	Publication Date	Title
HUT58056A (en)	1992-01-28	Process for producing quinolonecarboxylic acid derivatives
EP0351889B1 (en)	1994-06-29	Process for the preparation of a quinoline carboxylic acid
KR970005911B1 (ko)	1997-04-22	퀴놀린 카복실산 유도체를 제조하는 제조방법
DK175037B1 (da)	2004-05-10	Fremgangsmåde til fremstilling af quinolincarboxylsyrederivater samt mellemprodukt, der kan anvendes ved fremgangsmåden
CS261250B2 (en)	1989-01-12	Method of 1-methylaminoquinolinecarboxyl acid's and its derivatives production
SU1604156A3 (ru)	1990-10-30	Способ получени ангидридов 1-этил-6-фтор-7-хлор-4-оксо-1,4-дигидро-хинолин-3-карбоновой кислоты и борных кислот
US5294712A (en)	1994-03-15	Process for the preparation of quinoline carboxylic acids
RU2002744C1 (ru)	1993-11-15	Способ получени 1-замещенной 6-фтор-4-оксо-7-(1-пиперазинил)-1,4-дигидрохинолин-3-карбоновой кислоты
US5284950A (en)	1994-02-08	Process for the preparation of quinoline carboxyolic acids
CS265229B2 (en)	1989-10-13	Making of intermediate for amifloxacine production
RU2049783C1 (ru)	1995-12-10	Способ получения производных хинолинкарбоновых кислот или их фармацевтически приемлемых солей
US5380845A (en)	1995-01-10	Process for the preparation of quinoline carboxylic acid derivatives
EP0195135B1 (en)	1992-06-17	A process for the preparation of quinoline carboxylic acid derivatives
NO172743B (no)	1993-05-24	Fremgangsmaate for fremstilling av kinolincarboxylsyrederivater
IE58031B1 (en)	1993-06-16	A process for the preparation of quinoline carboxylic acid derivatives
CZ97496A3 (en)	1996-10-16	Process for preparing 1-cyclopropyl-6-fluoro-1, 4-dihydro-7-£(1s, 4s)\|-5-methyl-2,5-diazabicyclo £2.2.1\|hept-2-yl\|-4-oxo-3-quinolinecarboxylic acid and salts thereof