CA2547085A1 - Hydroxylamine and oxime substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines - Google Patents
Hydroxylamine and oxime substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines Download PDFInfo
- Publication number
- CA2547085A1 CA2547085A1 CA002547085A CA2547085A CA2547085A1 CA 2547085 A1 CA2547085 A1 CA 2547085A1 CA 002547085 A CA002547085 A CA 002547085A CA 2547085 A CA2547085 A CA 2547085A CA 2547085 A1 CA2547085 A1 CA 2547085A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- alkyl
- aryl
- heteroaryl
- alkylene
- 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.)
- Abandoned
Links
- VFTLXHXYGQSOEN-UHFFFAOYSA-N 1h-imidazo[4,5-b][1,8]naphthyridine Chemical class C1=CN=C2NC3=NC=NC3=CC2=C1 VFTLXHXYGQSOEN-UHFFFAOYSA-N 0.000 title abstract description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 title description 10
- RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical class C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 title description 4
- 150000005232 imidazopyridines Chemical class 0.000 title description 2
- 125000003544 oxime group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 168
- 241001465754 Metazoa Species 0.000 claims abstract description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 28
- 201000010099 disease Diseases 0.000 claims abstract description 27
- 102000004127 Cytokines Human genes 0.000 claims abstract description 24
- 108090000695 Cytokines Proteins 0.000 claims abstract description 24
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 19
- 230000003612 virological effect Effects 0.000 claims abstract description 11
- 230000001613 neoplastic effect Effects 0.000 claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 230000001939 inductive effect Effects 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 271
- 125000003118 aryl group Chemical group 0.000 claims description 179
- 125000001072 heteroaryl group Chemical group 0.000 claims description 174
- -1 heteroarylalkylenyl Chemical group 0.000 claims description 133
- 229910052739 hydrogen Inorganic materials 0.000 claims description 131
- 239000001257 hydrogen Substances 0.000 claims description 124
- 125000003342 alkenyl group Chemical group 0.000 claims description 118
- 125000000623 heterocyclic group Chemical group 0.000 claims description 114
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 106
- 150000003839 salts Chemical class 0.000 claims description 93
- 229920006395 saturated elastomer Polymers 0.000 claims description 86
- 229910052736 halogen Inorganic materials 0.000 claims description 85
- 125000003545 alkoxy group Chemical group 0.000 claims description 83
- 125000002947 alkylene group Chemical group 0.000 claims description 79
- 125000001424 substituent group Chemical group 0.000 claims description 76
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 74
- 125000001188 haloalkyl group Chemical group 0.000 claims description 74
- 150000002367 halogens Chemical class 0.000 claims description 69
- 125000005466 alkylenyl group Chemical group 0.000 claims description 66
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 62
- 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims description 59
- 125000005275 alkylenearyl group Chemical group 0.000 claims description 58
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 58
- 125000004414 alkyl thio group Chemical group 0.000 claims description 53
- 125000000304 alkynyl group Chemical group 0.000 claims description 50
- 125000004450 alkenylene group Chemical group 0.000 claims description 49
- 125000000732 arylene group Chemical group 0.000 claims description 37
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 37
- 125000005549 heteroarylene group Chemical group 0.000 claims description 36
- 125000004419 alkynylene group Chemical group 0.000 claims description 31
- 125000005532 aryl alkyleneoxy group Chemical group 0.000 claims description 30
- 125000004104 aryloxy group Chemical group 0.000 claims description 30
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 125000004122 cyclic group Chemical group 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 15
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 15
- 125000004043 oxo group Chemical group O=* 0.000 claims description 15
- 125000003282 alkyl amino group Chemical group 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 230000002452 interceptive effect Effects 0.000 claims description 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 8
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 230000001419 dependent effect Effects 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 12
- 239000000543 intermediate Substances 0.000 abstract description 3
- SQQXRXKYTKFFSM-UHFFFAOYSA-N chembl1992147 Chemical compound OC1=C(OC)C(OC)=CC=C1C1=C(C)C(C(O)=O)=NC(C=2N=C3C4=NC(C)(C)N=C4C(OC)=C(O)C3=CC=2)=C1N SQQXRXKYTKFFSM-UHFFFAOYSA-N 0.000 abstract description 2
- 229940124669 imidazoquinoline Drugs 0.000 abstract description 2
- 239000002955 immunomodulating agent Substances 0.000 abstract description 2
