AU2005322898B2 - Chiral fused (1,2)imidazo(4,5-c) ring compounds - Google Patents
Chiral fused (1,2)imidazo(4,5-c) ring compounds Download PDFInfo
- Publication number
- AU2005322898B2 AU2005322898B2 AU2005322898A AU2005322898A AU2005322898B2 AU 2005322898 B2 AU2005322898 B2 AU 2005322898B2 AU 2005322898 A AU2005322898 A AU 2005322898A AU 2005322898 A AU2005322898 A AU 2005322898A AU 2005322898 B2 AU2005322898 B2 AU 2005322898B2
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- Prior art keywords
- group
- alkyl
- aryl
- heterocyclyl
- heteroaryl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 299
- 238000000034 method Methods 0.000 claims abstract description 68
- 241001465754 Metazoa Species 0.000 claims abstract description 37
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 33
- 201000010099 disease Diseases 0.000 claims abstract description 31
- 102000004127 Cytokines Human genes 0.000 claims abstract description 27
- 108090000695 Cytokines Proteins 0.000 claims abstract description 27
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 22
- 230000003612 virological effect Effects 0.000 claims abstract description 12
- 230000001613 neoplastic effect Effects 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 230000001939 inductive effect Effects 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 317
- 125000000623 heterocyclic group Chemical group 0.000 claims description 242
- 125000003118 aryl group Chemical group 0.000 claims description 238
- 125000001072 heteroaryl group Chemical group 0.000 claims description 219
- 125000001424 substituent group Chemical group 0.000 claims description 204
- 125000003342 alkenyl group Chemical group 0.000 claims description 155
- 125000002947 alkylene group Chemical group 0.000 claims description 137
- 125000003545 alkoxy group Chemical group 0.000 claims description 128
- 125000000304 alkynyl group Chemical group 0.000 claims description 120
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 116
- 150000003839 salts Chemical class 0.000 claims description 110
- 229910052736 halogen Inorganic materials 0.000 claims description 108
- -1 arylalkylenyl Chemical group 0.000 claims description 101
- 150000002367 halogens Chemical group 0.000 claims description 94
- 229910052739 hydrogen Inorganic materials 0.000 claims description 84
- 125000004450 alkenylene group Chemical group 0.000 claims description 83
- 239000001257 hydrogen Substances 0.000 claims description 83
- 229910052799 carbon Inorganic materials 0.000 claims description 75
- 125000001188 haloalkyl group Chemical group 0.000 claims description 61
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 60
- 125000005842 heteroatom Chemical group 0.000 claims description 54
- 150000002431 hydrogen Chemical class 0.000 claims description 54
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 53
- 125000005466 alkylenyl group Chemical group 0.000 claims description 52
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 51
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 46
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 43
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 43
- 125000005532 aryl alkyleneoxy group Chemical group 0.000 claims description 42
- 125000004104 aryloxy group Chemical group 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 125000005843 halogen group Chemical group 0.000 claims description 39
- 125000004414 alkyl thio group Chemical group 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- 229920006395 saturated elastomer Polymers 0.000 claims description 33
- 125000004419 alkynylene group Chemical group 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 23
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 23
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 22
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 22
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 22
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 22
- 125000005419 heteroarylsulfonylamino group Chemical group 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 125000003282 alkyl amino group Chemical group 0.000 claims description 21
- 125000000732 arylene group Chemical group 0.000 claims description 20
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 19
- 125000005549 heteroarylene group Chemical group 0.000 claims description 19
- 125000004043 oxo group Chemical group O=* 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 125000004423 acyloxy group Chemical group 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
- 125000001589 carboacyl group Chemical group 0.000 claims description 14
- 125000005110 aryl thio group Chemical group 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 3
- ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical class C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 abstract description 21
- 239000000543 intermediate Substances 0.000 abstract description 18
- 238000011282 treatment Methods 0.000 abstract description 12
- 239000002955 immunomodulating agent Substances 0.000 abstract description 2
- 229940121354 immunomodulator Drugs 0.000 abstract description 2
- QNLFZRVIACOXAG-UHFFFAOYSA-N 3h-imidazo[4,5-c][1,8]naphthyridine Chemical class N1=CC=CC2=C(NC=N3)C3=CN=C21 QNLFZRVIACOXAG-UHFFFAOYSA-N 0.000 abstract 1
- VROCUHFCXAAFLK-UHFFFAOYSA-N 6,7,8,9-tetrahydro-3h-imidazo[4,5-c][1,8]naphthyridine Chemical class C1=C2NC=NC2=C2CCCNC2=N1 VROCUHFCXAAFLK-UHFFFAOYSA-N 0.000 abstract 1
- CZTQJCYFLGFVLG-UHFFFAOYSA-N 6,7,8,9-tetrahydro-3h-imidazo[4,5-c]quinoline Chemical class C1CCCC2=C1N=CC1=C2NC=N1 CZTQJCYFLGFVLG-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 255
- 239000000243 solution Substances 0.000 description 167
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 165
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 115
- 230000002829 reductive effect Effects 0.000 description 109
- 239000011541 reaction mixture Substances 0.000 description 108
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 103
- 239000007787 solid Substances 0.000 description 91
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 79
- 239000002904 solvent Substances 0.000 description 73
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 72
- 239000000203 mixture Substances 0.000 description 70
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 69
- 238000005481 NMR spectroscopy Methods 0.000 description 63
- 238000004587 chromatography analysis Methods 0.000 description 63
- 229910004298 SiO 2 Inorganic materials 0.000 description 58
- 239000011734 sodium Substances 0.000 description 53
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 50
- 239000012267 brine Substances 0.000 description 46
- 239000010410 layer Substances 0.000 description 46
