IL108424A - Reliable quinoline preparation - Google Patents

Reliable quinoline preparation

Info

Publication number: IL108424A
Authority: IL; Israel
Prior art keywords: substituted; amino; nitroquinoline; compound; carbon atoms
Prior art date: 1993-01-29

Application number

IL10842494A

Other languages

English (en)

Hebrew (he)

Other versions

IL108424A0 (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.)

1993-01-29

Filing date

1994-01-25

Publication date

1998-09-24

1994-01-25 Application filed by Minnesota Mining & Mfg filed Critical Minnesota Mining & Mfg

1994-04-12 Publication of IL108424A0 publication Critical patent/IL108424A0/xx

1998-09-24 Publication of IL108424A publication Critical patent/IL108424A/en

Links

-1 quinoline amines Chemical class 0.000 title claims description 46
SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title description 5
238000002360 preparation method Methods 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 40
150000001412 amines Chemical class 0.000 claims description 32
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
ZKMXEKRSQNHUEK-UHFFFAOYSA-N C1=CC=C2C(S(O)(=O)=O)=C([N+]([O-])=O)C(S(=O)(=O)O)=NC2=C1 Chemical compound C1=CC=C2C(S(O)(=O)=O)=C([N+]([O-])=O)C(S(=O)(=O)O)=NC2=C1 ZKMXEKRSQNHUEK-UHFFFAOYSA-N 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
DAISLHBVGZZCHJ-UHFFFAOYSA-N 1-[[3-amino-2-(dibenzylamino)quinolin-4-yl]amino]-2-methylpropan-2-ol Chemical compound N=1C2=CC=CC=C2C(NCC(C)(O)C)=C(N)C=1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 DAISLHBVGZZCHJ-UHFFFAOYSA-N 0.000 claims description 2
ZAFRPVCGWKBGJZ-UHFFFAOYSA-N 2-n,2-n-dibenzyl-4-n-(2-methylpropyl)-3-nitroquinoline-2,4-diamine Chemical compound N=1C2=CC=CC=C2C(NCC(C)C)=C([N+]([O-])=O)C=1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 ZAFRPVCGWKBGJZ-UHFFFAOYSA-N 0.000 claims description 2
QOWUOXGDRYUYIZ-UHFFFAOYSA-N 2-n,2-n-dibenzyl-4-n-(2-methylpropyl)quinoline-2,3,4-triamine Chemical compound N=1C2=CC=CC=C2C(NCC(C)C)=C(N)C=1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 QOWUOXGDRYUYIZ-UHFFFAOYSA-N 0.000 claims description 2
OWEHRXYFJFBXPQ-UHFFFAOYSA-N [3-nitro-2-(trifluoromethylsulfonyloxy)quinolin-4-yl] trifluoromethanesulfonate Chemical compound C1=CC=CC2=C(OS(=O)(=O)C(F)(F)F)C([N+](=O)[O-])=C(OS(=O)(=O)C(F)(F)F)N=C21 OWEHRXYFJFBXPQ-UHFFFAOYSA-N 0.000 claims description 2
QRRPJVLNUURIHH-UHFFFAOYSA-N (2-methylsulfonyloxy-3-nitroquinolin-4-yl) methanesulfonate Chemical compound C1=CC=C2C(OS(C)(=O)=O)=C([N+]([O-])=O)C(OS(=O)(=O)C)=NC2=C1 QRRPJVLNUURIHH-UHFFFAOYSA-N 0.000 claims 1
HRZCNADOWCCFKG-UHFFFAOYSA-N 1-[4-(dibenzylamino)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol Chemical compound N1=C2C=CC=CC2=C2N(CC(C)(O)C)C=NC2=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 HRZCNADOWCCFKG-UHFFFAOYSA-N 0.000 claims 1
ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical group C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 claims 1
UQUPJGMZYBOGDJ-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinoline-4-carboxamide Chemical compound NC(=O)C1=NC2=CC=CC=C2C2=C1N=CN2 UQUPJGMZYBOGDJ-UHFFFAOYSA-N 0.000 claims 1
PPRGWLXYLVMCBB-UHFFFAOYSA-N [4-(2-methylpropylamino)-3-nitroquinolin-2-yl] trifluoromethanesulfonate Chemical compound C1=CC=C2C(NCC(C)C)=C([N+]([O-])=O)C(OS(=O)(=O)C(F)(F)F)=NC2=C1 PPRGWLXYLVMCBB-UHFFFAOYSA-N 0.000 claims 1
HBARJZXLEKEICY-UHFFFAOYSA-N [4-[(2-hydroxy-2-methylpropyl)amino]-3-nitroquinolin-2-yl] trifluoromethanesulfonate Chemical compound C1=CC=C2C(NCC(C)(O)C)=C([N+]([O-])=O)C(OS(=O)(=O)C(F)(F)F)=NC2=C1 HBARJZXLEKEICY-UHFFFAOYSA-N 0.000 claims 1
AVHWBFRWIDCHNL-UHFFFAOYSA-N [4-[(2-hydroxy-2-methylpropyl)amino]-3-nitroquinolin-2-yl]methanesulfonic acid Chemical compound C1=CC=C2C(NCC(C)(O)C)=C([N+]([O-])=O)C(CS(O)(=O)=O)=NC2=C1 AVHWBFRWIDCHNL-UHFFFAOYSA-N 0.000 claims 1
