LU84773A1 - Nouvelles imidazoquinoxalines et leurs sels,leur preparation leurs application comme medicaments,les compositions les renfermant et les nouveaux intermediaires obtenus - Google Patents

Nouvelles imidazoquinoxalines et leurs sels,leur preparation leurs application comme medicaments,les compositions les renfermant et les nouveaux intermediaires obtenus Download PDF

Info

Publication number: LU84773A1
Authority: LU; Luxembourg
Prior art keywords: formula; carbon atoms; group; product; radical
Prior art date: 1982-04-28

Application number

LU84773A

Other languages

English (en)

French (fr)

Inventor

Peter David Kennewell

David Alun Rowlands

Alan Charles Barnes

David Paul Kay

Frederick Leonard Parker

Original Assignee

Roussel Uclaf

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1982-04-28

Filing date

1983-04-27

Publication date

1984-03-02

1983-04-27 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1984-03-02 Publication of LU84773A1 publication Critical patent/LU84773A1/fr

Links

150000003839 salts Chemical class 0.000 title claims description 40
239000000203 mixture Substances 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 18
239000003814 drug Substances 0.000 title claims description 16
239000000543 intermediate Substances 0.000 title description 4
-1 alkoxy radical Chemical class 0.000 claims description 105
125000004432 carbon atom Chemical group C* 0.000 claims description 78
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 39
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
238000000034 method Methods 0.000 claims description 31
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 16
229910052757 nitrogen Inorganic materials 0.000 claims description 14
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 13
239000003960 organic solvent Substances 0.000 claims description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
150000003254 radicals Chemical class 0.000 claims description 9
YELMWJNXDALKFE-UHFFFAOYSA-N 3h-imidazo[4,5-f]quinoxaline Chemical class N1=CC=NC2=C(NC=N3)C3=CC=C21 YELMWJNXDALKFE-UHFFFAOYSA-N 0.000 claims description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
239000002585 base Substances 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical group CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
238000010992 reflux Methods 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
229940079593 drug Drugs 0.000 claims description 5
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 5
UPUZGXILYFKSGE-UHFFFAOYSA-N quinoxaline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CN=C21 UPUZGXILYFKSGE-UHFFFAOYSA-N 0.000 claims description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
239000012948 isocyanate Substances 0.000 claims description 4
150000002513 isocyanates Chemical class 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052763 palladium Inorganic materials 0.000 claims description 3
229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
239000012279 sodium borohydride Substances 0.000 claims description 3
229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
SXATZFYWGOHLRZ-UHFFFAOYSA-N N1=C(C=NC=2C(=CC=CC1=2)C(=O)O)C(=O)O Chemical compound N1=C(C=NC=2C(=CC=CC1=2)C(=O)O)C(=O)O SXATZFYWGOHLRZ-UHFFFAOYSA-N 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims description 2
229910052808 lithium carbonate Inorganic materials 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
238000007127 saponification reaction Methods 0.000 claims description 2
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
239000000047 product Substances 0.000 description 50
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 22
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
HZMKSGSOBKQGJX-UHFFFAOYSA-N Ethyl 2-quinoxalinecarboxylate Chemical compound C1=CC=CC2=NC(C(=O)OCC)=CN=C21 HZMKSGSOBKQGJX-UHFFFAOYSA-N 0.000 description 10
UPUZGXILYFKSGE-UHFFFAOYSA-M quinoxaline-2-carboxylate Chemical compound C1=CC=CC2=NC(C(=O)[O-])=CN=C21 UPUZGXILYFKSGE-UHFFFAOYSA-M 0.000 description 10
AYNZKZHGLPSGRI-UHFFFAOYSA-N CCC(=O)O.N1=CC=NC2=CC=CC=C12 Chemical compound CCC(=O)O.N1=CC=NC2=CC=CC=C12 AYNZKZHGLPSGRI-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
BOZQXJCQJYEOSB-UHFFFAOYSA-N quinoxaline-2-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC=CC2=NC(C(=O)O)=CN=C21 BOZQXJCQJYEOSB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
239000013078 crystal Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
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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 2
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230000002378 acidificating effect Effects 0.000 description 2
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208000003455 anaphylaxis Diseases 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
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230000005764 inhibitory process Effects 0.000 description 2
239000007924 injection Substances 0.000 description 2
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239000008101 lactose Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
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125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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241000238097 Callinectes sapidus Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
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125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
230000001079 digestive effect Effects 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
229960003699 evans blue Drugs 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000005484 gravity Effects 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
229940057952 methanol Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
229940092253 ovalbumin Drugs 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
150000002913 oxalic acids Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
230000008313 sensitization Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pulmonology (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Immunology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