- 229940121354 immunomodulator Drugs 0.000 abstract description 2
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 524
- 238000006243 chemical reaction Methods 0.000 description 292
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 225
- 239000000243 solution Substances 0.000 description 173
- 230000002829 reductive effect Effects 0.000 description 156
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 143
- 239000011541 reaction mixture Substances 0.000 description 142
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 135
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 116
- 239000000203 mixture Substances 0.000 description 109
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 102
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 89
- 239000007787 solid Substances 0.000 description 81
- 229910001868 water Inorganic materials 0.000 description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 75
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 70
- 235000017557 sodium bicarbonate Nutrition 0.000 description 70
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 69
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 61
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
- 239000010410 layer Substances 0.000 description 49
- 238000007796 conventional method Methods 0.000 description 48
- 238000007429 general method Methods 0.000 description 47
- 239000000047 product Substances 0.000 description 47
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 45
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- 235000019341 magnesium sulphate Nutrition 0.000 description 44
- 239000000463 material Substances 0.000 description 42
- 239000002904 solvent Substances 0.000 description 39
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 38
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 36
- 239000012044 organic layer Substances 0.000 description 35
- 238000000746 purification Methods 0.000 description 34
- 239000003921 oil Substances 0.000 description 30
- 235000019198 oils Nutrition 0.000 description 30
- 229910000027 potassium carbonate Inorganic materials 0.000 description 30
- 239000000741 silica gel Substances 0.000 description 30
- 229910002027 silica gel Inorganic materials 0.000 description 30
- 238000001953 recrystallisation Methods 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 27
- 239000000908 ammonium hydroxide Substances 0.000 description 27
- 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 description 25
- 239000012267 brine Substances 0.000 description 23
- 239000000843 powder Substances 0.000 description 23
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- 238000003818 flash chromatography Methods 0.000 description 21
- 239000012071 phase Substances 0.000 description 21
- 238000010992 reflux Methods 0.000 description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
- 229910052938 sodium sulfate Inorganic materials 0.000 description 19
- 235000011152 sodium sulphate Nutrition 0.000 description 19
- 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 19
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 18
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 18
- 125000005843 halogen group Chemical group 0.000 description 17
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 16
- 229910052760 oxygen Inorganic materials 0.000 description 16
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 15
- 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 14
- 230000009467 reduction Effects 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 13
- 239000013058 crude material Substances 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 13
- UTOMICFLROGMAE-UHFFFAOYSA-N quinoline-3,4-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CN=C21 UTOMICFLROGMAE-UHFFFAOYSA-N 0.000 description 13
- JAFMOTJMRSZOJE-UHFFFAOYSA-N 1,1,1-trimethoxybutane Chemical compound CCCC(OC)(OC)OC JAFMOTJMRSZOJE-UHFFFAOYSA-N 0.000 description 12
- 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 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 12
- 150000002576 ketones Chemical class 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 10
- 238000010828 elution Methods 0.000 description 10
- 238000005984 hydrogenation reaction Methods 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 238000010189 synthetic method Methods 0.000 description 10
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical class C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 9
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 230000028993 immune response Effects 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 7
- QZLAVKQIKWPEEU-UHFFFAOYSA-N 3,4,5,6,10,12-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaene Chemical compound C1=CN2N=NN=C2C2=C1NC=N2 QZLAVKQIKWPEEU-UHFFFAOYSA-N 0.000 description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 7
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 7
- 206010028980 Neoplasm Diseases 0.000 description 7
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 7
