AU2004253929A1 - Sulfonamide substituted imidazoquinolines - Google Patents

Sulfonamide substituted imidazoquinolines Download PDF

Info

Publication number: AU2004253929A1
Authority: AU; Australia
Prior art keywords: imidazo; quinolin; amino; butyl; mmol
Prior art date: 2003-06-27
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

Application number

AU2004253929A

Other languages

English (en)

Inventor

George W. Griesgraber

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

3M Innovative Properties Co

Original Assignee

3M Innovative Properties Co

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.)

2003-06-27

Filing date

2004-06-25

Publication date

2005-01-13

2004-06-25 Application filed by 3M Innovative Properties Co filed Critical 3M Innovative Properties Co

2005-01-13 Publication of AU2004253929A1 publication Critical patent/AU2004253929A1/en

Status Abandoned legal-status Critical Current

Links

229940124530 sulfonamide Drugs 0.000 title description 8
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 7
125000000565 sulfonamide group Chemical group 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 82
102000004127 Cytokines Human genes 0.000 claims description 27
108090000695 Cytokines Proteins 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 21
241001465754 Metazoa Species 0.000 claims description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
201000010099 disease Diseases 0.000 claims description 14
238000000034 method Methods 0.000 claims description 12
230000015572 biosynthetic process Effects 0.000 claims description 11
230000003612 virological effect Effects 0.000 claims description 8
230000001939 inductive effect Effects 0.000 claims description 7
230000001613 neoplastic effect Effects 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 5
NVNWHRIYBUUBAJ-UHFFFAOYSA-N n-[1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-yl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CC(C)(C)NS(C)(=O)=O)C3=C(N)N=C21 NVNWHRIYBUUBAJ-UHFFFAOYSA-N 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 description 86
229910052799 carbon Inorganic materials 0.000 description 78
229910052757 nitrogen Inorganic materials 0.000 description 73
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
238000006243 chemical reaction Methods 0.000 description 70
239000007787 solid Substances 0.000 description 55
239000000243 solution Substances 0.000 description 48
238000007429 general method Methods 0.000 description 42
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
238000004458 analytical method Methods 0.000 description 35
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
239000011541 reaction mixture Substances 0.000 description 27
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
239000000463 material Substances 0.000 description 20
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
-1 Compounds Imidazoquinolines Chemical class 0.000 description 15
125000000623 heterocyclic group Chemical group 0.000 description 15
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 15
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
239000012359 Methanesulfonyl chloride Substances 0.000 description 14
238000005481 NMR spectroscopy Methods 0.000 description 14
239000000203 mixture Substances 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 13
102100040247 Tumor necrosis factor Human genes 0.000 description 13
125000000217 alkyl group Chemical group 0.000 description 13
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
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
125000001072 heteroaryl group Chemical group 0.000 description 12
108060008682 Tumor Necrosis Factor Proteins 0.000 description 11
230000006698 induction Effects 0.000 description 11
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
238000007796 conventional method Methods 0.000 description 10
238000001914 filtration Methods 0.000 description 10
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 10
239000000843 powder Substances 0.000 description 10
239000011734 sodium Substances 0.000 description 10
125000001424 substituent group Chemical group 0.000 description 10
229910052717 sulfur Inorganic materials 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
150000001412 amines Chemical class 0.000 description 9
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
239000001257 hydrogen Substances 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
102000014150 Interferons Human genes 0.000 description 8
108010050904 Interferons Proteins 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
125000004103 aminoalkyl group Chemical group 0.000 description 8
239000012267 brine Substances 0.000 description 8
229940079322 interferon Drugs 0.000 description 8
238000004519 manufacturing process Methods 0.000 description 8
IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
150000001204 N-oxides Chemical class 0.000 description 7
206010028980 Neoplasm Diseases 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
239000006260 foam Substances 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
GCGNWZMOENODOJ-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-h]quinoline Chemical class C1C=C2C=CC=NC2=C2C1NCN2 GCGNWZMOENODOJ-UHFFFAOYSA-N 0.000 description 6
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
125000004122 cyclic group Chemical group 0.000 description 6
230000000694 effects Effects 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
230000028993 immune response Effects 0.000 description 6
239000012948 isocyanate Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
238000003756 stirring Methods 0.000 description 6
150000003456 sulfonamides Chemical group 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
125000003342 alkenyl group Chemical group 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
150000002513 isocyanates Chemical class 0.000 description 5
239000010410 layer Substances 0.000 description 5
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
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 4
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
208000036142 Viral infection Diseases 0.000 description 4
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
238000010189 synthetic method Methods 0.000 description 4
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
238000012360 testing method Methods 0.000 description 4
230000009385 viral infection Effects 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
KZWUQTRMSBGBBN-UHFFFAOYSA-N 1-(3-aminopropyl)-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CCCN)C3=C(N)N=C21 KZWUQTRMSBGBBN-UHFFFAOYSA-N 0.000 description 3
ZPJBFQVJSMEECU-UHFFFAOYSA-N 2-butyl-1-[4-(1,1-dioxo-1,2-thiazolidin-2-yl)butyl]imidazo[4,5-c]quinolin-4-amine Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCN1CCCS1(=O)=O ZPJBFQVJSMEECU-UHFFFAOYSA-N 0.000 description 3
XYYKPSXKBVBMHJ-UHFFFAOYSA-N 3-(2-butylimidazo[4,5-c]quinolin-1-yl)propan-1-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCN)C3=CN=C21 XYYKPSXKBVBMHJ-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
238000002965 ELISA Methods 0.000 description 3
239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 3
229910004298 SiO 2 Inorganic materials 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 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 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
125000001188 haloalkyl group Chemical group 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
210000005260 human cell Anatomy 0.000 description 3
229940124669 imidazoquinoline Drugs 0.000 description 3
239000002955 immunomodulating agent Substances 0.000 description 3
229940121354 immunomodulator Drugs 0.000 description 3
VQDBDUUBRYJICF-UHFFFAOYSA-N n-[2-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)ethyl]-4-methylbenzenesulfonamide Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCNS(=O)(=O)C1=CC=C(C)C=C1 VQDBDUUBRYJICF-UHFFFAOYSA-N 0.000 description 3
ZGEPNYAAUQVVLM-UHFFFAOYSA-N n-[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl]benzenesulfonamide Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCNS(=O)(=O)C1=CC=CC=C1 ZGEPNYAAUQVVLM-UHFFFAOYSA-N 0.000 description 3
XKWXZYMYHSFUJW-UHFFFAOYSA-N n-[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl]-4-methylbenzenesulfonamide Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCNS(=O)(=O)C1=CC=C(C)C=C1 XKWXZYMYHSFUJW-UHFFFAOYSA-N 0.000 description 3
YODWHKFJJPXAQD-UHFFFAOYSA-N n-[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl]benzenesulfonamide Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCNS(=O)(=O)C1=CC=CC=C1 YODWHKFJJPXAQD-UHFFFAOYSA-N 0.000 description 3
FRXDVFQORNBEFL-UHFFFAOYSA-N n-[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CCCNS(C)(=O)=O)C3=C(N)N=C21 FRXDVFQORNBEFL-UHFFFAOYSA-N 0.000 description 3
OCGIGXADEWZZPL-UHFFFAOYSA-N n-[3-[4-amino-2-(3-phenoxypropyl)imidazo[4,5-c]quinolin-1-yl]propyl]methanesulfonamide Chemical compound N=1C2=C(N)N=C3C=CC=CC3=C2N(CCCNS(=O)(=O)C)C=1CCCOC1=CC=CC=C1 OCGIGXADEWZZPL-UHFFFAOYSA-N 0.000 description 3
FDURDVQGNXYXGG-UHFFFAOYSA-N n-[3-[4-amino-2-(ethoxymethyl)-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-1-yl]propyl]methanesulfonamide Chemical compound C1CCCC2=C(N(C(COCC)=N3)CCCNS(C)(=O)=O)C3=C(N)N=C21 FDURDVQGNXYXGG-UHFFFAOYSA-N 0.000 description 3
XHFIIYXNIHVLAV-UHFFFAOYSA-N n-[4-(2-hexylimidazo[4,5-c]quinolin-1-yl)butyl]benzenesulfonamide Chemical compound CCCCCCC1=NC2=CN=C3C=CC=CC3=C2N1CCCCNS(=O)(=O)C1=CC=CC=C1 XHFIIYXNIHVLAV-UHFFFAOYSA-N 0.000 description 3
YZOQZEXYFLXNKA-UHFFFAOYSA-N n-[4-(4-amino-2-ethylimidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CC)=N3)CCCCNS(C)(=O)=O)C3=C(N)N=C21 YZOQZEXYFLXNKA-UHFFFAOYSA-N 0.000 description 3
TWEWOQRUFLEQNL-UHFFFAOYSA-N n-[4-(4-amino-2-hexylimidazo[4,5-c]quinolin-1-yl)butyl]benzenesulfonamide Chemical compound CCCCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNS(=O)(=O)C1=CC=CC=C1 TWEWOQRUFLEQNL-UHFFFAOYSA-N 0.000 description 3
ZUFWEBGOLJHBJM-UHFFFAOYSA-N n-[4-(4-amino-2-hexylimidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CCCCCC)=N3)CCCCNS(C)(=O)=O)C3=C(N)N=C21 ZUFWEBGOLJHBJM-UHFFFAOYSA-N 0.000 description 3
CCJISYWPWXKKRX-UHFFFAOYSA-N n-[4-(4-amino-2-methylimidazo[4,5-c]quinolin-1-yl)butyl]ethanesulfonamide Chemical compound C1=CC=CC2=C3N(CCCCNS(=O)(=O)CC)C(C)=NC3=C(N)N=C21 CCJISYWPWXKKRX-UHFFFAOYSA-N 0.000 description 3
DOZGTYGEBVOOFZ-UHFFFAOYSA-N n-[4-(4-amino-2-methylimidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(C)=N3)CCCCNS(C)(=O)=O)C3=C(N)N=C21 DOZGTYGEBVOOFZ-UHFFFAOYSA-N 0.000 description 3
GYAGKIRWXLWSHY-UHFFFAOYSA-N n-[4-(4-amino-2-pentylimidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CCCCC)=N3)CCCCNS(C)(=O)=O)C3=C(N)N=C21 GYAGKIRWXLWSHY-UHFFFAOYSA-N 0.000 description 3
KCQWOAPKZGATTP-UHFFFAOYSA-N n-[4-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)butyl]benzenesulfonamide Chemical compound CCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNS(=O)(=O)C1=CC=CC=C1 KCQWOAPKZGATTP-UHFFFAOYSA-N 0.000 description 3
KSQUPKPKVHSLDC-UHFFFAOYSA-N n-[4-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCCNS(C)(=O)=O)C3=C(N)N=C21 KSQUPKPKVHSLDC-UHFFFAOYSA-N 0.000 description 3
ZOCPCRFSEJMATG-UHFFFAOYSA-N n-[8-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]octyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CCCCCCCCNS(C)(=O)=O)C3=C(N)N=C21 ZOCPCRFSEJMATG-UHFFFAOYSA-N 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
238000010992 reflux Methods 0.000 description 3
230000004044 response Effects 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
SVBZCXQPNPURIX-UHFFFAOYSA-N 1-(2-amino-2-methylpropyl)-2-(ethoxymethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CC(C)(C)N)C3=C(N)N=C21 SVBZCXQPNPURIX-UHFFFAOYSA-N 0.000 description 2
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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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Immunology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Oncology (AREA)
Virology (AREA)
Communicable Diseases (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