LU84773A 1982-04-28 1983-04-27 Nouvelles imidazoquinoxalines et leurs sels,leur preparation leurs application comme medicaments,les compositions les renfermant et les nouveaux intermediaires obtenus LU84773A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8212325		1982-04-28
GB8212325		1982-04-28

Publications (1)

Publication Number	Publication Date
LU84773A1 true LU84773A1 (fr)	1984-03-02

Family

ID=10530041

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU84773A LU84773A1 (fr)	1982-04-28	1983-04-27	Nouvelles imidazoquinoxalines et leurs sels,leur preparation leurs application comme medicaments,les compositions les renfermant et les nouveaux intermediaires obtenus

Country Status (15)

Country	Link
US (1)	US4464373A (de)
JP (1)	JPS58201784A (de)
AT (1)	AT390063B (de)
AU (1)	AU559651B2 (de)
BE (1)	BE896581A (de)
CA (1)	CA1205804A (de)
CH (1)	CH655725A5 (de)
DE (1)	DE3315460A1 (de)
DK (1)	DK186283A (de)
FR (1)	FR2526024B1 (de)
IE (1)	IE55357B1 (de)
IT (1)	IT1165595B (de)
LU (1)	LU84773A1 (de)
SE (1)	SE462338B (de)
ZA (1)	ZA832701B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5683998A (en) *	1991-04-23	1997-11-04	Toray Industries, Inc.	Tricyclic triazolo derivatives, processes for producing the same and the uses of the same
SI9520108A (en) *	1994-09-30	1997-10-31	Basf Ag	New heterocyclic substituted imidazoloquinoxalinones, their preparation and their use
CN108794485B (zh) *	2018-04-28	2020-04-24	北京施安泰医药技术开发有限公司	一类toll样受体调节剂、其药物组合物、制备方法与用途

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE439308B (sv) *	1978-08-02	1985-06-10	Roussel Uclaf	Imidazo(1,2-a)kinoxaliner och farmaceutiska kompositioner derav
GB2027707B (en) *	1978-08-02	1982-11-17	Roussel Lab Ltd	Heterocyclic compounds
GB2043637B (en) *	1979-02-09	1983-03-16	Roussel Lab Ltd	Heterotricyclic derivatives
SE441449B (sv) *	1979-02-09	1985-10-07	Roussel Uclaf	Heterocykliska derivat och farmaceutiska kompositioner innehallande dessa derivat
GB2043064B (en) *	1979-02-09	1983-04-13	Roussel Lab Ltd	Oximidazoquinoxaline derivatives

1983
- 1983-04-14 SE SE8302076A patent/SE462338B/sv not_active IP Right Cessation
- 1983-04-18 ZA ZA832701A patent/ZA832701B/xx unknown
- 1983-04-20 FR FR8306445A patent/FR2526024B1/fr not_active Expired
- 1983-04-22 US US06/487,617 patent/US4464373A/en not_active Expired - Fee Related
- 1983-04-27 CH CH2266/83A patent/CH655725A5/fr not_active IP Right Cessation
- 1983-04-27 IE IE963/83A patent/IE55357B1/en unknown
- 1983-04-27 LU LU84773A patent/LU84773A1/fr unknown
- 1983-04-27 CA CA000426842A patent/CA1205804A/fr not_active Expired
- 1983-04-27 DK DK186283A patent/DK186283A/da unknown
- 1983-04-27 IT IT48169/83A patent/IT1165595B/it active
- 1983-04-27 AU AU13983/83A patent/AU559651B2/en not_active Ceased
- 1983-04-27 BE BE0/210641A patent/BE896581A/fr not_active IP Right Cessation
- 1983-04-28 AT AT0154183A patent/AT390063B/de not_active IP Right Cessation
- 1983-04-28 JP JP58074160A patent/JPS58201784A/ja active Pending
- 1983-04-28 DE DE19833315460 patent/DE3315460A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
FR2526024B1 (fr)	1986-04-25
IE830963L (en)	1983-10-28
AU559651B2 (en)	1987-03-19
AU1398383A (en)	1983-11-03
SE462338B (sv)	1990-06-11
IT1165595B (it)	1987-04-22
CH655725A5 (fr)	1986-05-15
BE896581A (fr)	1983-10-27
DK186283A (da)	1983-10-29
JPS58201784A (ja)	1983-11-24
DE3315460A1 (de)	1983-11-03
IE55357B1 (en)	1990-08-29
ATA154183A (de)	1989-08-15
SE8302076D0 (sv)	1983-04-14
DK186283D0 (da)	1983-04-27
SE8302076L (sv)	1983-10-29
ZA832701B (en)	1984-06-27
AT390063B (de)	1990-03-12
CA1205804A (fr)	1986-06-10
US4464373A (en)	1984-08-07
IT8348169A0 (it)	1983-04-27
FR2526024A1 (fr)	1983-11-04

