FR2653663A1 - Novel benzo[1,8]naphthyridine derivatives, their preparation and compositions containing them - Google Patents
Novel benzo[1,8]naphthyridine derivatives, their preparation and compositions containing them Download PDFInfo
- Publication number
- FR2653663A1 FR2653663A1 FR8914203A FR8914203A FR2653663A1 FR 2653663 A1 FR2653663 A1 FR 2653663A1 FR 8914203 A FR8914203 A FR 8914203A FR 8914203 A FR8914203 A FR 8914203A FR 2653663 A1 FR2653663 A1 FR 2653663A1
- Authority
- FR
- France
- Prior art keywords
- benzo
- dihydro
- oxo
- naphthyridine
- fluoro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 66
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- BJVCSICIEDHBNI-UHFFFAOYSA-N benzo[b][1,8]naphthyridine Chemical class N1=CC=CC2=CC3=CC=CC=C3N=C21 BJVCSICIEDHBNI-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
- 229910052731 fluorine Chemical group 0.000 claims abstract description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 4
- 125000005605 benzo group Chemical group 0.000 claims description 72
- 239000002253 acid Substances 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 26
- -1 cyano, amino Chemical group 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 150000004885 piperazines Chemical class 0.000 claims description 6
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000003513 alkali Chemical group 0.000 abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 239000004599 antimicrobial Substances 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 203
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- 239000000047 product Substances 0.000 description 43
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
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- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- 239000011777 magnesium Substances 0.000 description 9
- 229910052749 magnesium Inorganic materials 0.000 description 9
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 9
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- MJIWQHRXSLOUJN-UHFFFAOYSA-N 1,2,4-triazin-3-amine Chemical compound NC1=NC=CN=N1 MJIWQHRXSLOUJN-UHFFFAOYSA-N 0.000 description 1
- JPZIBAJGRPFSMW-UHFFFAOYSA-N 1,4-dihydroquinoline-3-carbaldehyde Chemical compound C1=CC=C2CC(C=O)=CNC2=C1 JPZIBAJGRPFSMW-UHFFFAOYSA-N 0.000 description 1
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
- WRDGNXCXTDDYBZ-UHFFFAOYSA-N 2,3,4-trifluoroaniline Chemical compound NC1=CC=C(F)C(F)=C1F WRDGNXCXTDDYBZ-UHFFFAOYSA-N 0.000 description 1
- SSMMZAKIHWZSES-UHFFFAOYSA-N 2,7-dichloro-6-fluoro-1H-quinoline-2-carboxylic acid Chemical compound ClC1(NC2=CC(=C(C=C2C=C1)F)Cl)C(=O)O SSMMZAKIHWZSES-UHFFFAOYSA-N 0.000 description 1
- NGKHHEDLAUNMFD-UHFFFAOYSA-N 2-(4-methylphenyl)-2-oxoacetaldehyde Chemical compound CC1=CC=C(C(=O)C=O)C=C1 NGKHHEDLAUNMFD-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- FVXIPVHDRCDSRW-UHFFFAOYSA-N 2-[6-methoxy-6-(trifluoromethyl)cyclohexa-2,4-dien-1-yl]acetic acid Chemical compound COC1(C(F)(F)F)C=CC=CC1CC(O)=O FVXIPVHDRCDSRW-UHFFFAOYSA-N 0.000 description 1
- QGSOPZAYKHDVDO-UHFFFAOYSA-N 2-benzylpyrazine Chemical compound C=1N=CC=NC=1CC1=CC=CC=C1 QGSOPZAYKHDVDO-UHFFFAOYSA-N 0.000 description 1
- FSAIASGOPGKUTF-UHFFFAOYSA-N 2-chloro-6,7,8-trifluoro-1,4-dihydroquinoline-3-carbaldehyde Chemical compound C1C(C=O)=C(Cl)NC2=C1C=C(F)C(F)=C2F FSAIASGOPGKUTF-UHFFFAOYSA-N 0.000 description 1
- BVOUDZPODLRKHZ-UHFFFAOYSA-N 2-chloro-6,7-difluoro-1,4-dihydroquinoline-3-carbaldehyde Chemical compound C1C(C=O)=C(Cl)NC2=C1C=C(F)C(F)=C2 BVOUDZPODLRKHZ-UHFFFAOYSA-N 0.000 description 1
