KR100642703B1 - 이미다조나프티리딘, 및 그의 시토킨 생합성 유발시의 용도 - Google Patents

Info

Publication number

KR100642703B1

KR100642703B1 KR1020007006369A KR20007006369A KR100642703B1 KR 100642703 B1 KR100642703 B1 KR 100642703B1 KR 1020007006369 A KR1020007006369 A KR 1020007006369A KR 20007006369 A KR20007006369 A KR 20007006369A KR 100642703 B1 KR100642703 B1 KR 100642703B1

Authority

KR

South Korea

Prior art keywords

alkyl

formula

imidazo

butyl

compound

Prior art date

1997-12-11

Links

• Espacenet
• Global Dossier
• Discuss

• 102000004127 Cytokines Human genes 0.000 title abstract description 28
• 108090000695 Cytokines Proteins 0.000 title abstract description 28
• 230000015572 biosynthetic process Effects 0.000 title abstract description 15
• 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
• 230000001939 inductive effect Effects 0.000 title description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 262
• 229910052739 hydrogen Inorganic materials 0.000 claims description 228
• 229910052799 carbon Inorganic materials 0.000 claims description 181
• 125000000217 alkyl group Chemical group 0.000 claims description 109
• -1 -N 3 Chemical group 0.000 claims description 92
• 239000001257 hydrogen Substances 0.000 claims description 49
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 44
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
• 125000001424 substituent group Chemical group 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 150000003839 salts Chemical class 0.000 claims description 18
• 125000003118 aryl group Chemical group 0.000 claims description 11
• 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 11
• 125000000623 heterocyclic group Chemical group 0.000 claims description 10
• 125000001072 heteroaryl group Chemical group 0.000 claims description 9
• 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 8
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
• 150000002367 halogens Chemical class 0.000 claims description 7
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 150000002431 hydrogen Chemical group 0.000 claims description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• 230000008961 swelling Effects 0.000 claims description 4
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
• 208000009889 Herpes Simplex Diseases 0.000 claims description 3
• 239000004305 biphenyl Substances 0.000 claims description 3
• 235000010290 biphenyl Nutrition 0.000 claims description 3
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 3
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 3
• 208000015181 infectious disease Diseases 0.000 claims description 3
• 125000002757 morpholinyl group Chemical group 0.000 claims description 3
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
• 125000001984 thiazolidinyl group Chemical group 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• 206010004146 Basal cell carcinoma Diseases 0.000 claims description 2
• 206010058314 Dysplasia Diseases 0.000 claims description 2
• 208000005176 Hepatitis C Diseases 0.000 claims description 2
• 241000701806 Human papillomavirus Species 0.000 claims description 2
• 208000007766 Kaposi sarcoma Diseases 0.000 claims description 2
• 208000034578 Multiple myelomas Diseases 0.000 claims description 2
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 2
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
• 208000006265 Renal cell carcinoma Diseases 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 210000002768 hair cell Anatomy 0.000 claims description 2
• 208000002672 hepatitis B Diseases 0.000 claims description 2
• 206010020718 hyperplasia Diseases 0.000 claims description 2
• 230000002458 infectious effect Effects 0.000 claims description 2
• 208000032839 leukemia Diseases 0.000 claims description 2
• 201000001441 melanoma Diseases 0.000 claims description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
• 208000025113 myeloid leukemia Diseases 0.000 claims description 2
• 206010041823 squamous cell carcinoma Diseases 0.000 claims description 2
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 2
• 125000005053 dihydropyrimidinyl group Chemical group N1(CN=CC=C1)* 0.000 claims 2
• 125000002883 imidazolyl group Chemical group 0.000 claims 2
• 125000000842 isoxazolyl group Chemical group 0.000 claims 2
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
• 206010067639 Genital swelling Diseases 0.000 claims 1
• 208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 claims 1
• 201000007241 cutaneous T cell lymphoma Diseases 0.000 claims 1
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
• 201000005962 mycosis fungoides Diseases 0.000 claims 1
• 208000025638 primary cutaneous T-cell non-Hodgkin lymphoma Diseases 0.000 claims 1
• 238000012163 sequencing technique Methods 0.000 claims 1
• 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
• 238000000034 method Methods 0.000 abstract description 19
• 239000000543 intermediate Substances 0.000 abstract description 18
• 108060008682 Tumor Necrosis Factor Proteins 0.000 abstract description 12
• 238000002360 preparation method Methods 0.000 abstract description 11
• 230000028993 immune response Effects 0.000 abstract description 10
• 102000003390 tumor necrosis factor Human genes 0.000 abstract description 9
• 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
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 465
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 192
• 229910052757 nitrogen Inorganic materials 0.000 description 183
• 239000011541 reaction mixture Substances 0.000 description 144
• 239000007787 solid Substances 0.000 description 112
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 92
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 91
• 238000002844 melting Methods 0.000 description 86
• 230000008018 melting Effects 0.000 description 86
• 239000000243 solution Substances 0.000 description 84
• 238000006243 chemical reaction Methods 0.000 description 81
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 64
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 62
• 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
• 239000000203 mixture Substances 0.000 description 53
• 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
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 45
• 235000019341 magnesium sulphate Nutrition 0.000 description 45
• 239000000741 silica gel Substances 0.000 description 45
• 229910002027 silica gel Inorganic materials 0.000 description 45
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 40
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 38
• 239000010410 layer Substances 0.000 description 38
• 238000001914 filtration Methods 0.000 description 36
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 35
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
• 238000007429 general method Methods 0.000 description 34
• 238000010992 reflux Methods 0.000 description 34
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 32
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 30
• 239000000047 product Substances 0.000 description 29
• 239000003921 oil Substances 0.000 description 27
• 235000019198 oils Nutrition 0.000 description 27
• 239000002244 precipitate Substances 0.000 description 27
• 239000002904 solvent Substances 0.000 description 27
• 239000000463 material Substances 0.000 description 26
• 239000000843 powder Substances 0.000 description 25
• 238000004809 thin layer chromatography Methods 0.000 description 25
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
• 239000000725 suspension Substances 0.000 description 24
• 239000003054 catalyst Substances 0.000 description 23
• 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
• 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
• 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
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 17
• 235000011114 ammonium hydroxide Nutrition 0.000 description 17
• 230000003197 catalytic effect Effects 0.000 description 17
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 17
