JP2005519118A5 - - Google Patents

Info

Publication number

JP2005519118A5

JP2005519118A5 JP2003573002A JP2003573002A JP2005519118A5 JP 2005519118 A5 JP2005519118 A5 JP 2005519118A5 JP 2003573002 A JP2003573002 A JP 2003573002A JP 2003573002 A JP2003573002 A JP 2003573002A JP 2005519118 A5 JP2005519118 A5 JP 2005519118A5

Authority

JP

Japan

Prior art keywords

group

alkyl

aryl

heteroaryl

compound

Prior art date

2003-03-03

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.)

Pending

Links

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• 238000000034 method Methods 0.000 claims 91
• 150000001875 compounds Chemical class 0.000 claims 62
• 125000003118 aryl group Chemical group 0.000 claims 57
• 125000000217 alkyl group Chemical group 0.000 claims 55
• 125000001072 heteroaryl group Chemical group 0.000 claims 55
• 229910052739 hydrogen Inorganic materials 0.000 claims 49
• 239000001257 hydrogen Substances 0.000 claims 49
• 229910052760 oxygen Inorganic materials 0.000 claims 45
• 150000002431 hydrogen Chemical class 0.000 claims 36
• 239000000126 substance Substances 0.000 claims 33
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 29
• 239000001301 oxygen Substances 0.000 claims 29
• 229910052799 carbon Inorganic materials 0.000 claims 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 27
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 22
• 229910052736 halogen Inorganic materials 0.000 claims 17
• 150000002367 halogens Chemical class 0.000 claims 17
• 125000001931 aliphatic group Chemical group 0.000 claims 15
• 125000003545 alkoxy group Chemical group 0.000 claims 15
• 125000001769 aryl amino group Chemical group 0.000 claims 15
• 125000004986 diarylamino group Chemical group 0.000 claims 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 13
• 125000004104 aryloxy group Chemical group 0.000 claims 13
• 125000004663 dialkyl amino group Chemical group 0.000 claims 12
• -1 2-methoxy-2-propyl Chemical group 0.000 claims 11
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 11
• 238000004519 manufacturing process Methods 0.000 claims 8
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 5
• 229910052801 chlorine Inorganic materials 0.000 claims 5
• 239000000460 chlorine Substances 0.000 claims 5
• 239000002904 solvent Substances 0.000 claims 5
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 3
• 229910052744 lithium Inorganic materials 0.000 claims 3
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
• 150000002009 diols Chemical class 0.000 claims 2
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
• YSEUEZAVUMLQHK-WOJBJXKFSA-N (1r,2r)-2-n,2-n-bis[(4-bromophenyl)methyl]cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N(CC=1C=CC(Br)=CC=1)CC1=CC=C(Br)C=C1 YSEUEZAVUMLQHK-WOJBJXKFSA-N 0.000 claims 1
• LQJAICQUOQTPOR-FGZHOGPDSA-N (1r,2r)-2-n,2-n-bis[(4-methoxyphenyl)methyl]cyclohexane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1CN([C@H]1[C@@H](CCCC1)N)CC1=CC=C(OC)C=C1 LQJAICQUOQTPOR-FGZHOGPDSA-N 0.000 claims 1
• SXCIGPQHVCQIFJ-WOJBJXKFSA-N (1r,2r)-2-n,2-n-dibenzylcyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 SXCIGPQHVCQIFJ-WOJBJXKFSA-N 0.000 claims 1
• 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 claims 1
• 150000004985 diamines Chemical class 0.000 claims 1
• NBNHZZVUWIWERN-JGTWLXFQSA-N C=CC[Si](N(Cc(cc1)ccc1Br)[C@H]1[C@H]2CCCC1)([N]2(Cc(cc1)ccc1Br)#C)Cl Chemical compound C=CC[Si](N(Cc(cc1)ccc1Br)[C@H]1[C@H]2CCCC1)([N]2(Cc(cc1)ccc1Br)#C)Cl NBNHZZVUWIWERN-JGTWLXFQSA-N 0.000 description 1