NO803684L - Fremgangsmaate for fremstilling av terapeutisk aktive kinoksalinderivater. - Google Patents
Fremgangsmaate for fremstilling av terapeutisk aktive kinoksalinderivater.Info
- Publication number
- NO803684L NO803684L NO803684A NO803684A NO803684L NO 803684 L NO803684 L NO 803684L NO 803684 A NO803684 A NO 803684A NO 803684 A NO803684 A NO 803684A NO 803684 L NO803684 L NO 803684L
- Authority
- NO
- Norway
- Prior art keywords
- quinoxaline
- hydrogen
- amino
- bound
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title claims description 7
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000007858 starting material Substances 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- ALSFLCPIABLEPY-UHFFFAOYSA-N NC1=[N+](C2=CC(=CC=C2N(C1=O)C1=CC=C(C=C1)Cl)Cl)[O-] Chemical compound NC1=[N+](C2=CC(=CC=C2N(C1=O)C1=CC=C(C=C1)Cl)Cl)[O-] ALSFLCPIABLEPY-UHFFFAOYSA-N 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 150000003252 quinoxalines Chemical class 0.000 claims description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- QHKOXNRYHNAZSL-UHFFFAOYSA-N NC1=[N+](C2=CC(=CC=C2N(C1=O)C1=CC=C(C=C1)Cl)Br)[O-] Chemical compound NC1=[N+](C2=CC(=CC=C2N(C1=O)C1=CC=C(C=C1)Cl)Br)[O-] QHKOXNRYHNAZSL-UHFFFAOYSA-N 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 150000004965 peroxy acids Chemical class 0.000 claims description 3
- RLQYWHMZCFKYIA-UHFFFAOYSA-N NC1=[N+](C2=CC(=CC=C2N(C1=O)C1=CC=C(C=C1)Br)Br)[O-] Chemical compound NC1=[N+](C2=CC(=CC=C2N(C1=O)C1=CC=C(C=C1)Br)Br)[O-] RLQYWHMZCFKYIA-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 46
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- -1 phenyl-substituted quinoxaline Chemical class 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 9
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 239000003176 neuroleptic agent Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- MBJNPBIDWPNGPT-UHFFFAOYSA-N 3-amino-6-bromo-1-(4-chlorophenyl)quinoxalin-2-one Chemical compound O=C1C(N)=NC2=CC(Br)=CC=C2N1C1=CC=C(Cl)C=C1 MBJNPBIDWPNGPT-UHFFFAOYSA-N 0.000 description 4
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000003869 acetamides Chemical class 0.000 description 4
- 229960003878 haloperidol Drugs 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000000701 neuroleptic effect Effects 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 208000009132 Catalepsy Diseases 0.000 description 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 206010047853 Waxy flexibility Diseases 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000002920 convulsive effect Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- YOWAEZWWQFSEJD-UHFFFAOYSA-N quinoxalin-2-amine Chemical class C1=CC=CC2=NC(N)=CN=C21 YOWAEZWWQFSEJD-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 2
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 description 2
- HREBWUWWMBCBLO-UHFFFAOYSA-N 3-amino-6,7-dichloro-1-(4-chlorophenyl)quinoxalin-2-one Chemical compound O=C1C(N)=NC2=CC(Cl)=C(Cl)C=C2N1C1=CC=C(Cl)C=C1 HREBWUWWMBCBLO-UHFFFAOYSA-N 0.000 description 2
- OMYZYEJVZPLTMG-UHFFFAOYSA-N 7-(trifluoromethyl)-4-[4-(trifluoromethyl)phenyl]-1h-quinoxaline-2,3-dione Chemical compound C1=CC(C(F)(F)F)=CC=C1N1C(=O)C(=O)NC2=CC(C(F)(F)F)=CC=C21 OMYZYEJVZPLTMG-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 230000000561 anti-psychotic effect Effects 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 229960003965 antiepileptics Drugs 0.000 description 2
- 239000002249 anxiolytic agent Substances 0.000 description 2
- 230000000949 anxiolytic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000002903 catalepsic effect Effects 0.000 description 2
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 2
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- JAIKXXLHMUTGCF-UHFFFAOYSA-N n-(4-bromo-2-nitrophenyl)-n-(4-bromophenyl)-2-chloroacetamide Chemical compound [O-][N+](=O)C1=CC(Br)=CC=C1N(C(=O)CCl)C1=CC=C(Br)C=C1 JAIKXXLHMUTGCF-UHFFFAOYSA-N 0.000 description 2