• 235000017557 sodium bicarbonate Nutrition 0.000 description 17
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 16
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
• 238000007796 conventional method Methods 0.000 description 15
• 238000010438 heat treatment Methods 0.000 description 15
• FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 14
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 14
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
• 241001465754 Metazoa Species 0.000 description 14
• 239000012267 brine Substances 0.000 description 14
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 14
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
• 239000002253 acid Substances 0.000 description 13
• 238000004458 analytical method Methods 0.000 description 13
• 239000012044 organic layer Substances 0.000 description 13
• MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 13
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 13
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 12
• 150000001412 amines Chemical class 0.000 description 12
• PHFKUTFUFKZJMV-UHFFFAOYSA-N 1,7-naphthyridin-4-amine Chemical compound N1=CC=C2C(N)=CC=NC2=C1 PHFKUTFUFKZJMV-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 11
• 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
• 210000004027 cell Anatomy 0.000 description 11
• 239000003795 chemical substances by application Substances 0.000 description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
• 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 11
• 201000010099 disease Diseases 0.000 description 10
• 229910003446 platinum oxide Inorganic materials 0.000 description 10
• 230000003612 virological effect Effects 0.000 description 10
• 238000000354 decomposition reaction Methods 0.000 description 9
• 239000005457 ice water Substances 0.000 description 9
• 230000006698 induction Effects 0.000 description 9
• 238000004949 mass spectrometry Methods 0.000 description 9
• HGYRIIKTLQUTMA-UHFFFAOYSA-N 2-butyl-3H-imidazo[4,5-c][1,5]naphthyridin-4-amine Chemical compound NC1=NC=2C=CC=NC=2C2=C1N=C(N2)CCCC HGYRIIKTLQUTMA-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
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• 239000002027 dichloromethane extract Substances 0.000 description 8
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 8
• 239000002609 medium Substances 0.000 description 8
• XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 8
• 238000012360 testing method Methods 0.000 description 8
• 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 7
• IRUNKQSGDBYUDC-UHFFFAOYSA-N diethoxymethyl acetate Chemical compound CCOC(OCC)OC(C)=O IRUNKQSGDBYUDC-UHFFFAOYSA-N 0.000 description 7
• 230000005484 gravity Effects 0.000 description 7
• 238000004519 manufacturing process Methods 0.000 description 7
• 239000007858 starting material Substances 0.000 description 7
• KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 6
• BPZZDZZOBAZEPJ-UHFFFAOYSA-N 3-nitro-1h-1,5-naphthyridin-4-one Chemical compound C1=CN=C2C(O)=C([N+]([O-])=O)C=NC2=C1 BPZZDZZOBAZEPJ-UHFFFAOYSA-N 0.000 description 6
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-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
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
• 208000036142 Viral infection Diseases 0.000 description 6
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 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
• 230000000694 effects Effects 0.000 description 6
• 239000000284 extract Substances 0.000 description 6
• 239000012442 inert solvent Substances 0.000 description 6
• 239000012948 isocyanate Substances 0.000 description 6
• 229910017604 nitric acid Inorganic materials 0.000 description 6
• 239000012299 nitrogen atmosphere Substances 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 230000009385 viral infection Effects 0.000 description 6
• XUXVVQKJULMMKX-UHFFFAOYSA-N 1,1,1-trimethoxypentane Chemical compound CCCCC(OC)(OC)OC XUXVVQKJULMMKX-UHFFFAOYSA-N 0.000 description 5
• GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical class ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 description 5
• 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 5
• 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 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
• 0 CCCCC(*(CC(C)C)C1=C2C(*3)=C*C=C2)=C(C2)[C@]2CC1=C3*(I)=* Chemical compound CCCCC(*(CC(C)C)C1=C2C(*3)=C*C=C2)=C(C2)[C@]2CC1=C3*(I)=* 0.000 description 5
• 102000006992 Interferon-alpha Human genes 0.000 description 5
• 108010047761 Interferon-alpha Proteins 0.000 description 5
• 241000700605 Viruses Species 0.000 description 5
• 239000012230 colorless oil Substances 0.000 description 5
• 238000004440 column chromatography Methods 0.000 description 5
• 238000001816 cooling Methods 0.000 description 5
• 201000002491 encephalomyelitis Diseases 0.000 description 5
• 238000004128 high performance liquid chromatography Methods 0.000 description 5
• 150000002513 isocyanates Chemical class 0.000 description 5
• PEJBARJFGXOAIR-UHFFFAOYSA-N n-(2-methylpropyl)-3-nitro-1,5-naphthyridin-4-amine Chemical compound C1=CN=C2C(NCC(C)C)=C([N+]([O-])=O)C=NC2=C1 PEJBARJFGXOAIR-UHFFFAOYSA-N 0.000 description 5
• 238000011002 quantification Methods 0.000 description 5
• 230000009467 reduction Effects 0.000 description 5
• 239000000126 substance Substances 0.000 description 5
• 229940086542 triethylamine Drugs 0.000 description 5
• VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 4
• 125000004866 1,1-dimethylethylcarbonyl group Chemical group CC(C)(C(=O)*)C 0.000 description 4
• FPMFWNDLLWUVEH-UHFFFAOYSA-N 1,8-naphthyridin-4-amine Chemical compound C1=CC=C2C(N)=CC=NC2=N1 FPMFWNDLLWUVEH-UHFFFAOYSA-N 0.000 description 4
• 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 4
• ISZNKHPDTSCLJP-UHFFFAOYSA-N 5-(2-methylpropyl)-4-nitro-1H-tetrazolo[1,5-a][1,8]naphthyridin-5-amine Chemical compound CC(CC1(C(=C2N(C3=NC=CC=C13)NN=N2)[N+](=O)[O-])N)C ISZNKHPDTSCLJP-UHFFFAOYSA-N 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• HTMFCWPGVBRCEL-UHFFFAOYSA-N CC(CC1(C(=C2N(C3=NC=CC=C13)NN=N2)N)N)C Chemical compound CC(CC1(C(=C2N(C3=NC=CC=C13)NN=N2)N)N)C HTMFCWPGVBRCEL-UHFFFAOYSA-N 0.000 description 4
• PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 description 4
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
• 206010028980 Neoplasm Diseases 0.000 description 4
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
• 210000004369 blood Anatomy 0.000 description 4
• 239000008280 blood Substances 0.000 description 4
• 210000000601 blood cell Anatomy 0.000 description 4
• 230000000120 cytopathologic effect Effects 0.000 description 4
• 238000010828 elution Methods 0.000 description 4
• 229910052700 potassium Inorganic materials 0.000 description 4
• 239000011591 potassium Substances 0.000 description 4
• 230000002250 progressing effect Effects 0.000 description 4
• 229920005989 resin Polymers 0.000 description 4
• 239000011347 resin Substances 0.000 description 4
• 238000003786 synthesis reaction Methods 0.000 description 4
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
• WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
• 239000008096 xylene Substances 0.000 description 4
• MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 3
• 125000004747 1,1-dimethylethoxycarbonyl group Chemical group CC(C)(OC(=O)*)C 0.000 description 3
• OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
• BVBRKAGVHZKDHN-UHFFFAOYSA-N 1-(2-benzyl-2h-1,5-naphthyridin-1-yl)-2-methylpropan-2-ol Chemical compound C1=CC2=NC=CC=C2N(CC(C)(O)C)C1CC1=CC=CC=C1 BVBRKAGVHZKDHN-UHFFFAOYSA-N 0.000 description 3
• 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 3
• NSBWNRLMZCPZDQ-UHFFFAOYSA-N 1-[(3-amino-1,5-naphthyridin-4-yl)amino]-2-methylpropan-2-ol Chemical compound C1=CN=C2C(NCC(C)(O)C)=C(N)C=NC2=C1 NSBWNRLMZCPZDQ-UHFFFAOYSA-N 0.000 description 3
• KMHROXXCHDOGPR-UHFFFAOYSA-N 1-chloro-7-nitro-2h-1,5-naphthyridine Chemical compound C1=CCN(Cl)C2=CC([N+](=O)[O-])=CN=C21 KMHROXXCHDOGPR-UHFFFAOYSA-N 0.000 description 3
