NO742351L - - Google Patents
Info
- Publication number
- NO742351L NO742351L NO742351A NO742351A NO742351L NO 742351 L NO742351 L NO 742351L NO 742351 A NO742351 A NO 742351A NO 742351 A NO742351 A NO 742351A NO 742351 L NO742351 L NO 742351L
- Authority
- NO
- Norway
- Prior art keywords
- quinoxaline
- piperazinyl
- formula
- hydrogen
- chloro
- Prior art date
Links
- -1 .carbalkoxy Chemical group 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 33
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 238000002360 preparation method Methods 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- RELPOLSGTUYMFR-UHFFFAOYSA-N 2-piperazin-1-ylquinoxaline Chemical compound C1CNCCN1C1=CN=C(C=CC=C2)C2=N1 RELPOLSGTUYMFR-UHFFFAOYSA-N 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 239000002798 polar solvent Substances 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000004193 piperazinyl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 11
- 125000001589 carboacyl group Chemical group 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 10
- 229930194542 Keto Natural products 0.000 claims description 9
- 239000003638 chemical reducing agent Substances 0.000 claims description 9
- 125000000468 ketone group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 230000009467 reduction Effects 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000003435 aroyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 6
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 6
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 231100000252 nontoxic Toxicity 0.000 claims description 6
- 230000003000 nontoxic effect Effects 0.000 claims description 6
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 3
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 3
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 3
- 125000005277 alkyl imino group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
- 150000003949 imides Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 238000000197 pyrolysis Methods 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 235000019270 ammonium chloride Nutrition 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
- 239000000203 mixture Substances 0.000 description 48
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000000706 filtrate Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000012362 glacial acetic acid Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 238000006722 reduction reaction Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000000935 antidepressant agent Substances 0.000 description 6
- 229940005513 antidepressants Drugs 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229940076279 serotonin Drugs 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- WFOKVKYNVKVWFK-UHFFFAOYSA-N 2,6-dichloroquinoxaline Chemical compound N1=C(Cl)C=NC2=CC(Cl)=CC=C21 WFOKVKYNVKVWFK-UHFFFAOYSA-N 0.000 description 5
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 230000001430 anti-depressive effect Effects 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- SSNCMIDZGFCTST-UHFFFAOYSA-N 1,3-difluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=C(F)C=CC=C1F SSNCMIDZGFCTST-UHFFFAOYSA-N 0.000 description 4
- OBVIIEVSLRCJSF-UHFFFAOYSA-N 6-chloroquinoxalin-2-amine Chemical compound C1=C(Cl)C=CC2=NC(N)=CN=C21 OBVIIEVSLRCJSF-UHFFFAOYSA-N 0.000 description 4
- ZHHVHNXHZINQDX-UHFFFAOYSA-N 8-fluoro-1h-quinoxalin-2-one Chemical compound N1=CC(=O)NC2=C1C=CC=C2F ZHHVHNXHZINQDX-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 230000036528 appetite Effects 0.000 description 4
- 235000019789 appetite Nutrition 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000002026 chloroform extract Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000006187 pill 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
- 230000001105 regulatory effect Effects 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000011135 tin Substances 0.000 description 4
- 229910052718 tin Inorganic materials 0.000 description 4
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 3
- JJTQVWHSMBWEJX-UHFFFAOYSA-N 2,3-dichloro-6-(trifluoromethyl)quinoxaline Chemical compound N1=C(Cl)C(Cl)=NC2=CC(C(F)(F)F)=CC=C21 JJTQVWHSMBWEJX-UHFFFAOYSA-N 0.000 description 3
- KVYFAZZUKRBQDA-UHFFFAOYSA-N 2-chloroquinoxaline-6-carbonitrile Chemical compound C1=C(C#N)C=CC2=NC(Cl)=CN=C21 KVYFAZZUKRBQDA-UHFFFAOYSA-N 0.000 description 3
- BXIXXXYDDJVHDL-UHFFFAOYSA-N 4-Chloro-ortho-phenylenediamine Chemical compound NC1=CC=C(Cl)C=C1N BXIXXXYDDJVHDL-UHFFFAOYSA-N 0.000 description 3
- BQNVOJRAHONGMT-UHFFFAOYSA-N 6-(trifluoromethyl)-1,4-dihydroquinoxaline-2,3-dione Chemical compound N1C(=O)C(=O)NC2=CC(C(F)(F)F)=CC=C21 BQNVOJRAHONGMT-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 150000003252 quinoxalines Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 3
- GZEGFNCRZUGIOB-UHFFFAOYSA-N 2,3,6-trichloroquinoxaline Chemical compound N1=C(Cl)C(Cl)=NC2=CC(Cl)=CC=C21 GZEGFNCRZUGIOB-UHFFFAOYSA-N 0.000 description 2
- OTEQFJHSOHZDRR-UHFFFAOYSA-N 2,3-dichloroquinoxaline-6-carbonitrile Chemical compound C1=C(C#N)C=C2N=C(Cl)C(Cl)=NC2=C1 OTEQFJHSOHZDRR-UHFFFAOYSA-N 0.000 description 2
- RJXOVESYJFXCGI-UHFFFAOYSA-N 2,4-difluoro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1F RJXOVESYJFXCGI-UHFFFAOYSA-N 0.000 description 2
- QRPUYNGXCJIUFC-UHFFFAOYSA-N 2-chloro-3-phenylsulfanyl-6-(trifluoromethyl)quinoxaline Chemical compound FC(C=1C=C2N=C(C(=NC2=CC1)Cl)SC1=CC=CC=C1)(F)F QRPUYNGXCJIUFC-UHFFFAOYSA-N 0.000 description 2
- MQNHTEGDNKDMGU-UHFFFAOYSA-N 2-chloro-5-fluoroquinoxaline Chemical compound ClC1=CN=C2C(F)=CC=CC2=N1 MQNHTEGDNKDMGU-UHFFFAOYSA-N 0.000 description 2
- PKOWPBJJCLWQMY-UHFFFAOYSA-N 2-chloro-6-(trifluoromethyl)quinoxaline Chemical compound N1=C(Cl)C=NC2=CC(C(F)(F)F)=CC=C21 PKOWPBJJCLWQMY-UHFFFAOYSA-N 0.000 description 2
- HYIHNBVCPAPJKH-UHFFFAOYSA-N 2-oxo-1h-quinoxaline-6-carbonitrile Chemical compound N#CC1=CC=C2NC(=O)C=NC2=C1 HYIHNBVCPAPJKH-UHFFFAOYSA-N 0.000 description 2
- RQWJHUJJBYMJMN-UHFFFAOYSA-N 4-(trifluoromethyl)benzene-1,2-diamine Chemical compound NC1=CC=C(C(F)(F)F)C=C1N RQWJHUJJBYMJMN-UHFFFAOYSA-N 0.000 description 2
- QFMJFXFXQAFGBO-UHFFFAOYSA-N 4-methoxy-2-nitroaniline Chemical compound COC1=CC=C(N)C([N+]([O-])=O)=C1 QFMJFXFXQAFGBO-UHFFFAOYSA-N 0.000 description 2
- QQUYDLGJURPFCY-UHFFFAOYSA-N 5-fluoro-1h-quinoxalin-2-one Chemical compound N1C(=O)C=NC2=C1C=CC=C2F QQUYDLGJURPFCY-UHFFFAOYSA-N 0.000 description 2
- BDBWPIXISLYKEG-UHFFFAOYSA-N 6-bromo-1h-quinoxalin-2-one Chemical compound N1C(=O)C=NC2=CC(Br)=CC=C21 BDBWPIXISLYKEG-UHFFFAOYSA-N 0.000 description 2
- SJAZZQLTKBYDHN-UHFFFAOYSA-N 6-chloro-1h-quinoxalin-2-one Chemical compound C1=C(Cl)C=CC2=NC(O)=CN=C21 SJAZZQLTKBYDHN-UHFFFAOYSA-N 0.000 description 2
- VIVXQKBATRMVNT-UHFFFAOYSA-N 6-hydroxy-1h-quinoxalin-2-one Chemical compound N1C(=O)C=NC2=CC(O)=CC=C21 VIVXQKBATRMVNT-UHFFFAOYSA-N 0.000 description 2
- SYEUUDPGKMMKRU-UHFFFAOYSA-N 6-methoxy-1h-quinoxalin-2-one Chemical compound N1C(=O)C=NC2=CC(OC)=CC=C21 SYEUUDPGKMMKRU-UHFFFAOYSA-N 0.000 description 2
- QXFWGNWEKCTIIL-UHFFFAOYSA-N 6-methylsulfonyl-1h-quinoxalin-2-one Chemical compound N1C(=O)C=NC2=CC(S(=O)(=O)C)=CC=C21 QXFWGNWEKCTIIL-UHFFFAOYSA-N 0.000 description 2
- 208000020401 Depressive disease Diseases 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
