PL193915B1 - Imidazonaftyrydyny, kompozycje farmaceutyczne je zawierające i ich zastosowanie oraz związki pośrednie - Google Patents

Info

Publication number

PL193915B1

PL193915B1 PL98341159A PL34115998A PL193915B1 PL 193915 B1 PL193915 B1 PL 193915B1 PL 98341159 A PL98341159 A PL 98341159A PL 34115998 A PL34115998 A PL 34115998A PL 193915 B1 PL193915 B1 PL 193915B1

Authority

PL

Poland

Prior art keywords

group

6alkyl

optionally substituted

phenyl

halogen

Prior art date

1997-12-11

Links

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• 230000015572 biosynthetic process Effects 0.000 title claims description 15
• 230000001939 inductive effect Effects 0.000 title claims description 8
• UQHKFADEQIVWID-UHFFFAOYSA-N cytokinin Natural products C1=NC=2C(NCC=C(CO)C)=NC=NC=2N1C1CC(O)C(CO)O1 UQHKFADEQIVWID-UHFFFAOYSA-N 0.000 title 1
• 239000004062 cytokinin Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 294
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 110
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 105
• 150000002367 halogens Chemical class 0.000 claims abstract description 104
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 89
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 75
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 73
• 125000001424 substituent group Chemical group 0.000 claims abstract description 63
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 62
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 44
• 125000001544 thienyl group Chemical group 0.000 claims abstract description 30
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 29
• 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 29
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims abstract description 16
• 125000002541 furyl group Chemical group 0.000 claims abstract description 16
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 16
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract description 16
• 125000000842 isoxazolyl group Chemical group 0.000 claims abstract description 15
• 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 15
• 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 15
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 15
• 125000006376 (C3-C10) cycloalkyl group Chemical class 0.000 claims abstract description 14
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 13
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
• 229910052739 hydrogen Inorganic materials 0.000 claims description 250
• -1 tetrahydropyrimidinyl Chemical group 0.000 claims description 103
• 239000001257 hydrogen Substances 0.000 claims description 75
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 55
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 36
• 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 28
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 27
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 25
• 102000004127 Cytokines Human genes 0.000 claims description 25
• 108090000695 Cytokines Proteins 0.000 claims description 25
• 241001465754 Metazoa Species 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 23
• 125000003118 aryl group Chemical group 0.000 claims description 19
• 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 claims description 17
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 15
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 15
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 15
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• 125000005053 dihydropyrimidinyl group Chemical group N1(CN=CC=C1)* 0.000 claims description 14
• 125000002883 imidazolyl group Chemical group 0.000 claims description 14
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 13
• 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 13
• 238000004519 manufacturing process Methods 0.000 claims description 12
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 10
• 238000002360 preparation method Methods 0.000 claims description 10
• 208000036142 Viral infection Diseases 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
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
• 230000009385 viral infection Effects 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 6
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 5
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 4
• 125000004432 carbon atom Chemical group C* 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
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
• 101150009274 nhr-1 gene Proteins 0.000 claims description 2
• 229910052799 carbon Inorganic materials 0.000 abstract description 175
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 468
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 192
• 229910052757 nitrogen Inorganic materials 0.000 description 188
• 239000011541 reaction mixture Substances 0.000 description 151
• 239000007787 solid Substances 0.000 description 111
• 238000006243 chemical reaction Methods 0.000 description 100
• 239000000243 solution Substances 0.000 description 98
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 89
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 80
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 73
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 67
• 239000000203 mixture Substances 0.000 description 61
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 60
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 58
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 57
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 45
• 239000000741 silica gel Substances 0.000 description 45
• 229910002027 silica gel Inorganic materials 0.000 description 45
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 44
• 235000019341 magnesium sulphate Nutrition 0.000 description 44
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 41
• 239000010410 layer Substances 0.000 description 40
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
• 238000001914 filtration Methods 0.000 description 36
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 35
• 238000007429 general method Methods 0.000 description 35
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 33
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 30
• 239000002904 solvent Substances 0.000 description 30
• 239000003921 oil Substances 0.000 description 29