- 102100040247 Tumor necrosis factor Human genes 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 description 7
- LEMSZRCMNDFGPO-UHFFFAOYSA-N n-methoxy-5-(2-propylimidazo[4,5-c]quinolin-1-yl)pentan-2-amine Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCC(C)NOC)C3=CN=C21 LEMSZRCMNDFGPO-UHFFFAOYSA-N 0.000 description 7
- 150000002923 oximes Chemical class 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- UJTNVHOFQOMHHY-UHFFFAOYSA-N 1-[4-(methoxyamino)butyl]-2-propylimidazo[4,5-c][1,5]naphthyridin-4-amine Chemical compound C1=CC=NC2=C(N(C(CCC)=N3)CCCCNOC)C3=C(N)N=C21 UJTNVHOFQOMHHY-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 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
- SJQQWQZOHIXMOO-UHFFFAOYSA-N 4-(2-propylimidazo[4,5-c]quinolin-1-yl)butanal Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCC=O)C3=CN=C21 SJQQWQZOHIXMOO-UHFFFAOYSA-N 0.000 description 6
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 6
- 150000004795 grignard reagents Chemical class 0.000 description 6
- UHUHBFMZVCOEOV-UHFFFAOYSA-N 1h-imidazo[4,5-c]pyridin-4-amine Chemical class NC1=NC=CC2=C1N=CN2 UHUHBFMZVCOEOV-UHFFFAOYSA-N 0.000 description 5
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Classifications
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Landscapes
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Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52496103P | 2003-11-25 | 2003-11-25 | |
| US60/524,961 | 2003-11-25 | ||
| US58013904P | 2004-06-16 | 2004-06-16 | |
| US60/580,139 | 2004-06-16 | ||
| US58129304P | 2004-06-18 | 2004-06-18 | |
| US60/581,293 | 2004-06-18 | ||
| PCT/US2004/039673 WO2005051324A2 (en) | 2003-11-25 | 2004-11-24 | Hydroxylamine and oxime substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2547085A1 true CA2547085A1 (en) | 2005-06-09 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002547085A Abandoned CA2547085A1 (en) | 2003-11-25 | 2004-11-24 | Hydroxylamine and oxime substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
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| Country | Link |
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| US (1) | US8778963B2 (enExample) |
| EP (1) | EP1686992A4 (enExample) |
| JP (1) | JP2007512349A (enExample) |
| AU (1) | AU2004293096A1 (enExample) |
| CA (1) | CA2547085A1 (enExample) |
| WO (1) | WO2005051324A2 (enExample) |
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| US20040265351A1 (en) | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
| AU2004266641A1 (en) | 2003-08-12 | 2005-03-03 | 3M Innovative Properties Company | Oxime substituted imidazo-containing compounds |
| MY145983A (en) | 2003-08-27 | 2012-05-31 | 3M Innovative Properties Co | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| CA2537763A1 (en) | 2003-09-05 | 2005-03-17 | 3M Innovative Properties Company | Treatment for cd5+ b cell lymphoma |
| EP1673087B1 (en) | 2003-10-03 | 2015-05-13 | 3M Innovative Properties Company | Alkoxy substituted imidazoquinolines |
| BRPI0414867A (pt) | 2003-10-03 | 2006-11-21 | 3M Innovative Properties Co | pirazolopiridinas e seus análogos |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| US8598192B2 (en) | 2003-11-14 | 2013-12-03 | 3M Innovative Properties Company | Hydroxylamine substituted imidazoquinolines |
| CN1906193A (zh) | 2003-11-14 | 2007-01-31 | 3M创新有限公司 | 肟取代的咪唑环化合物 |
| WO2005051317A2 (en) | 2003-11-25 | 2005-06-09 | 3M Innovative Properties Company | Substituted imidazo ring systems and methods |
| WO2005066170A1 (en) | 2003-12-29 | 2005-07-21 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
| EP1699788A2 (en) | 2003-12-30 | 2006-09-13 | 3M Innovative Properties Company | Imidazoquinolinyl, imidazopyridinyl and imidazonaphthyridinyl sulfonamides |
| TW200612932A (en) * | 2004-03-24 | 2006-05-01 | 3M Innovative Properties Co | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| WO2005123080A2 (en) | 2004-06-15 | 2005-12-29 | 3M Innovative Properties Company | Nitrogen-containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
| WO2006009826A1 (en) | 2004-06-18 | 2006-01-26 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
| US7897609B2 (en) | 2004-06-18 | 2011-03-01 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
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- 2004-11-24 CA CA002547085A patent/CA2547085A1/en not_active Abandoned
- 2004-11-24 JP JP2006541442A patent/JP2007512349A/ja active Pending
- 2004-11-24 WO PCT/US2004/039673 patent/WO2005051324A2/en not_active Ceased
- 2004-11-24 US US10/595,895 patent/US8778963B2/en not_active Expired - Fee Related
- 2004-11-24 AU AU2004293096A patent/AU2004293096A1/en not_active Abandoned
- 2004-11-24 EP EP04812235A patent/EP1686992A4/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| US20070099901A1 (en) | 2007-05-03 |
| EP1686992A4 (en) | 2009-11-04 |
| AU2004293096A1 (en) | 2005-06-09 |
| US8778963B2 (en) | 2014-07-15 |
| WO2005051324A2 (en) | 2005-06-09 |
| JP2007512349A (ja) | 2007-05-17 |
| WO2005051324A3 (en) | 2006-01-05 |
| EP1686992A2 (en) | 2006-08-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |