JP2000512994A - テトラヒドロイミダゾキノリンアミン調製方法 - Google Patents
テトラヒドロイミダゾキノリンアミン調製方法Info
- Publication number
- JP2000512994A JP2000512994A JP10502897A JP50289798A JP2000512994A JP 2000512994 A JP2000512994 A JP 2000512994A JP 10502897 A JP10502897 A JP 10502897A JP 50289798 A JP50289798 A JP 50289798A JP 2000512994 A JP2000512994 A JP 2000512994A
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- alkyl
- group
- hydrogen
- formula
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 42
- BZBQNDWAMYFNIE-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-h]quinolin-2-amine Chemical compound C1C=C2C=CC=NC2=C2C1NC(N)N2 BZBQNDWAMYFNIE-UHFFFAOYSA-N 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 80
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- -1 2-hydroxy-2-methylpropyl Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 239000000725 suspension Substances 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 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 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 3
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims 2
- 229910003446 platinum oxide Inorganic materials 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- YHQPYMQQMBVULM-UHFFFAOYSA-N 6,7,8,9-tetrahydro-3h-imidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C1N=C(N)C1=C2NC=N1 YHQPYMQQMBVULM-UHFFFAOYSA-N 0.000 abstract description 5
- 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 abstract description 2
- BTHZSGJQDAHDGL-UHFFFAOYSA-N 2,3,4,5,8,10-hexazatetracyclo[10.4.0.02,6.07,11]hexadeca-1(16),3,5,7(11),9,12,14-heptaene Chemical compound C12=NN=NN2C2=CC=CC=C2C2=C1N=CN2 BTHZSGJQDAHDGL-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000007787 solid Substances 0.000 description 25
- 239000000203 mixture Substances 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 229910052799 carbon Inorganic materials 0.000 description 21
- 238000001914 filtration Methods 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 239000002904 solvent Substances 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- 238000007796 conventional method Methods 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 5
- 150000003461 sulfonyl halides Chemical class 0.000 description 5
- NBNGNWSQNBDVRI-UHFFFAOYSA-N 2-(tetrazolo[1,5-a]quinolin-6-yl)ethanol Chemical compound N1=NN=C2N1C=1C=CC=C(C=1C=C2)CCO NBNGNWSQNBDVRI-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- QOIPJVLRQGAKQX-UHFFFAOYSA-N 2-(5-methyltetrazol-1-yl)benzoic acid Chemical compound CC1=NN=NN1C1=CC=CC=C1C(O)=O QOIPJVLRQGAKQX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- HZMROPWEPUOJDK-UHFFFAOYSA-N C1=CC=C2C(O)=CC3=NN=NN3C2=C1 Chemical compound C1=CC=C2C(O)=CC3=NN=NN3C2=C1 HZMROPWEPUOJDK-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- VNBXNMHHSYIDJJ-UHFFFAOYSA-N 2-methyl-1-[(4-nitrotetrazolo[1,5-a]quinolin-5-yl)amino]propan-2-ol Chemical compound C1=CC=C2C(NCC(C)(O)C)=C([N+]([O-])=O)C3=NN=NN3C2=C1 VNBXNMHHSYIDJJ-UHFFFAOYSA-N 0.000 description 2
- WMQSKECCMQRJRX-UHFFFAOYSA-N 2-methyl-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(C)=NC2=C1 WMQSKECCMQRJRX-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- XHQDQIZPZORDNW-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-4-ylhydrazine Chemical compound NNC1=NC2=CC=CC=C2C2=C1N=CN2 XHQDQIZPZORDNW-UHFFFAOYSA-N 0.000 description 2
- HZJIVLDPBZTDHB-UHFFFAOYSA-N 4-nitrotetrazolo[1,5-a]quinolin-5-amine Chemical compound C1=CC=C2C(N)=C([N+]([O-])=O)C3=NN=NN3C2=C1 HZJIVLDPBZTDHB-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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VELKAUGRMHWKQT-UHFFFAOYSA-N C1=CC=C2C(O)=C([N+]([O-])=O)C3=NN=NN3C2=C1 Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C3=NN=NN3C2=C1 VELKAUGRMHWKQT-UHFFFAOYSA-N 0.000 description 2
- QQGCATIHQFRHII-UHFFFAOYSA-N C1=CC=C2C(S(=O)(=O)O)=C([N+]([O-])=O)C3=NN=NN3C2=C1 Chemical compound C1=CC=C2C(S(=O)(=O)O)=C([N+]([O-])=O)C3=NN=NN3C2=C1 QQGCATIHQFRHII-UHFFFAOYSA-N 0.000 description 2
