MXPA06001669A - Compuestos que contienen imidazo-oxima sustituidos. - Google Patents

Info

Publication number

MXPA06001669A

MXPA06001669A MXPA06001669A MXPA06001669A MXPA06001669A MX PA06001669 A MXPA06001669 A MX PA06001669A MX PA06001669 A MXPA06001669 A MX PA06001669A MX PA06001669 A MXPA06001669 A MX PA06001669A MX PA06001669 A MXPA06001669 A MX PA06001669A

Authority

MX

Mexico

Prior art keywords

group

alkyl

hydrogen

aryl

independently selected

Prior art date

2003-08-12

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 203
• 150000002923 oximes Chemical group 0.000 title abstract description 40
• 238000000034 method Methods 0.000 claims abstract description 53
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 29
• 102000004127 Cytokines Human genes 0.000 claims abstract description 27
• 108090000695 Cytokines Proteins 0.000 claims abstract description 27
• 201000010099 disease Diseases 0.000 claims abstract description 25
• 241001465754 Metazoa Species 0.000 claims abstract description 22
• 230000015572 biosynthetic process Effects 0.000 claims abstract description 20
• 230000003612 virological effect Effects 0.000 claims abstract description 11
• 230000001613 neoplastic effect Effects 0.000 claims abstract description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
• 230000001939 inductive effect Effects 0.000 claims abstract description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 574
• 239000001257 hydrogen Substances 0.000 claims description 574
• -1 heteroarylalkylenyl Chemical group 0.000 claims description 556
• 125000000217 alkyl group Chemical group 0.000 claims description 272
• 125000003118 aryl group Chemical group 0.000 claims description 183
• 125000001072 heteroaryl group Chemical group 0.000 claims description 163
• 125000003342 alkenyl group Chemical group 0.000 claims description 155
• 125000000623 heterocyclic group Chemical group 0.000 claims description 144
• 125000002947 alkylene group Chemical group 0.000 claims description 129
• 150000002431 hydrogen Chemical class 0.000 claims description 123
• 125000004450 alkenylene group Chemical group 0.000 claims description 98
• 229910052736 halogen Inorganic materials 0.000 claims description 87
• 150000002367 halogens Chemical class 0.000 claims description 86
• 125000003545 alkoxy group Chemical group 0.000 claims description 82
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 74
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 64
• 125000001188 haloalkyl group Chemical group 0.000 claims description 63
• 125000005842 heteroatom Chemical group 0.000 claims description 61
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 61
• 125000000304 alkynyl group Chemical group 0.000 claims description 60
• 125000001424 substituent group Chemical group 0.000 claims description 58
• 150000003839 salts Chemical class 0.000 claims description 57
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 48
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
• 229920006395 saturated elastomer Polymers 0.000 claims description 42
• 125000000732 arylene group Chemical group 0.000 claims description 39
• 125000004414 alkyl thio group Chemical group 0.000 claims description 37
• 125000005549 heteroarylene group Chemical group 0.000 claims description 37
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 36
• 125000004419 alkynylene group Chemical group 0.000 claims description 35
• 125000004122 cyclic group Chemical group 0.000 claims description 35
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
• 125000004104 aryloxy group Chemical group 0.000 claims description 31
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 30
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 29
• 125000004429 atom Chemical group 0.000 claims description 26
• 150000002825 nitriles Chemical class 0.000 claims description 19
• 125000003282 alkyl amino group Chemical group 0.000 claims description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 17
• 229910052757 nitrogen Inorganic materials 0.000 claims description 17
• 125000005529 alkyleneoxy group Chemical group 0.000 claims description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
• 125000004043 oxo group Chemical group O=* 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 11
• 125000005466 alkylenyl group Chemical group 0.000 claims description 11
• 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 9
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• 125000005275 alkylenearyl group Chemical group 0.000 claims description 5
• 125000006413 ring segment Chemical group 0.000 claims description 5
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 4
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
• 125000005015 aryl alkynyl group Chemical group 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 3
• 125000005133 alkynyloxy group Chemical group 0.000 claims 1
• 238000011282 treatment Methods 0.000 abstract description 12
• 239000000543 intermediate Substances 0.000 abstract description 6
• 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 abstract description 5
• RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical class C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 abstract description 3
• 239000002955 immunomodulating agent Substances 0.000 abstract description 3
• 229940121354 immunomodulator Drugs 0.000 abstract description 3
• 150000005232 imidazopyridines Chemical class 0.000 abstract description 2
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 209
• 238000006243 chemical reaction Methods 0.000 description 197
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 168
• 239000000243 solution Substances 0.000 description 139
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 122
• 239000007787 solid Substances 0.000 description 116
• 230000002829 reductive effect Effects 0.000 description 102
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 87
• 239000000203 mixture Substances 0.000 description 87
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 81
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 77
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 66
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
• 239000002904 solvent Substances 0.000 description 57
• 239000000047 product Substances 0.000 description 55
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
• 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 44
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 42
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 40
• 125000004076 pyridyl group Chemical group 0.000 description 40
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 39
• 238000007796 conventional method Methods 0.000 description 39
• 238000001914 filtration Methods 0.000 description 38
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 33
• 235000019341 magnesium sulphate Nutrition 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
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
• 239000010410 layer Substances 0.000 description 30
• 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 28
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 27
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 27
• 239000000741 silica gel Substances 0.000 description 27
• 229910002027 silica gel Inorganic materials 0.000 description 27