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 46
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- 150000001721 carbon Chemical group 0.000 description 42
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 229910052720 vanadium Inorganic materials 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 235000019439 ethyl acetate Nutrition 0.000 description 35
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 30
- 239000000706 filtrate Substances 0.000 description 28
- 239000012044 organic layer Substances 0.000 description 27
- 238000003756 stirring Methods 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 23
- 238000002360 preparation method Methods 0.000 description 23
- 239000006188 syrup Substances 0.000 description 23
- 235000020357 syrup Nutrition 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- 239000006260 foam Substances 0.000 description 21
- 238000010992 reflux Methods 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 229910001868 water Inorganic materials 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 239000000463 material Substances 0.000 description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 18
- 239000000651 prodrug Substances 0.000 description 17
- 229940002612 prodrug Drugs 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 150000001414 amino alcohols Chemical class 0.000 description 16
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 16
- 238000002425 crystallisation Methods 0.000 description 15
- 230000008025 crystallization Effects 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- 239000000843 powder Substances 0.000 description 15
- 125000003396 thiol group Chemical group [H]S* 0.000 description 15
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 14
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 14
- 230000004048 modification Effects 0.000 description 14
- 238000012986 modification Methods 0.000 description 14
- 125000004076 pyridyl group Chemical group 0.000 description 14
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 14
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000002585 base Substances 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 125000003386 piperidinyl group Chemical group 0.000 description 13
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 13
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 238000007796 conventional method Methods 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 11
- 238000010189 synthetic method Methods 0.000 description 11
- 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 10
- 239000012298 atmosphere Substances 0.000 description 10
- 230000028993 immune response Effects 0.000 description 10
- 125000002757 morpholinyl group Chemical group 0.000 description 10
- 125000006239 protecting group Chemical group 0.000 description 10
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 10
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 9
- IDUUCDZKSKUCOP-UHFFFAOYSA-N 3h-imidazo[4,5-c][1,5]naphthyridine Chemical compound C1=CC=NC2=C(NC=N3)C3=CN=C21 IDUUCDZKSKUCOP-UHFFFAOYSA-N 0.000 description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 239000000908 ammonium hydroxide Substances 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 150000004985 diamines Chemical class 0.000 description 8
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- FDOIXMGDTOEUQL-UHFFFAOYSA-N 4-chloro-3-nitro-1,5-naphthyridine Chemical compound C1=CC=NC2=C(Cl)C([N+](=O)[O-])=CN=C21 FDOIXMGDTOEUQL-UHFFFAOYSA-N 0.000 description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- BGWMHFKCAUBYJJ-UHFFFAOYSA-N ethyl 2-chloroethanimidate;hydrochloride Chemical compound Cl.CCOC(=N)CCl BGWMHFKCAUBYJJ-UHFFFAOYSA-N 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- 230000002452 interceptive effect Effects 0.000 description 7
- 229960004592 isopropanol Drugs 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- UTOMICFLROGMAE-UHFFFAOYSA-N quinoline-3,4-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CN=C21 UTOMICFLROGMAE-UHFFFAOYSA-N 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- IEIGFDMBSIRMEW-UHFFFAOYSA-N 3-chloro-4-nitroquinoline Chemical compound C1=CC=C2C([N+](=O)[O-])=C(Cl)C=NC2=C1 IEIGFDMBSIRMEW-UHFFFAOYSA-N 0.000 description 6
- YHEPBWTXCZVUHG-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-6-amine Chemical compound N1=C2C(N)=CC=CC2=C2NC=NC2=C1 YHEPBWTXCZVUHG-UHFFFAOYSA-N 0.000 description 6
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 6
- RJSRSRITMWVIQT-UHFFFAOYSA-N quinolin-6-amine Chemical compound N1=CC=CC2=CC(N)=CC=C21 RJSRSRITMWVIQT-UHFFFAOYSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 6
- 125000001984 thiazolidinyl group Chemical group 0.000 description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
- 150000008575 L-amino acids Chemical class 0.000 description 5
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 125000005605 benzo group Chemical group 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical class BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 5
- 230000006698 induction Effects 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 125000002971 oxazolyl group Chemical group 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 125000003226 pyrazolyl group Chemical group 0.000 description 5
- 125000006513 pyridinyl methyl group Chemical group 0.000 description 5
- 150000003335 secondary amines Chemical class 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- 125000001425 triazolyl group Chemical group 0.000 description 5
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- C07D471/12—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 three hetero rings
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- C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
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| PCT/US2005/047258 WO2006074003A2 (en) | 2004-12-30 | 2005-12-29 | CHIRAL FUSED [1,2]IMIDAZO[4,5-c] RING COMPOUNDS |
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2005
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2006074003A2 (en) | 2006-07-13 |
| CA2592904A1 (en) | 2006-07-13 |
| EP1831226A4 (en) | 2008-11-05 |
| US20110207725A1 (en) | 2011-08-25 |
| EP1831226A2 (en) | 2007-09-12 |
| EP1831226B1 (en) | 2012-08-08 |
| US8546383B2 (en) | 2013-10-01 |
| JP5543068B2 (ja) | 2014-07-09 |
| ES2392647T3 (es) | 2012-12-12 |
| US20120232057A1 (en) | 2012-09-13 |
| US20080269192A1 (en) | 2008-10-30 |
| WO2006074003A3 (en) | 2007-11-22 |
| JP2008526754A (ja) | 2008-07-24 |
| US8207162B2 (en) | 2012-06-26 |
| US7943609B2 (en) | 2011-05-17 |
| CA2592904C (en) | 2015-04-07 |
| AU2005322898A1 (en) | 2006-07-13 |
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