• RMFSFKGHOJGVIS-UHFFFAOYSA-N 2-(5-methyltetrazol-1-yl)pyridine-3-carboxylic acid Chemical compound CC1=NN=NN1C1=NC=CC=C1C(O)=O RMFSFKGHOJGVIS-UHFFFAOYSA-N 0.000 description 3
• KPIVDNYJNOPGBE-UHFFFAOYSA-N 2-aminonicotinic acid Chemical class NC1=NC=CC=C1C(O)=O KPIVDNYJNOPGBE-UHFFFAOYSA-N 0.000 description 3
• FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 3
• NGFASMKCGPFSKL-UHFFFAOYSA-N 2-methyl-1-(2-methylpropyl)imidazo[4,5-c][1,7]naphthyridin-4-amine Chemical compound C1=NC=CC2=C3N(CC(C)C)C(C)=NC3=C(N)N=C21 NGFASMKCGPFSKL-UHFFFAOYSA-N 0.000 description 3
• HMBBEVMGBHTFAV-UHFFFAOYSA-N 2-methyl-1-[(3-nitro-1,5-naphthyridin-4-yl)amino]propan-2-ol Chemical compound C1=CN=C2C(NCC(C)(O)C)=C([N+]([O-])=O)C=NC2=C1 HMBBEVMGBHTFAV-UHFFFAOYSA-N 0.000 description 3
• BGKRAURDUSXPJA-UHFFFAOYSA-N 3-nitro-n-(2-phenoxyethyl)-1,5-naphthyridin-4-amine Chemical compound [O-][N+](=O)C1=CN=C2C=CC=NC2=C1NCCOC1=CC=CC=C1 BGKRAURDUSXPJA-UHFFFAOYSA-N 0.000 description 3
• BSPFJSMHIAIXQW-UHFFFAOYSA-N 4-n-(2-methylpropyl)-1,5-naphthyridine-3,4-diamine Chemical compound C1=CN=C2C(NCC(C)C)=C(N)C=NC2=C1 BSPFJSMHIAIXQW-UHFFFAOYSA-N 0.000 description 3
• NACQOSQIBYXWLO-UHFFFAOYSA-N 4-n-(3-propan-2-yloxypropyl)-1,5-naphthyridine-3,4-diamine Chemical compound C1=CN=C2C(NCCCOC(C)C)=C(N)C=NC2=C1 NACQOSQIBYXWLO-UHFFFAOYSA-N 0.000 description 3
• KLQPYZBQTQCRGX-UHFFFAOYSA-N 5-chlorotetrazolo[1,5-a][1,7]naphthyridine Chemical compound N1=CC=C2C(Cl)=CC3=NN=NN3C2=C1 KLQPYZBQTQCRGX-UHFFFAOYSA-N 0.000 description 3
• RDKBGEUBCVGHKL-UHFFFAOYSA-N C1=CC=C2C(O)=C([N+]([O-])=O)C3=NN=NN3C2=N1 Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C3=NN=NN3C2=N1 RDKBGEUBCVGHKL-UHFFFAOYSA-N 0.000 description 3
• WMGVTQKSSVZODJ-UHFFFAOYSA-N CC(CC1(C(=C2N(C3=CN=CC=C13)NN=N2)N)N)C Chemical compound CC(CC1(C(=C2N(C3=CN=CC=C13)NN=N2)N)N)C WMGVTQKSSVZODJ-UHFFFAOYSA-N 0.000 description 3
• KETATWAOIHTGRE-UHFFFAOYSA-N CC(CN1C(C=CC2=NC=CC=C12)CCCC)(O)C Chemical compound CC(CN1C(C=CC2=NC=CC=C12)CCCC)(O)C KETATWAOIHTGRE-UHFFFAOYSA-N 0.000 description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
• NYXMAZJXRJFLOH-UHFFFAOYSA-N N1=CC=C2C(O)=CC3=NN=NN3C2=C1 Chemical compound N1=CC=C2C(O)=CC3=NN=NN3C2=C1 NYXMAZJXRJFLOH-UHFFFAOYSA-N 0.000 description 3
• 210000001744 T-lymphocyte Anatomy 0.000 description 3
• 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 3
• 150000004703 alkoxides Chemical class 0.000 description 3
• 229910052782 aluminium Inorganic materials 0.000 description 3
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
• 150000001408 amides Chemical class 0.000 description 3
• 239000006227 byproduct Substances 0.000 description 3
• 125000004432 carbon atom Chemical group C* 0.000 description 3
• 150000001793 charged compounds Chemical class 0.000 description 3
• 239000012320 chlorinating reagent Substances 0.000 description 3
• 230000001143 conditioned effect Effects 0.000 description 3
• 239000012043 crude product Substances 0.000 description 3
• 229940117389 dichlorobenzene Drugs 0.000 description 3
• 239000003480 eluent Substances 0.000 description 3
• TWSXTXIKUVDTET-UHFFFAOYSA-N ethyl 2-(5-methyltetrazol-1-yl)pyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC=CN=C1N1C(C)=NN=N1 TWSXTXIKUVDTET-UHFFFAOYSA-N 0.000 description 3
• ABXBSVKCTZCZAG-UHFFFAOYSA-N ethyl 3-(5-methyltetrazol-1-yl)pyridine-4-carboxylate Chemical compound CCOC(=O)C1=CC=NC=C1N1C(C)=NN=N1 ABXBSVKCTZCZAG-UHFFFAOYSA-N 0.000 description 3
• 239000011888 foil Substances 0.000 description 3
• 125000000524 functional group Chemical group 0.000 description 3
• 150000004820 halides Chemical class 0.000 description 3
• 230000007062 hydrolysis Effects 0.000 description 3
• 238000006460 hydrolysis reaction Methods 0.000 description 3
• 239000002955 immunomodulating agent Substances 0.000 description 3
• 229940121354 immunomodulator Drugs 0.000 description 3
• 238000011534 incubation Methods 0.000 description 3
• HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 3
• WKASZCYKAHCWPM-UHFFFAOYSA-N n-(2-methylpropyl)tetrazolo[1,5-a][1,7]naphthyridin-5-amine Chemical compound N1=CC=C2C(NCC(C)C)=CC3=NN=NN3C2=C1 WKASZCYKAHCWPM-UHFFFAOYSA-N 0.000 description 3
• AVOWLFVANBADTR-UHFFFAOYSA-N n-(3-butoxypropyl)-3-nitro-1,5-naphthyridin-4-amine Chemical compound C1=CN=C2C(NCCCOCCCC)=C([N+]([O-])=O)C=NC2=C1 AVOWLFVANBADTR-UHFFFAOYSA-N 0.000 description 3
• CTOMEIHIBBVOSE-UHFFFAOYSA-N n-benzyl-3-nitro-1,5-naphthyridin-4-amine Chemical compound [O-][N+](=O)C1=CN=C2C=CC=NC2=C1NCC1=CC=CC=C1 CTOMEIHIBBVOSE-UHFFFAOYSA-N 0.000 description 3
• MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
• 150000002905 orthoesters Chemical class 0.000 description 3
• 239000002245 particle Substances 0.000 description 3
• 239000011148 porous material Substances 0.000 description 3
• 229910000027 potassium carbonate Inorganic materials 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• HBADLRJMWQITCI-UHFFFAOYSA-N tert-butyl n-[2-[(3-amino-1,5-naphthyridin-4-yl)amino]ethyl]carbamate Chemical compound C1=CN=C2C(NCCNC(=O)OC(C)(C)C)=C(N)C=NC2=C1 HBADLRJMWQITCI-UHFFFAOYSA-N 0.000 description 3
• 201000008827 tuberculosis Diseases 0.000 description 3
• BWKAYBPLDRWMCJ-UHFFFAOYSA-N 1,1-diethoxy-n,n-dimethylmethanamine Chemical compound CCOC(N(C)C)OCC BWKAYBPLDRWMCJ-UHFFFAOYSA-N 0.000 description 2
• KFAJXZVDBVRZRC-UHFFFAOYSA-N 1,5-naphthyridin-4-amine Chemical compound C1=CN=C2C(N)=CC=NC2=C1 KFAJXZVDBVRZRC-UHFFFAOYSA-N 0.000 description 2
• MIDQVYLLSDOPIL-UHFFFAOYSA-N 1,5-naphthyridine-3,4-diamine Chemical compound C1=CC=NC2=C(N)C(N)=CN=C21 MIDQVYLLSDOPIL-UHFFFAOYSA-N 0.000 description 2
• 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 2
• UCPMSMNKGXUFCC-UHFFFAOYSA-N 1-(2-methylpropyl)imidazo[4,5-c][1,5]naphthyridin-4-amine Chemical compound C1=CC=NC2=C3N(CC(C)C)C=NC3=C(N)N=C21 UCPMSMNKGXUFCC-UHFFFAOYSA-N 0.000 description 2
• 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 2
• DUPLWUHVMVNESI-UHFFFAOYSA-N 1-(2-methylpropyl)imidazo[4,5-c][1,7]naphthyridin-4-amine Chemical compound C1=NC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DUPLWUHVMVNESI-UHFFFAOYSA-N 0.000 description 2
• LRTBNVRJDCCDCF-UHFFFAOYSA-N 1-benzyl-2-(ethoxymethyl)imidazo[4,5-c][1,5]naphthyridin-4-amine Chemical compound CCOCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CC1=CC=CC=C1 LRTBNVRJDCCDCF-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 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 2
• TZDMCKHDYUDRMB-UHFFFAOYSA-N 2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetic acid Chemical compound CC1=CN(CC(O)=O)C(=O)NC1=O TZDMCKHDYUDRMB-UHFFFAOYSA-N 0.000 description 2
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
• JPRWNUUKSJXRRK-UHFFFAOYSA-N 2-butyl-1-(2-methylpropyl)-6,7,8,9-tetrahydroimidazo[4,5-c][1,7]naphthyridin-4-amine Chemical compound C1NCCC2=C(N(C(CCCC)=N3)CC(C)C)C3=C(N)N=C21 JPRWNUUKSJXRRK-UHFFFAOYSA-N 0.000 description 2
• RPPZIQGNJARTFR-UHFFFAOYSA-N 2-butyl-1-(2-methylpropyl)-6,7,8,9-tetrahydroimidazo[4,5-c][1,8]naphthyridin-4-amine Chemical compound N1CCCC2=C(N(C(CCCC)=N3)CC(C)C)C3=C(N)N=C21 RPPZIQGNJARTFR-UHFFFAOYSA-N 0.000 description 2
• OQVONIYULORIOW-UHFFFAOYSA-N 2-butyl-1-(2-methylpropyl)imidazo[4,5-c][1,5]naphthyridin-4-amine Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CC(C)C)C3=C(N)N=C21 OQVONIYULORIOW-UHFFFAOYSA-N 0.000 description 2
• KPGOIOHDLTXDKJ-UHFFFAOYSA-N 2-butyl-1-(2-methylpropyl)imidazo[4,5-c][1,5]naphthyridine Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CC(C)C)C3=CN=C21 KPGOIOHDLTXDKJ-UHFFFAOYSA-N 0.000 description 2
• UPEZASYXNFGIBH-UHFFFAOYSA-N 2-butyl-1-(2-methylpropyl)imidazo[4,5-c][1,7]naphthyridin-4-amine Chemical compound C1=NC=CC2=C(N(C(CCCC)=N3)CC(C)C)C3=C(N)N=C21 UPEZASYXNFGIBH-UHFFFAOYSA-N 0.000 description 2
• XHIVHQOGWNVIKO-UHFFFAOYSA-N 2-butyl-1-(2-methylpropyl)imidazo[4,5-c][1,8]naphthyridin-4-amine Chemical compound N1=CC=CC2=C(N(C(CCCC)=N3)CC(C)C)C3=C(N)N=C21 XHIVHQOGWNVIKO-UHFFFAOYSA-N 0.000 description 2
• WZYYHTKEBYRGEZ-UHFFFAOYSA-N 2-butyl-1-(2-phenoxyethyl)imidazo[4,5-c][1,5]naphthyridine Chemical compound CCCCC1=NC2=CN=C3C=CC=NC3=C2N1CCOC1=CC=CC=C1 WZYYHTKEBYRGEZ-UHFFFAOYSA-N 0.000 description 2
• VQHSDXHNLUMCFA-UHFFFAOYSA-N 2-butyl-1-(3-propan-2-yloxypropyl)imidazo[4,5-c][1,5]naphthyridine Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CCCOC(C)C)C3=CN=C21 VQHSDXHNLUMCFA-UHFFFAOYSA-N 0.000 description 2
• LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
• VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 2
• BIGVMITVYSKPHR-UHFFFAOYSA-N 3-(5-methyltetrazol-1-yl)pyridine-4-carboxylic acid Chemical compound CC1=NN=NN1C1=CN=CC=C1C(O)=O BIGVMITVYSKPHR-UHFFFAOYSA-N 0.000 description 2
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
• FYEQKMAVRYRMBL-UHFFFAOYSA-N 3-aminopyridine-4-carboxylic acid Chemical compound NC1=CN=CC=C1C(O)=O FYEQKMAVRYRMBL-UHFFFAOYSA-N 0.000 description 2
• HFULIQZCEBYHHA-UHFFFAOYSA-N 3-nitro-1,5-naphthyridin-4-amine Chemical compound C1=CN=C2C(N)=C([N+]([O-])=O)C=NC2=C1 HFULIQZCEBYHHA-UHFFFAOYSA-N 0.000 description 2
• SXBSNCCBEXBWQL-UHFFFAOYSA-N 3-nitro-n-(3-propan-2-yloxypropyl)-1,5-naphthyridin-4-amine Chemical compound C1=CN=C2C(NCCCOC(C)C)=C([N+]([O-])=O)C=NC2=C1 SXBSNCCBEXBWQL-UHFFFAOYSA-N 0.000 description 2
• NYTAWQCHFDZOQR-UHFFFAOYSA-N 4-n-(2-phenoxyethyl)-1,5-naphthyridine-3,4-diamine Chemical compound NC1=CN=C2C=CC=NC2=C1NCCOC1=CC=CC=C1 NYTAWQCHFDZOQR-UHFFFAOYSA-N 0.000 description 2
• HRYURYZKAIVPOP-UHFFFAOYSA-N 4-n-(3-butoxypropyl)-1,5-naphthyridine-3,4-diamine Chemical compound C1=CN=C2C(NCCCOCCCC)=C(N)C=NC2=C1 HRYURYZKAIVPOP-UHFFFAOYSA-N 0.000 description 2
• FXRNYXRWMUFBSD-UHFFFAOYSA-N 5-chlorotetrazolo[1,5-a][1,8]naphthyridine Chemical compound C1=CC=C2C(Cl)=CC3=NN=NN3C2=N1 FXRNYXRWMUFBSD-UHFFFAOYSA-N 0.000 description 2
• ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 2
• 239000005711 Benzoic acid Substances 0.000 description 2
• QHHPCNDWJPGOFP-UHFFFAOYSA-N CC(CN1C(C=C(C2=NC=CC=C12)N)CCCC)(O)C Chemical compound CC(CN1C(C=C(C2=NC=CC=C12)N)CCCC)(O)C QHHPCNDWJPGOFP-UHFFFAOYSA-N 0.000 description 2
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
• 108010002352 Interleukin-1 Proteins 0.000 description 2
• 102000000589 Interleukin-1 Human genes 0.000 description 2
• 108010063738 Interleukins Proteins 0.000 description 2
• 102000015696 Interleukins Human genes 0.000 description 2
• ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
• 229930182816 L-glutamine Natural products 0.000 description 2
• 206010058467 Lung neoplasm malignant Diseases 0.000 description 2
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
• 208000031888 Mycoses Diseases 0.000 description 2
• BKGKDVXHKALOSR-UHFFFAOYSA-N N-[2-(dimethylamino)ethoxy-phenylmethyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NC(C1=CC=CC=C1)OCCN(C)C BKGKDVXHKALOSR-UHFFFAOYSA-N 0.000 description 2
• DVEZWJCEXOZQAL-UHFFFAOYSA-N N=1C=NC2=C(NC=3C=CC=NC3C21)N Chemical compound N=1C=NC2=C(NC=3C=CC=NC3C21)N DVEZWJCEXOZQAL-UHFFFAOYSA-N 0.000 description 2
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
• 229930182555 Penicillin Natural products 0.000 description 2
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
• 239000012980 RPMI-1640 medium Substances 0.000 description 2
• QTENRWWVYAAPBI-YZTFXSNBSA-N Streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@H]1[C@H](N=C(N)N)[C@@H](O)[C@H](N=C(N)N)[C@@H](O)[C@@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@H]1[C@H](N=C(N)N)[C@@H](O)[C@H](N=C(N)N)[C@@H](O)[C@@H]1O QTENRWWVYAAPBI-YZTFXSNBSA-N 0.000 description 2
• 150000001266 acyl halides Chemical class 0.000 description 2
• YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 2
• 229910021529 ammonia Inorganic materials 0.000 description 2
• 239000001099 ammonium carbonate Substances 0.000 description 2
• 239000008346 aqueous phase Substances 0.000 description 2
• 239000012298 atmosphere Substances 0.000 description 2
• CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 2
• 210000003719 b-lymphocyte Anatomy 0.000 description 2
• CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
• 235000010233 benzoic acid Nutrition 0.000 description 2
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
• 238000004166 bioassay Methods 0.000 description 2
• 238000004364 calculation method Methods 0.000 description 2
• 239000001569 carbon dioxide Substances 0.000 description 2
• 229910002092 carbon dioxide Inorganic materials 0.000 description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
• 238000004132 cross linking Methods 0.000 description 2
• 210000004748 cultured cell Anatomy 0.000 description 2
• 230000032050 esterification Effects 0.000 description 2
• 238000005886 esterification reaction Methods 0.000 description 2
• 238000009472 formulation Methods 0.000 description 2
• 125000005842 heteroatom Chemical group 0.000 description 2
• 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 2
• ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 description 2
• 210000005260 human cell Anatomy 0.000 description 2
• NSHFLKZNBPJNPA-UHFFFAOYSA-N imidazo[4,5-c]quinolin-2-one Chemical class C1=CC=C2C3=NC(=O)N=C3C=NC2=C1 NSHFLKZNBPJNPA-UHFFFAOYSA-N 0.000 description 2
• 238000000338 in vitro Methods 0.000 description 2
• 238000002347 injection Methods 0.000 description 2
• 239000007924 injection Substances 0.000 description 2
• 239000002054 inoculum Substances 0.000 description 2
• 229940047124 interferons Drugs 0.000 description 2
• 229940047122 interleukins Drugs 0.000 description 2
• 238000002955 isolation Methods 0.000 description 2
• 210000000265 leukocyte Anatomy 0.000 description 2
• 201000005296 lung carcinoma Diseases 0.000 description 2
• 210000002540 macrophage Anatomy 0.000 description 2
• 238000005259 measurement Methods 0.000 description 2
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 2
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
• ZNBIZPXNJOMSFQ-UHFFFAOYSA-N methyl 4-[hydroxy(phenyl)methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(O)C1=CC=CC=C1 ZNBIZPXNJOMSFQ-UHFFFAOYSA-N 0.000 description 2
• FWOBKHVPUNKFMI-UHFFFAOYSA-N n-(2-methylpropyl)-4-nitrotetrazolo[1,5-a][1,7]naphthyridin-5-amine Chemical compound N1=CC=C2C(NCC(C)C)=C([N+]([O-])=O)C3=NN=NN3C2=C1 FWOBKHVPUNKFMI-UHFFFAOYSA-N 0.000 description 2
• QJZFCQPRSYMNCQ-UHFFFAOYSA-N n-[4-(benzylamino)-1,5-naphthyridin-3-yl]-2-ethoxyacetamide;hydrochloride Chemical compound Cl.CCOCC(=O)NC1=CN=C2C=CC=NC2=C1NCC1=CC=CC=C1 QJZFCQPRSYMNCQ-UHFFFAOYSA-N 0.000 description 2
• OHDXDNUPVVYWOV-UHFFFAOYSA-N n-methyl-1-(2-naphthalen-1-ylsulfanylphenyl)methanamine Chemical compound CNCC1=CC=CC=C1SC1=CC=CC2=CC=CC=C12 OHDXDNUPVVYWOV-UHFFFAOYSA-N 0.000 description 2
• 230000000802 nitrating effect Effects 0.000 description 2
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
• KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
• 230000003647 oxidation Effects 0.000 description 2
• 238000007254 oxidation reaction Methods 0.000 description 2
• 229910052760 oxygen Inorganic materials 0.000 description 2
• 229940049954 penicillin Drugs 0.000 description 2
• XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 description 2
• 239000012071 phase Substances 0.000 description 2
• 239000004033 plastic Substances 0.000 description 2
• 229920005990 polystyrene resin Polymers 0.000 description 2
• 150000003141 primary amines Chemical class 0.000 description 2
• 230000004044 response Effects 0.000 description 2
• 238000004007 reversed phase HPLC Methods 0.000 description 2
• 210000002966 serum Anatomy 0.000 description 2
• 229910000029 sodium carbonate Inorganic materials 0.000 description 2
• HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 2
• 239000011973 solid acid Substances 0.000 description 2
• 238000010186 staining Methods 0.000 description 2
• 229910052717 sulfur Inorganic materials 0.000 description 2
• 239000006188 syrup Substances 0.000 description 2
• 235000020357 syrup Nutrition 0.000 description 2
• 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 2
• AOCSUUGBCMTKJH-UHFFFAOYSA-N tert-butyl n-(2-aminoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCN AOCSUUGBCMTKJH-UHFFFAOYSA-N 0.000 description 2
• VUQORGLMHLIGFY-UHFFFAOYSA-N tert-butyl n-[2-[(3-nitro-1,5-naphthyridin-4-yl)amino]ethyl]carbamate Chemical compound C1=CN=C2C(NCCNC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=NC2=C1 VUQORGLMHLIGFY-UHFFFAOYSA-N 0.000 description 2
• HBOOVKROVITRDE-UHFFFAOYSA-N tert-butyl n-[4-[(3-amino-1,5-naphthyridin-4-yl)amino]butyl]carbamate Chemical compound C1=CN=C2C(NCCCCNC(=O)OC(C)(C)C)=C(N)C=NC2=C1 HBOOVKROVITRDE-UHFFFAOYSA-N 0.000 description 2
• DTDCSSCKPBHWCA-UHFFFAOYSA-N tert-butyl n-[4-[(3-nitro-1,5-naphthyridin-4-yl)amino]butyl]carbamate Chemical compound C1=CN=C2C(NCCCCNC(=O)OC(C)(C)C)=C([N+]([O-])=O)C=NC2=C1 DTDCSSCKPBHWCA-UHFFFAOYSA-N 0.000 description 2
• 150000003512 tertiary amines Chemical class 0.000 description 2
• 238000010998 test method Methods 0.000 description 2
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
• 238000003260 vortexing Methods 0.000 description 2
• IIQILDHAOYRQRT-UHFFFAOYSA-N (4-methylphenyl)sulfonyl 4-methylbenzenesulfonate;hydrate Chemical compound O.C1=CC(C)=CC=C1S(=O)(=O)OS(=O)(=O)C1=CC=C(C)C=C1 IIQILDHAOYRQRT-UHFFFAOYSA-N 0.000 description 1
• AUTOLBMXDDTRRT-JGVFFNPUSA-N (4R,5S)-dethiobiotin Chemical compound C[C@@H]1NC(=O)N[C@@H]1CCCCCC(O)=O AUTOLBMXDDTRRT-JGVFFNPUSA-N 0.000 description 1
• QVADRSWDTZDDGR-VKHMYHEASA-N (S)-alpha-hydroxyglutaric acid-gamma-lactone Chemical compound OC(=O)[C@@H]1CCC(=O)O1 QVADRSWDTZDDGR-VKHMYHEASA-N 0.000 description 1
• FJKAXTTTWIHSDM-QPJJXVBHSA-N (e)-n-[2-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]but-2-enamide Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CCNC(=O)\C=C\C)C3=C(N)N=C21 FJKAXTTTWIHSDM-QPJJXVBHSA-N 0.000 description 1
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
• VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 1
• FVLLRUVQRRMQTI-UHFFFAOYSA-N 1,7-naphthyridin-5-amine Chemical compound C1=CC=C2C(N)=CN=CC2=N1 FVLLRUVQRRMQTI-UHFFFAOYSA-N 0.000 description 1
• MXBVNILGVJVVMH-UHFFFAOYSA-N 1,7-naphthyridine Chemical compound C1=NC=CC2=CC=CN=C21 MXBVNILGVJVVMH-UHFFFAOYSA-N 0.000 description 1
• BDCFMIICEGFLRO-UHFFFAOYSA-N 1-(2-methylpropyl)-6,7,8,9-tetrahydroimidazo[4,5-c][1,5]naphthyridin-4-amine Chemical compound C1CCNC2=C3N(CC(C)C)C=NC3=C(N)N=C21 BDCFMIICEGFLRO-UHFFFAOYSA-N 0.000 description 1
• JKVGLMNJBSNQMA-UHFFFAOYSA-N 1-(2-methylpropyl)-6,7,8,9-tetrahydroimidazo[4,5-c][1,7]naphthyridin-4-amine Chemical compound C1NCCC2=C3N(CC(C)C)C=NC3=C(N)N=C21 JKVGLMNJBSNQMA-UHFFFAOYSA-N 0.000 description 1
• HKSNTMPGCZLSAJ-UHFFFAOYSA-N 1-(2-methylpropyl)-6,7,8,9-tetrahydroimidazo[4,5-c][1,8]naphthyridin-4-amine Chemical compound N1CCCC2=C3N(CC(C)C)C=NC3=C(N)N=C21 HKSNTMPGCZLSAJ-UHFFFAOYSA-N 0.000 description 1
• CKZUQDWORWGTAH-UHFFFAOYSA-N 1-(2-methylpropyl)imidazo[4,5-c][1,8]naphthyridin-4-amine;hydrate Chemical compound O.N1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 CKZUQDWORWGTAH-UHFFFAOYSA-N 0.000 description 1
• YJKZDGOMTKOYQK-UHFFFAOYSA-N 1-(2-piperidin-4-ylethyl)imidazo[4,5-c]quinoline Chemical compound C1=NC2=CN=C3C=CC=CC3=C2N1CCC1CCNCC1 YJKZDGOMTKOYQK-UHFFFAOYSA-N 0.000 description 1
• GUGXWAQONJUXCP-UHFFFAOYSA-N 1-(3-butoxypropyl)-2-butylimidazo[4,5-c][1,5]naphthyridin-4-amine Chemical compound C1=CC=NC2=C3N(CCCOCCCC)C(CCCC)=NC3=C(N)N=C21 GUGXWAQONJUXCP-UHFFFAOYSA-N 0.000 description 1
• QIHPJMGAELEBDI-UHFFFAOYSA-N 1-(4-aminobutyl)imidazo[4,5-c][1,5]naphthyridin-4-amine Chemical compound C1=CC=NC2=C3N(CCCCN)C=NC3=C(N)N=C21 QIHPJMGAELEBDI-UHFFFAOYSA-N 0.000 description 1
• HDDNSPWJCZZICL-UHFFFAOYSA-N 1-(6-methoxyquinolin-8-yl)-2-methylimidazo[4,5-c]quinoline Chemical compound N1=CC=CC2=CC(OC)=CC(N3C4=C5C=CC=CC5=NC=C4N=C3C)=C21 HDDNSPWJCZZICL-UHFFFAOYSA-N 0.000 description 1
• CJUHSWCYPAVCHW-UHFFFAOYSA-N 1-[4-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]-2h-quinoline-6-carboxamide Chemical compound C1C=CC2=CC(C(N)=O)=CC=C2N1CCCCN1C2=C3N=CC=CC3=NC(N)=C2N=C1CCCC CJUHSWCYPAVCHW-UHFFFAOYSA-N 0.000 description 1
• LBASQHHLELWFKS-UHFFFAOYSA-N 1-[4-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]-3-benzylurea Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CCCCNC(=O)NCC1=CC=CC=C1 LBASQHHLELWFKS-UHFFFAOYSA-N 0.000 description 1
• RKHPJMXDRRZPGD-UHFFFAOYSA-N 1-[4-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]-3-butylurea Chemical compound C1=CC=NC2=C3N(CCCCNC(=O)NCCCC)C(CCCC)=NC3=C(N)N=C21 RKHPJMXDRRZPGD-UHFFFAOYSA-N 0.000 description 1
• GRGBJCMHYKWROJ-UHFFFAOYSA-N 1-[4-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]-3-cyclohexylurea Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CCCCNC(=O)NC1CCCCC1 GRGBJCMHYKWROJ-UHFFFAOYSA-N 0.000 description 1
• MBFWVQQVFIYYRG-UHFFFAOYSA-N 1-[4-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]-3-phenylurea Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CCCCNC(=O)NC1=CC=CC=C1 MBFWVQQVFIYYRG-UHFFFAOYSA-N 0.000 description 1
• SXHJHHGDOJEWNL-UHFFFAOYSA-N 1-[4-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]-6-morpholin-4-yl-2h-pyridine-3-carboxamide Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CCCCN1CC(C(N)=O)=CC=C1N1CCOCC1 SXHJHHGDOJEWNL-UHFFFAOYSA-N 0.000 description 1
• RMLSLDGDLTUNMS-UHFFFAOYSA-N 2-(2-phenoxyethyl)-1,5-naphthyridine-3,4-diamine Chemical compound NC1=C(N)C2=NC=CC=C2N=C1CCOC1=CC=CC=C1 RMLSLDGDLTUNMS-UHFFFAOYSA-N 0.000 description 1
• DXDGDCBZWVCDHG-UHFFFAOYSA-N 2-amino-n-[2-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-4-methylpentanamide Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CCNC(=O)C(N)CC(C)C)C3=C(N)N=C21 DXDGDCBZWVCDHG-UHFFFAOYSA-N 0.000 description 1
• MZRZAVKRACYKTJ-UHFFFAOYSA-N 2-butyl-1-(2-methylpropyl)-6,7,8,9-tetrahydroimidazo[4,5-c][1,5]naphthyridin-4-amine Chemical compound C1CCNC2=C(N(C(CCCC)=N3)CC(C)C)C3=C(N)N=C21 MZRZAVKRACYKTJ-UHFFFAOYSA-N 0.000 description 1
• TYFMBXUQBGXBTQ-UHFFFAOYSA-N 2-butyl-1-(2-phenoxyethyl)imidazo[4,5-c][1,5]naphthyridin-4-amine Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CCOC1=CC=CC=C1 TYFMBXUQBGXBTQ-UHFFFAOYSA-N 0.000 description 1
• QWRCCBHOAGNVOW-UHFFFAOYSA-N 2-butyl-1-(3-propan-2-yloxypropyl)imidazo[4,5-c][1,5]naphthyridin-4-amine Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CCCOC(C)C)C3=C(N)N=C21 QWRCCBHOAGNVOW-UHFFFAOYSA-N 0.000 description 1
• ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
• GSNFOKGMUXXBNX-UHFFFAOYSA-N 2-ethoxyacetamide;hydrochloride Chemical compound Cl.CCOCC(N)=O GSNFOKGMUXXBNX-UHFFFAOYSA-N 0.000 description 1
• ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 1
• OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 1
• RWYSIZOYCYKXGB-UHFFFAOYSA-N 2-methyl-1-(2-methylpropyl)-6,7,8,9-tetrahydroimidazo[4,5-c][1,7]naphthyridin-4-amine Chemical compound C1NCCC2=C3N(CC(C)C)C(C)=NC3=C(N)N=C21 RWYSIZOYCYKXGB-UHFFFAOYSA-N 0.000 description 1
• ZXBCLVSLRUWISJ-UHFFFAOYSA-N 2-methyl-1-(2-methylpropyl)imidazo[4,5-c][1,5]naphthyridin-4-amine Chemical compound C1=CC=NC2=C3N(CC(C)C)C(C)=NC3=C(N)N=C21 ZXBCLVSLRUWISJ-UHFFFAOYSA-N 0.000 description 1
• 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 1
• JDCQRGZSCOCTKK-UHFFFAOYSA-N 2-methylpyrido[2,3-d][1,3]oxazin-4-one Chemical compound C1=CC=C2C(=O)OC(C)=NC2=N1 JDCQRGZSCOCTKK-UHFFFAOYSA-N 0.000 description 1
• IMLAIXAZMVDRGA-UHFFFAOYSA-N 2-phenoxyethanamine Chemical compound NCCOC1=CC=CC=C1 IMLAIXAZMVDRGA-UHFFFAOYSA-N 0.000 description 1
• PGUPJAPHYIEKLT-UHFFFAOYSA-N 2-pyridin-4-ylsulfanylacetic acid Chemical compound OC(=O)CSC1=CC=NC=C1 PGUPJAPHYIEKLT-UHFFFAOYSA-N 0.000 description 1
• NIEOYUNNKKAQKI-UHFFFAOYSA-N 2-pyrimidin-2-ylsulfanylacetic acid Chemical compound OC(=O)CSC1=NC=CC=N1 NIEOYUNNKKAQKI-UHFFFAOYSA-N 0.000 description 1
• IJEUISLJVBUNRE-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazole-4-carboxylic acid Chemical compound CC1=NOC(C)=C1C(O)=O IJEUISLJVBUNRE-UHFFFAOYSA-N 0.000 description 1
• AIPCSKRJJOUNEM-UHFFFAOYSA-N 3,5-ditert-butyl-4-hydroxybenzoyl chloride Chemical compound CC(C)(C)C1=CC(C(Cl)=O)=CC(C(C)(C)C)=C1O AIPCSKRJJOUNEM-UHFFFAOYSA-N 0.000 description 1
• DWYQVYQPUQINMM-UHFFFAOYSA-N 3-(2-methylpropyl)-2,3,4,5,8,10,15-heptazatetracyclo[10.4.0.02,6.07,11]hexadeca-1(12),4,6,8,10,13,15-heptaene Chemical compound C12=CC=NC=C2N2N(CC(C)C)N=NC2=C2C1=NC=N2 DWYQVYQPUQINMM-UHFFFAOYSA-N 0.000 description 1
