BRPI0609047A2 - composto ou sal farmaceuticamente aceitável do mesmo, formulação farmacêutica, e, uso de um composto - Google Patents

Info

Publication number

BRPI0609047A2

BRPI0609047A2 BRPI0609047-8A BRPI0609047A BRPI0609047A2 BR PI0609047 A2 BRPI0609047 A2 BR PI0609047A2 BR PI0609047 A BRPI0609047 A BR PI0609047A BR PI0609047 A2 BRPI0609047 A2 BR PI0609047A2

Authority

BR

Brazil

Prior art keywords

mmol

pyridin

phenyl

imidazo

add

Prior art date

2005-02-24

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 170
• 150000003839 salts Chemical class 0.000 title claims abstract description 25
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
• -1 imidazolia Chemical group 0.000 claims description 256
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 185
• 229910052757 nitrogen Inorganic materials 0.000 claims description 97
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 32
• 125000004076 pyridyl group Chemical group 0.000 claims description 32
• 125000001424 substituent group Chemical group 0.000 claims description 32
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 31
• 125000000217 alkyl group Chemical group 0.000 claims description 27
• 125000002757 morpholinyl group Chemical group 0.000 claims description 25
• 206010028980 Neoplasm Diseases 0.000 claims description 24
• 125000000335 thiazolyl group Chemical group 0.000 claims description 22
• 101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims description 20
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
• 230000033115 angiogenesis Effects 0.000 claims description 15
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 14
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 12
• 229910052739 hydrogen Inorganic materials 0.000 claims description 11
• 239000001257 hydrogen Substances 0.000 claims description 11
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 11
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 11
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 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 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 10
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
• 125000001544 thienyl group Chemical group 0.000 claims description 9
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 8
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 8
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 125000001425 triazolyl group Chemical group 0.000 claims description 4
• 208000035269 cancer or benign tumor Diseases 0.000 claims description 3
• 125000001475 halogen functional group Chemical group 0.000 claims 4
• 239000012453 solvate Substances 0.000 claims 2
• GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 claims 1
• 239000003085 diluting agent Substances 0.000 claims 1
• 229940079593 drug Drugs 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 103
• 239000003112 inhibitor Substances 0.000 abstract description 5
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 658
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 584
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 286
• 239000012141 concentrate Substances 0.000 description 190
• 238000003756 stirring Methods 0.000 description 165
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 153
• 239000007787 solid Substances 0.000 description 142
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 128
• 238000006243 chemical reaction Methods 0.000 description 126
• 239000000203 mixture Substances 0.000 description 123
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 120
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 108
• 239000000243 solution Substances 0.000 description 107
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 106
• 235000019439 ethyl acetate Nutrition 0.000 description 104
• 238000002360 preparation method Methods 0.000 description 100
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 90
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 84
• 239000000047 product Substances 0.000 description 75
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 70
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 54
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 54
• 235000019341 magnesium sulphate Nutrition 0.000 description 54
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 52
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 50
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
• 239000000284 extract Substances 0.000 description 46
• 239000011541 reaction mixture Substances 0.000 description 46
• 239000000377 silicon dioxide Substances 0.000 description 45
• 239000000725 suspension Substances 0.000 description 43
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
• 229920006395 saturated elastomer Polymers 0.000 description 42
• 239000012044 organic layer Substances 0.000 description 41
• 239000000126 substance Substances 0.000 description 41
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 40
• 238000010992 reflux Methods 0.000 description 36
• 238000012799 strong cation exchange Methods 0.000 description 35
• 239000003921 oil Substances 0.000 description 34
• 235000019198 oils Nutrition 0.000 description 34
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 33
• 239000000741 silica gel Substances 0.000 description 33
• 229910002027 silica gel Inorganic materials 0.000 description 33
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 29
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 27
• 239000011780 sodium chloride Substances 0.000 description 27
• 239000000706 filtrate Substances 0.000 description 25
• 230000002829 reductive effect Effects 0.000 description 25
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• 239000010410 layer Substances 0.000 description 24
• 125000005843 halogen group Chemical group 0.000 description 22
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 21
• 239000002904 solvent Substances 0.000 description 21
• 239000000543 intermediate Substances 0.000 description 20
• 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 20
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 19
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 19
• 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 19
• 238000004587 chromatography analysis Methods 0.000 description 19
• 229910000069 nitrogen hydride Inorganic materials 0.000 description 18
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 17
• 238000004440 column chromatography Methods 0.000 description 17
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
• 239000004202 carbamide Substances 0.000 description 16
• 238000010898 silica gel chromatography Methods 0.000 description 16
• 229940086542 triethylamine Drugs 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
• 239000000872 buffer Substances 0.000 description 14
• 239000000463 material Substances 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• 238000000746 purification Methods 0.000 description 14
• 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 14
• 201000011510 cancer Diseases 0.000 description 13
• 239000012458 free base Substances 0.000 description 13
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 13
• 235000011056 potassium acetate Nutrition 0.000 description 13
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical group BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
• 239000002253 acid Substances 0.000 description 12
• 125000003386 piperidinyl group Chemical group 0.000 description 12
• 238000011282 treatment Methods 0.000 description 12
• 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 11
• 229910004298 SiO 2 Inorganic materials 0.000 description 11
• 150000001408 amides Chemical class 0.000 description 11
• 150000001412 amines Chemical class 0.000 description 11
• 230000000694 effects Effects 0.000 description 11
• 239000012299 nitrogen atmosphere Substances 0.000 description 11
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 10
• 239000012043 crude product Substances 0.000 description 10
• 150000002148 esters Chemical class 0.000 description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
• 239000006260 foam Substances 0.000 description 10
• 238000004128 high performance liquid chromatography Methods 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
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 10
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
• 241000124008 Mammalia Species 0.000 description 9
• 125000003118 aryl group Chemical group 0.000 description 9
• 239000003480 eluent Substances 0.000 description 9
• 238000010438 heat treatment Methods 0.000 description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
• 239000012071 phase Substances 0.000 description 9
• 229910000029 sodium carbonate Inorganic materials 0.000 description 9
• 235000017550 sodium carbonate Nutrition 0.000 description 9
• 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 8
• 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 8
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
• CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 8
• 229910052681 coesite Inorganic materials 0.000 description 8
• 229910052906 cristobalite Inorganic materials 0.000 description 8
• 230000002401 inhibitory effect Effects 0.000 description 8
• 239000012074 organic phase Substances 0.000 description 8
• LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 8
• 235000012239 silicon dioxide Nutrition 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
• VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 8
• 229910052682 stishovite Inorganic materials 0.000 description 8
• WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 8
• 229910052905 tridymite Inorganic materials 0.000 description 8
• 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
• LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Substances IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 7
• 229910021529 ammonia Inorganic materials 0.000 description 7
• 235000019270 ammonium chloride Nutrition 0.000 description 7
• 239000008346 aqueous phase Substances 0.000 description 7
• NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 7
• 125000001207 fluorophenyl group Chemical group 0.000 description 7
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical group C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
• 238000010926 purge Methods 0.000 description 7
• 230000002441 reversible effect Effects 0.000 description 7
• 238000005406 washing Methods 0.000 description 7
• 238000005160 1H NMR spectroscopy Methods 0.000 description 6
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
• 108091000080 Phosphotransferase Proteins 0.000 description 6
• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 description 6
• 210000004027 cell Anatomy 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• 238000010168 coupling process Methods 0.000 description 6
• 238000005859 coupling reaction Methods 0.000 description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
• 102000020233 phosphotransferase Human genes 0.000 description 6
• 125000004193 piperazinyl group Chemical group 0.000 description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
• 229910052708 sodium Inorganic materials 0.000 description 6
• 235000017557 sodium bicarbonate Nutrition 0.000 description 6
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• 229910000404 tripotassium phosphate Inorganic materials 0.000 description 6
• 235000019798 tripotassium phosphate Nutrition 0.000 description 6
• QNOVBSWPRKSYCR-UHFFFAOYSA-N 3-iodo-7-(4-methylsulfonylphenyl)imidazo[1,2-a]pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC2=NC=C(I)N2C=C1 QNOVBSWPRKSYCR-UHFFFAOYSA-N 0.000 description 5
• 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 5
• 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 5
• QOWSWEBLNVACCL-UHFFFAOYSA-N 4-Bromophenyl acetate Chemical compound OC(=O)CC1=CC=C(Br)C=C1 QOWSWEBLNVACCL-UHFFFAOYSA-N 0.000 description 5
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
• 208000007766 Kaposi sarcoma Diseases 0.000 description 5
• 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 5
• 201000004681 Psoriasis Diseases 0.000 description 5
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
• 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 description 5
• 150000001499 aryl bromides Chemical class 0.000 description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
• 230000015572 biosynthetic process Effects 0.000 description 5
• 230000008878 coupling Effects 0.000 description 5
• 125000000753 cycloalkyl group Chemical group 0.000 description 5
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