AU2004253929A 2003-06-27 2004-06-25 Sulfonamide substituted imidazoquinolines Abandoned AU2004253929A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US48320003P	2003-06-27	2003-06-27
US60/483,200		2003-06-27
PCT/US2004/020607 WO2005003065A2 (fr)	2003-06-27	2004-06-25	Imidazo-quinolines a substitution sulfonamide

Publications (1)

Publication Number	Publication Date
AU2004253929A1 true AU2004253929A1 (en)	2005-01-13

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Family Applications (1)

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AU2004253929A Abandoned AU2004253929A1 (en)	2003-06-27	2004-06-25	Sulfonamide substituted imidazoquinolines

Country Status (16)

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EP (1)	EP1638566A4 (fr)
JP (1)	JP2007521280A (fr)
KR (1)	KR20060035637A (fr)
CN (1)	CN1812789B (fr)
AR (2)	AR044923A1 (fr)
AU (1)	AU2004253929A1 (fr)
BR (1)	BRPI0411916A (fr)
CA (1)	CA2529322A1 (fr)
IL (1)	IL172427A0 (fr)
MX (1)	MXPA06000144A (fr)
MY (1)	MY157827A (fr)
NZ (1)	NZ544330A (fr)
RU (1)	RU2374246C2 (fr)
TW (2)	TW200514784A (fr)
WO (2)	WO2005003064A2 (fr)
ZA (1)	ZA200600769B (fr)

