SE441449B - Heterocykliska derivat och farmaceutiska kompositioner innehallande dessa derivat - Google Patents
Heterocykliska derivat och farmaceutiska kompositioner innehallande dessa derivatInfo
- Publication number
- SE441449B SE441449B SE8000205A SE8000205A SE441449B SE 441449 B SE441449 B SE 441449B SE 8000205 A SE8000205 A SE 8000205A SE 8000205 A SE8000205 A SE 8000205A SE 441449 B SE441449 B SE 441449B
- Authority
- SE
- Sweden
- Prior art keywords
- ethyl
- formula
- compounds
- group
- quinoxaline
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 73
- 150000001875 compounds Chemical class 0.000 claims description 61
- 229910052757 nitrogen Inorganic materials 0.000 claims description 58
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 43
- -1 hydroxymethyl- Chemical group 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000011203 carbon fibre reinforced carbon Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 4
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical group [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 68
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 53
- 239000000203 mixture Substances 0.000 description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- 239000000243 solution Substances 0.000 description 42
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- 229910052799 carbon Inorganic materials 0.000 description 39
- 239000000126 substance Substances 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 33
- 238000004458 analytical method Methods 0.000 description 31
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 17
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 16
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 16
- 238000002329 infrared spectrum Methods 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 239000000725 suspension Substances 0.000 description 12
- 239000003826 tablet Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 10
- 241000700159 Rattus Species 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000012448 Lithium borohydride Substances 0.000 description 8
- 235000019270 ammonium chloride Nutrition 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 239000000546 pharmaceutical excipient Substances 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- UAJUXJSXCLUTNU-UHFFFAOYSA-N pranlukast Chemical compound C=1C=C(OCCCCC=2C=CC=CC=2)C=CC=1C(=O)NC(C=1)=CC=C(C(C=2)=O)C=1OC=2C=1N=NNN=1 UAJUXJSXCLUTNU-UHFFFAOYSA-N 0.000 description 7
- 229960004583 pranlukast Drugs 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 239000001632 sodium acetate Substances 0.000 description 6
- 235000017281 sodium acetate Nutrition 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 230000008313 sensitization Effects 0.000 description 5
- UMVYPMIZWHTLFF-UHFFFAOYSA-N 2,5-Dichloroquinoxaline Chemical compound ClC1=CC=CC2=NC(Cl)=CN=C21 UMVYPMIZWHTLFF-UHFFFAOYSA-N 0.000 description 4
- ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 description 4
- 206010002198 Anaphylactic reaction Diseases 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 206010070834 Sensitisation Diseases 0.000 description 4
- 208000003455 anaphylaxis Diseases 0.000 description 4
- 239000000427 antigen Substances 0.000 description 4
- 102000036639 antigens Human genes 0.000 description 4