IDIYRPYPRNQNOB-UHFFFAOYSA-N n,n-dibenzyl-1-(2-methylpropyl)imidazo[4,5-c]quinolin-4-amine Chemical compound N1=C2C=CC=CC2=C2N(CC(C)C)C=NC2=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 IDIYRPYPRNQNOB-UHFFFAOYSA-N 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
125000004432 carbon atom Chemical group C* 0.000 description 74
125000000217 alkyl group Chemical group 0.000 description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 30
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 28
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
229910052739 hydrogen Inorganic materials 0.000 description 23
239000011541 reaction mixture Substances 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000000047 product Substances 0.000 description 21
238000000034 method Methods 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
125000003545 alkoxy group Chemical group 0.000 description 18
125000001424 substituent group Chemical group 0.000 description 18
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
239000010410 layer Substances 0.000 description 15
239000007787 solid Substances 0.000 description 15
239000001257 hydrogen Substances 0.000 description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
229910052799 carbon Inorganic materials 0.000 description 12
229910052736 halogen Inorganic materials 0.000 description 12
150000002367 halogens Chemical class 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
239000003921 oil Substances 0.000 description 11
235000019198 oils Nutrition 0.000 description 11
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
238000010992 reflux Methods 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
239000006260 foam Substances 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 7
238000010898 silica gel chromatography Methods 0.000 description 7
KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 6
SHZUGBYEPDMAPC-UHFFFAOYSA-N 4-hydroxy-3-nitro-1h-quinolin-2-one Chemical compound C1=CC=C2C(=O)C([N+]([O-])=O)=C(O)NC2=C1 SHZUGBYEPDMAPC-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000008064 anhydrides Chemical class 0.000 description 6
125000000753 cycloalkyl group Chemical group 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
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 6
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 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
239000006227 byproduct Substances 0.000 description 5
235000019253 formic acid Nutrition 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
150000003461 sulfonyl halides Chemical class 0.000 description 5
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 4
125000003342 alkenyl group Chemical group 0.000 description 4
125000004183 alkoxy alkyl group Chemical group 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
125000002768 hydroxyalkyl group Chemical group 0.000 description 4
239000000463 material Substances 0.000 description 4
150000003512 tertiary amines Chemical class 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
239000000284 extract Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
241000894007 species Species 0.000 description 3
230000003595 spectral effect Effects 0.000 description 3
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 3
239000000725 suspension Substances 0.000 description 3
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 description 2
FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 2
150000005011 4-aminoquinolines Chemical class 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
229910021586 Nickel(II) chloride Inorganic materials 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
235000019502 Orange oil Nutrition 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
125000005041 acyloxyalkyl group Chemical group 0.000 description 2
