IL101110A - H1-Amidazo] -C-4,5 [-Quinoline-4-Amines converted at position 2, pharmaceutical preparations containing them and certain intermediates new to them - Google Patents

H1-Amidazo] -C-4,5 [-Quinoline-4-Amines converted at position 2, pharmaceutical preparations containing them and certain intermediates new to them

Info

Publication number: IL101110A
Authority: IL; Israel
Prior art keywords: carbon atoms; imidazo; alkyl; methylpropyl; compound according
Prior art date: 1991-03-01

Application number

IL10111092A

Other languages

English (en)

Hebrew (he)

Other versions

IL101110A0 (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.)

1991-03-01

Filing date

1992-03-01

Publication date

1995-12-08

1992-03-01 Application filed by Minnesota Mining & Mfg filed Critical Minnesota Mining & Mfg

1992-03-01 Priority to IL11457092A priority Critical patent/IL114570A/en

1992-11-15 Publication of IL101110A0 publication Critical patent/IL101110A0/xx

1995-12-08 Publication of IL101110A publication Critical patent/IL101110A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 5
239000000543 intermediate Substances 0.000 title abstract description 19
HQBUPOAKJGJGCD-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-4-amine Chemical class NC1=NC2=CC=CC=C2C2=C1N=CN2 HQBUPOAKJGJGCD-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 143
-1 alkylamido Chemical group 0.000 claims abstract description 60
125000000217 alkyl group Chemical group 0.000 claims abstract description 58
125000003545 alkoxy group Chemical group 0.000 claims abstract description 24
125000001424 substituent group Chemical group 0.000 claims abstract description 18
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 12
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 8
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 6
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 181
125000004432 carbon atom Chemical group C* 0.000 claims description 123
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 111
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 74
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 43
229910052739 hydrogen Inorganic materials 0.000 claims description 41
239000001257 hydrogen Substances 0.000 claims description 41
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
229910052799 carbon Inorganic materials 0.000 claims description 30
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
229910052736 halogen Inorganic materials 0.000 claims description 18
150000002367 halogens Chemical class 0.000 claims description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
125000000753 cycloalkyl group Chemical group 0.000 claims description 16
125000004423 acyloxy group Chemical group 0.000 claims description 13
125000003342 alkenyl group Chemical group 0.000 claims description 12
150000002431 hydrogen Chemical group 0.000 claims description 12
230000000840 anti-viral effect Effects 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
125000005041 acyloxyalkyl group Chemical group 0.000 claims description 7
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 7
125000005333 aroyloxy group Chemical group 0.000 claims description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
208000036142 Viral infection Diseases 0.000 claims description 3
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
230000009385 viral infection Effects 0.000 claims description 3
INMPPEDAPCJKNV-UHFFFAOYSA-N (4-amino-1-benzylimidazo[4,5-c]quinolin-2-yl)methanol Chemical compound OCC1=NC=2C(N)=NC3=CC=CC=C3C=2N1CC1=CC=CC=C1 INMPPEDAPCJKNV-UHFFFAOYSA-N 0.000 claims description 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
RXNTZIJLOZMJTM-UHFFFAOYSA-N 2-(2h-quinolin-1-yl)ethanol Chemical compound C1=CC=C2N(CCO)CC=CC2=C1 RXNTZIJLOZMJTM-UHFFFAOYSA-N 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
GJWIWOYILQFPJK-UHFFFAOYSA-N 1-(2-methoxyethyl)-2-(methoxymethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C3N(CCOC)C(COC)=NC3=C(N)N=C21 GJWIWOYILQFPJK-UHFFFAOYSA-N 0.000 claims 1
GTTJKTPDYQMDLA-UHFFFAOYSA-N 1-(2-methylpropyl)-2-(morpholin-4-ylmethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound N=1C2=C(N)N=C3C=CC=CC3=C2N(CC(C)C)C=1CN1CCOCC1 GTTJKTPDYQMDLA-UHFFFAOYSA-N 0.000 claims 1
OEQKMAKSZQARAT-UHFFFAOYSA-N 1-(2-methylpropyl)-2-(pyrrolidin-1-ylmethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound N=1C2=C(N)N=C3C=CC=CC3=C2N(CC(C)C)C=1CN1CCCC1 OEQKMAKSZQARAT-UHFFFAOYSA-N 0.000 claims 1
ZDUUNVSWBCZIAS-UHFFFAOYSA-N 1-benzyl-2-(methylsulfanylmethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound CSCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CC1=CC=CC=C1 ZDUUNVSWBCZIAS-UHFFFAOYSA-N 0.000 claims 1
