KR100226184B1 - 이미다조(4,5-c)퀴놀린-4-아민 및 그 제조 방법 - Google Patents
이미다조(4,5-c)퀴놀린-4-아민 및 그 제조 방법 Download PDFInfo
- Publication number
- KR100226184B1 KR100226184B1 KR1019930702603A KR930702603A KR100226184B1 KR 100226184 B1 KR100226184 B1 KR 100226184B1 KR 1019930702603 A KR1019930702603 A KR 1019930702603A KR 930702603 A KR930702603 A KR 930702603A KR 100226184 B1 KR100226184 B1 KR 100226184B1
- Authority
- KR
- South Korea
- Prior art keywords
- group
- alkyl
- phenyl
- substituted
- straight
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- HQBUPOAKJGJGCD-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-4-amine Chemical compound NC1=NC2=CC=CC=C2C2=C1N=CN2 HQBUPOAKJGJGCD-UHFFFAOYSA-N 0.000 title claims description 9
- 238000000034 method Methods 0.000 claims abstract description 26
- -1 1-substituted-1H-imidazo [4,5-c] quinoline Chemical class 0.000 claims abstract description 23
- 239000012948 isocyanate Substances 0.000 claims abstract description 14
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 13
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 238000007792 addition Methods 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 125000000524 functional group Chemical group 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 claims description 8
- GIIWGCBLYNDKBO-UHFFFAOYSA-N Quinoline 1-oxide Chemical compound C1=CC=C2[N+]([O-])=CC=CC2=C1 GIIWGCBLYNDKBO-UHFFFAOYSA-N 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 125000000962 organic group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 125000005333 aroyloxy group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 11
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical class C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 238000006243 chemical reaction Methods 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 241000593992 Blicca bjoerkna Species 0.000 description 6
- 150000001204 N-oxides Chemical class 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical compound C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 5
- ZWISCKSGNCMAQO-UHFFFAOYSA-N 3-nitro-1H-quinolin-4-one Chemical compound C1=CC=C2C(=O)C([N+](=O)[O-])=CNC2=C1 ZWISCKSGNCMAQO-UHFFFAOYSA-N 0.000 description 4
- 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 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000006239 protecting group Chemical group 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 230000000269 nucleophilic effect Effects 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XNPJZZIARKSZAN-UHFFFAOYSA-N [(4-chlorophenyl)-[1-(2-methylpropyl)imidazo[4,5-c]quinolin-2-yl]methyl] acetate Chemical compound N=1C2=CN=C3C=CC=CC3=C2N(CC(C)C)C=1C(OC(C)=O)C1=CC=C(Cl)C=C1 XNPJZZIARKSZAN-UHFFFAOYSA-N 0.000 description 2
- CMNIDDIBCYMXTD-UHFFFAOYSA-N [1-(2-methylpropyl)imidazo[4,5-c]quinolin-2-yl]-phenylmethanol Chemical compound N=1C2=CN=C3C=CC=CC3=C2N(CC(C)C)C=1C(O)C1=CC=CC=C1 CMNIDDIBCYMXTD-UHFFFAOYSA-N 0.000 description 2
- KJGZTPSSMHUCJY-UHFFFAOYSA-N [4-amino-1-(2-methylpropyl)imidazo[4,5-c]quinolin-2-yl]-(4-chlorophenyl)methanol Chemical compound N=1C2=C(N)N=C3C=CC=CC3=C2N(CC(C)C)C=1C(O)C1=CC=C(Cl)C=C1 KJGZTPSSMHUCJY-UHFFFAOYSA-N 0.000 description 2
- BVXHHEFUCZFNTQ-UHFFFAOYSA-N [[1-(2-methylpropyl)imidazo[4,5-c]quinolin-2-yl]-phenylmethyl] acetate Chemical compound N=1C2=CN=C3C=CC=CC3=C2N(CC(C)C)C=1C(OC(C)=O)C1=CC=CC=C1 BVXHHEFUCZFNTQ-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- CDUWBBGUDMBQDE-UHFFFAOYSA-N n-(2-methylpropyl)-3-nitroquinolin-4-amine Chemical compound C1=CC=C2C(NCC(C)C)=C([N+]([O-])=O)C=NC2=C1 CDUWBBGUDMBQDE-UHFFFAOYSA-N 0.000 description 2
- TZTHLAVJQIFKRJ-UHFFFAOYSA-N n-[1-(2-methylpropyl)imidazo[4,5-c]quinolin-4-yl]benzamide Chemical compound N1=C2C=CC=CC2=C2N(CC(C)C)C=NC2=C1NC(=O)C1=CC=CC=C1 TZTHLAVJQIFKRJ-UHFFFAOYSA-N 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- 150000002905 orthoesters Chemical class 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RSZODAWNBKUNFT-UHFFFAOYSA-N (4-chlorophenyl)-(3h-imidazo[4,5-c]quinolin-2-yl)methanol Chemical compound N=1C(C2=CC=CC=C2N=C2)=C2NC=1C(O)C1=CC=C(Cl)C=C1 RSZODAWNBKUNFT-UHFFFAOYSA-N 0.000 description 1
- ZRFUZDDJSQVQBY-UHFFFAOYSA-N 4-chloro-3-nitroquinoline Chemical compound C1=CC=CC2=C(Cl)C([N+](=O)[O-])=CN=C21 ZRFUZDDJSQVQBY-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- 150000004331 4-hydroxyquinolines Chemical class 0.000 description 1