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2004
- 2004-06-24 MY MYPI20042461A patent/MY157827A/en unknown
- 2004-06-25 CA CA002529322A patent/CA2529322A1/fr not_active Abandoned
- 2004-06-25 AR ARP040102248A patent/AR044923A1/es unknown
- 2004-06-25 BR BRPI0411916-9A patent/BRPI0411916A/pt not_active IP Right Cessation
- 2004-06-25 WO PCT/US2004/020606 patent/WO2005003064A2/fr not_active Ceased
- 2004-06-25 EP EP04756208A patent/EP1638566A4/fr not_active Withdrawn
- 2004-06-25 MX MXPA06000144A patent/MXPA06000144A/es unknown
- 2004-06-25 AR ARP040102247A patent/AR044922A1/es unknown
- 2004-06-25 TW TW093118635A patent/TW200514784A/zh unknown
- 2004-06-25 TW TW093118636A patent/TW200511992A/zh unknown
- 2004-06-25 CN CN2004800181459A patent/CN1812789B/zh not_active Expired - Fee Related
- 2004-06-25 WO PCT/US2004/020607 patent/WO2005003065A2/fr not_active Ceased
- 2004-06-25 RU RU2005138915/04A patent/RU2374246C2/ru not_active IP Right Cessation
- 2004-06-25 KR KR1020057024904A patent/KR20060035637A/ko not_active Ceased
- 2004-06-25 AU AU2004253929A patent/AU2004253929A1/en not_active Abandoned
- 2004-06-25 NZ NZ544330A patent/NZ544330A/en unknown
- 2004-06-25 JP JP2006517711A patent/JP2007521280A/ja active Pending
2005
- 2005-12-07 IL IL172427A patent/IL172427A0/en unknown
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- 2006-01-26 ZA ZA200600769A patent/ZA200600769B/en unknown

Also Published As

Publication number	Publication date
WO2005003065A2 (fr)	2005-01-13
TW200511992A (en)	2005-04-01
WO2005003064A2 (fr)	2005-01-13
MY157827A (en)	2016-07-29
JP2007521280A (ja)	2007-08-02
IL172427A0 (en)	2006-04-10
CN1812789B (zh)	2010-07-14
CN1812789A (zh)	2006-08-02
WO2005003064A3 (fr)	2005-03-31
MXPA06000144A (es)	2006-04-07
EP1638566A4 (fr)	2009-03-25
NZ544330A (en)	2009-06-26
KR20060035637A (ko)	2006-04-26
AR044923A1 (es)	2005-10-12
RU2374246C2 (ru)	2009-11-27
ZA200600769B (en)	2007-05-30
RU2005138915A (ru)	2006-06-27
BRPI0411916A (pt)	2006-08-15
WO2005003065A3 (fr)	2005-03-10
TW200514784A (en)	2005-05-01
CA2529322A1 (fr)	2005-01-13
AR044922A1 (es)	2005-10-12
EP1638566A2 (fr)	2006-03-29

Publication	Publication Date	Title
AU2004253929A1 (en)	2005-01-13	Sulfonamide substituted imidazoquinolines
US6677349B1 (en)	2004-01-13	Sulfonamide and sulfamide substituted imidazoquinolines
KR100781428B1 (ko)	2007-12-03	술폰아미드 및 술파미드 치환된 이미다조퀴놀린
AU2002232482B2 (en)	2006-10-19	Amido ether substituted imidazoquinolines
US6969722B2 (en)	2005-11-29	Amide substituted imidazopyridines
AU766565B2 (en)	2003-10-16	Urea substituted imidazoquinolines
US6903113B2 (en)	2005-06-07	Urea substituted imidazopyridines
AU2002312414B2 (en)	2009-02-19	Sulfonamido substituted imidazopyridines
AU2002239547B2 (en)	2006-11-30	Substituted imidazopyridines
AU2002232497A1 (en)	2002-08-22	Urea substituted imidazoquinoline ethers
EP1642580A1 (fr)	2006-04-05	Sulfonamides d' imidazoquinoline
HK1088836A (en)	2006-11-17	Sulfonamide substituted imidazoquinolines

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Date	Code	Title	Description
2010-12-16	MK5	Application lapsed section 142(2)(e) - patent request and compl. specification not accepted