• HZVFHZZVBGAISK-UHFFFAOYSA-N 3-(ethyliminomethylideneamino)-n,n-dimethoxypropan-1-amine;hydrochloride Chemical compound Cl.CCN=C=NCCCN(OC)OC HZVFHZZVBGAISK-UHFFFAOYSA-N 0.000 description 1
• LPUBRQWGZPPVBS-UHFFFAOYSA-N 3-butoxypropan-1-amine Chemical compound CCCCOCCCN LPUBRQWGZPPVBS-UHFFFAOYSA-N 0.000 description 1
• BPZIZKUCGNLPTL-UHFFFAOYSA-N 3-butyl-4-(2-methylpropyl)-2h-tetrazole Chemical compound CCCCN1NN=CN1CC(C)C BPZIZKUCGNLPTL-UHFFFAOYSA-N 0.000 description 1
• FVMDYYGIDFPZAX-UHFFFAOYSA-N 3-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=CC(O)=C1 FVMDYYGIDFPZAX-UHFFFAOYSA-N 0.000 description 1
• MFEILWXBDBCWKF-UHFFFAOYSA-N 3-phenylpropanoyl chloride Chemical compound ClC(=O)CCC1=CC=CC=C1 MFEILWXBDBCWKF-UHFFFAOYSA-N 0.000 description 1
• VHYUNSUGCNKWSO-UHFFFAOYSA-N 3-propan-2-yloxypropan-1-amine Chemical compound CC(C)OCCCN VHYUNSUGCNKWSO-UHFFFAOYSA-N 0.000 description 1
• FULSSJUSJYSWAE-UHFFFAOYSA-N 3h-imidazo[4,5-c][1,5]naphthyridin-4-amine Chemical compound NC1=NC2=CC=CN=C2C2=C1N=CN2 FULSSJUSJYSWAE-UHFFFAOYSA-N 0.000 description 1
• 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 1
• YDPJFCNFRRNGPD-UHFFFAOYSA-N 3h-imidazo[4,5-c][1,7]naphthyridin-4-amine Chemical compound NC1=NC2=CN=CC=C2C2=C1N=CN2 YDPJFCNFRRNGPD-UHFFFAOYSA-N 0.000 description 1
• KGEGVJJFFQXJTG-UHFFFAOYSA-N 3h-imidazo[4,5-c][1,8]naphthyridin-4-amine Chemical compound NC1=NC2=NC=CC=C2C2=C1N=CN2 KGEGVJJFFQXJTG-UHFFFAOYSA-N 0.000 description 1
• 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 1
• RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical group C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 description 1
• KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
• IFQUPKAISSPFTE-UHFFFAOYSA-N 4-benzoylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)C1=CC=CC=C1 IFQUPKAISSPFTE-UHFFFAOYSA-N 0.000 description 1
• XLTDPMSJFUDVTK-UHFFFAOYSA-N 4-butyl-5-(2-methylpropyl)-2,3,4,5,8,10,16-heptazatetracyclo[10.4.0.02,6.07,11]hexadeca-1(12),6,8,10,13,15-hexaene Chemical compound C12=CC=CN=C2N2NN(CCCC)N(CC(C)C)C2=C2C1=NC=N2 XLTDPMSJFUDVTK-UHFFFAOYSA-N 0.000 description 1
• BHTHYWZAOOGGMJ-UHFFFAOYSA-N 4-imidazo[4,5-c][1,5]naphthyridin-1-ylbutan-1-amine Chemical compound C1=CC=NC2=C3N(CCCCN)C=NC3=CN=C21 BHTHYWZAOOGGMJ-UHFFFAOYSA-N 0.000 description 1
• AHIQCNDMKDZKGY-UHFFFAOYSA-N 4-methyl-3-(2-methylpropyl)-2,3,4,5,8,10,15-heptazatetracyclo[10.4.0.02,6.07,11]hexadeca-1(12),6,8,10,13,15-hexaene Chemical compound N1=CC=C2C3=NC=NC3=C3NN(C)N(CC(C)C)N3C2=C1 AHIQCNDMKDZKGY-UHFFFAOYSA-N 0.000 description 1
• YWZRZEOMKRGIBS-UHFFFAOYSA-N 4-n-(2-methylpropyl)tetrazolo[1,5-a][1,7]naphthyridine-4,5-diamine Chemical compound CC(C)CNC1=C(N)C2=CC=NC=C2N2C1=NN=N2 YWZRZEOMKRGIBS-UHFFFAOYSA-N 0.000 description 1
• BQTHFBTXQQCIJN-UHFFFAOYSA-N 4-nitrotetrazolo[1,5-a][1,8]naphthyridin-5-amine Chemical compound C1=CC=C2C(N)=C([N+]([O-])=O)C3=NN=NN3C2=N1 BQTHFBTXQQCIJN-UHFFFAOYSA-N 0.000 description 1
• ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 1
• PBJUPLPTWVIDAH-UHFFFAOYSA-N 6,7,8,9-tetrahydro-3h-imidazo[4,5-c][1,8]naphthyridin-4-amine Chemical compound N1CCCC2=C1N=C(N)C1=C2NC=N1 PBJUPLPTWVIDAH-UHFFFAOYSA-N 0.000 description 1
• VRCWSYYXUCKEED-UHFFFAOYSA-N 6-Hydroxypicolinic acid Chemical compound OC(=O)C1=CC=CC(=O)N1 VRCWSYYXUCKEED-UHFFFAOYSA-N 0.000 description 1
• XXDSDFLDYNISKD-UHFFFAOYSA-N 6-morpholin-4-ylpyridine-3-carboxylic acid Chemical compound N1=CC(C(=O)O)=CC=C1N1CCOCC1 XXDSDFLDYNISKD-UHFFFAOYSA-N 0.000 description 1
• CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
• 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 1
• FYMYHJWHCPGNMD-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-[4-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]carbamate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1COC(=O)NCCCCN1C2=C3N=CC=CC3=NC(N)=C2N=C1CCCC FYMYHJWHCPGNMD-UHFFFAOYSA-N 0.000 description 1
• 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
• 239000004254 Ammonium phosphate Substances 0.000 description 1
• 206010059313 Anogenital warts Diseases 0.000 description 1
• 241000228212 Aspergillus Species 0.000 description 1
• 206010003645 Atopy Diseases 0.000 description 1
• 208000035143 Bacterial infection Diseases 0.000 description 1
• 241000283690 Bos taurus Species 0.000 description 1
• 208000013165 Bowen disease Diseases 0.000 description 1
• 208000019337 Bowen disease of the skin Diseases 0.000 description 1
• KDCWTYMVLCKDRC-UHFFFAOYSA-N C(CCC)C=1NC2=C(C=NC=3C=CC=NC23)N1 Chemical compound C(CCC)C=1NC2=C(C=NC=3C=CC=NC23)N1 KDCWTYMVLCKDRC-UHFFFAOYSA-N 0.000 description 1
• IGZGXYBDLGEMQI-UHFFFAOYSA-N C1=CN=C2N(N=NN3)C3=C3N=CN=C3C2=C1 Chemical compound C1=CN=C2N(N=NN3)C3=C3N=CN=C3C2=C1 IGZGXYBDLGEMQI-UHFFFAOYSA-N 0.000 description 1
• LIDRJGJEIJHOAR-UHFFFAOYSA-N C1=NC=C2N(NN=N3)C3=C3N=CN=C3C2=C1 Chemical compound C1=NC=C2N(NN=N3)C3=C3N=CN=C3C2=C1 LIDRJGJEIJHOAR-UHFFFAOYSA-N 0.000 description 1
• NZQDVFXCYCJJHB-UHFFFAOYSA-N CC(CN1C(C=C(C2=NC=CC=C12)N)CC1=CC=CC=C1)(O)C Chemical compound CC(CN1C(C=C(C2=NC=CC=C12)N)CC1=CC=CC=C1)(O)C NZQDVFXCYCJJHB-UHFFFAOYSA-N 0.000 description 1
• TZEPUKAEPQOHOW-UHFFFAOYSA-N CC(CN1C=NC=2C=NC=3N=CC=CC3C21)C Chemical compound CC(CN1C=NC=2C=NC=3N=CC=CC3C21)C TZEPUKAEPQOHOW-UHFFFAOYSA-N 0.000 description 1
• HSNIKLATDAIQRH-UHFFFAOYSA-N CC=1OCC2=C(N1)N=CC=C2 Chemical compound CC=1OCC2=C(N1)N=CC=C2 HSNIKLATDAIQRH-UHFFFAOYSA-N 0.000 description 1
• 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
• 241000283707 Capra Species 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
• 241000606161 Chlamydia Species 0.000 description 1
• 208000000907 Condylomata Acuminata Diseases 0.000 description 1
• 241001337994 Cryptococcus <scale insect> Species 0.000 description 1
• 208000008953 Cryptosporidiosis Diseases 0.000 description 1
• 206010011502 Cryptosporidiosis infection Diseases 0.000 description 1
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
• 201000004624 Dermatitis Diseases 0.000 description 1
• 206010012438 Dermatitis atopic Diseases 0.000 description 1
• 238000008157 ELISA kit Methods 0.000 description 1
• 206010014950 Eosinophilia Diseases 0.000 description 1
• 239000007995 HEPES buffer Substances 0.000 description 1
• 201000002563 Histoplasmosis Diseases 0.000 description 1
• 206010020751 Hypersensitivity Diseases 0.000 description 1
• 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 description 1
• 108010074328 Interferon-gamma Proteins 0.000 description 1
• 206010024229 Leprosy Diseases 0.000 description 1
• 206010025323 Lymphomas Diseases 0.000 description 1
• 201000009906 Meningitis Diseases 0.000 description 1
• AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
• UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
• NDCGVLJXFQKXOF-UHFFFAOYSA-N N-hydroxy-2-methylpropanamine Chemical compound CC(C)CNO NDCGVLJXFQKXOF-UHFFFAOYSA-N 0.000 description 1
• APLILVSDIXWYPA-UHFFFAOYSA-N N-pyrimidin-2-ylsulfanylacetamide Chemical compound C(C)(=O)NSC1=NC=CC=N1 APLILVSDIXWYPA-UHFFFAOYSA-N 0.000 description 1
• WCEMNEVRGROOFT-UHFFFAOYSA-N NC1=NC=2C=CC=NC2C2=C1N=CN2CCCC Chemical compound NC1=NC=2C=CC=NC2C2=C1N=CN2CCCC WCEMNEVRGROOFT-UHFFFAOYSA-N 0.000 description 1
• OZYONUNLDSGZFT-UHFFFAOYSA-N O.N1=CC=C2C(O)=CC3=NN=NN3C2=C1 Chemical compound O.N1=CC=C2C(O)=CC3=NN=NN3C2=C1 OZYONUNLDSGZFT-UHFFFAOYSA-N 0.000 description 1
• 235000019502 Orange oil Nutrition 0.000 description 1
• 241000283973 Oryctolagus cuniculus Species 0.000 description 1
• 206010033733 Papule Diseases 0.000 description 1
• 208000030852 Parasitic disease Diseases 0.000 description 1
• 241000233870 Pneumocystis Species 0.000 description 1
• 239000004743 Polypropylene Substances 0.000 description 1
• 206010039085 Rhinitis allergic Diseases 0.000 description 1
• 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 1
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
• 206010042674 Swelling Diseases 0.000 description 1
• 201000005485 Toxoplasmosis Diseases 0.000 description 1
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
• 239000012346 acetyl chloride Substances 0.000 description 1
• ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 1
• 239000004480 active ingredient Substances 0.000 description 1