- 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 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- HYVOYDDYZPOQOW-UHFFFAOYSA-N [4-amino-1-(2-methylpropyl)imidazo[4,5-c]quinolin-2-yl]-phenylmethanol Chemical compound N=1C2=C(N)N=C3C=CC=CC3=C2N(CC(C)C)C=1C(O)C1=CC=CC=C1 HYVOYDDYZPOQOW-UHFFFAOYSA-N 0.000 description 1
- HDUHSISAGHHYRW-UHFFFAOYSA-N [N].N1=CC=CC2=CC=CC=C21 Chemical compound [N].N1=CC=CC2=CC=CC=C21 HDUHSISAGHHYRW-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 1
- IRUNKQSGDBYUDC-UHFFFAOYSA-N diethoxymethyl acetate Chemical compound CCOC(OCC)OC(C)=O IRUNKQSGDBYUDC-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- IRFHMTUHTBSEBK-QGZVFWFLSA-N tert-butyl n-[(2s)-2-(2,5-difluorophenyl)-3-quinolin-3-ylpropyl]carbamate Chemical compound C1([C@H](CC=2C=C3C=CC=CC3=NC=2)CNC(=O)OC(C)(C)C)=CC(F)=CC=C1F IRFHMTUHTBSEBK-QGZVFWFLSA-N 0.000 description 1
- 239000012970 tertiary amine catalyst Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/663,110 US5175296A (en) | 1991-03-01 | 1991-03-01 | Imidazo[4,5-c]quinolin-4-amines and processes for their preparation |
| US663,110 | 1991-03-01 | ||
| PCT/US1992/001212 WO1992015581A1 (en) | 1991-03-01 | 1992-02-13 | PROCESS FOR IMIDAZO[4,5-c]QUINOLIN-4-AMINES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR930703317A KR930703317A (ko) | 1993-11-29 |
| KR100226184B1 true KR100226184B1 (ko) | 1999-10-15 |
Family
ID=24660514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019930702603A Expired - Lifetime KR100226184B1 (ko) | 1991-03-01 | 1992-02-13 | 이미다조(4,5-c)퀴놀린-4-아민 및 그 제조 방법 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5175296A (enExample) |
| EP (1) | EP0575549B1 (enExample) |
| JP (2) | JP3313708B2 (enExample) |
| KR (1) | KR100226184B1 (enExample) |
| AT (1) | ATE142632T1 (enExample) |
| AU (1) | AU657958B2 (enExample) |
| CA (1) | CA2104781C (enExample) |
| CZ (1) | CZ291368B6 (enExample) |
| DE (1) | DE69213720T2 (enExample) |
| DK (1) | DK0575549T3 (enExample) |
| ES (1) | ES2091463T3 (enExample) |
| HU (1) | HU218219B (enExample) |
| IE (1) | IE920524A1 (enExample) |
| IL (1) | IL100998A (enExample) |
| NO (1) | NO301714B1 (enExample) |
| NZ (1) | NZ241645A (enExample) |
| WO (1) | WO1992015581A1 (enExample) |
Families Citing this family (171)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5389640A (en) * | 1991-03-01 | 1995-02-14 | Minnesota Mining And Manufacturing Company | 1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
| US6608201B2 (en) * | 1992-08-28 | 2003-08-19 | 3M Innovative Properties Company | Process for preparing 1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
| US5395937A (en) * | 1993-01-29 | 1995-03-07 | Minnesota Mining And Manufacturing Company | Process for preparing quinoline amines |
| US5352784A (en) * | 1993-07-15 | 1994-10-04 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
| ATE195735T1 (de) * | 1993-07-15 | 2000-09-15 | Minnesota Mining & Mfg | Imidazo (4,5-c)pyridin-4-amine |
| US5648516A (en) * | 1994-07-20 | 1997-07-15 | Minnesota Mining And Manufacturing Company | Fused cycloalkylimidazopyridines |
| US5644063A (en) * | 1994-09-08 | 1997-07-01 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-c]pyridin-4-amine intermediates |
| US5741908A (en) | 1996-06-21 | 1998-04-21 | Minnesota Mining And Manufacturing Company | Process for reparing imidazoquinolinamines |
| US5693811A (en) * | 1996-06-21 | 1997-12-02 | Minnesota Mining And Manufacturing Company | Process for preparing tetrahdroimidazoquinolinamines |
| UA67760C2 (uk) | 1997-12-11 | 2004-07-15 | Міннесота Майнінг Енд Мануфакчурінг Компані | Імідазонафтиридин та тетрагідроімідазонафтиридин, фармацевтична композиція, спосіб індукування біосинтезу цитокінів та спосіб лікування вірусної інфекції, проміжні сполуки |
| US20020058674A1 (en) | 1999-01-08 | 2002-05-16 | Hedenstrom John C. | Systems and methods for treating a mucosal surface |
| US6486168B1 (en) | 1999-01-08 | 2002-11-26 | 3M Innovative Properties Company | Formulations and methods for treatment of mucosal associated conditions with an immune response modifier |
| KR20010101420A (ko) | 1999-01-08 | 2001-11-14 | 캐롤린 에이. 베이츠 | 면역반응 조절제로 점막 관련 질환을 치료하기 위한조성물 및 방법 |
| US6558951B1 (en) * | 1999-02-11 | 2003-05-06 | 3M Innovative Properties Company | Maturation of dendritic cells with immune response modifying compounds |
| US6541485B1 (en) | 1999-06-10 | 2003-04-01 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6573273B1 (en) | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6331539B1 (en) * | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US6756382B2 (en) | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6916925B1 (en) | 1999-11-05 | 2005-07-12 | 3M Innovative Properties Co. | Dye labeled imidazoquinoline compounds |