AIOJIIMJRSQGDU-UHFFFAOYSA-N 1-benzyl-2-(morpholin-4-ylmethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1COCCN1CC1=NC=2C(N)=NC3=CC=CC=C3C=2N1CC1=CC=CC=C1 AIOJIIMJRSQGDU-UHFFFAOYSA-N 0.000 claims 1
HDEFYLRCCSPRQE-UHFFFAOYSA-N 2-(1-methoxypentyl)-1-(2-methylpropyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(C(OC)CCCC)=N3)CC(C)C)C3=C(N)N=C21 HDEFYLRCCSPRQE-UHFFFAOYSA-N 0.000 claims 1
BZKZXCFPTOAPSV-UHFFFAOYSA-N 2-(2-methoxyethyl)-1-(2-methylpropyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CC(C)C)C3=C(N)N=C21 BZKZXCFPTOAPSV-UHFFFAOYSA-N 0.000 claims 1
DDKLJBYHXBQCMI-UHFFFAOYSA-N 2-(methoxymethyl)-1-(2-methylpropyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(COC)=N3)CC(C)C)C3=C(N)N=C21 DDKLJBYHXBQCMI-UHFFFAOYSA-N 0.000 claims 1
ZEPMDUKBOAODEV-UHFFFAOYSA-N [4-(4-aminobutyl)-1-(2-methylpropyl)imidazo[4,5-c]quinolin-2-yl]methanol Chemical compound C1=CC=CC2=C3N(CC(C)C)C(CO)=NC3=C(CCCCN)N=C21 ZEPMDUKBOAODEV-UHFFFAOYSA-N 0.000 claims 1
YGXQRRLAJLTBSH-UHFFFAOYSA-N [4-amino-1-(2-methylpropyl)imidazo[4,5-c]quinolin-2-yl]methanol Chemical compound C1=CC=CC2=C3N(CC(C)C)C(CO)=NC3=C(N)N=C21 YGXQRRLAJLTBSH-UHFFFAOYSA-N 0.000 claims 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
102000014150 Interferons Human genes 0.000 abstract description 33
108010050904 Interferons Proteins 0.000 abstract description 33
229940079322 interferon Drugs 0.000 abstract description 32
230000015572 biosynthetic process Effects 0.000 abstract description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 3
125000004414 alkyl thio group Chemical group 0.000 abstract description 2
239000003443 antiviral agent Substances 0.000 abstract description 2
230000005740 tumor formation Effects 0.000 abstract description 2
238000010171 animal model Methods 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 192
239000007787 solid Substances 0.000 description 123
239000000203 mixture Substances 0.000 description 103
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 77
239000000047 product Substances 0.000 description 76
238000004458 analytical method Methods 0.000 description 67
239000000243 solution Substances 0.000 description 63
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 62
238000006243 chemical reaction Methods 0.000 description 48
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 44
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
238000007429 general method Methods 0.000 description 39
241000699670 Mus sp. Species 0.000 description 31
229910052943 magnesium sulfate Inorganic materials 0.000 description 31
235000019341 magnesium sulphate Nutrition 0.000 description 31
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
239000011541 reaction mixture Substances 0.000 description 29
238000005481 NMR spectroscopy Methods 0.000 description 28
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
239000000908 ammonium hydroxide Substances 0.000 description 24
239000002244 precipitate Substances 0.000 description 22
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
239000012043 crude product Substances 0.000 description 19
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 18
239000003921 oil Substances 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
238000000034 method Methods 0.000 description 16
238000003756 stirring Methods 0.000 description 16
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
239000000706 filtrate Substances 0.000 description 15
230000006698 induction Effects 0.000 description 15
235000017557 sodium bicarbonate Nutrition 0.000 description 14
229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
210000004027 cell Anatomy 0.000 description 13
239000003480 eluent Substances 0.000 description 13
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 13
238000010992 reflux Methods 0.000 description 13
239000002904 solvent Substances 0.000 description 12
239000000725 suspension Substances 0.000 description 12
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
241000700198 Cavia Species 0.000 description 11
239000003795 chemical substances by application Substances 0.000 description 11
230000003902 lesion Effects 0.000 description 11
239000000523 sample Substances 0.000 description 11
YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 10
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 10
210000002966 serum Anatomy 0.000 description 10
238000010898 silica gel chromatography Methods 0.000 description 10
150000001204 N-oxides Chemical class 0.000 description 9
239000008280 blood Substances 0.000 description 9
238000010438 heat treatment Methods 0.000 description 9