- 108091007433 antigens Proteins 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 150000002923 oximes Chemical class 0.000 description 4
- 239000002504 physiological saline solution Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 4
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 3
- AYGOPKCNRLLVRH-UHFFFAOYSA-N 5-(1H-imidazol-2-yl)-2H-tetrazole Chemical compound C1=CNC(C=2NN=NN=2)=N1 AYGOPKCNRLLVRH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000036783 anaphylactic response Effects 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
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 3
- VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 3
- 239000002024 ethyl acetate extract Substances 0.000 description 3
- 229960003699 evans blue Drugs 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- DQMFHJPQTMTOEV-UHFFFAOYSA-N 2-(2h-tetrazol-5-yl)imidazo[1,2-a]quinoxaline Chemical compound N1=C2C=NC3=CC=CC=C3N2C=C1C1=NN=NN1 DQMFHJPQTMTOEV-UHFFFAOYSA-N 0.000 description 2
- BWQHDBZIQZDFCY-UHFFFAOYSA-N 5-chloroquinoxalin-2-amine Chemical compound ClC1=CC=CC2=NC(N)=CN=C21 BWQHDBZIQZDFCY-UHFFFAOYSA-N 0.000 description 2
- 108010088751 Albumins Proteins 0.000 description 2
- 102000009027 Albumins Human genes 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 108010058846 Ovalbumin Proteins 0.000 description 2
- 240000003801 Sigesbeckia orientalis Species 0.000 description 2
- 235000003407 Sigesbeckia orientalis Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 230000003266 anti-allergic effect Effects 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- HARFQJNTXRLUGN-UHFFFAOYSA-N ethyl 3-(2-aminoquinoxalin-1-ium-1-yl)-2-oxopropanoate;bromide Chemical compound [Br-].C1=CC=C2[N+](CC(=O)C(=O)OCC)=C(N)C=NC2=C1 HARFQJNTXRLUGN-UHFFFAOYSA-N 0.000 description 2
- UMZALKINSDJRCY-UHFFFAOYSA-N ethyl imidazo[1,2-a]quinoxaline-2-carboxylate Chemical compound C1=CC=C2N3C=C(C(=O)OCC)N=C3C=NC2=C1 UMZALKINSDJRCY-UHFFFAOYSA-N 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- VRFWNFBIGLWUCR-UHFFFAOYSA-N imidazo[1,2-a]quinoxaline-2-carbaldehyde Chemical compound C1=CC=C2N3C=C(C=O)N=C3C=NC2=C1 VRFWNFBIGLWUCR-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229940092253 ovalbumin Drugs 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 2
- PZLGAOXMPNXQBW-UHFFFAOYSA-N quinoxalin-2-ylmethanol Chemical compound C1=CC=CC2=NC(CO)=CN=C21 PZLGAOXMPNXQBW-UHFFFAOYSA-N 0.000 description 2
- UPUZGXILYFKSGE-UHFFFAOYSA-M quinoxaline-2-carboxylate Chemical compound C1=CC=CC2=NC(C(=O)[O-])=CN=C21 UPUZGXILYFKSGE-UHFFFAOYSA-M 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- IQPCLDKBSXJSNZ-UHFFFAOYSA-N (5-ethyl-1h-imidazol-2-yl)methanol Chemical compound CCC1=CN=C(CO)N1 IQPCLDKBSXJSNZ-UHFFFAOYSA-N 0.000 description 1
- UNLHKHZVPKHOBX-UHFFFAOYSA-N 1,2-benzoxazin-2-ylmethanol Chemical compound O1N(C=CC2=C1C=CC=C2)CO UNLHKHZVPKHOBX-UHFFFAOYSA-N 0.000 description 1
- BJLRVFDWAOVFCI-UHFFFAOYSA-N 1h-imidazole;quinoline Chemical compound C1=CNC=N1.N1=CC=CC2=CC=CC=C21 BJLRVFDWAOVFCI-UHFFFAOYSA-N 0.000 description 1
- WLODWTPNUWYZKN-UHFFFAOYSA-N 1h-pyrrol-2-ol Chemical compound OC1=CC=CN1 WLODWTPNUWYZKN-UHFFFAOYSA-N 0.000 description 1
- SDXJSSHDXMAEQX-UHFFFAOYSA-N 2,3-dihydroimidazo[4,5-f]quinoxalin-1-ylmethanol Chemical compound OCN1CNC=2C=CC=3N=CC=NC3C21 SDXJSSHDXMAEQX-UHFFFAOYSA-N 0.000 description 1