| US6376669B1 (en) | 1999-11-05 | 2002-04-23 | 3M Innovative Properties Company | Dye labeled imidazoquinoline compounds |
| EP1256582A1 (en) * | 2000-02-09 | 2002-11-13 | Hokuriku Seiyaku Co., Ltd. | 1h-imidazopyridine derivatives |
| CA2598144A1 (en) * | 2000-12-08 | 2006-08-31 | 3M Innovative Properties Company | Compositions and methods for targeted delivery of immune response modifiers |
| US6677347B2 (en) * | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamido ether substituted imidazoquinolines |
| US6660735B2 (en) | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Urea substituted imidazoquinoline ethers |
| UA75622C2 (en) * | 2000-12-08 | 2006-05-15 | 3M Innovative Properties Co | Aryl ether substituted imidazoquinolines, pharmaceutical composition based thereon |
| US6545017B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Urea substituted imidazopyridines |
| US6664264B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US6545016B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Amide substituted imidazopyridines |
| US6677348B2 (en) | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Aryl ether substituted imidazoquinolines |
| US6664265B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| US6525064B1 (en) | 2000-12-08 | 2003-02-25 | 3M Innovative Properties Company | Sulfonamido substituted imidazopyridines |
| US6660747B2 (en) * | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
| US6667312B2 (en) * | 2000-12-08 | 2003-12-23 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| US7226928B2 (en) * | 2001-06-15 | 2007-06-05 | 3M Innovative Properties Company | Methods for the treatment of periodontal disease |
| JP2005501550A (ja) * | 2001-08-30 | 2005-01-20 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫反応調整剤分子を用いた形質細胞様樹状細胞を成熟させる方法 |
| AU2002343728A1 (en) * | 2001-11-16 | 2003-06-10 | 3M Innovative Properties Company | Methods and compositions related to irm compounds and toll-like receptor pathways |
| JP4447914B2 (ja) * | 2001-11-29 | 2010-04-07 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫応答調節物質を含む医薬品 |
| CA2365732A1 (en) * | 2001-12-20 | 2003-06-20 | Ibm Canada Limited-Ibm Canada Limitee | Testing measurements |
| US6677349B1 (en) * | 2001-12-21 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| HUE025145T2 (en) * | 2002-02-22 | 2016-01-28 | Meda Ab | A method for reducing and treating immunosuppression induced by ultraviolet B radiation |
| AU2003233519A1 (en) | 2002-05-29 | 2003-12-19 | 3M Innovative Properties Company | Process for imidazo(4,5-c)pyridin-4-amines |
| CA2488801A1 (en) * | 2002-06-07 | 2003-12-18 | 3M Innovative Properties Company | Ether substituted imidazopyridines |
| PT1543002E (pt) | 2002-07-23 | 2006-11-30 | Teva Gyogyszergyar Zartkoeruen | Preparação de intermediários 1h-imidazo ( 4,5-c )quinolin-4-aminas via 1h- imidazo (4,5-c ) quinolina-4-ftalimida |
| JP2005537287A (ja) | 2002-07-26 | 2005-12-08 | テバ ジョジセルジャール レースベニュタールシャシャーグ | 新規１Ｈ−イミダゾ［４，５−ｃ］キノリン−４−シアノ及び１Ｈ−イミダゾ［４，５−ｃ］キノリン−４−カルボキサミド中間体による１Ｈ−イミダゾ［４，５−ｃ］キノリン−４−アミン類の製造 |
| DK1545597T3 (da) | 2002-08-15 | 2011-01-31 | 3M Innovative Properties Co | Immunstimulerende sammensætninger og fremgangsmåde til stimulering af en immunrespons |
| EP1542688A4 (en) * | 2002-09-26 | 2010-06-02 | 3M Innovative Properties Co | 1H-imidazo dimers |
| AU2003287316A1 (en) * | 2002-12-11 | 2004-06-30 | 3M Innovative Properties Company | Assays relating to toll-like receptor activity |
| AU2003287324A1 (en) * | 2002-12-11 | 2004-06-30 | 3M Innovative Properties Company | Gene expression systems and recombinant cell lines |
| NZ540826A (en) | 2002-12-20 | 2008-07-31 | 3M Innovative Properties Co | Aryl / hetaryl substituted imidazoquinolines |
| EP2572715A1 (en) | 2002-12-30 | 2013-03-27 | 3M Innovative Properties Company | Immunostimulatory Combinations |
| WO2004071459A2 (en) * | 2003-02-13 | 2004-08-26 | 3M Innovative Properties Company | Methods and compositions related to irm compounds and toll-like receptor 8 |
| WO2004075865A2 (en) * | 2003-02-27 | 2004-09-10 | 3M Innovative Properties Company | Selective modulation of tlr-mediated biological activity |
| EP1601365A4 (en) | 2003-03-04 | 2009-11-11 | 3M Innovative Properties Co | PROPHYLACTIC TREATMENT OF UV-INDUCED EPIDERMAL NEOPLASIA |
