IL116566A - 1, 2-Bridged imidazo [4,5-c] quinolinamines and pharmaceutical compositions containing them - Google Patents

1, 2-Bridged imidazo [4,5-c] quinolinamines and pharmaceutical compositions containing them

Info

Publication number: IL116566A
Authority: IL; Israel
Prior art keywords: imidazo; amine; quinolin; carbon atoms; alkyl
Prior art date: 1995-01-12

Application number

IL11656695A

Other languages

English (en)

Other versions

IL116566A0 (en

Original Assignee

Minnesota Mining & Mfg

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.)

1995-01-12

Filing date

1995-12-26

Publication date

1998-10-30

1995-12-26 Application filed by Minnesota Mining & Mfg filed Critical Minnesota Mining & Mfg

1996-03-31 Publication of IL116566A0 publication Critical patent/IL116566A0/xx

1998-10-30 Publication of IL116566A publication Critical patent/IL116566A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
PPDAXUPXBAMEFZ-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-2-amine Chemical class C1=CC=CC2=C(NC(N)=N3)C3=CN=C21 PPDAXUPXBAMEFZ-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 73
102000014150 Interferons Human genes 0.000 claims abstract description 24
108010050904 Interferons Proteins 0.000 claims abstract description 24
229940079322 interferon Drugs 0.000 claims abstract description 23
150000003839 salts Chemical class 0.000 claims abstract description 18
238000000034 method Methods 0.000 claims abstract description 12
230000015572 biosynthetic process Effects 0.000 claims abstract description 9
241001465754 Metazoa Species 0.000 claims abstract description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 14
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 claims description 13
YHEPBWTXCZVUHG-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-6-amine Chemical compound N1=C2C(N)=CC=CC2=C2NC=NC2=C1 YHEPBWTXCZVUHG-UHFFFAOYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
RJSRSRITMWVIQT-UHFFFAOYSA-N quinolin-6-amine Chemical compound N1=CC=CC2=CC(N)=CC=C21 RJSRSRITMWVIQT-UHFFFAOYSA-N 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
GCMNJUJAKQGROZ-UHFFFAOYSA-N 1,2-Dihydroquinolin-2-imine Chemical compound C1=CC=CC2=NC(N)=CC=C21 GCMNJUJAKQGROZ-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
230000001939 inductive effect Effects 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims 1
OIHMHGZJVLNEMD-UHFFFAOYSA-N N12CCCCC2=NC2=C1C1=CC=CC=C1N=C2N Chemical compound N12CCCCC2=NC2=C1C1=CC=CC=C1N=C2N OIHMHGZJVLNEMD-UHFFFAOYSA-N 0.000 claims 1
HQBUPOAKJGJGCD-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-4-amine Chemical group NC1=NC2=CC=CC=C2C2=C1N=CN2 HQBUPOAKJGJGCD-UHFFFAOYSA-N 0.000 abstract description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 144
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
239000011541 reaction mixture Substances 0.000 description 45
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
238000006243 chemical reaction Methods 0.000 description 32
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
239000000243 solution Substances 0.000 description 29
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
239000000741 silica gel Substances 0.000 description 24
229910002027 silica gel Inorganic materials 0.000 description 24
229910052943 magnesium sulfate Inorganic materials 0.000 description 21
235000019341 magnesium sulphate Nutrition 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
239000010410 layer Substances 0.000 description 18
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 18
238000004440 column chromatography Methods 0.000 description 17
239000000203 mixture Substances 0.000 description 17
238000010992 reflux Methods 0.000 description 16
239000007787 solid Substances 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
-1 imidazo[4,5-c]quinoline amine compounds Chemical class 0.000 description 13
229910052757 nitrogen Inorganic materials 0.000 description 13
239000002904 solvent Substances 0.000 description 13
229910052799 carbon Inorganic materials 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
235000011167 hydrochloric acid Nutrition 0.000 description 11
235000002639 sodium chloride Nutrition 0.000 description 11
239000000725 suspension Substances 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
241000699670 Mus sp. Species 0.000 description 8
210000004027 cell Anatomy 0.000 description 8
238000009472 formulation Methods 0.000 description 8
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 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
235000019253 formic acid Nutrition 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
241000711975 Vesicular stomatitis virus Species 0.000 description 6
235000011054 acetic acid Nutrition 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
210000004369 blood Anatomy 0.000 description 6
239000008280 blood Substances 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
230000006698 induction Effects 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
239000000047 product Substances 0.000 description 6
235000009518 sodium iodide Nutrition 0.000 description 6
239000012980 RPMI-1640 medium Substances 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 5
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 5