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical group F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- LUTSRLYCMSCGCS-BWOMAWGNSA-N [(3s,8r,9s,10r,13s)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,16-decahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC=C3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 LUTSRLYCMSCGCS-BWOMAWGNSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 239000002955 immunomodulating agent Substances 0.000 description 2
- 229940121354 immunomodulator Drugs 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- GYESAYHWISMZOK-UHFFFAOYSA-N quinolin-5-ol Chemical compound C1=CC=C2C(O)=CC=CC2=N1 GYESAYHWISMZOK-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- HHFCAUSIBNOUOP-UHFFFAOYSA-N tetrazolo[1,5-a]quinoline Chemical compound C1=CC2=NN=NN2C2=CC=CC=C21 HHFCAUSIBNOUOP-UHFFFAOYSA-N 0.000 description 2
- KDXKKSGAKJPGNY-UHFFFAOYSA-N tetrazolo[1,5-a]quinoline-4,5-diamine Chemical compound NC1=C(N)C2=CC=CC=C2N2C1=NN=N2 KDXKKSGAKJPGNY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZAPSNGHNEPUZEG-UHFFFAOYSA-N 1-(4-amino-2-methylimidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol Chemical compound C1=CC=CC2=C(N(C(C)=N3)CC(C)(C)O)C3=C(N)N=C21 ZAPSNGHNEPUZEG-UHFFFAOYSA-N 0.000 description 1
- CNBOKXFMODKQCT-UHFFFAOYSA-N 1-(4-aminoimidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol Chemical compound C1=CC=CC2=C3N(CC(C)(O)C)C=NC3=C(N)N=C21 CNBOKXFMODKQCT-UHFFFAOYSA-N 0.000 description 1
- JTQRHJOAARSHIV-UHFFFAOYSA-N 1-[(2-chloro-3-nitroquinolin-4-yl)amino]-2-methylpropan-2-ol Chemical compound C1=CC=C2C(NCC(C)(O)C)=C([N+]([O-])=O)C(Cl)=NC2=C1 JTQRHJOAARSHIV-UHFFFAOYSA-N 0.000 description 1
- LXQMHOKEXZETKB-UHFFFAOYSA-N 1-amino-2-methylpropan-2-ol Chemical compound CC(C)(O)CN LXQMHOKEXZETKB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KMMHZIBWCXYAAH-UHFFFAOYSA-N 4-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(Br)C=C1 KMMHZIBWCXYAAH-UHFFFAOYSA-N 0.000 description 1
- SHKUAAUCZDOPDI-UHFFFAOYSA-N 4-chloro-3h-imidazo[4,5-c]quinoline Chemical compound ClC1=NC2=CC=CC=C2C2=C1N=CN2 SHKUAAUCZDOPDI-UHFFFAOYSA-N 0.000 description 1
- JODWMMXXVZOUJQ-UHFFFAOYSA-N 4-hydroxy-3-nitro-5,6,7,8-tetrahydro-1h-quinolin-2-one Chemical compound C1CCCC2=C1N=C(O)C([N+]([O-])=O)=C2O JODWMMXXVZOUJQ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- JNAUXELXFGUHAD-UHFFFAOYSA-N N1=NN=C2N1C1=CC=CC=C1C(=C2)O.O.[N+](=O)([O-])C=2C=1N(C3=CC=CC=C3C2O)N=NN1 Chemical compound N1=NN=C2N1C1=CC=CC=C1C(=C2)O.O.[N+](=O)([O-])C=2C=1N(C3=CC=CC=C3C2O)N=NN1 JNAUXELXFGUHAD-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000002584 immunomodulator Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 239000002798 polar solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- XMIAFAKRAAMSGX-UHFFFAOYSA-N quinolin-5-amine Chemical compound C1=CC=C2C(N)=CC=CC2=N1 XMIAFAKRAAMSGX-UHFFFAOYSA-N 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- TVBIVRGNYNBFCD-UHFFFAOYSA-N triethylazanium;trifluoromethanesulfonate Chemical compound CC[NH+](CC)CC.[O-]S(=O)(=O)C(F)(F)F TVBIVRGNYNBFCD-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/669,895 | 1996-06-21 | ||
| US08/669,895 US5693811A (en) | 1996-06-21 | 1996-06-21 | Process for preparing tetrahdroimidazoquinolinamines |
| PCT/US1996/016913 WO1997048703A1 (en) | 1996-06-21 | 1996-10-22 | Process for preparing tetrahydroimidazoquinolinamines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000512994A true JP2000512994A (ja) | 2000-10-03 |
| JP2000512994A5 JP2000512994A5 (OSRAM) | 2004-10-28 |
Family
ID=24688154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10502897A Withdrawn JP2000512994A (ja) | 1996-06-21 | 1996-10-22 | テトラヒドロイミダゾキノリンアミン調製方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5693811A (OSRAM) |
| EP (1) | EP0912564B1 (OSRAM) |