- YTEHWAFIZXWKAA-UHFFFAOYSA-N 2-(2h-tetrazol-5-yl)imidazo[1,2-a]quinoline Chemical compound N1=C2C=CC3=CC=CC=C3N2C=C1C1=NN=NN1 YTEHWAFIZXWKAA-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
- NBOQCTZQZWICLB-UHFFFAOYSA-N 2-ethyl-1,4-dihydroimidazol-5-one Chemical compound CCC1=NCC(=O)N1 NBOQCTZQZWICLB-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- QLVSLJAXURJSAR-UHFFFAOYSA-N 3-(hydroxymethyl)-1h-quinoxalin-2-one Chemical compound C1=CC=C2N=C(O)C(CO)=NC2=C1 QLVSLJAXURJSAR-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- RGNDUQAJWUSZET-UHFFFAOYSA-N 4,5-dihydroimidazo[1,2-a]quinoxalin-2-ylmethanol Chemical compound C1=CC=C2N3C=C(CO)N=C3CNC2=C1 RGNDUQAJWUSZET-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- DJWQOBDHRKYSIJ-UHFFFAOYSA-N 4-(hydroxymethyl)imidazo[4,5-f]quinoxalin-2-one Chemical compound OCC1=CC=2N=CC=NC2C=2C1=NC(N2)=O DJWQOBDHRKYSIJ-UHFFFAOYSA-N 0.000 description 1
- RPXIFCHQYBLRKC-UHFFFAOYSA-N 5-ethyl-2-(hydroxyiminomethyl)imidazo[1,2-a]quinoxalin-4-one Chemical compound O=C1N(CC)C2=CC=CC=C2N2C1=NC(C=NO)=C2 RPXIFCHQYBLRKC-UHFFFAOYSA-N 0.000 description 1
- IICQXIBDCKGJBZ-UHFFFAOYSA-N 5-ethyl-2-(hydroxymethyl)imidazo[1,2-a]quinoxalin-4-one Chemical compound O=C1N(CC)C2=CC=CC=C2N2C1=NC(CO)=C2 IICQXIBDCKGJBZ-UHFFFAOYSA-N 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
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- 150000003138 primary alcohols Chemical class 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-M quinaldate Chemical compound C1=CC=CC2=NC(C(=O)[O-])=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-M 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- WDXARTMCIRVMAE-UHFFFAOYSA-N quinoline-2-carbonitrile Chemical compound C1=CC=CC2=NC(C#N)=CC=C21 WDXARTMCIRVMAE-UHFFFAOYSA-N 0.000 description 1
- YOWAEZWWQFSEJD-UHFFFAOYSA-N quinoxalin-2-amine Chemical compound C1=CC=CC2=NC(N)=CN=C21 YOWAEZWWQFSEJD-UHFFFAOYSA-N 0.000 description 1
- UJEHWLFUEQHEEZ-UHFFFAOYSA-N quinoxaline-2-carbaldehyde Chemical compound C1=CC=CC2=NC(C=O)=CN=C21 UJEHWLFUEQHEEZ-UHFFFAOYSA-N 0.000 description 1
- UPUZGXILYFKSGE-UHFFFAOYSA-N quinoxaline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CN=C21 UPUZGXILYFKSGE-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
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- NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7904648 | 1979-02-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8000205L SE8000205L (sv) | 1980-08-10 |
| SE441449B true SE441449B (sv) | 1985-10-07 |
Family
ID=10503082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8000205A SE441449B (sv) | 1979-02-09 | 1980-01-10 | Heterocykliska derivat och farmaceutiska kompositioner innehallande dessa derivat |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US4333934A (en]) |
| JP (3) | JPS55105685A (en]) |
| AU (1) | AU530820B2 (en]) |
| BE (2) | BE881631A (en]) |
| CA (1) | CA1131633A (en]) |
| CH (1) | CH643257A5 (en]) |
| DE (1) | DE3004750A1 (en]) |
| DK (1) | DK54280A (en]) |
| ES (1) | ES488386A0 (en]) |
| FI (1) | FI66868C (en]) |
| FR (1) | FR2448535A1 (en]) |
| HU (1) | HU178380B (en]) |
| IE (1) | IE49388B1 (en]) |
| IL (1) | IL59104A (en]) |
| IT (1) | IT1144033B (en]) |
| NL (1) | NL8000812A (en]) |