- AXNUZKSSQHTNPZ-UHFFFAOYSA-N 3,4-difluoroaniline Chemical compound NC1=CC=C(F)C(F)=C1 AXNUZKSSQHTNPZ-UHFFFAOYSA-N 0.000 description 1
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- QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
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- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- WJGAPUXHSQQWQF-UHFFFAOYSA-N acetic acid;hydrochloride Chemical compound Cl.CC(O)=O WJGAPUXHSQQWQF-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal 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
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N anhydrous methyl chloride Natural products ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 229960003121 arginine Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000020176 deacylation Effects 0.000 description 1
- 238000005947 deacylation reaction Methods 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 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
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000015092 herbal tea Nutrition 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- RKLUHJIBJTXOQU-UHFFFAOYSA-N n-chloro-n-phenylpropanamide Chemical compound CCC(=O)N(Cl)C1=CC=CC=C1 RKLUHJIBJTXOQU-UHFFFAOYSA-N 0.000 description 1
- 150000005054 naphthyridines Chemical class 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 229960000948 quinine Drugs 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (26)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8914203A FR2653663A1 (en) | 1989-10-30 | 1989-10-30 | Novel benzo[1,8]naphthyridine derivatives, their preparation and compositions containing them |
| RO146164A RO108347B1 (ro) | 1989-10-30 | 1990-10-22 | DERIVATI DE BENZO-(b)-NAFTIRIDIN-1,8 SI PROCEDEU DE PREPARARE A ACESTORA |
| HU906926A HU208138B (en) | 1989-10-30 | 1990-10-29 | Process for producing benzo-1,8-naphthyridine derivatives and pharmaceutical compositions comprising same |
| ES90403047T ES2062455T3 (es) | 1989-10-30 | 1990-10-29 | Nuevos derivados de benzonaftiridina-1,8, su preparacion y las composiciones que les contienen. |
| BG93114A BG60915B1 (bg) | 1989-10-30 | 1990-10-29 | Производни на бензонафтиридин-1,8 ,методи за получаването им и състави които ги съдържат |
| AU65551/90A AU629997B2 (en) | 1989-10-30 | 1990-10-29 | New benzo(1,8)naphthyridine derivatives, their preparation and compositions containing them |
| IL9615990A IL96159A (en) | 1989-10-30 | 1990-10-29 | Acids 8-) 3-Transformed-1-piperazinyl (-7-fluoro-4-exo-1,4-dihydrobenzo] B [] 1,8 [naphthyridine-3-carboxylates, their preparation and preparations containing or |
| ZA908639A ZA908639B (en) | 1989-10-30 | 1990-10-29 | New benzo(1,8)naphthyridine derivatives,their preparation and compositions containing them |
| DK90403047.5T DK0431991T3 (da) | 1989-10-30 | 1990-10-29 | Derivater af 1,8-benzonaphthyridin, fremstilling af disse forbindelser samt midler indeholdende forbindelserne |
| FI905329A FI92068C (fi) | 1989-10-30 | 1990-10-29 | Menetelmä uusien terapeuttisesti käyttökelpoisten 7-fluori-4-okso-8-(1-piperatsinyyli)-1,4-dihydro-1,8-bentso/b/naftyridiini-3-karboksyylihappojen valmistamiseksi |
| NO904683A NO175433C (no) | 1989-10-30 | 1990-10-29 | Analogifremgangsmåte for fremstilling av nye, terapeutisk aktive 1,8-benzonaftyridinderivater |
| CA002028730A CA2028730A1 (fr) | 1989-10-30 | 1990-10-29 | Derives de benzonaphtyridine-1-8, leur preparation et les compositions qui les contiennent |
| PL90287563A PL164270B1 (pl) | 1989-10-30 | 1990-10-29 | Sposób wytwarzania nowych pochodnych 1,8-benzo-[b]naftyrydyny PL PL |