| JP (1) | JP2000512994A (OSRAM) |
| AT (1) | ATE230744T1 (OSRAM) |
| AU (1) | AU717564B2 (OSRAM) |
| CA (1) | CA2258262A1 (OSRAM) |
| DE (1) | DE69625712T2 (OSRAM) |
| DK (1) | DK0912564T3 (OSRAM) |
| ES (1) | ES2185808T3 (OSRAM) |
| IL (1) | IL127347A (OSRAM) |
| NO (1) | NO315086B1 (OSRAM) |
| NZ (1) | NZ333168A (OSRAM) |
| PT (1) | PT912564E (OSRAM) |
| WO (1) | WO1997048703A1 (OSRAM) |
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|---|---|---|---|---|
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| US11306083B2 (en) | 2017-12-20 | 2022-04-19 | 3M Innovative Properties Company | Amide substituted imidazo[4,5-C]quinoline compounds with a branched chain linking group for use as an immune response modifier |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3891653A (en) * | 1970-07-08 | 1975-06-24 | Lilly Co Eli | Substituted 4-5 dehydro-tetrazolo(1,5-a)quinolenes |
| US3764681A (en) * | 1970-07-08 | 1973-10-09 | Lilly Co Eli | Certain tetrazolo-(1,5-a) quinoline compounds as fungus control agents |
| ZA848968B (en) * | 1983-11-18 | 1986-06-25 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinolines and 1h-imidazo(4,5-c)quinolin-4-amines |
| CA1271477A (en) * | 1983-11-18 | 1990-07-10 | John F. Gerster | 1h-imidazo[4,5-c]quinolin-4-amines |
| 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 |
| US5035420A (en) * | 1988-11-28 | 1991-07-30 | Therabite Corporation | Jaw exerciser |
| 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 |
| ES2071340T3 (es) * | 1990-10-05 | 1995-06-16 | Minnesota Mining & Mfg | Procedimiento para la preparacion de imidazo(4,5-c)quinolin-4-aminas. |
| 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 |
| US5175296A (en) * | 1991-03-01 | 1992-12-29 | Minnesota Mining And Manufacturing Company | Imidazo[4,5-c]quinolin-4-amines and processes for their preparation |
| US5268376A (en) * | 1991-09-04 | 1993-12-07 | Minnesota Mining And Manufacturing Company | 1-substituted 1H-imidazo[4,5-c]quinolin-4-amines |
| US5266575A (en) * | 1991-11-06 | 1993-11-30 | Minnesota Mining And Manufacturing Company | 2-ethyl 1H-imidazo[4,5-ciquinolin-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 |
-
1996
- 1996-06-21 US US08/669,895 patent/US5693811A/en not_active Expired - Lifetime
- 1996-10-22 WO PCT/US1996/016913 patent/WO1997048703A1/en not_active Ceased
- 1996-10-22 PT PT96936832T patent/PT912564E/pt unknown
- 1996-10-22 NZ NZ333168A patent/NZ333168A/xx unknown
- 1996-10-22 EP EP96936832A patent/EP0912564B1/en not_active Expired - Lifetime
- 1996-10-22 DK DK96936832T patent/DK0912564T3/da active
- 1996-10-22 AT AT96936832T patent/ATE230744T1/de not_active IP Right Cessation
- 1996-10-22 CA CA002258262A patent/CA2258262A1/en not_active Abandoned
- 1996-10-22 AU AU74658/96A patent/AU717564B2/en not_active Ceased
- 1996-10-22 JP JP10502897A patent/JP2000512994A/ja not_active Withdrawn
- 1996-10-22 ES ES96936832T patent/ES2185808T3/es not_active Expired - Lifetime
- 1996-10-22 IL IL12734796A patent/IL127347A/en not_active IP Right Cessation
- 1996-10-22 DE DE69625712T patent/DE69625712T2/de not_active Expired - Fee Related
-
1998
- 1998-12-18 NO NO19986001A patent/NO315086B1/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT912564E (pt) | 2003-04-30 |
| ES2185808T3 (es) | 2003-05-01 |
| IL127347A (en) | 2002-03-10 |
| NO986001D0 (no) | 1998-12-18 |
| ATE230744T1 (de) | 2003-01-15 |
| US5693811A (en) | 1997-12-02 |
| NO315086B1 (no) | 2003-07-07 |
| NZ333168A (en) | 1999-05-28 |
| CA2258262A1 (en) | 1997-12-24 |
| IL127347A0 (en) | 1999-10-28 |
| EP0912564A1 (en) | 1999-05-06 |
| EP0912564B1 (en) | 2003-01-08 |
| NO986001L (no) | 1998-12-18 |
| AU7465896A (en) | 1998-01-07 |
| DE69625712D1 (de) | 2003-02-13 |
| AU717564B2 (en) | 2000-03-30 |
| DE69625712T2 (de) | 2003-11-13 |
| DK0912564T3 (da) | 2003-04-22 |
| WO1997048703A1 (en) | 1997-12-24 |
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