NO300327B1 - 1,8-benzonaftyridinderivater og antimikrobielle preparater - Google Patents
1,8-benzonaftyridinderivater og antimikrobielle preparater Download PDFInfo
- Publication number
- NO300327B1 NO300327B1 NO941035A NO941035A NO300327B1 NO 300327 B1 NO300327 B1 NO 300327B1 NO 941035 A NO941035 A NO 941035A NO 941035 A NO941035 A NO 941035A NO 300327 B1 NO300327 B1 NO 300327B1
- Authority
- NO
- Norway
- Prior art keywords
- benzo
- oxo
- dihydro
- naphthyridine
- methyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 18
- 230000000845 anti-microbial effect Effects 0.000 title 1
- UWRGLMZRYNFMAB-UHFFFAOYSA-N pyrido[4,3-g]quinoline Chemical class C1=NC=CC2=CC3=CC=CN=C3C=C21 UWRGLMZRYNFMAB-UHFFFAOYSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 53
- 239000002253 acid Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
- 125000004212 difluorophenyl group Chemical group 0.000 abstract description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 abstract description 3
- 125000001207 fluorophenyl group Chemical group 0.000 abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 239000004599 antimicrobial Substances 0.000 abstract description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 87
- 239000007787 solid Substances 0.000 description 69
- CGXLVFZJJOXEDF-UHFFFAOYSA-N 1,8-naphthyridine-3-carboxylic acid Chemical compound N1=CC=CC2=CC(C(=O)O)=CN=C21 CGXLVFZJJOXEDF-UHFFFAOYSA-N 0.000 description 58
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000002844 melting Methods 0.000 description 26
- 230000008018 melting Effects 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000000725 suspension Substances 0.000 description 17
- -1 I 2 is H Chemical group 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 238000001816 cooling Methods 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 238000000746 purification Methods 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 239000002198 insoluble material Substances 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000000155 melt Substances 0.000 description 9
- 229940098779 methanesulfonic acid Drugs 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical compound CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- ZIKVTWBPKCIGPD-UHFFFAOYSA-N methanesulfonic acid;3-methylazetidin-3-amine Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.CC1(N)CNC1 ZIKVTWBPKCIGPD-UHFFFAOYSA-N 0.000 description 5
- KBKDCBZELBBQQI-UHFFFAOYSA-N n-methylazetidin-3-amine;dihydrochloride Chemical compound Cl.Cl.CNC1CNC1 KBKDCBZELBBQQI-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- HLYCKHOZSJZTKH-UHFFFAOYSA-N (1-benzhydryl-3-methylazetidin-3-yl) methanesulfonate Chemical compound C1C(C)(OS(C)(=O)=O)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 HLYCKHOZSJZTKH-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- BJVCSICIEDHBNI-UHFFFAOYSA-N benzo[b][1,8]naphthyridine Chemical class N1=CC=CC2=CC3=CC=CC=C3N=C21 BJVCSICIEDHBNI-UHFFFAOYSA-N 0.000 description 4
- 244000309464 bull Species 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- DHXXDTCOJUYKOQ-UHFFFAOYSA-N n,n-dimethylazetidin-3-amine;dihydrochloride Chemical compound Cl.Cl.CN(C)C1CNC1 DHXXDTCOJUYKOQ-UHFFFAOYSA-N 0.000 description 4
- IETLPNNWMHRUGS-UHFFFAOYSA-N n-ethylazetidin-3-amine;dihydrochloride Chemical compound Cl.Cl.CCNC1CNC1 IETLPNNWMHRUGS-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- GNUNZSHNXGMTQA-UHFFFAOYSA-N (1-benzhydryl-3-propylazetidin-3-yl) methanesulfonate Chemical compound C1C(CCC)(OS(C)(=O)=O)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 GNUNZSHNXGMTQA-UHFFFAOYSA-N 0.000 description 3