| EP1605943A4 (en) * | 2003-03-07 | 2008-01-16 | 3M Innovative Properties Co | 1-AMINO-1H-imidazoquinolines |
| US7163947B2 (en) * | 2003-03-07 | 2007-01-16 | 3M Innovative Properties Company | 1-Amino 1H-imidazoquinolines |
| US8426457B2 (en) * | 2003-03-13 | 2013-04-23 | Medicis Pharmaceutical Corporation | Methods of improving skin quality |
| US7179253B2 (en) * | 2003-03-13 | 2007-02-20 | 3M Innovative Properties Company | Method of tattoo removal |
| CA2518082C (en) * | 2003-03-13 | 2013-02-12 | 3M Innovative Properties Company | Methods for diagnosing skin lesions |
| US20040192585A1 (en) * | 2003-03-25 | 2004-09-30 | 3M Innovative Properties Company | Treatment for basal cell carcinoma |
| WO2004108072A2 (en) * | 2003-04-10 | 2004-12-16 | 3M Innovative Properties Company | Delivery of immune response modifier compounds using metal-containing particulate support materials |
| US20040265351A1 (en) | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
| US20050032829A1 (en) * | 2003-06-06 | 2005-02-10 | 3M Innovative Properties Company | Process for imidazo[4,5-c]pyridin-4-amines |
| WO2004110991A2 (en) * | 2003-06-06 | 2004-12-23 | 3M Innovative Properties Company | PROCESS FOR IMIDAZO[4,5-c]PYRIDIN-4-AMINES |
| CA2533128A1 (en) * | 2003-07-31 | 2005-02-10 | 3M Innovative Properties Company | Bioactive compositions comprising triazines |
| WO2005016273A2 (en) * | 2003-08-05 | 2005-02-24 | 3M Innovative Properties Company | Infection prophylaxis using immune response modifier compounds |
| AU2004266658A1 (en) * | 2003-08-12 | 2005-03-03 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo-containing compounds |
| US7799800B2 (en) * | 2003-08-14 | 2010-09-21 | 3M Innovative Properties Company | Lipid-modified immune response modifiers |
| CA2536249A1 (en) | 2003-08-25 | 2005-03-10 | 3M Innovative Properties Company | Delivery of immune response modifier compounds |
| US20050048072A1 (en) * | 2003-08-25 | 2005-03-03 | 3M Innovative Properties Company | Immunostimulatory combinations and treatments |
| BRPI0413998A (pt) | 2003-08-27 | 2006-11-07 | 3M Innovative Properties Co | imidazoquinolinas arilóxi e arilalquilenóxi substituìdas |
| US20060216333A1 (en) * | 2003-09-02 | 2006-09-28 | Miller Richard L | Methods related to the treatment of mucosal associated conditions |
| US20050054665A1 (en) * | 2003-09-05 | 2005-03-10 | 3M Innovative Properties Company | Treatment for CD5+ B cell lymphoma |
| WO2005029037A2 (en) * | 2003-09-17 | 2005-03-31 | 3M Innovative Properties Company | Selective modulation of tlr gene expression |
| WO2005033049A2 (en) * | 2003-10-01 | 2005-04-14 | Taro Pharmaceuticals U.S.A., Inc. | METHOD OF PREPARING 4-AMINO-1H-IMIDAZO(4,5-c)QUINOLINES AND ACID ADDITION SALTS THEREOF |
| BRPI0414856A (pt) | 2003-10-03 | 2006-11-21 | 3M Innovative Properties Co | imidazoquinolinas alcóxi-substituìdas |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| JP2007508305A (ja) | 2003-10-03 | 2007-04-05 | スリーエム イノベイティブ プロパティズ カンパニー | ピラゾロピリジンおよびその類似物 |
| US20050096259A1 (en) * | 2003-10-31 | 2005-05-05 | 3M Innovative Properties Company | Neutrophil activation by immune response modifier compounds |
| WO2005048933A2 (en) * | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Oxime substituted imidazo ring compounds |
| CA2545825A1 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo ring compounds |
| CA2547020C (en) | 2003-11-25 | 2014-03-25 | 3M Innovative Properties Company | 1h-imidazo[4,5-c]pyridine-4-amine derivatives as immune response modifier |
| WO2005051324A2 (en) * | 2003-11-25 | 2005-06-09 | 3M Innovative Properties Company | Hydroxylamine and oxime substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| US8940755B2 (en) * | 2003-12-02 | 2015-01-27 | 3M Innovative Properties Company | Therapeutic combinations and methods including IRM compounds |
| US20050226878A1 (en) * | 2003-12-02 | 2005-10-13 | 3M Innovative Properties Company | Therapeutic combinations and methods including IRM compounds |
| WO2005076783A2 (en) * | 2003-12-04 | 2005-08-25 | 3M Innovative Properties Company | Sulfone substituted imidazo ring ethers |
| JP2007530450A (ja) * | 2003-12-29 | 2007-11-01 | スリーエム イノベイティブ プロパティズ カンパニー | ピペラジン、［１，４］ジアゼパン、［１，４］ジアゾカン、および［１，５］ジアゾカン縮合イミダゾ環化合物 |
| WO2005066170A1 (en) | 2003-12-29 | 2005-07-21 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
| AU2004312508A1 (en) | 2003-12-30 | 2005-07-21 | 3M Innovative Properties Company | Imidazoquinolinyl, imidazopyridinyl, and imidazonaphthyridinyl sulfonamides |