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- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- RFRSVYCGLNMJBT-UHFFFAOYSA-N ethyl 2-(5-fluoro-2-nitroanilino)acetate Chemical compound CCOC(=O)CNC1=CC(F)=CC=C1[N+]([O-])=O RFRSVYCGLNMJBT-UHFFFAOYSA-N 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 239000012054 flavored emulsion Substances 0.000 description 1
- 235000020375 flavoured syrup Nutrition 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000010575 fractional recrystallization Methods 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- MSQACBWWAIBWIC-UHFFFAOYSA-N hydron;piperazine;chloride Chemical compound Cl.C1CNCCN1 MSQACBWWAIBWIC-UHFFFAOYSA-N 0.000 description 1
- TVZISJTYELEYPI-UHFFFAOYSA-N hypodiphosphoric acid Chemical compound OP(O)(=O)P(O)(O)=O TVZISJTYELEYPI-UHFFFAOYSA-N 0.000 description 1
- BSRDNMMLQYNQQD-UHFFFAOYSA-N iminodiacetonitrile Chemical compound N#CCNCC#N BSRDNMMLQYNQQD-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000001640 nerve ending Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229940005654 nitrite ion Drugs 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- SAEMKKTVBSCOFX-UHFFFAOYSA-N quinoxalin-1-ium;chloride Chemical compound Cl.N1=CC=NC2=CC=CC=C21 SAEMKKTVBSCOFX-UHFFFAOYSA-N 0.000 description 1
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- PTLRDCMBXHILCL-UHFFFAOYSA-M sodium arsenite Chemical compound [Na+].[O-][As]=O PTLRDCMBXHILCL-UHFFFAOYSA-M 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- PTISTKLWEJDJID-UHFFFAOYSA-N sulfanylidenemolybdenum Chemical compound [Mo]=S PTISTKLWEJDJID-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37902273A | 1973-07-13 | 1973-07-13 | |
| US46538174A | 1974-04-29 | 1974-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO742351L true NO742351L (fr) | 1975-02-10 |
Family
ID=27008442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO742351A NO742351L (fr) | 1973-07-13 | 1974-06-27 |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5037791A (fr) |
| AU (1) | AU7073174A (fr) |
| BG (1) | BG21606A3 (fr) |
| CH (1) | CH605919A5 (fr) |
| DD (1) | DD112127A5 (fr) |
| DE (1) | DE2433397A1 (fr) |
| DK (1) | DK342674A (fr) |
| ES (1) | ES428107A1 (fr) |
| FI (1) | FI193974A (fr) |
| FR (1) | FR2236499B1 (fr) |
| GB (1) | GB1440722A (fr) |
| IE (1) | IE39869B1 (fr) |
| IL (1) | IL45158A0 (fr) |
| LU (1) | LU70510A1 (fr) |
| NL (1) | NL7408705A (fr) |
| NO (1) | NO742351L (fr) |
| RO (1) | RO63539A (fr) |
| SE (1) | SE417316B (fr) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4082845A (en) * | 1977-04-25 | 1978-04-04 | Merck & Co., Inc. | 3-(1-Piperazinyl)-pyrido[2,3-b]pyrazines |
| US4091098A (en) * | 1977-04-25 | 1978-05-23 | Merck & Co., Inc. | 3-(1-PIPERAZINYL)-1,2,4-BENZOTRIAZINES AND N-oxides |
| US4107309A (en) * | 1977-05-23 | 1978-08-15 | American Cyanamid Company | Substituted imidazo[1,2-d]-as-triazines |
| US4091101A (en) * | 1977-06-15 | 1978-05-23 | Merck & Co., Inc. | 6-(1-Piperazinyl)quinoxaline |
| EP0094498A3 (fr) * | 1982-05-06 | 1985-04-03 | American Cyanamid Company | Dérivés de 1-pipérazine utiles contre l'arthériosclérose |
| ES2042395B1 (es) * | 1992-02-27 | 1994-06-16 | Promotora Catalana De Inversio | Procedimiento para la obtencion de derivados de 2-ciano-3-piperacinilquinoxalinas. |
| FR2731221B1 (fr) * | 1995-03-01 | 1997-05-30 | Pf Medicament | Nouveaux derives de l'ethyl-1 dihydro-1, 2 oxo-2 methylamino-3 quinoxaline, leur utilisation a titre de medicament et les compositions pharmaceutiques les comprenant |
| WO1999021850A1 (fr) * | 1997-10-24 | 1999-05-06 | Neurogen Corporation | Piperazines de 1-(2-naphtyle) et de 1-(2-azanaphtyle)-4-(1-phenylmethyle)en tant que ligands pour le sous-type du recepteur de la dopamine d¿4? |
| US6040448A (en) | 1997-10-24 | 2000-03-21 | Neurogen Corporation | Certain 1-(2-naphthyl) and 1-(2-azanaphthyl)-4-(1-phenylmethyl) piperazines, dopamine receptor subtype specific ligands |
