DE69826518T2 - Imidazonaphthyridinderivate und ihre verwendung zur induzierung von biosythese von cytokin - Google Patents

Info

Publication number

DE69826518T2

DE69826518T2 DE69826518T DE69826518T DE69826518T2 DE 69826518 T2 DE69826518 T2 DE 69826518T2 DE 69826518 T DE69826518 T DE 69826518T DE 69826518 T DE69826518 T DE 69826518T DE 69826518 T2 DE69826518 T2 DE 69826518T2

Authority

DE

Germany

Prior art keywords

alkyl

group

aryl

heteroaryl

heterocyclyl

Prior art date

1997-12-11

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.)

Expired - Fee Related

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• 230000006698 induction Effects 0.000 title claims description 19
• 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 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 274
• 102000004127 Cytokines Human genes 0.000 claims abstract description 28
• 108090000695 Cytokines Proteins 0.000 claims abstract description 28
• 238000000034 method Methods 0.000 claims abstract description 25
• 230000015572 biosynthetic process Effects 0.000 claims abstract description 15
• 238000002360 preparation method Methods 0.000 claims abstract description 14
• 229910052739 hydrogen Inorganic materials 0.000 claims description 246
• 229910052799 carbon Inorganic materials 0.000 claims description 195
• 125000000217 alkyl group Chemical group 0.000 claims description 113
• -1 pyrrolidinyl Tetrahydrofuranyl Chemical group 0.000 claims description 91
• 239000001257 hydrogen Substances 0.000 claims description 64
• 125000003118 aryl group Chemical group 0.000 claims description 44
• 125000001424 substituent group Chemical group 0.000 claims description 42
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
• 125000000623 heterocyclic group Chemical group 0.000 claims description 39
• 229910052736 halogen Inorganic materials 0.000 claims description 38
• 125000001072 heteroaryl group Chemical group 0.000 claims description 32
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 31
• 125000004043 oxo group Chemical group O=* 0.000 claims description 22
• 241001465754 Metazoa Species 0.000 claims description 20
• 125000004432 carbon atom Chemical group C* 0.000 claims description 19
• 150000002367 halogens Chemical class 0.000 claims description 19
• 150000003839 salts Chemical class 0.000 claims description 19
• 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 17
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
• 150000002431 hydrogen Chemical group 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• 230000009385 viral infection Effects 0.000 claims description 9
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 8
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 239000004305 biphenyl Substances 0.000 claims description 8
• 235000010290 biphenyl Nutrition 0.000 claims description 8
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 8
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 8
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 8
• 125000002883 imidazolyl group Chemical group 0.000 claims description 8
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 8
• 125000002757 morpholinyl group Chemical group 0.000 claims description 8
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000001624 naphthyl group Chemical group 0.000 claims description 8
• 150000002825 nitriles Chemical class 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
• 125000001984 thiazolidinyl group Chemical group 0.000 claims description 8
• 125000001544 thienyl group Chemical group 0.000 claims description 8
• 125000004953 trihalomethyl group Chemical group 0.000 claims description 8
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 7
• 208000036142 Viral infection Diseases 0.000 claims description 7
• 125000002541 furyl group Chemical group 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 4
• 239000003814 drug Substances 0.000 claims description 3
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
• 230000001939 inductive effect Effects 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
• 125000001475 halogen functional group Chemical group 0.000 claims 6
• 125000002252 acyl group Chemical group 0.000 claims 4
• 125000004414 alkyl thio group Chemical group 0.000 claims 4
• 108010050904 Interferons Proteins 0.000 abstract description 21
• 102000014150 Interferons Human genes 0.000 abstract description 21
• 229940079322 interferon Drugs 0.000 abstract description 19
• 239000000543 intermediate Substances 0.000 abstract description 13
• 108060008682 Tumor Necrosis Factor Proteins 0.000 abstract description 11
• 102000003390 tumor necrosis factor Human genes 0.000 abstract description 8
• ZZXQWFQBPSUCAF-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-b][1,8]naphthyridine Chemical class N1C2=NC=CC=C2C=C2C1NCN2 ZZXQWFQBPSUCAF-UHFFFAOYSA-N 0.000 abstract description 4
• 230000000840 anti-viral effect Effects 0.000 abstract description 2
• 230000000259 anti-tumor effect Effects 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 460
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 192
• 229910052757 nitrogen Inorganic materials 0.000 description 185
• 239000011541 reaction mixture Substances 0.000 description 141
• 239000007787 solid Substances 0.000 description 112
• 239000000243 solution Substances 0.000 description 104
• 238000004458 analytical method Methods 0.000 description 98
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 88
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 73
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
• 238000006243 chemical reaction Methods 0.000 description 64