| EP90403047A EP0431991B1 (fr) | 1989-10-30 | 1990-10-29 | Nouveaux dérivés de benzonaphtyridine-1,8 leur préparation et les compositions qui les contiennent |
| DE90403047T DE69005994T2 (de) | 1989-10-30 | 1990-10-29 | 1,8-Benzonaphthyridinderivate, ihre Herstellung und diese enthaltende Zusammensetzungen. |
| CS905297A CZ280513B6 (cs) | 1989-10-30 | 1990-10-29 | Deriváty 1,8-benzo/b/naftyridinu, způsob jejich přípravy a antibakteriální kompozice tyto deriváty obsahující |
| AT90403047T ATE100103T1 (de) | 1989-10-30 | 1990-10-29 | 1,8-benzonaphthyridinderivate, ihre herstellung und diese enthaltende zusammensetzungen. |
| IE389790A IE65099B1 (en) | 1989-10-30 | 1990-10-30 | New benzo[1,8]naphthyridine derivatives their preparation and compositions containing them |
| PT95743A PT95743B (pt) | 1989-10-30 | 1990-10-30 | /processo para a preparacao de derivados da-benzo{b//1,8/ naftiridina e de composicoes farmaceuticas que os contem |
| YU205390A YU47694B (sh) | 1989-10-30 | 1990-10-30 | Novi derivati 1,8-benzonaftiridina, postupak za njihovo dobivanje i postupak za dobivanje farmaceutske smeše |
| US07/605,340 US5053509A (en) | 1989-10-30 | 1990-10-30 | Benzo[1,8]naphthyridine derivatives, their preparation and compositions containing them |
| JP2293501A JPH03151384A (ja) | 1989-10-30 | 1990-10-30 | 新規なベンゾ〔b〕〔1,8〕ナフチリジン誘導体、その製造及びそれを含む組成物 |
| KR1019900017460A KR910007928A (ko) | 1989-10-30 | 1990-10-30 | 신규 벤조[1,8] 나프티리딘 유도체, 그의 제조 및 그를 함유하는 조성물 |
| TW079109196A TW214550B (enExample) | 1989-10-30 | 1990-10-30 | |
| NZ235890A NZ235890A (en) | 1989-10-30 | 1990-10-30 | Benzo (1,8) naphthyridine derivatives and antibacterial compositions |
| SU925011989A RU2047613C1 (ru) | 1989-10-30 | 1992-07-08 | Производные 1,8-бензо(b)нафтиридина и фармацевтическая композиция на их основе |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8914203A FR2653663A1 (en) | 1989-10-30 | 1989-10-30 | Novel benzo[1,8]naphthyridine derivatives, their preparation and compositions containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2653663A1 true FR2653663A1 (en) | 1991-05-03 |
| FR2653663B1 FR2653663B1 (enExample) | 1992-01-10 |
Family
ID=9386910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8914203A Granted FR2653663A1 (en) | 1989-10-30 | 1989-10-30 | Novel benzo[1,8]naphthyridine derivatives, their preparation and compositions containing them |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR2653663A1 (enExample) |
| ZA (1) | ZA908639B (enExample) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0169993A2 (de) * | 1984-06-04 | 1986-02-05 | Bayer Ag | 7-(3-Aryl-1-piperazinyl)-sowie 7-(3-Cyclohexyl-1-piperazinyl)-3-chinoloncarbonsäuren |
| EP0230053A2 (en) * | 1986-01-17 | 1987-07-29 | American Cyanamid Company | 7-(Substituted)piperazinyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids |
-
1989
- 1989-10-30 FR FR8914203A patent/FR2653663A1/fr active Granted
-
1990
- 1990-10-29 ZA ZA908639A patent/ZA908639B/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0169993A2 (de) * | 1984-06-04 | 1986-02-05 | Bayer Ag | 7-(3-Aryl-1-piperazinyl)-sowie 7-(3-Cyclohexyl-1-piperazinyl)-3-chinoloncarbonsäuren |
| EP0230053A2 (en) * | 1986-01-17 | 1987-07-29 | American Cyanamid Company | 7-(Substituted)piperazinyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2653663B1 (enExample) | 1992-01-10 |
| ZA908639B (en) | 1991-08-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ER | Errata listed in the french official journal (bopi) |
Free format text: 18/91 |
|
| ST | Notification of lapse |