| WO2000012500A2 (fr) * | 1998-09-02 | 2000-03-09 | Neurogen Corporation | 2-aryl-4-[4-heteroaryl]piperazin-1-yl methylimidazoles: ligands pour le sous-type de recepteur d4 de la dopamine |
| SE9901884D0 (sv) * | 1999-05-21 | 1999-05-21 | Pharmacia & Upjohn Ab | Novel compounds their use and preparation |
| US6465467B1 (en) | 1999-05-21 | 2002-10-15 | Biovitrum Ab | Certain aryl-aliphatic and heteroaryl-aliphatic piperazinyl pyrazines and their use in the treatment of serotonin-related diseases |
| WO2000076984A2 (fr) * | 1999-05-21 | 2000-12-21 | Biovitrum Ab | Nouveaux composes, et utilisation et preparation de ces derniers |
| JP4707261B2 (ja) * | 2001-05-15 | 2011-06-22 | 日本エンバイロケミカルズ株式会社 | キノキサリン系化合物および工業用殺菌組成物 |
| ATE454383T1 (de) | 2002-06-19 | 2010-01-15 | Biovitrum Ab Publ | Neue verbindungen, deren verwendung und herstellung |
| WO2004009586A1 (fr) * | 2002-07-19 | 2004-01-29 | Biovitrum Ab | Nouveaux derives de piperazinyl-pyrazinone pour le traitement des troubles lies au recepteur 5-ht2a |
| SE0202287D0 (sv) * | 2002-07-19 | 2002-07-19 | Biovitrum Ab | New compounds |
| AU2004221812B2 (en) | 2003-03-19 | 2010-02-18 | Exelixis Inc. | Tie-2 modulators and methods of use |
| MXPA06003578A (es) * | 2003-09-30 | 2006-08-31 | Johnson & Johnson | Compuestos de quinoxalina. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL260335A (fr) * | 1960-01-22 | |||
| CH450434A (de) * | 1961-12-14 | 1968-01-31 | Ciba Geigy | Verfahren zur Herstellung von Diazinen |
| BE788451A (fr) * | 1971-09-08 | 1973-03-06 | Bayer Ag | Nouvelles 2-amino-quinoxalines, leur procede de preparation et leur application comme insecticides, acaricides et fongicides |
| GB1457400A (en) * | 1972-11-20 | 1976-12-01 | Pfizer | Pharmaceutical compositions containing 2-substituted quinoxa lines |
-
1974
- 1974-06-25 FI FI1939/74A patent/FI193974A/fi unknown
- 1974-06-26 DK DK342674A patent/DK342674A/da unknown
- 1974-06-27 NO NO742351A patent/NO742351L/no unknown
- 1974-06-27 SE SE7408486A patent/SE417316B/xx unknown
- 1974-06-27 NL NL7408705A patent/NL7408705A/xx not_active Application Discontinuation
- 1974-07-01 IL IL45158A patent/IL45158A0/xx unknown
- 1974-07-02 AU AU70731/74A patent/AU7073174A/en not_active Expired
- 1974-07-02 IE IE1397/74A patent/IE39869B1/xx unknown
- 1974-07-08 GB GB3017674A patent/GB1440722A/en not_active Expired
- 1974-07-09 ES ES428107A patent/ES428107A1/es not_active Expired
- 1974-07-11 LU LU70510A patent/LU70510A1/xx unknown
- 1974-07-11 DE DE2433397A patent/DE2433397A1/de active Pending
- 1974-07-11 FR FR7424114A patent/FR2236499B1/fr not_active Expired
- 1974-07-11 DD DD179871A patent/DD112127A5/xx unknown
- 1974-07-12 CH CH964874A patent/CH605919A5/xx not_active IP Right Cessation
- 1974-07-13 BG BG27222A patent/BG21606A3/xx unknown
- 1974-07-13 JP JP49079774A patent/JPS5037791A/ja active Pending
- 1974-07-13 RO RO7400079481A patent/RO63539A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU7073174A (en) | 1976-01-08 |
| NL7408705A (nl) | 1975-01-15 |
| IE39869B1 (en) | 1979-01-17 |
| RO63539A (fr) | 1978-07-15 |
| ES428107A1 (es) | 1976-11-16 |
| SE417316B (sv) | 1981-03-09 |
| IE39869L (en) | 1975-01-13 |
| JPS5037791A (fr) | 1975-04-08 |
| DD112127A5 (fr) | 1975-03-20 |
| IL45158A0 (en) | 1974-11-29 |
| GB1440722A (en) | 1976-06-23 |
| FR2236499B1 (fr) | 1977-04-15 |
| CH605919A5 (fr) | 1978-10-13 |
| DE2433397A1 (de) | 1975-02-06 |
| LU70510A1 (fr) | 1975-03-27 |
| FI193974A (fr) | 1975-01-14 |
| SE7408486L (sv) | 1975-01-14 |
| BG21606A3 (fr) | 1976-07-20 |
| FR2236499A1 (fr) | 1975-02-07 |
| DK342674A (fr) | 1975-03-03 |
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