Publication	Publication Date	Title
CH651561A5 (fr)	1985-09-30	Derives des nor-tropane et granatane et leur procede de preparation.
FR2529548A1 (fr)	1984-01-06	Nouveaux derives de l'amino-3 quinuclidine, leur procede et leur application en therapeutique
FR2534257A1 (fr)	1984-04-13	Nouveaux derives de la 6-amino 7-hydroxy 4,5,6,7-tetrahydro-imidazo/4,5,1-j-k/ /1/ benzazepin-2(1h)-one, leurs sels, application a titre de medicaments, compositions les renfermant et un intermediaire
EP0507672B1 (de)	1997-06-04	N-Cyclohexyl Benzamide Derivate, ihre Herstellungen und therapeutischen Anwendungen
EP0080941B1 (de)	1986-09-17	Pyrimidoquinoxaline, ihre Herstellung, ihre Verwendung als Arzneimittel und diese enthaltende Zubereitungen
FR2528043A1 (fr)	1983-12-09	Nouveaux derives de la 1,3-dihydro 4-/1-hydroxy-2-amino-ethyl/2h-indol-2-one, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant
CH649994A5 (fr)	1985-06-28	Derives du 4h-1,2,4-triazole, procedes de preparation et compositions les renfermant.
EP0076199B1 (de)	1986-12-30	Triazoloquinazolone und deren Salze, Verfahren und Zwischenprodukte zu ihrer Herstellung, ihre Verwendung als Arzneimittel und diese enthaltende Zusammensetzungen
FR2595695A1 (fr)	1987-09-18	Derives de n-(((hydroxy-2 phenyl) (phenyl) methylene) amino-2) ethyl) acetamide, leur preparation et leur application en therapeutique
EP0213984A1 (de)	1987-03-11	Indolcarboxamidderivate, ihre Salze, Verfahren und Zwischenprodukte, Anwendung als Heilmittel und Zusammensetzungen die sie enthalten
LU84773A1 (fr)	1984-03-02	Nouvelles imidazoquinoxalines et leurs sels,leur preparation leurs application comme medicaments,les compositions les renfermant et les nouveaux intermediaires obtenus
EP0153230B1 (de)	1989-07-19	Pyrimido(2,1-b)benzothiazolderivate und ihre Salze, Verfahren und Zwischenprodukte zu ihrer Herstellung, ihre Verwendung als Arzneimittel und diese enthaltende pharmazeutische Zubereitungen
CH644124A5 (fr)	1984-07-13	Oxoimidazoquinoxalines et leurs sels, leurs procedes de preparation et les medicaments les renfermant.
FR2551063A1 (fr)	1985-03-01	Nouveaux dimethyl-2,5 pyrroles, leur procede de preparation et leur application en therapeutique
EP0201400B1 (de)	1989-07-19	4-Phenylpropylindolderivate und ihre Salze, Verfahren zur Herstellung, deren Anwendung als Heilmittel und sie enthaltende pharmazeutische Zusammensetzungen
FR2772766A1 (fr)	1999-06-25	Nouveaux composes heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
FR2559771A1 (fr)	1985-08-23	Derives de la 3-pyrrolidinopropiophenone et procede pour leur preparation
CH674845A5 (de)	1990-07-31
FR2584070A1 (fr)	1987-01-02	Nouveaux derives de l'hydroxy alkoxy 4-phenyl propyl indole, leurs sels, procede et intermediaires de preparation, application a titre de medicaments et compositions les renfermant.
EP0347305B1 (de)	1993-05-12	[(Aryl-4-piperazinyl-1)-2-ethoxy]-3p-cymole, die ortho-, meta-, para-monosubstituierten oder disubstituierten Derivate, das Verfahren zu deren Herstellung und die als aktives Prinzip diese Verbindungen enthaltenden Arzneimittel
EP0280627B1 (de)	1993-04-21	N-substituierte alpha-Mercaptomethylbenzenpropanamid-Derivate, ihre Herstellung, ihre Verwendung als Arzneimittel und diese enthaltende Zusammensetzungen
CA1099290A (fr)	1981-04-14	Procede de preparation du 7-amino 6,7 dihydro (5h) benzocycloheptene
EP0275221B1 (de)	1991-04-17	N-(1H-indol-4-yl)-Benzamidderivate, ihre Salze und deren Anwendung als Heilmittel und Zusammenstellungen, die sie enthalten
CH636350A5 (fr)	1983-05-31	Derives de l'acide 2-/(4-quinoleinyl) amino/ 5-fluorobenzoique, leurs procedes de preparation et les compositions pharmaceutiques les renfermant.
EP0275762A1 (de)	1988-07-27	Indol-Carboxamid-Derivate und ihre Salze, Verfahren und Zwischenprodukte zur Herstellung, Anwendung als Heilmittel und Zusammenstellungen, die sie enthalten