230000003612 virological effect Effects 0.000 description 5
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
238000004166 bioassay Methods 0.000 description 4
230000000120 cytopathologic effect Effects 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
239000002955 immunomodulating agent Substances 0.000 description 4
229940121354 immunomodulator Drugs 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000002798 polar solvent Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
210000002966 serum Anatomy 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
150000003461 sulfonyl halides Chemical class 0.000 description 4
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 4
150000003512 tertiary amines Chemical class 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
230000000699 topical effect Effects 0.000 description 4
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical group FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 3
239000006071 cream Substances 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
239000000284 extract Substances 0.000 description 3
210000005260 human cell Anatomy 0.000 description 3
230000002584 immunomodulator Effects 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
238000011534 incubation Methods 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
239000002674 ointment Substances 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
NGIJXKWZUVOTKD-UHFFFAOYSA-N 2-[[4-(dibenzylamino)-3h-imidazo[4,5-c]quinolin-2-yl]methoxy]ethanol Chemical compound N1=C2C=CC=CC2=C2NC(COCCO)=NC2=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 NGIJXKWZUVOTKD-UHFFFAOYSA-N 0.000 description 2
WAPDTLJMHILPJB-UHFFFAOYSA-N 2-[[4-(dibenzylamino)-3h-imidazo[4,5-c]quinolin-2-yl]methoxy]ethyl methanesulfonate Chemical compound N1=C2C=CC=CC2=C2NC(COCCOS(=O)(=O)C)=NC2=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 WAPDTLJMHILPJB-UHFFFAOYSA-N 0.000 description 2
JHQURTLKGWGJHY-UHFFFAOYSA-N 2-n,2-n-dibenzylquinoline-2,3,4-triamine;hydrochloride Chemical compound Cl.NC1=C(N)C2=CC=CC=C2N=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 JHQURTLKGWGJHY-UHFFFAOYSA-N 0.000 description 2
PGWYDDRGIXJIRG-UHFFFAOYSA-N 3-[4-(dibenzylamino)-1-(ethoxymethyl)imidazo[4,5-c]quinolin-2-yl]propan-1-ol Chemical compound N1=C2C=CC=CC2=C2N(COCC)C(CCCO)=NC2=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 PGWYDDRGIXJIRG-UHFFFAOYSA-N 0.000 description 2
FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 2
SHZUGBYEPDMAPC-UHFFFAOYSA-N 4-hydroxy-3-nitro-1h-quinolin-2-one Chemical compound C1=CC=C2C(=O)C([N+]([O-])=O)=C(O)NC2=C1 SHZUGBYEPDMAPC-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
DSYDNDIXUDMIIN-UHFFFAOYSA-N Cl.N=1C2=CC=CC=C2C(N)=C([N+]([O-])=O)C=1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 Chemical compound Cl.N=1C2=CC=CC=C2C(N)=C([N+]([O-])=O)C=1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 DSYDNDIXUDMIIN-UHFFFAOYSA-N 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
239000004264 Petrolatum Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
241000700605 Viruses Species 0.000 description 2
ZABNVWZCJRFGNQ-UHFFFAOYSA-N [4-(dibenzylamino)-1-(ethoxymethyl)imidazo[4,5-c]quinolin-2-yl]methanol Chemical compound N1=C2C=CC=CC2=C2N(COCC)C(CO)=NC2=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 ZABNVWZCJRFGNQ-UHFFFAOYSA-N 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
230000000840 anti-viral effect Effects 0.000 description 2
239000003443 antiviral agent Substances 0.000 description 2
238000003556 assay Methods 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
210000000601 blood cell Anatomy 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
235000010980 cellulose Nutrition 0.000 description 2
229960000541 cetyl alcohol Drugs 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
238000006073 displacement reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000003974 emollient agent Substances 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
239000012997 ficoll-paque Substances 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose 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
238000004519 manufacturing process Methods 0.000 description 2
238000005259 measurement Methods 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
PKKJSCKAYCPOAP-UHFFFAOYSA-N n,n-dibenzyl-1-(ethoxymethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound N1=C2C=CC=CC2=C2N(COCC)C=NC2=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 PKKJSCKAYCPOAP-UHFFFAOYSA-N 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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IL11656695A 1995-01-12 1995-12-26 1, 2-Bridged imidazo [4,5-c] quinolinamines and pharmaceutical compositions containing them IL116566A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US08/371,845 US5482936A (en)	1995-01-12	1995-01-12	Imidazo[4,5-C]quinoline amines

Publications (2)

Publication Number	Publication Date
IL116566A0 IL116566A0 (en)	1996-03-31
IL116566A true IL116566A (en)	1998-10-30

Family

ID=23465639

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL11656695A IL116566A (en)	1995-01-12	1995-12-26	1, 2-Bridged imidazo [4,5-c] quinolinamines and pharmaceutical compositions containing them

Country Status (22)

Country	Link
US (1)	US5482936A (de)
EP (1)	EP0802913B1 (de)
JP (1)	JPH10512256A (de)
KR (1)	KR100404166B1 (de)
CN (1)	CN1066447C (de)
AT (1)	ATE192153T1 (de)
AU (1)	AU692033B2 (de)
CA (1)	CA2209487C (de)
CZ (1)	CZ285682B6 (de)
DE (1)	DE69516540T2 (de)
DK (1)	DK0802913T3 (de)
ES (1)	ES2145318T3 (de)
FI (1)	FI113866B (de)
GR (1)	GR3033869T3 (de)
HU (1)	HU221430B (de)
IL (1)	IL116566A (de)
NO (2)	NO308538B1 (de)
NZ (1)	NZ298296A (de)
PT (1)	PT802913E (de)
SK (1)	SK282145B6 (de)
WO (1)	WO1996021663A1 (de)
ZA (1)	ZA96101B (de)

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1995
- 1995-01-12 US US08/371,845 patent/US5482936A/en not_active Expired - Lifetime
- 1995-12-06 DK DK95942556T patent/DK0802913T3/da active
- 1995-12-06 NZ NZ298296A patent/NZ298296A/xx unknown
- 1995-12-06 AU AU43743/96A patent/AU692033B2/en not_active Ceased
- 1995-12-06 CA CA002209487A patent/CA2209487C/en not_active Expired - Fee Related
- 1995-12-06 DE DE69516540T patent/DE69516540T2/de not_active Expired - Fee Related
- 1995-12-06 CZ CZ972204A patent/CZ285682B6/cs not_active IP Right Cessation
- 1995-12-06 WO PCT/US1995/015828 patent/WO1996021663A1/en not_active Ceased
- 1995-12-06 SK SK872-97A patent/SK282145B6/sk unknown
- 1995-12-06 CN CN95197310A patent/CN1066447C/zh not_active Expired - Fee Related
- 1995-12-06 EP EP95942556A patent/EP0802913B1/de not_active Expired - Lifetime
- 1995-12-06 KR KR1019970704686A patent/KR100404166B1/ko not_active Expired - Fee Related
- 1995-12-06 AT AT95942556T patent/ATE192153T1/de not_active IP Right Cessation
- 1995-12-06 HU HU9800545A patent/HU221430B/hu not_active IP Right Cessation
- 1995-12-06 PT PT95942556T patent/PT802913E/pt unknown
- 1995-12-06 JP JP8521653A patent/JPH10512256A/ja not_active Withdrawn
- 1995-12-06 ES ES95942556T patent/ES2145318T3/es not_active Expired - Lifetime
- 1995-12-26 IL IL11656695A patent/IL116566A/en not_active IP Right Cessation
1996
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1997
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2000
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Publication number	Publication date
NO308538B1 (no)	2000-09-25
NO3198A (no)	1997-08-19
ATE192153T1 (de)	2000-05-15
DE69516540D1 (de)	2000-05-31
ZA96101B (en)	1997-07-08
CA2209487C (en)	2005-04-26
CZ220497A3 (en)	1997-12-17
AU692033B2 (en)	1998-05-28
HUT77667A (hu)	1998-07-28
GR3033869T3 (en)	2000-10-31
DE69516540T2 (de)	2000-08-10
IL116566A0 (en)	1996-03-31
US5482936A (en)	1996-01-09
WO1996021663A1 (en)	1996-07-18
EP0802913A1 (de)	1997-10-29
SK282145B6 (sk)	2001-11-06
SK87297A3 (en)	1997-12-10
JPH10512256A (ja)	1998-11-24
FI113866B (fi)	2004-06-30
NO972801D0 (no)	1997-06-17
CN1173178A (zh)	1998-02-11
MX9705283A (es)	1998-06-30
HU221430B (en)	2002-10-28
CZ285682B6 (cs)	1999-10-13
DK0802913T3 (da)	2000-09-25
EP0802913B1 (de)	2000-04-26
ES2145318T3 (es)	2000-07-01
NO20003198D0 (no)	2000-06-20
NO972801L (no)	1997-08-19
CA2209487A1 (en)	1996-07-18
CN1066447C (zh)	2001-05-30
AU4374396A (en)	1996-07-31
NZ298296A (en)	1999-11-29
KR19980701297A (ko)	1998-05-15
KR100404166B1 (ko)	2004-04-28
FI972967A0 (fi)	1997-07-11
FI972967L (fi)	1997-07-11
PT802913E (pt)	2000-09-29

Legal Events

Date	Code	Title
1999-03-12	FF	Patent granted
1999-09-22	KB	Patent renewed
2002-02-10	KB	Patent renewed
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