| PT (1) | PT70804B (en]) |
| SE (1) | SE441449B (en]) |
| ZA (1) | ZA80234B (en]) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL66835A (en) * | 1981-09-24 | 1988-05-31 | Roussel Uclaf | 1,4-disubstituted(1,2,4)triazolo(4,3-alpha)quinazolin-5(4h)-one derivatives and their salts,their preparation and pharmaceutical compositions containing them |
| US4472401A (en) * | 1981-11-27 | 1984-09-18 | Roussel Uclaf | Pyrimido-quinoxalines having antiallergic properties |
| US4510143A (en) * | 1982-02-17 | 1985-04-09 | Roussel Uclaf | Antiallergic pyrimido[1,2-a]quinoxalin-2-carboxylic acid derivatives |
| SE462338B (sv) * | 1982-04-28 | 1990-06-11 | Roussel Uclaf | Nya imidazo /1,2-a/ kinoxaliner och deras salter, foerfarande foer framstaellning daerav samt farmaceutiska kompositioner innehaallande densamma |
| US4696928A (en) * | 1985-09-09 | 1987-09-29 | G. D. Searle & Co. | Substituted dihydroimidazo[1,2-a]quinoxalines |
| US5055465A (en) * | 1989-05-31 | 1991-10-08 | Berlex Laboratories, Inc. | Imidazoquinoxalinones, their aza analogs and process for their preparation |
| US5182386A (en) * | 1991-08-27 | 1993-01-26 | Neurogen Corporation | Certain imidazoquinoxalinones; a new class of gaba brain receptor ligands |
| GB9212486D0 (en) * | 1992-06-12 | 1992-07-22 | Erba Carlo Spa | Derivatives of substituted imidazo benzoxazin-1-one and process for their preparation |
| DE4310523A1 (de) * | 1993-03-31 | 1994-10-06 | Basf Ag | Imidazolo-chinoxalinone zur Behandlung zentralnervöser Erkrankungen |
| FR2722789B1 (fr) * | 1994-07-20 | 1996-08-23 | Rhone Poulenc Rorer Sa | Derives d'acide imidazo (1,2-a)indeno(1,2-e) pyrazine-2-carboxylique, leur preparation et les medicaments les contenant |
| CA2200358A1 (en) * | 1994-09-30 | 1996-04-11 | Hans-Jorg Treiber | New heterocyclic substituted imidazoloquinoxalinones, their preparation and their use |
| CN1075498C (zh) * | 1997-05-08 | 2001-11-28 | 车庆明 | 一种查尔酮c甙和它的用途 |
| WO2001014348A1 (en) * | 1999-08-20 | 2001-03-01 | The Scripps Research Institute | Formation of heterocycles |
| HUP0105406A3 (en) * | 2001-12-21 | 2003-12-29 | Sanofi Aventis | Imidazo[1,2-a]quinolin derivatives, process for their preparation, pharmaceutical compositions thereof and intermediates |
| HUP0203976A3 (en) * | 2002-11-15 | 2004-08-30 | Sanofi Aventis | Adenozine a3 receptors, process for their preparation and pharmaceutical compositions containing them |
| CN103524436B (zh) * | 2004-11-17 | 2015-09-23 | 瑞恩药品公司 | 1-[(6,7-取代的烷氧基喹喔啉基)氨基羰基]-4-(杂)芳基哌嗪衍生物 |
| EA201490610A1 (ru) * | 2011-10-21 | 2014-09-30 | ГЛАКСОСМИТКЛАЙН ЭлЭлСи | Соединения и способы усиления врожденных иммунных ответов |
| JP6827237B2 (ja) * | 2016-11-02 | 2021-02-10 | 株式会社大阪製薬 | 害虫駆除シート |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE759292A (fr) * | 1969-11-27 | 1971-05-24 | Allen & Hanburys Ltd | Derives de xanthone, leur preparation et leur emploi |
| US4145419A (en) * | 1976-05-21 | 1979-03-20 | Roussel Uclaf | Novel imidazobenzoxazines |
| GB1538479A (en) * | 1976-05-21 | 1979-01-17 | Roussel Labor Ltd | Imidazobenzoxazines |
| US4075343A (en) * | 1976-09-13 | 1978-02-21 | Pfizer Inc. | Anti-allergenic 5-alkoxyimidazo[1,2-A]quinoline-2-carboxylic acids and derivatives thereof |
| US4229452A (en) * | 1977-01-07 | 1980-10-21 | Westwood Pharmaceuticals, Inc. | Treatment of inflammatory disorders with 4-trifluoromethylimidazo[1,2-a]quinoxaline |
