NO822918L - Nye imidazokinazolinderivater. - Google Patents

Nye imidazokinazolinderivater.

Info

Publication number: NO822918L
Authority: NO; Norway
Prior art keywords: formula; compounds; tautomers; acid addition; well
Prior art date: 1981-08-28

Application number

NO822918A

Other languages

English (en)

Norwegian (no)

Inventor

Frank Kienzle

Original Assignee

Hoffmann La Roche

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.)

1981-08-28

Filing date

1982-08-27

Publication date

1983-03-01

1982-08-27 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1983-03-01 Publication of NO822918L publication Critical patent/NO822918L/no

Links

150000001875 compounds Chemical class 0.000 claims description 37
150000003839 salts Chemical class 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
238000000034 method Methods 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 7
150000002431 hydrogen Chemical class 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
KJMFQJFNQYWQAV-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinazoline Chemical class C1=NC=NC2=C(NC=N3)C3=CC=C21 KJMFQJFNQYWQAV-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
230000027119 gastric acid secretion Effects 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 2
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
239000007858 starting material Substances 0.000 claims 4
PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
208000010110 spontaneous platelet aggregation Diseases 0.000 claims 1
AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
239000000126 substance Substances 0.000 description 7
241001465754 Metazoa Species 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
-1 3-substituted 2-amino-3,4-dihydroquinazoline Chemical class 0.000 description 5
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
239000000725 suspension Substances 0.000 description 5
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
230000002776 aggregation Effects 0.000 description 4
238000004220 aggregation Methods 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
235000019439 ethyl acetate Nutrition 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000047 product Substances 0.000 description 4
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
CQAXGKSICSSBMI-UHFFFAOYSA-N 2-(chloromethyl)-n,n-dimethyl-4-nitroaniline Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C=C1CCl CQAXGKSICSSBMI-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
208000001871 Tachycardia Diseases 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
230000009090 positive inotropic effect Effects 0.000 description 3
230000002265 prevention Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
230000006794 tachycardia Effects 0.000 description 3
150000005341 2-nitrobenzoic acids Chemical class 0.000 description 2
HZDJJUGMLAMVSA-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methyl]-6-n,6-n-dimethyl-4h-quinazoline-2,6-diamine Chemical compound C1=CC(OC)=CC=C1CN1C(N)=NC2=CC=C(N(C)C)C=C2C1 HZDJJUGMLAMVSA-UHFFFAOYSA-N 0.000 description 2
RIBZKYVKDZGFBP-UHFFFAOYSA-N 5-(dimethylamino)-2-nitrobenzoic acid Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C(C(O)=O)=C1 RIBZKYVKDZGFBP-UHFFFAOYSA-N 0.000 description 2
229910015900 BF3 Inorganic materials 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
206010019280 Heart failures Diseases 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
208000007536 Thrombosis Diseases 0.000 description 2
125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000031709 bromination Effects 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
150000001649 bromium compounds Chemical class 0.000 description 2
239000002775 capsule Substances 0.000 description 2
238000005660 chlorination reaction Methods 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
210000004051 gastric juice Anatomy 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 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
229940126601 medicinal product Drugs 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
230000009467 reduction Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
WBNZUUIFTPNYRN-UHFFFAOYSA-N 1,3-dichloro-2-methyl-4-nitrobenzene Chemical compound CC1=C(Cl)C=CC([N+]([O-])=O)=C1Cl WBNZUUIFTPNYRN-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 1
BXCBUWKTXLWPSB-UHFFFAOYSA-N 1-(chloromethyl)-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1CCl BXCBUWKTXLWPSB-UHFFFAOYSA-N 0.000 description 1
MKLDLMXFDMZYAD-UHFFFAOYSA-N 1h-quinazolin-2-one;hydrochloride Chemical compound Cl.C1=CC=C2NC(=O)N=CC2=C1 MKLDLMXFDMZYAD-UHFFFAOYSA-N 0.000 description 1
OCAYPMMBIIAXSY-UHFFFAOYSA-N 3-(dimethylamino)-2-methyl-6-nitrobenzoic acid Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C(C(O)=O)=C1C OCAYPMMBIIAXSY-UHFFFAOYSA-N 0.000 description 1
FHWPBBMYWHFORO-UHFFFAOYSA-N 3-chloro-2-methyl-6-nitrobenzoic acid Chemical compound CC1=C(Cl)C=CC([N+]([O-])=O)=C1C(O)=O FHWPBBMYWHFORO-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
102000008186 Collagen Human genes 0.000 description 1
108010035532 Collagen Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
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 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
241000700159 Rattus Species 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
208000007107 Stomach Ulcer Diseases 0.000 description 1
AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 1
ZKAHOBKUYXIJGT-UHFFFAOYSA-N [5-(dimethylamino)-2-nitrophenyl]methanol Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C(CO)=C1 ZKAHOBKUYXIJGT-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
125000005228 aryl sulfonate group Chemical group 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000001772 blood platelet Anatomy 0.000 description 1
239000000872 buffer Substances 0.000 description 1
244000309464 bull Species 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000001734 carboxylic acid salts Chemical class 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
229920001436 collagen Polymers 0.000 description 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
230000006806 disease prevention Effects 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
MFFXVVHUKRKXCI-UHFFFAOYSA-N ethyl iodoacetate Chemical compound CCOC(=O)CI MFFXVVHUKRKXCI-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000004992 fission Effects 0.000 description 1
235000013305 food Nutrition 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
210000002381 plasma Anatomy 0.000 description 1
210000004623 platelet-rich plasma Anatomy 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
239000004304 potassium nitrite Substances 0.000 description 1
235000010289 potassium nitrite Nutrition 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000001187 pylorus Anatomy 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
230000002861 ventricular Effects 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
238000009736 wetting 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/58—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/84—Nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO822918A 1981-08-28 1982-08-27 Nye imidazokinazolinderivater. NO822918L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH554881		1981-08-28
CH374482		1982-06-17

Publications (1)

Publication Number	Publication Date
NO822918L true NO822918L (no)	1983-03-01

Family

ID=25693751

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO822918A NO822918L (no)	1981-08-28	1982-08-27	Nye imidazokinazolinderivater.

Country Status (14)

Country	Link
US (1)	US4455311A (fr)
EP (1)	EP0073060A1 (fr)
AR (1)	AR242389A1 (fr)
AU (1)	AU8752482A (fr)
DK (1)	DK349682A (fr)
ES (1)	ES515295A0 (fr)
FI (1)	FI822785L (fr)
HU (1)	HU185109B (fr)
IL (1)	IL66618A0 (fr)
MC (1)	MC1478A1 (fr)
NO (1)	NO822918L (fr)
NZ (1)	NZ201659A (fr)
PH (1)	PH19683A (fr)
PT (1)	PT75472A (fr)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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1982
- 1982-07-28 US US06/402,471 patent/US4455311A/en not_active Expired - Fee Related
- 1982-08-04 DK DK349682A patent/DK349682A/da not_active Application Discontinuation
- 1982-08-10 FI FI822785A patent/FI822785L/fi not_active Application Discontinuation
- 1982-08-20 NZ NZ201659A patent/NZ201659A/en unknown
- 1982-08-23 AU AU87524/82A patent/AU8752482A/en not_active Abandoned
- 1982-08-23 IL IL66618A patent/IL66618A0/xx unknown
- 1982-08-24 HU HU822714A patent/HU185109B/hu unknown
- 1982-08-25 EP EP82107787A patent/EP0073060A1/fr not_active Ceased
- 1982-08-26 PH PH27784A patent/PH19683A/en unknown
- 1982-08-26 PT PT75472A patent/PT75472A/pt unknown
- 1982-08-26 MC MC821603A patent/MC1478A1/fr unknown
- 1982-08-27 ES ES515295A patent/ES515295A0/es active Granted
- 1982-08-27 AR AR82290468A patent/AR242389A1/es active
- 1982-08-27 NO NO822918A patent/NO822918L/no unknown

Also Published As

Publication number	Publication date
PT75472A (en)	1982-09-01
FI822785L (fi)	1983-03-01
MC1478A1 (fr)	1983-06-17
AR242389A1 (es)	1993-03-31
PH19683A (en)	1986-06-13
US4455311A (en)	1984-06-19
FI822785A0 (fi)	1982-08-10
EP0073060A1 (fr)	1983-03-02
HU185109B (en)	1984-12-28
NZ201659A (en)	1984-07-31
IL66618A0 (en)	1982-12-31
ES8306375A1 (es)	1983-06-01
AU8752482A (en)	1983-03-03
ES515295A0 (es)	1983-06-01
DK349682A (da)	1983-03-01

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CA1328871C (fr)	1994-04-26	Derives carboxamide aromatiques et heterocycliques, utilises comme agents antineoplastiques
US20040063673A1 (en)	2004-04-01	Cyclic compounds containing zinc binding groups as matrix metalloproteinase inhibitors
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JPS5846088A (ja)	1983-03-17	イミダゾキナゾリン類
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