- 150000004987 o-phenylenediamines Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000002990 phenothiazines Chemical class 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- YHYKLKNNBYLTQY-UHFFFAOYSA-N 1,1-diphenylhydrazine Chemical class C=1C=CC=CC=1N(N)C1=CC=CC=C1 YHYKLKNNBYLTQY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ABJFBJGGLJVMAQ-UHFFFAOYSA-N 1,4-dihydroquinoxaline-2,3-dione Chemical class C1=CC=C2NC(=O)C(=O)NC2=C1 ABJFBJGGLJVMAQ-UHFFFAOYSA-N 0.000 description 1
- RLKSQLJFGCDUOX-UHFFFAOYSA-N 1-(4-tert-butylphenyl)-4-chlorobutan-1-one Chemical compound CC(C)(C)C1=CC=C(C(=O)CCCCl)C=C1 RLKSQLJFGCDUOX-UHFFFAOYSA-N 0.000 description 1
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
- XVKLMYQMVPHUPN-UHFFFAOYSA-N 2-bromoquinoxaline Chemical class C1=CC=CC2=NC(Br)=CN=C21 XVKLMYQMVPHUPN-UHFFFAOYSA-N 0.000 description 1
- ZCXBSQNQBCUMKO-UHFFFAOYSA-N 2-chloro-n-(4-chloro-2-nitrophenyl)-n-(4-chlorophenyl)acetamide Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1N(C(=O)CCl)C1=CC=C(Cl)C=C1 ZCXBSQNQBCUMKO-UHFFFAOYSA-N 0.000 description 1
- FKVQOLBOVYHLMN-UHFFFAOYSA-N 2-chloro-n-(5-chloro-2-nitrophenyl)-n-phenylacetamide Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1N(C(=O)CCl)C1=CC=CC=C1 FKVQOLBOVYHLMN-UHFFFAOYSA-N 0.000 description 1
- BKXHYVROFOOKFE-UHFFFAOYSA-N 2-chloro-n-[6,7-dichloro-4-(4-chlorophenyl)-3-oxoquinoxalin-2-yl]acetamide Chemical compound O=C1C(NC(=O)CCl)=NC2=CC(Cl)=C(Cl)C=C2N1C1=CC=C(Cl)C=C1 BKXHYVROFOOKFE-UHFFFAOYSA-N 0.000 description 1
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 1
- XQEASBVRKVDWDU-UHFFFAOYSA-N 3-amino-1-(4-bromophenyl)-6-chloroquinoxalin-2-one Chemical compound O=C1C(N)=NC2=CC(Cl)=CC=C2N1C1=CC=C(Br)C=C1 XQEASBVRKVDWDU-UHFFFAOYSA-N 0.000 description 1
- YPVVFAYMDYLOGV-UHFFFAOYSA-N 4-(4-chlorophenyl)-7-nitro-1h-quinoxaline-2,3-dione Chemical compound O=C1C(=O)NC2=CC([N+](=O)[O-])=CC=C2N1C1=CC=C(Cl)C=C1 YPVVFAYMDYLOGV-UHFFFAOYSA-N 0.000 description 1
- YZNREZUEQIAYDY-UHFFFAOYSA-N 6-bromo-3-chloro-1-(4-chlorophenyl)quinoxalin-2-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(Cl)=NC2=CC(Br)=CC=C21 YZNREZUEQIAYDY-UHFFFAOYSA-N 0.000 description 1
- ZTWWKJOHRIBAGY-UHFFFAOYSA-N 7-bromo-4-(4-chlorophenyl)-1h-quinoxaline-2,3-dione Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(=O)NC2=CC(Br)=CC=C21 ZTWWKJOHRIBAGY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OOPUXKSDXLCVGQ-UHFFFAOYSA-N C(C)(=O)NC1=[N+](C2=CC(=CC=C2N(C1=O)C1=CC=C(C=C1)Cl)Cl)[O-] Chemical compound C(C)(=O)NC1=[N+](C2=CC(=CC=C2N(C1=O)C1=CC=C(C=C1)Cl)Cl)[O-] OOPUXKSDXLCVGQ-UHFFFAOYSA-N 0.000 description 1
- AXKMETHWRPXZST-UHFFFAOYSA-N C(C)(=O)NC1=[N+](C2=CC=CC=C2N(C1=O)C1=CC=C(C=C1)Cl)[O-] Chemical compound C(C)(=O)NC1=[N+](C2=CC=CC=C2N(C1=O)C1=CC=C(C=C1)Cl)[O-] AXKMETHWRPXZST-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VXOGMDZYGQXIFO-UHFFFAOYSA-N ClC1=CC=C2N(C(C(=[N+](C2=C1)[O-])NC(CC)=O)=O)C1=CC=C(C=C1)Cl Chemical compound ClC1=CC=C2N(C(C(=[N+](C2=C1)[O-])NC(CC)=O)=O)C1=CC=C(C=C1)Cl VXOGMDZYGQXIFO-UHFFFAOYSA-N 0.000 description 1
- XTHYYBALTCKPDP-UHFFFAOYSA-N ClC1=CC=C2N(C(C(=[N+](C2=C1)[O-])NC(CCC)=O)=O)C1=CC=C(C=C1)Cl Chemical compound ClC1=CC=C2N(C(C(=[N+](C2=C1)[O-])NC(CCC)=O)=O)C1=CC=C(C=C1)Cl XTHYYBALTCKPDP-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 241000557626 Corvus corax Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 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 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- YKCNWWMWMLTKFP-UHFFFAOYSA-N NC1=[N+](C2=CC=C(C=C2N(C1=O)C1=CC=CC=C1)Cl)[O-] Chemical compound NC1=[N+](C2=CC=C(C=C2N(C1=O)C1=CC=CC=C1)Cl)[O-] YKCNWWMWMLTKFP-UHFFFAOYSA-N 0.000 description 1
