AU2006216710B2 - Imidazo (1, 2-A) pyridine compounds as VEGF-R2 inhibitors - Google Patents

Info

Publication number

AU2006216710B2

AU2006216710B2 AU2006216710A AU2006216710A AU2006216710B2 AU 2006216710 B2 AU2006216710 B2 AU 2006216710B2 AU 2006216710 A AU2006216710 A AU 2006216710A AU 2006216710 A AU2006216710 A AU 2006216710A AU 2006216710 B2 AU2006216710 B2 AU 2006216710B2

Authority

AU

Australia

Prior art keywords

pyridin

phenyl

imidazo

mmol

tert

Prior art date

2005-02-24

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Ceased

Links

• Espacenet
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• 239000003112 inhibitor Substances 0.000 title abstract description 8
• 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 199
• 238000000034 method Methods 0.000 claims abstract description 111
• -1 N-oxo-pyridinyl Chemical group 0.000 claims description 291
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 200
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 177
• 229910052757 nitrogen Inorganic materials 0.000 claims description 105
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 83
• 150000003839 salts Chemical class 0.000 claims description 41
• 125000004076 pyridyl group Chemical group 0.000 claims description 32
• 125000001424 substituent group Chemical group 0.000 claims description 32
• 206010028980 Neoplasm Diseases 0.000 claims description 27
• 125000002757 morpholinyl group Chemical group 0.000 claims description 27
• 125000000335 thiazolyl group Chemical group 0.000 claims description 25
• 239000012453 solvate Substances 0.000 claims description 24
• 241000124008 Mammalia Species 0.000 claims description 23
• 238000011282 treatment Methods 0.000 claims description 23
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
• 101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims description 18
• 230000002401 inhibitory effect Effects 0.000 claims description 17
• 230000033115 angiogenesis Effects 0.000 claims description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
• 125000003386 piperidinyl group Chemical group 0.000 claims description 15
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 15
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 14
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims description 13
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 13
• 229910052739 hydrogen Inorganic materials 0.000 claims description 12
• 239000001257 hydrogen Substances 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 10
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
• 125000001544 thienyl group Chemical group 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 9
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 9
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 125000004193 piperazinyl group Chemical group 0.000 claims description 6
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
• 125000002971 oxazolyl group Chemical group 0.000 claims description 5
• 125000001425 triazolyl group Chemical group 0.000 claims description 5
• 230000000903 blocking effect Effects 0.000 claims description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
• 230000005747 tumor angiogenesis Effects 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
• HTQYWLPDWPCWTF-UHFFFAOYSA-N 2-[2-fluoro-4-[7-(2-methylpyridin-4-yl)imidazo[1,2-a]pyridin-3-yl]phenyl]-n-[3-(trifluoromethyl)phenyl]acetamide Chemical compound C1=NC(C)=CC(C2=CC3=NC=C(N3C=C2)C=2C=C(F)C(CC(=O)NC=3C=C(C=CC=3)C(F)(F)F)=CC=2)=C1 HTQYWLPDWPCWTF-UHFFFAOYSA-N 0.000 claims 1
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 724
• YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 577
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 309
• 239000012141 concentrate Substances 0.000 description 188
• 238000003756 stirring Methods 0.000 description 180
• 238000006243 chemical reaction Methods 0.000 description 147
• 239000007787 solid Substances 0.000 description 146
• 239000004202 carbamide Substances 0.000 description 137
• 238000002360 preparation method Methods 0.000 description 133
• 239000000203 mixture Substances 0.000 description 120
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 120
• 235000019439 ethyl acetate Nutrition 0.000 description 113
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 111
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 110
• 239000000243 solution Substances 0.000 description 109
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 105
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 99
• 229940093499 ethyl acetate Drugs 0.000 description 75
• 239000000047 product Substances 0.000 description 75
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 74
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 70
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 64
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 58
• 239000011541 reaction mixture Substances 0.000 description 58
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 57
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 45
• 239000000284 extract Substances 0.000 description 44
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 43
• 239000012044 organic layer Substances 0.000 description 41
• 239000000377 silicon dioxide Substances 0.000 description 40
• 238000010992 reflux Methods 0.000 description 36
• 239000002002 slurry Substances 0.000 description 35
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 34
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
• 239000003921 oil Substances 0.000 description 33
• 235000019198 oils Nutrition 0.000 description 33
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 33
• 238000012799 strong cation exchange Methods 0.000 description 30
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 29
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 29
• 239000000741 silica gel Substances 0.000 description 29
• 229910002027 silica gel Inorganic materials 0.000 description 29
• 229960001866 silicon dioxide Drugs 0.000 description 29
• 235000019341 magnesium sulphate Nutrition 0.000 description 28
• 239000000706 filtrate Substances 0.000 description 26
• 229920006395 saturated elastomer Polymers 0.000 description 26
• 125000000217 alkyl group Chemical group 0.000 description 25
• 239000010410 layer Substances 0.000 description 25
• 239000000725 suspension Substances 0.000 description 25
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• 125000005843 halogen group Chemical group 0.000 description 24
• 230000002829 reductive effect Effects 0.000 description 24
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
• 239000002904 solvent Substances 0.000 description 22
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 21
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 21
• 239000000543 intermediate Substances 0.000 description 19
• 238000010898 silica gel chromatography Methods 0.000 description 19
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 18
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 17
• YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 17
• 238000010791 quenching Methods 0.000 description 17
• 229940086542 triethylamine Drugs 0.000 description 17
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 16
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• 238000000746 purification Methods 0.000 description 16
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 15
• 238000004440 column chromatography Methods 0.000 description 15
• 239000007789 gas Substances 0.000 description 15
• 235000011056 potassium acetate Nutrition 0.000 description 15
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 14
• 235000013877 carbamide Nutrition 0.000 description 14
• VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 14
• 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 13
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 13
• 229910004298 SiO 2 Inorganic materials 0.000 description 13
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
• IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 13
• 201000011510 cancer Diseases 0.000 description 13
• 239000012458 free base Substances 0.000 description 13
• 239000012299 nitrogen atmosphere Substances 0.000 description 13
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 12
• 239000012043 crude product Substances 0.000 description 12
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 11
• 150000001412 amines Chemical class 0.000 description 11
• CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 11
• 238000004587 chromatography analysis Methods 0.000 description 11
• 239000000463 material Substances 0.000 description 11
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 11
• JBLWSEJYQSQFKW-UHFFFAOYSA-N 7-pyridin-4-ylimidazo[1,2-a]pyridine Chemical compound C=1C2=NC=CN2C=CC=1C1=CC=NC=C1 JBLWSEJYQSQFKW-UHFFFAOYSA-N 0.000 description 10
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
• SECXISVLQFMRJM-UHFFFAOYSA-N NMP Substances CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
• METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 10
• 150000002148 esters Chemical class 0.000 description 10
• 239000006260 foam Substances 0.000 description 10
• 238000004128 high performance liquid chromatography Methods 0.000 description 10
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical group C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 10
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 10
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
• LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Substances IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 9
• 125000003342 alkenyl group Chemical group 0.000 description 9
• 150000001408 amides Chemical class 0.000 description 9
• 125000003118 aryl group Chemical group 0.000 description 9
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
• 125000000753 cycloalkyl group Chemical group 0.000 description 9
• 230000000694 effects Effects 0.000 description 9
• 238000003818 flash chromatography Methods 0.000 description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
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• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 description 8
• 102000016549 Vascular Endothelial Growth Factor Receptor-2 Human genes 0.000 description 8
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 8
• 238000010438 heat treatment Methods 0.000 description 8
• 239000012074 organic phase Substances 0.000 description 8
• 229910000027 potassium carbonate Inorganic materials 0.000 description 8
• 229940080818 propionamide Drugs 0.000 description 8
• 229910000029 sodium carbonate Inorganic materials 0.000 description 8
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical group [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
• WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 8
• BGKDWGHFISLPAE-UHFFFAOYSA-N 2-[4-(7-pyridin-4-ylimidazo[1,2-a]pyridin-3-yl)phenyl]-n-[3-(trifluoromethyl)phenyl]acetamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)CC=2C=CC(=CC=2)C=2N3C=CC(=CC3=NC=2)C=2C=CN=CC=2)=C1 BGKDWGHFISLPAE-UHFFFAOYSA-N 0.000 description 7
• BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 description 7
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 7
• NGHRUBVFDAKWBC-UHFFFAOYSA-N 7-chloroimidazo[1,2-a]pyridine Chemical compound C1=C(Cl)C=CN2C=CN=C21 NGHRUBVFDAKWBC-UHFFFAOYSA-N 0.000 description 7
• 108091000080 Phosphotransferase Proteins 0.000 description 7
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• 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 7
• 238000005406 washing Methods 0.000 description 7
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• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 6
• LKXGEUZSNQCIAO-UHFFFAOYSA-N 3-iodo-7-pyridin-4-ylimidazo[1,2-a]pyridine Chemical compound C1=CN2C(I)=CN=C2C=C1C1=CC=NC=C1 LKXGEUZSNQCIAO-UHFFFAOYSA-N 0.000 description 6
• OXFRWJAGUOTHEH-UHFFFAOYSA-N 7-chloro-3-iodoimidazo[1,2-a]pyridine Chemical compound C1=C(Cl)C=CN2C(I)=CN=C21 OXFRWJAGUOTHEH-UHFFFAOYSA-N 0.000 description 6
• 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 6
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• 239000002253 acid Substances 0.000 description 6
• 235000019270 ammonium chloride Nutrition 0.000 description 6
• 239000002585 base Substances 0.000 description 6
• 230000005587 bubbling Effects 0.000 description 6
• VZSXFJPZOCRDPW-UHFFFAOYSA-N carbanide;trioxorhenium Chemical compound [CH3-].O=[Re](=O)=O VZSXFJPZOCRDPW-UHFFFAOYSA-N 0.000 description 6
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