238000005576 amination reaction Methods 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000005002 aryl methyl group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000011203 carbon fibre reinforced carbon Chemical group 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001914 filtration Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
238000004949 mass spectrometry Methods 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000000203 mixture Substances 0.000 description 2
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 2
239000010502 orange oil Substances 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
150000002905 orthoesters Chemical class 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
150000003141 primary amines Chemical class 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
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 description 2
239000008096 xylene Substances 0.000 description 2
FPDFOFSQEVGKSO-UHFFFAOYSA-N 2-benzyl-1-(2-methylpropyl)imidazo[4,5-c]quinolin-4-amine Chemical compound N=1C2=C(N)N=C3C=CC=CC3=C2N(CC(C)C)C=1CC1=CC=CC=C1 FPDFOFSQEVGKSO-UHFFFAOYSA-N 0.000 description 1
ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-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
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
102000004127 Cytokines Human genes 0.000 description 1
108090000695 Cytokines Proteins 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
102000014150 Interferons Human genes 0.000 description 1
108010050904 Interferons Proteins 0.000 description 1
102000015696 Interleukins Human genes 0.000 description 1
108010063738 Interleukins Proteins 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
NDCGVLJXFQKXOF-UHFFFAOYSA-N N-hydroxy-2-methylpropanamine Chemical compound CC(C)CNO NDCGVLJXFQKXOF-UHFFFAOYSA-N 0.000 description 1
229910015346 Ni2B Inorganic materials 0.000 description 1
241000276498 Pollachius virens Species 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
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 1
GZIFYJOWLKZURP-UHFFFAOYSA-N [4-(2-methylpropylamino)-3-nitroquinolin-2-yl] methanesulfonate Chemical compound C1=CC=C2C(NCC(C)C)=C([N+]([O-])=O)C(OS(C)(=O)=O)=NC2=C1 GZIFYJOWLKZURP-UHFFFAOYSA-N 0.000 description 1
WRLJWIVBUPYRTE-UHFFFAOYSA-N [B].[Ni].[Ni] Chemical compound [B].[Ni].[Ni] WRLJWIVBUPYRTE-UHFFFAOYSA-N 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000000840 anti-viral effect Effects 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000000852 azido group Chemical group *N=[N+]=[N-] 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
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
HGGYAQHDNDUIIQ-UHFFFAOYSA-L dichloronickel;hydrate Chemical compound O.Cl[Ni]Cl HGGYAQHDNDUIIQ-UHFFFAOYSA-L 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
125000005059 halophenyl group Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
239000002955 immunomodulating agent Substances 0.000 description 1
229940121354 immunomodulator Drugs 0.000 description 1
230000002584 immunomodulator Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229940047124 interferons Drugs 0.000 description 1
229940047122 interleukins Drugs 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000005065 mining Methods 0.000 description 1
KQYREKISXCBRQB-UHFFFAOYSA-N n,n-diethylethanamine;methanesulfonic acid Chemical compound CS(O)(=O)=O.CCN(CC)CC KQYREKISXCBRQB-UHFFFAOYSA-N 0.000 description 1
HKFZDVPCCOOGEV-UHFFFAOYSA-N nickel(3+);borate Chemical compound [Ni+3].[O-]B([O-])[O-] HKFZDVPCCOOGEV-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
125000005010 perfluoroalkyl group Chemical group 0.000 description 1
125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
238000004809 thin layer chromatography Methods 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
102000003390 tumor necrosis factor Human genes 0.000 description 1