| US20050201959A1 (en) * | 2004-03-11 | 2005-09-15 | Vvii Newco 2003, Inc. | Methods and compositions for altering skin coloration |
| EP1729768B1 (en) * | 2004-03-15 | 2018-01-10 | Meda AB | Immune response modifier formulations and methods |
| TW200612932A (en) | 2004-03-24 | 2006-05-01 | 3M Innovative Properties Co | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| AU2005244260B2 (en) * | 2004-04-09 | 2010-08-05 | 3M Innovative Properties Company | Methods, compositions, and preparations for delivery of immune response modifiers |
| MXPA06012451A (es) * | 2004-04-28 | 2007-01-31 | 3M Innovative Properties Co | Composiciones y metodos para vacunacion por la mucosa. |
| US20080015184A1 (en) * | 2004-06-14 | 2008-01-17 | 3M Innovative Properties Company | Urea Substituted Imidazopyridines, Imidazoquinolines, and Imidazonaphthyridines |
| WO2005123080A2 (en) | 2004-06-15 | 2005-12-29 | 3M Innovative Properties Company | Nitrogen-containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
| US7915281B2 (en) | 2004-06-18 | 2011-03-29 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and method |
| US7897609B2 (en) | 2004-06-18 | 2011-03-01 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
| WO2006009826A1 (en) | 2004-06-18 | 2006-01-26 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
| US8541438B2 (en) | 2004-06-18 | 2013-09-24 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| CA2571360C (en) * | 2004-06-18 | 2014-11-25 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines useful in inducing cytokine biosynthesis in animals |
| ITMI20041282A1 (it) * | 2004-06-24 | 2004-09-24 | Dipharma Spa | Procedimento per la preparazione di imiquimod |
| WO2006026470A2 (en) * | 2004-08-27 | 2006-03-09 | 3M Innovative Properties Company | Hiv immunostimulatory compositions |
| ATE555786T1 (de) * | 2004-09-02 | 2012-05-15 | 3M Innovative Properties Co | 1-alkoxy 1h-imidazo-ringsysteme und verfahren |
| EP1784180A4 (en) | 2004-09-02 | 2009-07-22 | 3M Innovative Properties Co | 2-AMINO-1H-IMIDAZO RING SYSTEMS AND METHOD |
| WO2007001448A2 (en) | 2004-11-04 | 2007-01-04 | Massachusetts Institute Of Technology | Coated controlled release polymer particles as efficient oral delivery vehicles for biopharmaceuticals |
| US8034938B2 (en) | 2004-12-30 | 2011-10-11 | 3M Innovative Properties Company | Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds |
| HUE025749T2 (en) * | 2004-12-30 | 2016-04-28 | Meda Ab | Use of Imiquimod to treat skin metastases from breast cancer |
| NZ556399A (en) * | 2004-12-30 | 2009-03-31 | Takeda Pharmaceutical | 1-(2-methylpropyl)-1H-imidazo[4,5-C][1,5]naphthyridin-4-amine ethanesulfonate and 1-(2-methylpropyl)-1H-imidazo[4,5-C][1,5]naphthyridin-4-amine methanesulfonate |
| AU2005322898B2 (en) | 2004-12-30 | 2011-11-24 | 3M Innovative Properties Company | Chiral fused (1,2)imidazo(4,5-c) ring compounds |
| US8436176B2 (en) * | 2004-12-30 | 2013-05-07 | Medicis Pharmaceutical Corporation | Process for preparing 2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine |
| US9248127B2 (en) | 2005-02-04 | 2016-02-02 | 3M Innovative Properties Company | Aqueous gel formulations containing immune response modifiers |
| CA2602083A1 (en) | 2005-02-09 | 2006-08-09 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted thiazolo(4,5-c) ring compounds and methods |
| AU2006212765B2 (en) | 2005-02-09 | 2012-02-02 | 3M Innovative Properties Company | Alkyloxy substituted thiazoloquinolines and thiazolonaphthyridines |
| US7968563B2 (en) | 2005-02-11 | 2011-06-28 | 3M Innovative Properties Company | Oxime and hydroxylamine substituted imidazo[4,5-c] ring compounds and methods |
| CA2597446A1 (en) | 2005-02-11 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Substituted imidazoquinolines and imidazonaphthyridines |
| US8343993B2 (en) | 2005-02-23 | 2013-01-01 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazonaphthyridines |
| EP1850849A2 (en) | 2005-02-23 | 2007-11-07 | Coley Pharmaceutical Group, Inc. | Method of preferentially inducing the biosynthesis of interferon |
| US8158794B2 (en) | 2005-02-23 | 2012-04-17 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazoquinoline compounds and methods |
| US8178677B2 (en) | 2005-02-23 | 2012-05-15 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazoquinolines |
| BRPI0608011A2 (pt) * | 2005-03-14 | 2009-11-03 | Graceway Pharmaceuticals Llc | uso de uma formulação para o tratamento da queratose actìnica e uso de 2-metil-1-(2-metilpropil)-1h-imidazo[4,5-c][1,5] naftiridin-4-amina |