• 125000002015 acyclic group Chemical group 0.000 description 1
• 125000002252 acyl group Chemical group 0.000 description 1
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
• 125000004414 alkyl thio group Chemical group 0.000 description 1
• 208000026935 allergic disease Diseases 0.000 description 1
• 201000010105 allergic rhinitis Diseases 0.000 description 1
• 230000007815 allergy Effects 0.000 description 1
• 125000003368 amide group Chemical group 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
• 235000012501 ammonium carbonate Nutrition 0.000 description 1
• 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
• 235000019289 ammonium phosphates Nutrition 0.000 description 1
• 150000003863 ammonium salts Chemical class 0.000 description 1
• 208000025009 anogenital human papillomavirus infection Diseases 0.000 description 1
• 201000004201 anogenital venereal wart Diseases 0.000 description 1
• 230000001773 anti-convulsant effect Effects 0.000 description 1
• 230000000840 anti-viral effect Effects 0.000 description 1
• 229940125681 anticonvulsant agent Drugs 0.000 description 1
• 239000001961 anticonvulsive agent Substances 0.000 description 1
• 239000003430 antimalarial agent Substances 0.000 description 1
• 239000003443 antiviral agent Substances 0.000 description 1
• 239000012223 aqueous fraction Substances 0.000 description 1
• 239000012300 argon atmosphere Substances 0.000 description 1
• 125000003710 aryl alkyl group Chemical group 0.000 description 1
• 208000006673 asthma Diseases 0.000 description 1
• 201000008937 atopic dermatitis Diseases 0.000 description 1
• 208000010668 atopic eczema Diseases 0.000 description 1
• 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 description 1
• 208000022362 bacterial infectious disease Diseases 0.000 description 1
• 239000002585 base Substances 0.000 description 1
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
• LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 1
• HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
• LPDKRJUGFJHJBE-UHFFFAOYSA-N benzyl n-[4-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]carbamate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CCCCNC(=O)OCC1=CC=CC=C1 LPDKRJUGFJHJBE-UHFFFAOYSA-N 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• 125000001246 bromo group Chemical group Br* 0.000 description 1
• 229940124630 bronchodilator Drugs 0.000 description 1
• 239000000168 bronchodilator agent Substances 0.000 description 1
• 239000000872 buffer Substances 0.000 description 1
• 239000001273 butane Substances 0.000 description 1
• 125000002837 carbocyclic group Chemical group 0.000 description 1
• JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
• 229940125692 cardiovascular agent Drugs 0.000 description 1
• 239000002327 cardiovascular agent Substances 0.000 description 1
• 238000004113 cell culture Methods 0.000 description 1
• 239000013553 cell monolayer Substances 0.000 description 1
• OIQPTROHQCGFEF-UHFFFAOYSA-L chembl1371409 Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 OIQPTROHQCGFEF-UHFFFAOYSA-L 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• 238000004587 chromatography analysis Methods 0.000 description 1
• 229940125904 compound 1 Drugs 0.000 description 1
• 229940125782 compound 2 Drugs 0.000 description 1
• 229940126214 compound 3 Drugs 0.000 description 1
• 229940125898 compound 5 Drugs 0.000 description 1
• 235000008504 concentrate Nutrition 0.000 description 1
• 239000012141 concentrate Substances 0.000 description 1
• 239000007822 coupling agent Substances 0.000 description 1
• 239000006071 cream Substances 0.000 description 1
• 239000012228 culture supernatant Substances 0.000 description 1
• 125000000392 cycloalkenyl group Chemical group 0.000 description 1
• 125000000753 cycloalkyl group Chemical group 0.000 description 1
• RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 210000004443 dendritic cell Anatomy 0.000 description 1
• 238000009795 derivation Methods 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
• 230000004069 differentiation Effects 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• 208000035475 disorder Diseases 0.000 description 1
• 239000002552 dosage form Substances 0.000 description 1
• 230000003828 downregulation Effects 0.000 description 1
• RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
• YYXKAGAJFBAITG-UHFFFAOYSA-N ethyl n-[4-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]carbamate Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CCCCNC(=O)OCC)C3=C(N)N=C21 YYXKAGAJFBAITG-UHFFFAOYSA-N 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 238000000556 factor analysis Methods 0.000 description 1
• 229960000301 factor viii Drugs 0.000 description 1
• 230000001605 fetal effect Effects 0.000 description 1
• 239000012997 ficoll-paque Substances 0.000 description 1
• IRXSLJNXXZKURP-UHFFFAOYSA-N fluorenylmethyloxycarbonyl chloride Chemical compound C1=CC=C2C(COC(=O)Cl)C3=CC=CC=C3C2=C1 IRXSLJNXXZKURP-UHFFFAOYSA-N 0.000 description 1
• ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 description 1
• 238000005984 hydrogenation reaction Methods 0.000 description 1
• 230000003301 hydrolyzing effect Effects 0.000 description 1
• MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 1
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
• 229960002751 imiquimod Drugs 0.000 description 1
• DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 description 1
• 230000002519 immonomodulatory effect Effects 0.000 description 1
• 230000036039 immunity Effects 0.000 description 1
• 239000012535 impurity Substances 0.000 description 1
• 230000002779 inactivation Effects 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 230000015788 innate immune response Effects 0.000 description 1
• 230000022023 interleukin-5 production Effects 0.000 description 1
• 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
• YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 1
• 239000010977 jade Substances 0.000 description 1
• 231100000225 lethality Toxicity 0.000 description 1
• 239000007937 lozenge Substances 0.000 description 1
• 206010025135 lupus erythematosus Diseases 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• FEIOASZZURHTHB-UHFFFAOYSA-N methyl 4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1 FEIOASZZURHTHB-UHFFFAOYSA-N 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 125000002950 monocyclic group Chemical group 0.000 description 1
• 210000001616 monocyte Anatomy 0.000 description 1
• 201000006417 multiple sclerosis Diseases 0.000 description 1
• OELWIDHVUIWCQU-UHFFFAOYSA-N n-[2-(4-amino-2-butyl-6,7,8,9-tetrahydroimidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-3,5-ditert-butyl-4-hydroxybenzamide Chemical compound CCCCC1=NC2=C(N)N=C3CCCNC3=C2N1CCNC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 OELWIDHVUIWCQU-UHFFFAOYSA-N 0.000 description 1
• NQVTVSISVQJWEF-UHFFFAOYSA-N n-[2-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-2-(3-hydroxyphenyl)acetamide Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CCNC(=O)CC1=CC=CC(O)=C1 NQVTVSISVQJWEF-UHFFFAOYSA-N 0.000 description 1
• AFSZBLIXCUNBNU-UHFFFAOYSA-N n-[2-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-3,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CCNC(=O)C=1C(C)=NOC=1C AFSZBLIXCUNBNU-UHFFFAOYSA-N 0.000 description 1
• KABDODXUQRCYGI-UHFFFAOYSA-N n-[2-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-3,5-ditert-butyl-4-hydroxybenzamide Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CCNC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 KABDODXUQRCYGI-UHFFFAOYSA-N 0.000 description 1
• ODINERYGXDPLPN-UHFFFAOYSA-N n-[2-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-3-phenylpropanamide;hydrochloride Chemical compound Cl.CCCCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CCNC(=O)CCC1=CC=CC=C1 ODINERYGXDPLPN-UHFFFAOYSA-N 0.000 description 1
• CPRUTIXYUMZWKM-UHFFFAOYSA-N n-[2-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]acetamide Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CCNC(C)=O)C3=C(N)N=C21 CPRUTIXYUMZWKM-UHFFFAOYSA-N 0.000 description 1