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
• 239000000706 filtrate Substances 0.000 description 24
• 239000012044 organic layer Substances 0.000 description 24
• 238000005481 NMR spectroscopy Methods 0.000 description 22
• 238000010828 elution Methods 0.000 description 21
• 235000017557 sodium bicarbonate Nutrition 0.000 description 21
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 21
• 150000001299 aldehydes Chemical class 0.000 description 20
• 239000012043 crude product Substances 0.000 description 20
• 150000002576 ketones Chemical class 0.000 description 20
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 19
• 239000000908 ammonium hydroxide Substances 0.000 description 19
• 239000012267 brine Substances 0.000 description 19
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
• 239000003921 oil Substances 0.000 description 18
• 235000019198 oils Nutrition 0.000 description 18
• KFAJXZVDBVRZRC-UHFFFAOYSA-N 1,5-naphthyridin-4-amine Chemical compound C1=CN=C2C(N)=CC=NC2=C1 KFAJXZVDBVRZRC-UHFFFAOYSA-N 0.000 description 17
• 239000000843 powder Substances 0.000 description 17
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 17
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 16
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 16
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
• AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 16
• 239000011541 reaction mixture Substances 0.000 description 16
• 238000010992 reflux Methods 0.000 description 16
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 15
• 239000002244 precipitate Substances 0.000 description 15
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
• 239000000463 material Substances 0.000 description 14
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
• 125000003396 thiol group Chemical group [H]S* 0.000 description 14
• 101150041968 CDC13 gene Proteins 0.000 description 13
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 13
• 229910052938 sodium sulfate Inorganic materials 0.000 description 13
• 235000011152 sodium sulphate Nutrition 0.000 description 13
• 238000003756 stirring Methods 0.000 description 13
• 239000000725 suspension Substances 0.000 description 13
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
• 238000010438 heat treatment Methods 0.000 description 12
• VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 12
• 238000012360 testing method Methods 0.000 description 12
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
• 239000002585 base Substances 0.000 description 11
• 238000000746 purification Methods 0.000 description 11
• CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 10
• 102100040247 Tumor necrosis factor Human genes 0.000 description 10
• 239000002253 acid Substances 0.000 description 10
• 238000004587 chromatography analysis Methods 0.000 description 10
• 229910000027 potassium carbonate Inorganic materials 0.000 description 10
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 9
• 238000004458 analytical method Methods 0.000 description 9
• 235000011181 potassium carbonates Nutrition 0.000 description 9
• 238000001308 synthesis method Methods 0.000 description 9
• FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical class C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
• 125000004432 carbon atom Chemical group C* 0.000 description 8
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
• 238000005859 coupling reaction Methods 0.000 description 8
• 238000004519 manufacturing process Methods 0.000 description 8
• 230000009467 reduction Effects 0.000 description 8
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
• 229910000029 sodium carbonate Inorganic materials 0.000 description 8
• 235000017550 sodium carbonate Nutrition 0.000 description 8
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 7
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 7
• ZRFUZDDJSQVQBY-UHFFFAOYSA-N 4-chloro-3-nitroquinoline Chemical compound C1=CC=CC2=C(Cl)C([N+](=O)[O-])=CN=C21 ZRFUZDDJSQVQBY-UHFFFAOYSA-N 0.000 description 7
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 7
• 206010028980 Neoplasm Diseases 0.000 description 7
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 7
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
• 239000003795 chemical substances by application Substances 0.000 description 7
• 230000036039 immunity Effects 0.000 description 7
• 230000006698 induction Effects 0.000 description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 7
• 238000003786 synthesis reaction Methods 0.000 description 7
• GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 7
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
• 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 6
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 6
• 150000001204 N-oxides Chemical class 0.000 description 6
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
• 150000001412 amines Chemical class 0.000 description 6
• 150000001502 aryl halides Chemical class 0.000 description 6
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
• 125000001246 bromo group Chemical group Br* 0.000 description 6
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 6
• 230000008878 coupling Effects 0.000 description 6
• 238000010168 coupling process Methods 0.000 description 6
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
• VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 6
• 238000007429 general method Methods 0.000 description 6
• 230000002452 interceptive effect Effects 0.000 description 6
• 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 6
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
• 230000004044 response Effects 0.000 description 6
• MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 5
• JAFMOTJMRSZOJE-UHFFFAOYSA-N 1,1,1-trimethoxybutane Chemical compound CCCC(OC)(OC)OC JAFMOTJMRSZOJE-UHFFFAOYSA-N 0.000 description 5
• VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 5
• ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 5
• 238000002965 ELISA Methods 0.000 description 5
• 238000006751 Mitsunobu reaction Methods 0.000 description 5
• PXAJQJMDEXJWFB-UHFFFAOYSA-N Oxime-Acetone Natural products CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 5
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 5
• 241000700605 Viruses Species 0.000 description 5
• 229910052799 carbon Inorganic materials 0.000 description 5
• 239000003054 catalyst Substances 0.000 description 5
• 238000005119 centrifugation Methods 0.000 description 5
• 239000012065 filter cake Substances 0.000 description 5
• 238000005984 hydrogenation reaction Methods 0.000 description 5
• 239000012299 nitrogen atmosphere Substances 0.000 description 5
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
• 238000002953 preparative HPLC Methods 0.000 description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
• 239000007858 starting material Substances 0.000 description 5
• QSQCKOLRUAEGEE-UHFFFAOYSA-N 1-[2-[(3-nitroquinolin-4-yl)amino]ethoxy]ethanol Chemical compound C1=CC=C2C(NCCOC(O)C)=C([N+]([O-])=O)C=NC2=C1 QSQCKOLRUAEGEE-UHFFFAOYSA-N 0.000 description 4
• 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 4
• AGMZSYQMSHMXLT-UHFFFAOYSA-N 3-aminobutan-1-ol Chemical compound CC(N)CCO AGMZSYQMSHMXLT-UHFFFAOYSA-N 0.000 description 4
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