| CA2602683A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridine-1,4-diamines and analogs thereof |
| WO2006107851A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | 1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases |
| EP1931352B1 (en) * | 2005-08-22 | 2016-04-13 | The Regents of The University of California | Tlr agonists |
| BRPI0615788A2 (pt) | 2005-09-09 | 2011-05-24 | Coley Pharm Group Inc | derivados de amida e carbamato de n-{2-[4-amino (etoximetil)-1h-imidazo [4,5-c] quinolin-1-il]-1,1-dimetiletil} metanossulfonamida, composição farmacêutica destes e seus usos |
| ZA200803029B (en) | 2005-09-09 | 2009-02-25 | Coley Pharm Group Inc | Amide and carbamate derivatives of alkyl substituted /V-[4-(4-amino-1H-imidazo[4,5-c] quinolin-1-yl)butyl] methane-sulfonamides and methods |
| US20070081962A1 (en) * | 2005-10-06 | 2007-04-12 | Amit Munshi | Novel delivery of immune response modifiers for removal of chronic tattoos |
| US7629027B2 (en) * | 2005-10-14 | 2009-12-08 | 3M Innovative Properties Company | Method for making chromonic nanoparticles |
| US7718716B2 (en) * | 2005-10-14 | 2010-05-18 | 3M Innovative Properties Company | Chromonic nanoparticles containing bioactive compounds |
| KR20080083270A (ko) | 2005-11-04 | 2008-09-17 | 콜레이 파마시티컬 그룹, 인코포레이티드 | 하이드록시 및 알콕시 치환된 1에이치 이미다조퀴놀린 및방법 |
| US20070128291A1 (en) * | 2005-12-07 | 2007-06-07 | Tokie Jeffrey H | Method and Apparatus for Forming Chromonic Nanoparticles |
| US7807661B2 (en) * | 2005-12-08 | 2010-10-05 | 3M Innovative Properties Company | Silver ion releasing articles and methods of manufacture |
| US7323568B2 (en) * | 2005-12-12 | 2008-01-29 | Chemagis Ltd. | Process for preparing Imiquimod |
| US9267937B2 (en) | 2005-12-15 | 2016-02-23 | Massachusetts Institute Of Technology | System for screening particles |
| US8951528B2 (en) | 2006-02-22 | 2015-02-10 | 3M Innovative Properties Company | Immune response modifier conjugates |
| US8329721B2 (en) | 2006-03-15 | 2012-12-11 | 3M Innovative Properties Company | Hydroxy and alkoxy substituted 1H-imidazonaphthyridines and methods |
| WO2007106852A2 (en) | 2006-03-15 | 2007-09-20 | Coley Pharmaceutical Group, Inc. | Substituted fused[1,2]imidazo[4,5-c] ring compounds and methods |
| CA2648099C (en) | 2006-03-31 | 2012-05-29 | The Brigham And Women's Hospital, Inc | System for targeted delivery of therapeutic agents |
| US8367113B2 (en) | 2006-05-15 | 2013-02-05 | Massachusetts Institute Of Technology | Polymers for functional particles |
| US20070275185A1 (en) * | 2006-05-23 | 2007-11-29 | 3M Innovative Properties Company | Method of making ordered nanostructured layers |
| CA2653941C (en) | 2006-05-31 | 2013-01-08 | The Regents Of The University Of California | Substituted amino purine derivatives and uses thereof |
| US9381477B2 (en) | 2006-06-23 | 2016-07-05 | Massachusetts Institute Of Technology | Microfluidic synthesis of organic nanoparticles |
| WO2008008432A2 (en) | 2006-07-12 | 2008-01-17 | Coley Pharmaceutical Group, Inc. | Substituted chiral fused( 1,2) imidazo (4,5-c) ring compounds and methods |
| US8178539B2 (en) | 2006-09-06 | 2012-05-15 | 3M Innovative Properties Company | Substituted 3,4,6,7-tetrahydro-5H-1,2a,4a,8-tetraazacyclopenta[cd]phenalenes and methods |
| US20080149123A1 (en) | 2006-12-22 | 2008-06-26 | Mckay William D | Particulate material dispensing hairbrush with combination bristles |
| US7943771B2 (en) * | 2007-01-24 | 2011-05-17 | Chemagis Ltd. | Imiquimod production process |
| JP5425642B2 (ja) | 2007-02-07 | 2014-02-26 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 合成ｔｌｒアゴニストの結合体およびそのための使用 |
| US9217129B2 (en) | 2007-02-09 | 2015-12-22 | Massachusetts Institute Of Technology | Oscillating cell culture bioreactor |
| US7659398B2 (en) * | 2007-02-14 | 2010-02-09 | Chemagis Ltd. | Imiquimod production process |
| JP2010523595A (ja) | 2007-04-04 | 2010-07-15 | マサチューセッツ インスティテュート オブ テクノロジー | ポリ（アミノ酸）ターゲッティング部分 |
| CA2917512C (en) | 2007-10-12 | 2025-08-05 | President And Fellows Of Harvard College | VACCINE NANOTECHNOLOGY |
| WO2009099650A2 (en) * | 2008-02-07 | 2009-08-13 | Carson Dennis A | Treatment of bladder diseases with a tlr7 activator |
| US8343498B2 (en) | 2008-10-12 | 2013-01-01 | Massachusetts Institute Of Technology | Adjuvant incorporation in immunonanotherapeutics |
| US8343497B2 (en) | 2008-10-12 | 2013-01-01 | The Brigham And Women's Hospital, Inc. | Targeting of antigen presenting cells with immunonanotherapeutics |