Classifications

- 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- 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
- 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)
Quinoline Compounds (AREA)

IL10842494A 1993-01-29 1994-01-25 Reliable quinoline preparation IL108424A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US08/011,405 US5395937A (en)	1993-01-29	1993-01-29	Process for preparing quinoline amines

Publications (2)

Publication Number	Publication Date
IL108424A0 IL108424A0 (en)	1994-04-12
IL108424A true IL108424A (en)	1998-09-24

Family

ID=21750245

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10842494A IL108424A (en)	1993-01-29	1994-01-25	Reliable quinoline preparation

Country Status (9)

Country	Link
US (1)	US5395937A (es)
EP (1)	EP0681570B1 (es)
JP (1)	JP3703829B2 (es)
AU (1)	AU677381B2 (es)
DE (1)	DE69426870T2 (es)
ES (1)	ES2154672T3 (es)
HU (1)	HUT73671A (es)
IL (1)	IL108424A (es)
WO (1)	WO1994017043A1 (es)

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1994
- 1994-01-25 IL IL10842494A patent/IL108424A/en not_active IP Right Cessation
- 1994-01-25 AU AU61656/94A patent/AU677381B2/en not_active Expired
- 1994-01-25 WO PCT/US1994/000906 patent/WO1994017043A1/en not_active Ceased
- 1994-01-25 HU HU9501973A patent/HUT73671A/hu not_active Application Discontinuation
- 1994-01-25 EP EP94908641A patent/EP0681570B1/en not_active Expired - Lifetime
- 1994-01-25 ES ES94908641T patent/ES2154672T3/es not_active Expired - Lifetime
- 1994-01-25 DE DE69426870T patent/DE69426870T2/de not_active Expired - Lifetime
- 1994-01-25 JP JP51729094A patent/JP3703829B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
WO1994017043A1 (en)	1994-08-04
ES2154672T3 (es)	2001-04-16
DE69426870T2 (de)	2001-10-25
HUT73671A (en)	1996-09-30
JPH08505881A (ja)	1996-06-25
DE69426870D1 (de)	2001-04-19
HU9501973D0 (en)	1995-09-28
IL108424A0 (en)	1994-04-12
EP0681570B1 (en)	2001-03-14
US5395937A (en)	1995-03-07
AU6165694A (en)	1994-08-15
JP3703829B2 (ja)	2005-10-05
EP0681570A1 (en)	1995-11-15
AU677381B2 (en)	1997-04-24

Legal Events

Date	Code	Title
1999-01-26	FF	Patent granted
1999-07-14	KB	Patent renewed
2000-07-16	FF	Patent granted
2004-03-28	KB	Patent renewed
2008-02-10	KB	Patent renewed
2012-01-31	KB	Patent renewed
2014-09-30	EXP	Patent expired

Publication	Publication Date	Title
AU677381B2 (en)	1997-04-24	Process for preparing quinoline amines
US5741908A (en)	1998-04-21	Process for reparing imidazoquinolinamines
US5693811A (en)	1997-12-02	Process for preparing tetrahdroimidazoquinolinamines
WO1992006093A1 (en)	1992-04-16	Process for the preparation of imidazo[4,5-c]quinolin-4-amines
HU217715B (hu)	2000-04-28	Közbenső termékként alkalmazható kinolin-4-amin-származékok
EP0708773A1 (en)	1996-05-01	Fused cycloalkylimidazopyridines
US4474953A (en)	1984-10-02	Process and intermediates for the preparation of 3(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-ones
KR100459583B1 (ko)	2005-05-18	이미다조퀴놀린아민류의제조방법
HU220667B1 (hu)	2002-04-29	1- és 2-helyzetben szubsztituált 1H-imidazo[4,5-c]kinolin-4-amin-származékok előállításában alkalmazható kinolinszármazékok
IL152040A (en)	2006-08-20	4 - triphenylphosphinylamino - 1h - imidazo [4,5-c] quinolines, their preparation and use as intermediates in processes for preparing 1h - imidazo [4,5-c] quinolin - 4 - amines