• 235000019198 oils Nutrition 0.000 description 29
• 239000000047 product Substances 0.000 description 27
• FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 26
• 239000000843 powder Substances 0.000 description 26
• 239000002244 precipitate Substances 0.000 description 26
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
• 238000004809 thin layer chromatography Methods 0.000 description 25
• 239000000463 material Substances 0.000 description 24
• 239000003054 catalyst Substances 0.000 description 23
• 102000014150 Interferons Human genes 0.000 description 22
• 108010050904 Interferons Proteins 0.000 description 22
• 239000000706 filtrate Substances 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
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 21
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 21
• 229940079322 interferon Drugs 0.000 description 20
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
• 238000010992 reflux Methods 0.000 description 19
• 239000000725 suspension Substances 0.000 description 19
• 230000003197 catalytic effect Effects 0.000 description 18
• 238000010438 heat treatment Methods 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
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
• 239000000543 intermediate Substances 0.000 description 17
• 235000011114 ammonium hydroxide Nutrition 0.000 description 16
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 16
• 238000000034 method Methods 0.000 description 16
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
• 235000017557 sodium bicarbonate Nutrition 0.000 description 16
• 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
• 239000000908 ammonium hydroxide Substances 0.000 description 15
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 15
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
• 239000002253 acid Substances 0.000 description 14
• 239000012267 brine Substances 0.000 description 14
• 238000007796 conventional method Methods 0.000 description 14
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
• 239000000460 chlorine Substances 0.000 description 13
• 239000012044 organic layer Substances 0.000 description 13
• 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 12
• 210000004027 cell Anatomy 0.000 description 12
• 239000003795 chemical substances by application Substances 0.000 description 12
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 12
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 11
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 11
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 11
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 11
• 230000006698 induction Effects 0.000 description 11
• 230000003612 virological effect Effects 0.000 description 11
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 10
• 150000001412 amines Chemical class 0.000 description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
• 239000005457 ice water Substances 0.000 description 9
• 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 9
• 230000009467 reduction Effects 0.000 description 9
• 102000003390 tumor necrosis factor Human genes 0.000 description 9
• PHFKUTFUFKZJMV-UHFFFAOYSA-N 1,7-naphthyridin-4-amine Chemical compound N1=CC=C2C(N)=CC=NC2=C1 PHFKUTFUFKZJMV-UHFFFAOYSA-N 0.000 description 8
• FPMFWNDLLWUVEH-UHFFFAOYSA-N 1,8-naphthyridin-4-amine Chemical class C1=CC=C2C(N)=CC=NC2=N1 FPMFWNDLLWUVEH-UHFFFAOYSA-N 0.000 description 8
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• 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
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• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• 239000012298 atmosphere Substances 0.000 description 8
• 238000000354 decomposition reaction Methods 0.000 description 8
• 239000002027 dichloromethane extract Substances 0.000 description 8
• 201000010099 disease Diseases 0.000 description 8
• 230000028993 immune response Effects 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 group CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 8
• 229910003446 platinum oxide Inorganic materials 0.000 description 8
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 7
• 238000004166 bioassay Methods 0.000 description 7
• IRUNKQSGDBYUDC-UHFFFAOYSA-N diethoxymethyl acetate Chemical compound CCOC(OCC)OC(C)=O IRUNKQSGDBYUDC-UHFFFAOYSA-N 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 239000012948 isocyanate Substances 0.000 description 7
• 238000001819 mass spectrum Methods 0.000 description 7
• 239000007858 starting material Substances 0.000 description 7
• 238000012360 testing method Methods 0.000 description 7
• 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 6
• KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 6
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
• 150000001204 N-oxides Chemical class 0.000 description 6
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 6
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
• 125000004122 cyclic group Chemical group 0.000 description 6
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• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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• XUXVVQKJULMMKX-UHFFFAOYSA-N 1,1,1-trimethoxypentane Chemical group CCCCC(OC)(OC)OC XUXVVQKJULMMKX-UHFFFAOYSA-N 0.000 description 5
• VICOWBWHKDBEJY-UHFFFAOYSA-N 1-(2-methylpropyl)imidazo[4,5-c][1,5]naphthyridine Chemical compound C1=CC=NC2=C3N(CC(C)C)C=NC3=CN=C21 VICOWBWHKDBEJY-UHFFFAOYSA-N 0.000 description 5
• HNLGOZWJKYAZPD-UHFFFAOYSA-N C1=CC=C2C(O)=CC3=NN=NN3C2=N1 Chemical compound C1=CC=C2C(O)=CC3=NN=NN3C2=N1 HNLGOZWJKYAZPD-UHFFFAOYSA-N 0.000 description 5
• 206010028980 Neoplasm Diseases 0.000 description 5
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• VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 4
• TVJWZRNFQQLPIJ-UHFFFAOYSA-N 1-(3-butoxypropyl)-2-butylimidazo[4,5-c][1,5]naphthyridine Chemical compound C1=CC=NC2=C3N(CCCOCCCC)C(CCCC)=NC3=CN=C21 TVJWZRNFQQLPIJ-UHFFFAOYSA-N 0.000 description 4
• KVVRQUKUTARMLZ-UHFFFAOYSA-N 1-benzyl-2-(ethoxymethyl)imidazo[4,5-c][1,5]naphthyridine Chemical compound CCOCC1=NC2=CN=C3C=CC=NC3=C2N1CC1=CC=CC=C1 KVVRQUKUTARMLZ-UHFFFAOYSA-N 0.000 description 4
• GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical compound ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 description 4
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