• DDGPFJVDVOLRKP-UHFFFAOYSA-N n-[2-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]cyclohexanecarboxamide Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CCNC(=O)C1CCCCC1 DDGPFJVDVOLRKP-UHFFFAOYSA-N 0.000 description 1
• DBMNXPQADUWRES-UHFFFAOYSA-N n-[4-(2-methylpropylamino)-1,5-naphthyridin-3-yl]pentanamide Chemical compound C1=CC=NC2=C(NCC(C)C)C(NC(=O)CCCC)=CN=C21 DBMNXPQADUWRES-UHFFFAOYSA-N 0.000 description 1
• HPXYJNCRUPPYPN-UHFFFAOYSA-N n-[4-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]-2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetamide Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CCCCNC(=O)CN1C=C(C)C(O)=NC1=O HPXYJNCRUPPYPN-UHFFFAOYSA-N 0.000 description 1
• LEDOCKFUDFUJKH-UHFFFAOYSA-N n-[4-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]-2-phenylacetamide Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CCCCNC(=O)CC1=CC=CC=C1 LEDOCKFUDFUJKH-UHFFFAOYSA-N 0.000 description 1
• JMZCAXZZTNFGIA-UHFFFAOYSA-N n-[4-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]-2-pyridin-4-ylsulfanylacetamide Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CCCCNC(=O)CSC1=CC=NC=C1 JMZCAXZZTNFGIA-UHFFFAOYSA-N 0.000 description 1
• ASIJFEOADJGNKV-UHFFFAOYSA-N n-[4-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]-4-benzoylbenzamide Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CCCCNC(=O)C(C=C1)=CC=C1C(=O)C1=CC=CC=C1 ASIJFEOADJGNKV-UHFFFAOYSA-N 0.000 description 1
• PZFNMLHAPUIOLN-UHFFFAOYSA-N n-[4-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]benzamide Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CCCCNC(=O)C1=CC=CC=C1 PZFNMLHAPUIOLN-UHFFFAOYSA-N 0.000 description 1
• YZMYSQHIKATPDR-UHFFFAOYSA-N n-[4-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]furan-2-carboxamide Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CCCCNC(=O)C1=CC=CO1 YZMYSQHIKATPDR-UHFFFAOYSA-N 0.000 description 1
• DITNETKTNUQAAC-UHFFFAOYSA-N n-[4-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]pyridine-3-carboxamide Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CCCCNC(=O)C1=CC=CN=C1 DITNETKTNUQAAC-UHFFFAOYSA-N 0.000 description 1
• HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
• OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
• 210000000822 natural killer cell Anatomy 0.000 description 1
• 230000007935 neutral effect Effects 0.000 description 1
• 238000006386 neutralization reaction Methods 0.000 description 1
• 235000005152 nicotinamide Nutrition 0.000 description 1
• 239000011570 nicotinamide Substances 0.000 description 1
• 229960003966 nicotinamide Drugs 0.000 description 1
• 235000001968 nicotinic acid Nutrition 0.000 description 1
• 239000011664 nicotinic acid Substances 0.000 description 1
• 229960003512 nicotinic acid Drugs 0.000 description 1
• PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Natural products OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
• 150000002825 nitriles Chemical class 0.000 description 1
• 125000006574 non-aromatic ring group Chemical group 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• 239000010502 orange oil Substances 0.000 description 1
• 239000012074 organic phase Substances 0.000 description 1
• 230000001151 other effect Effects 0.000 description 1
• IVKNUIVDQMARCO-UHFFFAOYSA-N oxazin-4-one Chemical compound O=C1C=CON=C1 IVKNUIVDQMARCO-UHFFFAOYSA-N 0.000 description 1
• 239000007800 oxidant agent Substances 0.000 description 1
• 125000004043 oxo group Chemical group O=* 0.000 description 1
• SEVSMVUOKAMPDO-UHFFFAOYSA-N para-Acetoxybenzaldehyde Natural products CC(=O)OC1=CC=C(C=O)C=C1 SEVSMVUOKAMPDO-UHFFFAOYSA-N 0.000 description 1
• DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
• AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
• DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
• NQVKBTDUFXDUGU-UHFFFAOYSA-N phenyl n-[4-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]carbamate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=NC3=C2N1CCCCNC(=O)OC1=CC=CC=C1 NQVKBTDUFXDUGU-UHFFFAOYSA-N 0.000 description 1
• ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
• UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
• 229910052697 platinum Inorganic materials 0.000 description 1
• 201000000317 pneumocystosis Diseases 0.000 description 1
• 125000003367 polycyclic group Chemical group 0.000 description 1
• 229920001155 polypropylene Polymers 0.000 description 1
• GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
• 238000002953 preparative HPLC Methods 0.000 description 1
• 230000035755 proliferation Effects 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• VXGYRCVTBHVXMZ-UHFFFAOYSA-N quinoline-6-carboxylic acid Chemical compound N1=CC=CC2=CC(C(=O)O)=CC=C21 VXGYRCVTBHVXMZ-UHFFFAOYSA-N 0.000 description 1
• 230000000306 recurrent effect Effects 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 206010039073 rheumatoid arthritis Diseases 0.000 description 1
• 229920006395 saturated elastomer Polymers 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
• 239000001632 sodium acetate Substances 0.000 description 1
• 235000017281 sodium acetate Nutrition 0.000 description 1
• 239000012453 solvate Substances 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 230000004936 stimulating effect Effects 0.000 description 1
• 239000006228 supernatant Substances 0.000 description 1
• 208000011580 syndromic disease Diseases 0.000 description 1
• 230000002194 synthesizing effect Effects 0.000 description 1
• 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
• 239000003826 tablet Substances 0.000 description 1
• ZFQWJXFJJZUVPI-UHFFFAOYSA-N tert-butyl n-(4-aminobutyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCCN ZFQWJXFJJZUVPI-UHFFFAOYSA-N 0.000 description 1
• UHTFTBRABUWYME-UHFFFAOYSA-N tert-butyl n-(4-imidazo[4,5-c][1,5]naphthyridin-1-ylbutyl)carbamate Chemical compound C1=CC=NC2=C3N(CCCCNC(=O)OC(C)(C)C)C=NC3=CN=C21 UHTFTBRABUWYME-UHFFFAOYSA-N 0.000 description 1
• LFYHTJJDBDTWEN-UHFFFAOYSA-N tert-butyl n-[1-[2-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)ethylamino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CCNC(=O)C(CC(C)C)NC(=O)OC(C)(C)C)C3=C(N)N=C21 LFYHTJJDBDTWEN-UHFFFAOYSA-N 0.000 description 1
• VDVGTASSHOLSKP-UHFFFAOYSA-N tert-butyl n-[2-(2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]carbamate Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CCNC(=O)OC(C)(C)C)C3=CN=C21 VDVGTASSHOLSKP-UHFFFAOYSA-N 0.000 description 1
• JAXIHJSNTPBIQU-UHFFFAOYSA-N tert-butyl n-[2-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]carbamate Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CCNC(=O)OC(C)(C)C)C3=C(N)N=C21 JAXIHJSNTPBIQU-UHFFFAOYSA-N 0.000 description 1
• UVRYAPOGGJJJJX-UHFFFAOYSA-N tert-butyl n-[4-(2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]carbamate Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CCCCNC(=O)OC(C)(C)C)C3=CN=C21 UVRYAPOGGJJJJX-UHFFFAOYSA-N 0.000 description 1
• RANGKIAISHUOCO-UHFFFAOYSA-N tert-butyl n-[4-(4-amino-2-butylimidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]carbamate Chemical compound C1=CC=NC2=C(N(C(CCCC)=N3)CCCCNC(=O)OC(C)(C)C)C3=C(N)N=C21 RANGKIAISHUOCO-UHFFFAOYSA-N 0.000 description 1
• PHXUIGRGPODXIF-UHFFFAOYSA-N tetrazolo[1,5-a][1,7]naphthyridine-4,5-diamine Chemical compound NC1=C(N)C2=CC=NC=C2N2C1=NN=N2 PHXUIGRGPODXIF-UHFFFAOYSA-N 0.000 description 1
• WVOUCGZOQPSJCR-UHFFFAOYSA-N tetrazolo[1,5-a][1,8]naphthyridine-4,5-diamine Chemical compound NC1=C(N)C2=CC=CN=C2N2C1=NN=N2 WVOUCGZOQPSJCR-UHFFFAOYSA-N 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
• 125000004953 trihalomethyl group Chemical group 0.000 description 1
• 238000001665 trituration Methods 0.000 description 1
• 210000004881 tumor cell Anatomy 0.000 description 1
• 230000004614 tumor growth Effects 0.000 description 1
• 230000003827 upregulation Effects 0.000 description 1
• 239000012646 vaccine adjuvant Substances 0.000 description 1
• 229940124931 vaccine adjuvant Drugs 0.000 description 1
• 230000000007 visual effect Effects 0.000 description 1
• WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1