• 239000000203 mixture Substances 0.000 description 61
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 60
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 58
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 51
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 43
• 235000019341 magnesium sulphate Nutrition 0.000 description 43
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 40
• 239000000741 silica gel Substances 0.000 description 39
• 229910002027 silica gel Inorganic materials 0.000 description 39
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 37
• 239000010410 layer Substances 0.000 description 35
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• 239000003921 oil Substances 0.000 description 29
• 235000019198 oils Nutrition 0.000 description 29
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 28
• 239000000047 product Substances 0.000 description 27
• 239000002904 solvent Substances 0.000 description 27
• 239000000843 powder Substances 0.000 description 26
• 239000002244 precipitate Substances 0.000 description 26
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 23
• 239000003054 catalyst Substances 0.000 description 23
• 239000000706 filtrate Substances 0.000 description 23
• 239000000725 suspension Substances 0.000 description 23
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
• 238000003818 flash chromatography Methods 0.000 description 22
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 22
• 238000010992 reflux Methods 0.000 description 22
• 239000000126 substance Substances 0.000 description 22
• 238000004809 thin layer chromatography Methods 0.000 description 22
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 21
• UDPCXSIHDFYJJJ-UHFFFAOYSA-N 1-(4-aminobutyl)-2-butylimidazo[4,5-c][1,5]naphthyridin-4-amine Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CCCCN)C3=C(N)N=C21 UDPCXSIHDFYJJJ-UHFFFAOYSA-N 0.000 description 21
• 238000005160 1H NMR spectroscopy Methods 0.000 description 21
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 18
• 235000017557 sodium bicarbonate Nutrition 0.000 description 18
• 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 18
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 239000002253 acid Substances 0.000 description 15
• 239000000908 ammonium hydroxide Substances 0.000 description 15
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
• 210000004027 cell Anatomy 0.000 description 14
• URVRUEIJYPBVSU-UHFFFAOYSA-N 1-(2-aminoethyl)-2-butylimidazo[4,5-c][1,5]naphthyridin-4-amine Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CCN)C3=C(N)N=C21 URVRUEIJYPBVSU-UHFFFAOYSA-N 0.000 description 13
• 239000012267 brine Substances 0.000 description 13
• 239000003795 chemical substances by application Substances 0.000 description 13
• 239000012044 organic layer Substances 0.000 description 13
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 13
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 12
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 11
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 11
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 10
• 150000001412 amines Chemical class 0.000 description 10
• 238000003756 stirring Methods 0.000 description 10
• 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 10
• FPMFWNDLLWUVEH-UHFFFAOYSA-N 1,8-naphthyridin-4-amine Chemical compound C1=CC=C2C(N)=CC=NC2=N1 FPMFWNDLLWUVEH-UHFFFAOYSA-N 0.000 description 9
• 201000010099 disease Diseases 0.000 description 9
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• 239000005457 ice water Substances 0.000 description 9
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• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 8
• MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 8
• XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 8
• 229910003446 platinum oxide Inorganic materials 0.000 description 8
• 238000000926 separation method Methods 0.000 description 8
• 238000012360 testing method Methods 0.000 description 8
• PHFKUTFUFKZJMV-UHFFFAOYSA-N 1,7-naphthyridin-4-amine Chemical compound N1=CC=C2C(N)=CC=NC2=C1 PHFKUTFUFKZJMV-UHFFFAOYSA-N 0.000 description 7
• 241000700605 Viruses Species 0.000 description 7
• 238000004166 bioassay Methods 0.000 description 7
• 239000002027 dichloromethane extract Substances 0.000 description 7
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• 230000000694 effects Effects 0.000 description 7
• 239000000284 extract Substances 0.000 description 7
• 230000028993 immune response Effects 0.000 description 7
• 239000012948 isocyanate Substances 0.000 description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
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• 0 CCC(C(C*)*=C1N)c2c1nc(*)[n]2* Chemical compound CCC(C(C*)*=C1N)c2c1nc(*)[n]2* 0.000 description 6
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• 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 5
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• 125000004866 1,1-dimethylethylcarbonyl group Chemical group CC(C)(C(=O)*)C 0.000 description 4
• ICJQRUDUVJQLKN-UHFFFAOYSA-N 1-(2-methylpropyl)-1h-tetrazolo[1,5-a]imidazo[4,5-c][1,8]naphthyridine Chemical compound C12=CC=CN=C2N2N=NN(CC(C)C)C2=C2C1=NC=N2 ICJQRUDUVJQLKN-UHFFFAOYSA-N 0.000 description 4
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• KRULLMMDEYYKGQ-UHFFFAOYSA-N 2-methyl-1-(2-methylpropyl)imidazo[4,5-c][1,5]naphthyridine Chemical compound C1=CC=NC2=C3N(CC(C)C)C(C)=NC3=CN=C21 KRULLMMDEYYKGQ-UHFFFAOYSA-N 0.000 description 4
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