| GB1596652A (en) * | 1977-01-20 | 1981-08-26 | Roussel Lab Ltd | Imidazo (1,2-a) quinoline-2-carboxylic acid and derivatives |
| GB1576077A (en) * | 1977-04-13 | 1980-10-01 | Roussel Lab Ltd | 4,5-dihydro-4-oxophyrrolo(1,2-)-quinoxaline-2-carboxylic acids and derivatives |
| SE444319B (sv) * | 1977-11-18 | 1986-04-07 | Roussel Uclaf | Nya imidazobensoxazinderivat, forfarande for framstellning derav och farmaceutiska kompositioner innehallande dessa foreningar |
-
1980
- 1980-01-10 SE SE8000205A patent/SE441449B/sv not_active IP Right Cessation
- 1980-01-10 IL IL59104A patent/IL59104A/xx unknown
- 1980-01-15 ZA ZA00800234A patent/ZA80234B/xx unknown
- 1980-01-24 HU HU8080148A patent/HU178380B/hu not_active IP Right Cessation
- 1980-01-30 FR FR8002003A patent/FR2448535A1/fr active Granted
- 1980-02-04 US US06/118,445 patent/US4333934A/en not_active Expired - Lifetime
- 1980-02-08 JP JP1376880A patent/JPS55105685A/ja active Granted
- 1980-02-08 JP JP1376780A patent/JPS55105683A/ja active Pending
- 1980-02-08 NL NL8000812A patent/NL8000812A/nl not_active Application Discontinuation
- 1980-02-08 PT PT70804A patent/PT70804B/pt unknown
- 1980-02-08 IE IE249/80A patent/IE49388B1/en unknown
- 1980-02-08 FI FI800391A patent/FI66868C/fi not_active IP Right Cessation
- 1980-02-08 BE BE0/199331A patent/BE881631A/fr not_active IP Right Cessation
- 1980-02-08 AU AU55351/80A patent/AU530820B2/en not_active Ceased
- 1980-02-08 CH CH104580A patent/CH643257A5/fr not_active IP Right Cessation
- 1980-02-08 DK DK54280A patent/DK54280A/da not_active Application Discontinuation
- 1980-02-08 BE BE0/199330A patent/BE881630A/fr unknown
- 1980-02-08 CA CA345,337A patent/CA1131633A/en not_active Expired
- 1980-02-08 IT IT47848/80A patent/IT1144033B/it active
- 1980-02-08 ES ES488386A patent/ES488386A0/es active Granted
- 1980-02-08 DE DE19803004750 patent/DE3004750A1/de not_active Withdrawn
-
1982
- 1982-03-01 US US06/353,052 patent/US4474784A/en not_active Expired - Fee Related
-
1987
- 1987-11-19 JP JP62290801A patent/JPS6456677A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BE881630A (fr) | 1980-08-08 |
| SE8000205L (sv) | 1980-08-10 |
| FI800391A7 (fi) | 1980-08-10 |
| AU5535180A (en) | 1980-08-14 |
| PT70804A (fr) | 1980-03-01 |
| ES8102129A1 (es) | 1980-12-16 |
| IT8047848A0 (it) | 1980-02-08 |
| AU530820B2 (en) | 1983-07-28 |
| JPS55105683A (en) | 1980-08-13 |
| JPS6456677A (en) | 1989-03-03 |
| IE800249L (en) | 1980-08-09 |
| ES488386A0 (es) | 1980-12-16 |
| US4333934A (en) | 1982-06-08 |
| JPH0144712B2 (en]) | 1989-09-29 |
| US4474784A (en) | 1984-10-02 |
| FI66868B (fi) | 1984-08-31 |
| IE49388B1 (en) | 1985-10-02 |
| NL8000812A (nl) | 1980-08-12 |
| IT1144033B (it) | 1986-10-29 |
| FR2448535A1 (fr) | 1980-09-05 |
| PT70804B (fr) | 1981-08-04 |
| JPS55105685A (en) | 1980-08-13 |
| CH643257A5 (fr) | 1984-05-30 |
| ZA80234B (en) | 1981-08-26 |
| DE3004750A1 (de) | 1980-08-21 |
| FR2448535B1 (en]) | 1983-10-21 |
| IL59104A (en) | 1984-02-29 |
| FI66868C (fi) | 1984-12-10 |
| IL59104A0 (en) | 1980-05-30 |
| HU178380B (en) | 1982-04-28 |
| BE881631A (fr) | 1980-08-08 |
| CA1131633A (en) | 1982-09-14 |
| DK54280A (da) | 1980-08-10 |
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