- MSVZMUILYMLJCF-UHFFFAOYSA-N (1-benzhydrylazetidin-3-yl) methanesulfonate Chemical compound C1C(OS(=O)(=O)C)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 MSVZMUILYMLJCF-UHFFFAOYSA-N 0.000 description 3
- BZHZHKVKNMHJKE-UHFFFAOYSA-N 1-benzhydryl-3-methylazetidin-2-amine Chemical compound NC1C(C)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 BZHZHKVKNMHJKE-UHFFFAOYSA-N 0.000 description 3
- OCGJXJHKZPGHMI-UHFFFAOYSA-N 1-benzhydryl-3-propylazetidin-3-amine Chemical compound C1C(CCC)(N)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 OCGJXJHKZPGHMI-UHFFFAOYSA-N 0.000 description 3
- IOTQIOOILSHDFQ-UHFFFAOYSA-N 1-benzhydryl-n-cyclopropyl-3-methylazetidin-3-amine Chemical compound C1C(C)(NC2CC2)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 IOTQIOOILSHDFQ-UHFFFAOYSA-N 0.000 description 3
- GIQZZQOLZXEHCN-UHFFFAOYSA-N 1-benzhydryl-n-ethyl-3-methylazetidin-3-amine Chemical compound C1C(NCC)(C)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 GIQZZQOLZXEHCN-UHFFFAOYSA-N 0.000 description 3
- HXZUGDDOYXGRRP-UHFFFAOYSA-N 1-benzhydryl-n-ethylazetidin-3-amine;dihydrochloride Chemical compound Cl.Cl.C1C(NCC)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 HXZUGDDOYXGRRP-UHFFFAOYSA-N 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- YGRAOQOZCJDXJM-UHFFFAOYSA-N 3-ethylazetidin-3-amine;methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.CCC1(N)CNC1 YGRAOQOZCJDXJM-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- NAHCDGOPMRQUDS-UHFFFAOYSA-N azetidin-3-amine;methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.NC1CNC1 NAHCDGOPMRQUDS-UHFFFAOYSA-N 0.000 description 3
- 150000001539 azetidines Chemical class 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- VNSYPJWBNWZJPW-UHFFFAOYSA-N n-cyclopropylazetidin-3-amine;dihydrochloride Chemical compound Cl.Cl.C1CC1NC1CNC1 VNSYPJWBNWZJPW-UHFFFAOYSA-N 0.000 description 3
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- JTSMALYOTZFJCF-UHFFFAOYSA-N (1-benzhydryl-3-ethylazetidin-3-yl) methanesulfonate Chemical compound C1C(CC)(OS(C)(=O)=O)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 JTSMALYOTZFJCF-UHFFFAOYSA-N 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 2
- RHQCPDGKOWRALN-UHFFFAOYSA-N 1-benzhydryl-3-ethylazetidin-3-amine Chemical compound C1C(CC)(N)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 RHQCPDGKOWRALN-UHFFFAOYSA-N 0.000 description 2
- JLNKQCMINZIWID-UHFFFAOYSA-N 1-benzhydryl-3-propylazetidin-3-ol Chemical compound C1C(CCC)(O)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 JLNKQCMINZIWID-UHFFFAOYSA-N 0.000 description 2
- SVYKKXALMSZXPC-UHFFFAOYSA-N 1-benzhydryl-n-cyclopropylazetidin-3-amine;dihydrochloride Chemical compound Cl.Cl.C1CC1NC1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 SVYKKXALMSZXPC-UHFFFAOYSA-N 0.000 description 2
- AVUDXLOVIBJFQA-UHFFFAOYSA-N 1-benzhydrylazetidin-3-one Chemical compound C1C(=O)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 AVUDXLOVIBJFQA-UHFFFAOYSA-N 0.000 description 2
- AGGVXRCHGLRVQN-UHFFFAOYSA-N 2,2-dimethylazetidin-3-amine;methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.CC1(C)NCC1N AGGVXRCHGLRVQN-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- HPDSPTCURBEIAT-UHFFFAOYSA-N 3-propylazetidin-3-amine Chemical compound CCCC1(N)CNC1 HPDSPTCURBEIAT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- FDPKMJDUXJFKOI-UHFFFAOYSA-N azetidin-3-amine Chemical compound NC1CNC1 FDPKMJDUXJFKOI-UHFFFAOYSA-N 0.000 description 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- COMYBBUQYYTAQX-UHFFFAOYSA-N ethyl 2-(2-chloro-6,7-difluoroquinoline-3-carbonyl)-3-(dimethylamino)prop-2-enoate Chemical compound FC1=C(F)C=C2N=C(Cl)C(C(=O)C(=CN(C)C)C(=O)OCC)=CC2=C1 COMYBBUQYYTAQX-UHFFFAOYSA-N 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- FZDQWGJDOUXSRV-UHFFFAOYSA-N methanesulfonic acid;3-propylazetidin-3-amine Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.CCCC1(N)CNC1 FZDQWGJDOUXSRV-UHFFFAOYSA-N 0.000 description 2