- MYYIJLGWQSBTQV-UHFFFAOYSA-N NC1=[N+](C2=CC=CC=C2N(C1=O)C1=CC=C(C=C1)Cl)[O-] Chemical compound NC1=[N+](C2=CC=CC=C2N(C1=O)C1=CC=C(C=C1)Cl)[O-] MYYIJLGWQSBTQV-UHFFFAOYSA-N 0.000 description 1
- HEDRFPZLKQSYRI-UHFFFAOYSA-N NC1=[N+]([O-])C2=CC(Cl)=CC=C2N(C2=CC=CC=C2)C1=O Chemical compound NC1=[N+]([O-])C2=CC(Cl)=CC=C2N(C2=CC=CC=C2)C1=O HEDRFPZLKQSYRI-UHFFFAOYSA-N 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229940054053 antipsychotics butyrophenone derivative Drugs 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical class CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 229960001076 chlorpromazine Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- XNFVGEUMTFIVHQ-UHFFFAOYSA-N disodium;sulfide;hydrate Chemical compound O.[Na+].[Na+].[S-2] XNFVGEUMTFIVHQ-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003210 dopamine receptor blocking agent Substances 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 229940102213 injectable suspension Drugs 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- VGONTRNFWQASIP-UHFFFAOYSA-N n-(6,7-dichloro-3-oxo-4-phenylquinoxalin-2-yl)acetamide Chemical compound O=C1C(NC(=O)C)=NC2=CC(Cl)=C(Cl)C=C2N1C1=CC=CC=C1 VGONTRNFWQASIP-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 231100000862 numbness Toxicity 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical class C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000021542 voluntary musculoskeletal movement Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7942090 | 1979-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO803684L true NO803684L (no) | 1981-06-09 |
Family
ID=10509650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO803684A NO803684L (no) | 1979-12-06 | 1980-12-05 | Fremgangsmaate for fremstilling av terapeutisk aktive kinoksalinderivater. |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0030795A3 (da) |
| JP (1) | JPS5692277A (da) |
| AU (1) | AU6461080A (da) |
| DK (1) | DK514280A (da) |
| FI (1) | FI803762L (da) |
| GR (1) | GR82323B (da) |
| NO (1) | NO803684L (da) |
| ZA (1) | ZA807311B (da) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO179551C (no) * | 1987-11-10 | 1996-10-30 | Novo Nordisk As | Analogifremgangsmåte for fremstilling av terapeutisk virksomme kinoxalinforbindelser |
| HUT76302A (en) * | 1995-11-30 | 1997-07-28 | Chinoin Gyogyszer Es Vegyeszet | Quinoxaline derivatives, pharmaceutical compositions containing them and process for producing them |
| DE102007050673A1 (de) | 2007-10-19 | 2009-04-23 | Friedrich-Schiller-Universität Jena | Neue Hexaaza-acene und Verfahren zu ihrer Herstellung |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0008864A1 (en) * | 1978-08-15 | 1980-03-19 | FISONS plc | Pyridopyrazine and quinoxaline derivatives, processes for their preparation, and pharmaceutical compositions containing them |
| US4181724A (en) * | 1978-09-11 | 1980-01-01 | The Upjohn Company | Quinoxalinone compounds useful for expanding the lumina or air passages in mammals |
-
1980
- 1980-11-14 EP EP80304092A patent/EP0030795A3/en not_active Withdrawn
- 1980-11-21 ZA ZA00807311A patent/ZA807311B/xx unknown
- 1980-11-21 AU AU64610/80A patent/AU6461080A/en not_active Abandoned
- 1980-12-01 GR GR63515A patent/GR82323B/el unknown
- 1980-12-02 DK DK514280A patent/DK514280A/da not_active Application Discontinuation
- 1980-12-03 FI FI803762A patent/FI803762L/fi not_active Application Discontinuation
- 1980-12-05 JP JP17107680A patent/JPS5692277A/ja active Pending
- 1980-12-05 NO NO803684A patent/NO803684L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI803762L (fi) | 1981-06-07 |
| EP0030795A2 (en) | 1981-06-24 |
| GR82323B (da) | 1984-12-13 |
| AU6461080A (en) | 1981-06-11 |
| ZA807311B (en) | 1981-11-25 |
| JPS5692277A (en) | 1981-07-25 |
| EP0030795A3 (en) | 1981-09-09 |
| DK514280A (da) | 1981-06-07 |
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