239000000463 material Substances 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
210000004369 blood Anatomy 0.000 description 8
239000000284 extract Substances 0.000 description 8
230000005764 inhibitory process Effects 0.000 description 8
239000010410 layer Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
241000711975 Vesicular stomatitis virus Species 0.000 description 7
210000005260 human cell Anatomy 0.000 description 7
239000012948 isocyanate Substances 0.000 description 7
239000002609 medium Substances 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
241000700199 Cavia porcellus Species 0.000 description 6
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
239000012980 RPMI-1640 medium Substances 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
241000700605 Viruses Species 0.000 description 6
239000013078 crystal Substances 0.000 description 6
230000000120 cytopathologic effect Effects 0.000 description 6
150000002513 isocyanates Chemical class 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
238000010998 test method Methods 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
230000003612 virological effect Effects 0.000 description 6
206010028980 Neoplasm Diseases 0.000 description 5
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
238000001816 cooling Methods 0.000 description 5
150000004985 diamines Chemical class 0.000 description 5
238000010790 dilution Methods 0.000 description 5
239000012895 dilution Substances 0.000 description 5
239000012259 ether extract Substances 0.000 description 5
238000003818 flash chromatography Methods 0.000 description 5
125000000524 functional group Chemical group 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
HREHOXSRYOZKNT-UHFFFAOYSA-N quinolin-2-ylmethanol Chemical compound C1=CC=CC2=NC(CO)=CC=C21 HREHOXSRYOZKNT-UHFFFAOYSA-N 0.000 description 5
JFMKIQOIIMSWIM-UHFFFAOYSA-N 4-n-(2-methylpropyl)quinoline-3,4-diamine Chemical compound C1=CC=C2C(NCC(C)C)=C(N)C=NC2=C1 JFMKIQOIIMSWIM-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
241000699666 Mus <mouse, genus> Species 0.000 description 4
241000700584 Simplexvirus Species 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
238000003556 assay Methods 0.000 description 4
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 4
238000004166 bioassay Methods 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000012512 characterization method Methods 0.000 description 4
238000009472 formulation Methods 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 4
230000000269 nucleophilic effect Effects 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
CXYOCSTZCULCAE-UHFFFAOYSA-N 1-(2-methylpropyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=CN=C21 CXYOCSTZCULCAE-UHFFFAOYSA-N 0.000 description 3
SIEDJWXHTNOOMX-UHFFFAOYSA-N 1-benzyl-2-(chloromethyl)imidazo[4,5-c]quinolin-4-amine;hydrochloride Chemical compound Cl.ClCC1=NC=2C(N)=NC3=CC=CC=C3C=2N1CC1=CC=CC=C1 SIEDJWXHTNOOMX-UHFFFAOYSA-N 0.000 description 3
ZWISCKSGNCMAQO-UHFFFAOYSA-N 3-nitro-1H-quinolin-4-one Chemical class C1=CC=C2C(=O)C([N+](=O)[O-])=CNC2=C1 ZWISCKSGNCMAQO-UHFFFAOYSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 3
210000000601 blood cell Anatomy 0.000 description 3
239000012267 brine Substances 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
239000006071 cream Substances 0.000 description 3
238000006073 displacement reaction Methods 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
238000011534 incubation Methods 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
238000005259 measurement Methods 0.000 description 3
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
238000010186 staining Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
LHBODUUXCWHZLN-UHFFFAOYSA-N 1-[(3-aminoquinolin-4-yl)amino]-2-methylpropan-2-ol Chemical compound C1=CC=C2C(NCC(C)(O)C)=C(N)C=NC2=C1 LHBODUUXCWHZLN-UHFFFAOYSA-N 0.000 description 2
CYOHXZCGGOMRPN-UHFFFAOYSA-N 1-benzyl-2-(ethoxymethyl)imidazo[4,5-c]quinoline Chemical compound CCOCC1=NC2=CN=C3C=CC=CC3=C2N1CC1=CC=CC=C1 CYOHXZCGGOMRPN-UHFFFAOYSA-N 0.000 description 2
DZCWNQSANNLVLU-UHFFFAOYSA-N 2-(1-methoxyethyl)-1-(2-methylpropyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(C(C)OC)=N3)CC(C)C)C3=CN=C21 DZCWNQSANNLVLU-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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- 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
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Virology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Quinoline Compounds (AREA)
Lubricants (AREA)
Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