| US8277812B2 (en) | 2008-10-12 | 2012-10-02 | Massachusetts Institute Of Technology | Immunonanotherapeutics that provide IgG humoral response without T-cell antigen |
| US8591905B2 (en) | 2008-10-12 | 2013-11-26 | The Brigham And Women's Hospital, Inc. | Nicotine immunonanotherapeutics |
| WO2010088924A1 (en) | 2009-02-06 | 2010-08-12 | Telormedix Sa | Pharmaceutical compositions comprising imidazoquinolin(amines) and derivatives thereof suitable for local administration |
| AU2010214112B2 (en) * | 2009-02-11 | 2015-04-09 | The Regents Of The University Of California | Toll-like receptor modulators and treatment of diseases |
| US20110033515A1 (en) * | 2009-08-04 | 2011-02-10 | Rst Implanted Cell Technology | Tissue contacting material |
| WO2011150264A2 (en) | 2010-05-26 | 2011-12-01 | Selecta Biosciences, Inc. | Synthetic nanocarrier combination vaccines |
| SI2606047T1 (sl) | 2010-08-17 | 2017-04-26 | 3M Innovative Properties Company | Lipidirani sestavki spojine, ki modificira imunski odgovor, formulacije in postopki |
| WO2012061717A1 (en) | 2010-11-05 | 2012-05-10 | Selecta Biosciences, Inc. | Modified nicotinic compounds and related methods |
| EP2718292B1 (en) | 2011-06-03 | 2018-03-14 | 3M Innovative Properties Company | Hydrazino 1h-imidazoquinolin-4-amines and conjugates made therefrom |
| US9475804B2 (en) | 2011-06-03 | 2016-10-25 | 3M Innovative Properties Company | Heterobifunctional linkers with polyethylene glycol segments and immune response modifier conjugates made therefrom |
| US20130023736A1 (en) | 2011-07-21 | 2013-01-24 | Stanley Dale Harpstead | Systems for drug delivery and monitoring |
| CA2843274A1 (en) | 2011-07-29 | 2013-02-07 | Selecta Biosciences, Inc. | Synthetic nanocarriers that generate humoral and cytotoxic t lymphocyte (ctl) immune responses |
| NZ701324A (en) | 2012-05-04 | 2016-09-30 | Pfizer | Prostate-associated antigens and vaccine-based immunotherapy regimens |
| WO2015092592A1 (en) | 2013-12-17 | 2015-06-25 | Pfizer Inc. | Novel 3,4-disubstituted-1h-pyrrolo[2,3-b]pyridines and 4,5-disubstituted-7h-pyrrolo[2,3-c]pyridazines as lrrk2 inhibitors |
| CN104402878A (zh) * | 2014-10-22 | 2015-03-11 | 天方药业有限公司 | 一种咪喹莫特的制备方法 |
| KR102161364B1 (ko) | 2015-09-14 | 2020-09-29 | 화이자 인코포레이티드 | LRRK2 억제제로서 이미다조[4,5-c]퀴놀린 및 이미다조[4,5-c][1,5]나프티리딘 유도체 |
| US11697851B2 (en) | 2016-05-24 | 2023-07-11 | The Regents Of The University Of California | Early ovarian cancer detection diagnostic test based on mRNA isoforms |
| CN111511740B (zh) | 2017-12-20 | 2023-05-16 | 3M创新有限公司 | 用作免疫应答调节剂的带有支链连接基团的酰胺取代的咪唑并[4,5-c]喹啉化合物 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL73534A (en) * | 1983-11-18 | 1990-12-23 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinoline-4-amines,their preparation and pharmaceutical compositions containing certain such compounds |
| US4929624A (en) * | 1989-03-23 | 1990-05-29 | Minnesota Mining And Manufacturing Company | Olefinic 1H-imidazo(4,5-c)quinolin-4-amines |
| US4988815A (en) * | 1989-10-26 | 1991-01-29 | Riker Laboratories, Inc. | 3-Amino or 3-nitro quinoline compounds which are intermediates in preparing 1H-imidazo[4,5-c]quinolines |
-
1991
- 1991-03-01 US US07/663,110 patent/US5175296A/en not_active Expired - Lifetime
-
1992
- 1992-02-13 AT AT92909690T patent/ATE142632T1/de active
- 1992-02-13 AU AU16993/92A patent/AU657958B2/en not_active Expired
- 1992-02-13 CZ CZ19931787A patent/CZ291368B6/cs not_active IP Right Cessation
- 1992-02-13 WO PCT/US1992/001212 patent/WO1992015581A1/en not_active Ceased
- 1992-02-13 EP EP92909690A patent/EP0575549B1/en not_active Expired - Lifetime
- 1992-02-13 DK DK92909690.7T patent/DK0575549T3/da active
- 1992-02-13 DE DE69213720T patent/DE69213720T2/de not_active Expired - Lifetime
- 1992-02-13 JP JP50932392A patent/JP3313708B2/ja not_active Expired - Lifetime
- 1992-02-13 CA CA002104781A patent/CA2104781C/en not_active Expired - Lifetime
- 1992-02-13 ES ES92909690T patent/ES2091463T3/es not_active Expired - Lifetime
- 1992-02-13 KR KR1019930702603A patent/KR100226184B1/ko not_active Expired - Lifetime
- 1992-02-18 NZ NZ241645A patent/NZ241645A/en not_active IP Right Cessation
- 1992-02-18 IL IL10099892A patent/IL100998A/en not_active IP Right Cessation
- 1992-02-19 IE IE052492A patent/IE920524A1/en not_active IP Right Cessation
- 1992-06-02 HU HU9302456A patent/HU218219B/hu unknown
-
1993
- 1993-08-31 NO NO933105A patent/NO301714B1/no not_active IP Right Cessation
-
1999
- 1999-02-09 JP JP03146599A patent/JP3450736B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CZ291368B6 (cs) | 2003-02-12 |
| EP0575549B1 (en) | 1996-09-11 |
| CZ178793A3 (en) | 1995-05-17 |
| KR930703317A (ko) | 1993-11-29 |
| HUT66968A (en) | 1995-01-30 |
| CA2104781C (en) | 2002-07-09 |
| CA2104781A1 (en) | 1992-09-02 |
| IL100998A (en) | 1995-10-31 |
| DK0575549T3 (enExample) | 1997-02-24 |
| ATE142632T1 (de) | 1996-09-15 |
| IL100998A0 (en) | 1992-11-15 |
| HU218219B (hu) | 2000-06-28 |
| HU9302456D0 (en) | 1993-11-29 |
| WO1992015581A1 (en) | 1992-09-17 |
| NO933105D0 (no) | 1993-08-31 |
| EP0575549A1 (en) | 1993-12-29 |
| DE69213720D1 (de) | 1996-10-17 |
| JPH11269177A (ja) | 1999-10-05 |
| AU657958B2 (en) | 1995-03-30 |
| NO301714B1 (no) | 1997-12-01 |
| IE920524A1 (en) | 1992-09-09 |
| JP3313708B2 (ja) | 2002-08-12 |
| JPH06505499A (ja) | 1994-06-23 |
| NO933105L (no) | 1993-08-31 |
| JP3450736B2 (ja) | 2003-09-29 |
| ES2091463T3 (es) | 1996-11-01 |
| AU1699392A (en) | 1992-10-06 |
| US5175296A (en) | 1992-12-29 |
| NZ241645A (en) | 1995-05-26 |
| DE69213720T2 (de) | 1997-04-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100226184B1 (ko) | 이미다조(4,5-c)퀴놀린-4-아민 및 그 제조 방법 | |
| EP0553202B1 (en) | Process for the preparation of imidazo[4,5-c]quinolin-4-amines | |
| IL114570A (en) | Compounds H1 – imidazo] C – 4,5 [quinoline | |
| EP0912564A1 (en) | Process for preparing tetrahydroimidazoquinolinamines | |
| HU223947B1 (hu) | Közbenső termékként alkalmazható 1H-imidazo[4,5-c]kinolin-származékok | |
| EP0595111B1 (en) | Carbazolone derivatives and process for preparing the same | |
| EP0063747B1 (en) | 2-substituted or unsubstituted aminocarbonyloxyalkyl-1,4-dihydropyridines | |
| EP0331899A2 (en) | A method for the sequential oxidation of substituted-8-hydroxy-quinolines to produce substituted-pyridine-2,3-dicarboxylic acids | |
| KR870000234B1 (ko) | 트랜스-dI-5-치환된-7-임의 치환된-4,4a,5,6,7,8,8a,9-옥타하이드로-1H(및 2H)피라졸로[3,4-g] 퀴나졸린의 제조 방법 | |
| JPH07121931B2 (ja) | ベンゾ〔ｂ〕フラン誘導体 | |
| JP3448635B2 (ja) | スルフェンアミド化合物及びその製造方法 | |
| EP0220917B1 (en) | 1,4-dihydropyridine pharmaceutical derivatives and their salts, and the preparation thereof | |
| EP0393109B1 (en) | Novel 2,3-thiomorpholinedione-2-oxime derivatives, pharmaceutical compositions containing them and process for preparing same | |
| EP0435995A1 (en) | New quinoline derivatives and process for the preparation thereof | |
| AU627609B2 (en) | New quinoline derivatives and process for the preparation thereof | |
| KR880000154B1 (ko) | 아미노니트로피리딘의 제조방법 | |
| HU220667B1 (hu) | 1- és 2-helyzetben szubsztituált 1H-imidazo[4,5-c]kinolin-4-amin-származékok előállításában alkalmazható kinolinszármazékok |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 19930831 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19970211 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19981223 Patent event code: PE09021S01D |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 19990428 |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 19990726 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 19990727 End annual number: 3 Start annual number: 1 |
|
| PG1601 | Publication of registration | ||
| PR1001 | Payment of annual fee |
Payment date: 20020719 Start annual number: 4 End annual number: 4 |
|
| PR1001 | Payment of annual fee |
Payment date: 20030716 Start annual number: 5 End annual number: 5 |
|
| PR1001 | Payment of annual fee |
Payment date: 20040723 Start annual number: 6 End annual number: 6 |
|
| PR1001 | Payment of annual fee |
Payment date: 20050721 Start annual number: 7 End annual number: 7 |
|
| PR1001 | Payment of annual fee |
Payment date: 20060724 Start annual number: 8 End annual number: 8 |
|
| PR1001 | Payment of annual fee |
Payment date: 20071005 Start annual number: 9 End annual number: 9 |
|
| PR1001 | Payment of annual fee |
Payment date: 20080507 Start annual number: 10 End annual number: 10 |
|
| PR1001 | Payment of annual fee |
Payment date: 20090508 Start annual number: 11 End annual number: 11 |
|
| PR1001 | Payment of annual fee |
Payment date: 20100519 Start annual number: 12 End annual number: 12 |
|
| FPAY | Annual fee payment |
Payment date: 20110425 Year of fee payment: 13 |
|
| PR1001 | Payment of annual fee |
Payment date: 20110425 Start annual number: 13 End annual number: 13 |
|
| EXPY | Expiration of term | ||
| PC1801 | Expiration of term |
Termination date: 20121109 Termination category: Expiration of duration |