- WUUOIPQMONXIGC-UHFFFAOYSA-N n,3-dimethylazetidin-3-amine;methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.CNC1(C)CNC1 WUUOIPQMONXIGC-UHFFFAOYSA-N 0.000 description 2
- HVPRNFJOJFQOMZ-UHFFFAOYSA-N n-(azetidin-3-yl)-2,2,2-trifluoroacetamide;hydrochloride Chemical compound Cl.FC(F)(F)C(=O)NC1CNC1 HVPRNFJOJFQOMZ-UHFFFAOYSA-N 0.000 description 2
- OYPPTIMLOJPLGO-UHFFFAOYSA-N n-(azetidin-3-yl)acetamide;hydrochloride Chemical compound Cl.CC(=O)NC1CNC1 OYPPTIMLOJPLGO-UHFFFAOYSA-N 0.000 description 2
- MPYKSZSCJSIWDW-UHFFFAOYSA-N n-ethyl-3-methylazetidin-3-amine;methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.CCNC1(C)CNC1 MPYKSZSCJSIWDW-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- KUSISHXBHVFQPM-UHFFFAOYSA-N 1-(azetidin-3-yl)pyrrolidine Chemical compound C1NCC1N1CCCC1 KUSISHXBHVFQPM-UHFFFAOYSA-N 0.000 description 1
- CEKVJXURIPHORX-UHFFFAOYSA-N 1-(azetidin-3-yl)pyrrolidine;dihydrochloride Chemical compound Cl.Cl.C1NCC1N1CCCC1 CEKVJXURIPHORX-UHFFFAOYSA-N 0.000 description 1
- OZVGFUVCECQOHG-UHFFFAOYSA-N 1-benzhydryl-3-ethylazetidin-3-ol Chemical compound C1C(CC)(O)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 OZVGFUVCECQOHG-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9112058A FR2681865B1 (fr) | 1991-10-01 | 1991-10-01 | Nouveaux derives de la benzonaphtyridine-1,8 leur preparation et les compositions qui les contiennent. |
| PCT/FR1992/000901 WO1993007144A1 (fr) | 1991-10-01 | 1992-09-29 | Derives de benzonaphtyridine-1,8 et compositions antimicrobiennes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO941035D0 NO941035D0 (no) | 1994-03-22 |
| NO941035L NO941035L (no) | 1994-03-22 |
| NO300327B1 true NO300327B1 (no) | 1997-05-12 |
Family
ID=9417466
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO941035A NO300327B1 (no) | 1991-10-01 | 1994-03-22 | 1,8-benzonaftyridinderivater og antimikrobielle preparater |
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| Country | Link |
|---|---|
| EP (2) | EP0606382B1 (de) |
| JP (1) | JPH07501047A (de) |
| AT (1) | ATE166054T1 (de) |
| AU (1) | AU665787B2 (de) |
| CA (1) | CA2119755A1 (de) |
| CZ (1) | CZ282257B6 (de) |
| DE (1) | DE69225490D1 (de) |
| FI (1) | FI941517A (de) |
| FR (1) | FR2681865B1 (de) |
| GE (1) | GEP19981300B (de) |
| HU (1) | HU214599B (de) |
| IL (1) | IL103271A (de) |
| MX (1) | MX9205539A (de) |
| NO (1) | NO300327B1 (de) |
| NZ (1) | NZ244518A (de) |
| PL (1) | PL170866B1 (de) |
| RU (1) | RU2105006C1 (de) |
| SK (1) | SK37394A3 (de) |
| TW (1) | TW263510B (de) |
| WO (1) | WO1993007144A1 (de) |
| YU (1) | YU48244B (de) |
| ZA (1) | ZA927455B (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2682384B1 (fr) * | 1991-10-10 | 1995-04-07 | Bellon Laboratoires | Procede de preparation de benzo (b) naphtyridines. |
| GB9823103D0 (en) * | 1998-10-23 | 1998-12-16 | Pfizer Ltd | Pharmaceutically active compounds |
| ES2216606T3 (es) * | 1998-12-21 | 2004-10-16 | Aventis Pharma S.A. | Derivados de la benzo-1,8-naftiridina. |
| FR2787452B1 (fr) * | 1998-12-21 | 2004-10-22 | Aventis Pharma Sa | Nouveaux derives de la benzonaphtyridine-1,8, leur preparation et les compositions pharmaceutiques qui les contiennent |
| WO2000063168A1 (en) * | 1999-04-16 | 2000-10-26 | Coelacanth Chemical Corporation | Synthesis of azetidine derivatives |
| US6355631B1 (en) * | 2000-03-03 | 2002-03-12 | Aventis Pharma S.A. | Pharmaceutical compositions containing azetidine derivatives, novel azetidine derivatives and their preparation |
| TWI520963B (zh) | 2014-12-24 | 2016-02-11 | 國立清華大學 | １，９－二氮萉衍生物及其製法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO177302C (no) * | 1989-03-16 | 1995-08-23 | Esteve Labor Dr | Analogifremgangsmåte til fremstilling av terapeutisk aktive substituerte azetidinylkinolon(naftyridon)karboksylsyrederivater |
| RO108347B1 (ro) * | 1989-10-30 | 1994-04-28 | Bellon Labor Sa Roger | DERIVATI DE BENZO-(b)-NAFTIRIDIN-1,8 SI PROCEDEU DE PREPARARE A ACESTORA |
-
1991
- 1991-10-01 FR FR9112058A patent/FR2681865B1/fr not_active Expired - Fee Related
-
1992
- 1992-09-24 IL IL10327192A patent/IL103271A/en not_active IP Right Cessation
- 1992-09-28 NZ NZ244518A patent/NZ244518A/en unknown
- 1992-09-29 SK SK373-94A patent/SK37394A3/sk unknown
- 1992-09-29 WO PCT/FR1992/000901 patent/WO1993007144A1/fr active IP Right Grant
- 1992-09-29 RU RU94019969A patent/RU2105006C1/ru active
- 1992-09-29 PL PL92303093A patent/PL170866B1/pl unknown
- 1992-09-29 EP EP92921665A patent/EP0606382B1/de not_active Expired - Lifetime
- 1992-09-29 MX MX9205539A patent/MX9205539A/es not_active IP Right Cessation
- 1992-09-29 ZA ZA927455A patent/ZA927455B/xx unknown
- 1992-09-29 HU HU9400941A patent/HU214599B/hu not_active IP Right Cessation
- 1992-09-29 GE GEAP19922400A patent/GEP19981300B/en unknown
- 1992-09-29 AT AT92921665T patent/ATE166054T1/de not_active IP Right Cessation
- 1992-09-29 EP EP92402655A patent/EP0536035A1/de active Pending
- 1992-09-29 JP JP5506650A patent/JPH07501047A/ja active Pending
- 1992-09-29 AU AU27860/92A patent/AU665787B2/en not_active Ceased
- 1992-09-29 CZ CZ94752A patent/CZ282257B6/cs unknown
- 1992-09-29 DE DE69225490T patent/DE69225490D1/de not_active Expired - Lifetime
- 1992-09-29 TW TW081107683A patent/TW263510B/zh active
- 1992-09-29 CA CA002119755A patent/CA2119755A1/fr not_active Abandoned
- 1992-10-01 YU YU88192A patent/YU48244B/sh unknown
-
1994
- 1994-03-22 NO NO941035A patent/NO300327B1/no unknown
- 1994-03-31 FI FI941517A patent/FI941517A/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU665787B2 (en) | 1996-01-18 |
| PL170866B1 (pl) | 1997-01-31 |
| WO1993007144A1 (fr) | 1993-04-15 |
| HU214599B (hu) | 1998-04-28 |
| CA2119755A1 (fr) | 1993-04-15 |
| RU2105006C1 (ru) | 1998-02-20 |
| FR2681865B1 (fr) | 1993-11-19 |
| FR2681865A1 (fr) | 1993-04-02 |
| SK37394A3 (en) | 1994-12-07 |
| AU2786092A (en) | 1993-05-03 |
| EP0606382B1 (de) | 1998-05-13 |
| YU48244B (sh) | 1997-08-22 |
| CZ282257B6 (cs) | 1997-06-11 |
| NO941035D0 (no) | 1994-03-22 |
| ZA927455B (en) | 1993-04-07 |
| NZ244518A (en) | 1994-04-27 |
| IL103271A0 (en) | 1993-02-21 |
| TW263510B (de) | 1995-11-21 |
| HU9400941D0 (en) | 1994-06-28 |
| MX9205539A (es) | 1993-04-01 |
| FI941517A (fi) | 1994-05-02 |
| ATE166054T1 (de) | 1998-05-15 |
| JPH07501047A (ja) | 1995-02-02 |
| CZ75294A3 (en) | 1994-07-13 |
| HUT72463A (en) | 1996-04-29 |
| EP0536035A1 (de) | 1993-04-07 |
| EP0606382A1 (de) | 1994-07-20 |
| NO941035L (no) | 1994-03-22 |
| FI941517A0 (fi) | 1994-03-31 |
| YU88192A (sh) | 1995-10-03 |
| IL103271A (en) | 1996-03-31 |
| GEP19981300B (en) | 1998-05-01 |
| DE69225490D1 (de) | 1998-06-18 |
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