IL10111092A 1991-03-01 1992-03-01 H1-Amidazo] -C-4,5 [-Quinoline-4-Amines converted at position 2, pharmaceutical preparations containing them and certain intermediates new to them IL101110A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
IL11457092A IL114570A (en)	1991-03-01	1992-03-01	Compounds H1 – imidazo] C – 4,5 [quinoline

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US66292691A	1991-03-01	1991-03-01
US68732691A	1991-04-18	1991-04-18

Publications (2)

Publication Number	Publication Date
IL101110A0 IL101110A0 (en)	1992-11-15
IL101110A true IL101110A (en)	1995-12-08

Family

ID=27098631

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
IL10111092A IL101110A (en)	1991-03-01	1992-03-01	H1-Amidazo] -C-4,5 [-Quinoline-4-Amines converted at position 2, pharmaceutical preparations containing them and certain intermediates new to them
IL11457092A IL114570A (en)	1991-03-01	1992-03-01	Compounds H1 – imidazo] C – 4,5 [quinoline

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
IL11457092A IL114570A (en)	1991-03-01	1992-03-01	Compounds H1 – imidazo] C – 4,5 [quinoline

Country Status (18)

Country	Link
EP (2)	EP0872478B1 (de)
JP (1)	JP2955019B2 (de)
AT (2)	ATE179711T1 (de)
AU (2)	AU658621B2 (de)
CA (2)	CA2289219C (de)
CZ (1)	CZ285050B6 (de)
DE (2)	DE69229114T2 (de)
DK (2)	DK0582581T3 (de)
ES (2)	ES2131070T3 (de)
HU (5)	HU222247B1 (de)
IE (1)	IE920605A1 (de)
IL (2)	IL101110A (de)
NO (1)	NO303729B1 (de)
NZ (1)	NZ241784A (de)
PH (1)	PH31614A (de)
SG (2)	SG70625A1 (de)
UA (1)	UA32546C2 (de)
WO (1)	WO1992015582A1 (de)

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1992
- 1992-02-20 DE DE69229114T patent/DE69229114T2/de not_active Expired - Lifetime
- 1992-02-20 SG SG1998000326A patent/SG70625A1/en unknown
- 1992-02-20 SG SG1996005108A patent/SG46492A1/en unknown
- 1992-02-20 HU HU9701083A patent/HU222247B1/hu not_active IP Right Cessation
- 1992-02-20 AU AU15669/92A patent/AU658621B2/en not_active Expired
- 1992-02-20 HU HU9302457A patent/HU222111B1/hu not_active IP Right Cessation
- 1992-02-20 AT AT92906763T patent/ATE179711T1/de not_active IP Right Cessation
- 1992-02-20 DK DK92906763T patent/DK0582581T3/da active
- 1992-02-20 CZ CZ931788A patent/CZ285050B6/cs not_active IP Right Cessation
- 1992-02-20 ES ES92906763T patent/ES2131070T3/es not_active Expired - Lifetime
- 1992-02-20 HU HU9701084A patent/HU222251B1/hu not_active IP Right Cessation
- 1992-02-20 CA CA002289219A patent/CA2289219C/en not_active Expired - Lifetime
- 1992-02-20 DK DK98105754T patent/DK0872478T3/da active
- 1992-02-20 DE DE69232878T patent/DE69232878T2/de not_active Expired - Fee Related
- 1992-02-20 AT AT98105754T patent/ATE229943T1/de not_active IP Right Cessation
- 1992-02-20 EP EP98105754A patent/EP0872478B1/de not_active Expired - Lifetime
- 1992-02-20 EP EP92906763A patent/EP0582581B1/de not_active Expired - Lifetime
- 1992-02-20 UA UA94020490A patent/UA32546C2/uk unknown
- 1992-02-20 ES ES98105754T patent/ES2186034T3/es not_active Expired - Lifetime
- 1992-02-20 CA CA002104782A patent/CA2104782C/en not_active Expired - Lifetime
- 1992-02-20 WO PCT/US1992/001305 patent/WO1992015582A1/en not_active Ceased
- 1992-02-20 HU HU9701089A patent/HU222250B1/hu not_active IP Right Cessation
- 1992-02-20 JP JP4506455A patent/JP2955019B2/ja not_active Expired - Lifetime
- 1992-02-26 IE IE060592A patent/IE920605A1/en not_active IP Right Cessation
- 1992-02-28 PH PH43994A patent/PH31614A/en unknown
- 1992-02-28 NZ NZ241784A patent/NZ241784A/en not_active IP Right Cessation
- 1992-03-01 IL IL10111092A patent/IL101110A/en not_active IP Right Cessation
- 1992-03-01 IL IL11457092A patent/IL114570A/en not_active IP Right Cessation
1993
- 1993-08-27 NO NO933069A patent/NO303729B1/no not_active IP Right Cessation
1995
- 1995-07-03 HU HU95P/P00753P patent/HU211242A9/hu unknown
- 1995-07-25 AU AU27157/95A patent/AU673309B2/en not_active Ceased

Also Published As

Publication number	Publication date
IL114570A0 (en)	1995-11-27
SG70625A1 (en)	2000-02-22
HU9302457D0 (en)	1993-11-29
EP0582581B1 (de)	1999-05-06
IE920605A1 (en)	1992-09-09
CA2289219C (en)	2003-05-20
JPH06504789A (ja)	1994-06-02
CZ178893A3 (en)	1995-10-18
NO303729B1 (no)	1998-08-24
EP0872478A3 (de)	1998-11-04
HU9701089D0 (en)	1997-08-28
EP0872478B1 (de)	2002-12-18
HU9701084D0 (en)	1997-08-28
IL101110A0 (en)	1992-11-15
DE69229114T2 (de)	1999-11-04
HU222251B1 (hu)	2003-05-28
JP2955019B2 (ja)	1999-10-04
AU673309B2 (en)	1996-10-31
NO933069L (no)	1993-11-01
AU658621B2 (en)	1995-04-27
CA2104782A1 (en)	1992-09-02
CA2289219A1 (en)	1992-09-02
PH31614A (en)	1999-01-12
UA32546C2 (uk)	2001-02-15
HU222111B1 (hu)	2003-04-28
DK0582581T3 (da)	1999-11-08
WO1992015582A1 (en)	1992-09-17
AU1566992A (en)	1992-10-06
ATE229943T1 (de)	2003-01-15
DE69232878T2 (de)	2003-11-20
DE69229114D1 (de)	1999-06-10
HU222247B1 (hu)	2003-05-28
SG46492A1 (en)	1998-02-20
IL114570A (en)	1996-10-31
IE990988A1 (en)	2000-12-13
CZ285050B6 (cs)	1999-05-12
EP0582581A1 (de)	1994-02-16
HU222250B1 (hu)	2003-05-28
EP0872478A2 (de)	1998-10-21
HU211242A9 (en)	1995-11-28
HUT67026A (en)	1995-01-30
ES2131070T3 (es)	1999-07-16
CA2104782C (en)	2001-08-07
NO933069D0 (no)	1993-08-27
DK0872478T3 (da)	2003-03-31
NZ241784A (en)	1995-06-27
AU2715795A (en)	1995-09-21
DE69232878D1 (de)	2003-01-30
HU9701083D0 (en)	1997-08-28
ES2186034T3 (es)	2003-05-01
ATE179711T1 (de)	1999-05-15

Legal Events

Date	Code	Title
1996-06-18	FF	Patent granted
1998-09-24	KB	Patent renewed
2006-06-18	KB	Patent renewed
2010-10-31	KB	Patent renewed
2012-10-31	EXP	Patent expired

Publication	Publication Date	Title
AU658621B2 (en)	1995-04-27	1-substituted, 2-substituted 1H-imidazo(4,5-c)quinolin-4-amines
US5605899A (en)	1997-02-25	1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines
US6790961B2 (en)	2004-09-14	Process for preparing 1-substituted, 2-substituted 1H-imidazo[4,5-C]quinolin-4-amines
JP3571342B2 (ja)	2004-09-29	縮合シクロアルキルイミダゾピリジン
US5525612A (en)	1996-06-11	1-substituted 1H-imidazo-[4,5-c]quinolin-4-amines
US5648516A (en)	1997-07-15	Fused cycloalkylimidazopyridines
EP0389302B1 (de)	1994-08-31	Olefinisch substitierte 1H-Imidazo[4,5-c]chinolin-4-amine
KR100235389B1 (ko)	1999-12-15	1-치환된, 2-치환된 1H-이미다조[4,5-c]퀴놀린-4-아민
IE19990988A1 (en)	2000-12-13	Intermediates for the preparation of 1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines
IE83826B1 (en)	2005-03-09	Intermediates for the preparation of 1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines