TW200524607A - Compounds - Google Patents

Info

Publication number

TW200524607A

TW200524607A TW093140595A TW93140595A TW200524607A TW 200524607 A TW200524607 A TW 200524607A TW 093140595 A TW093140595 A TW 093140595A TW 93140595 A TW93140595 A TW 93140595A TW 200524607 A TW200524607 A TW 200524607A

Authority

TW

Taiwan

Prior art keywords

alkyl

group

alkoxy

saturated

formula

Prior art date

2003-12-24

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 187
• 150000003839 salts Chemical class 0.000 claims abstract description 68
• 238000000034 method Methods 0.000 claims abstract description 66
• 238000004519 manufacturing process Methods 0.000 claims abstract description 39
• 238000002360 preparation method Methods 0.000 claims abstract description 34
• 239000000651 prodrug Substances 0.000 claims abstract description 29
• 229940002612 prodrug Drugs 0.000 claims abstract description 29
• 239000012453 solvate Substances 0.000 claims abstract description 27
• 239000003814 drug Substances 0.000 claims abstract description 19
• 230000001772 anti-angiogenic effect Effects 0.000 claims abstract description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
• 125000000217 alkyl group Chemical group 0.000 claims description 682
• -1 amino, aminocarbamoyl Chemical group 0.000 claims description 450
• 229920006395 saturated elastomer Polymers 0.000 claims description 376
• 125000003545 alkoxy group Chemical group 0.000 claims description 366
• 239000001257 hydrogen Substances 0.000 claims description 206
• 229910052739 hydrogen Inorganic materials 0.000 claims description 206
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 159
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 150
• 150000001412 amines Chemical class 0.000 claims description 148
• 125000003282 alkyl amino group Chemical group 0.000 claims description 137
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 128
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 126
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 110
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 107
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 97
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 89
• 238000006243 chemical reaction Methods 0.000 claims description 84
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 80
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 78
• 235000019000 fluorine Nutrition 0.000 claims description 68
• 125000005843 halogen group Chemical group 0.000 claims description 64
• 125000003118 aryl group Chemical group 0.000 claims description 63
• 239000011737 fluorine Substances 0.000 claims description 60
• 229910052731 fluorine Inorganic materials 0.000 claims description 60
• 125000000623 heterocyclic group Chemical group 0.000 claims description 52
• 125000001072 heteroaryl group Chemical group 0.000 claims description 50
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 46
• 238000006467 substitution reaction Methods 0.000 claims description 42
• 125000001153 fluoro group Chemical group F* 0.000 claims description 40
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 40
• 150000002431 hydrogen Chemical class 0.000 claims description 39
• 125000002971 oxazolyl group Chemical group 0.000 claims description 38
• 125000000524 functional group Chemical group 0.000 claims description 35
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 34
• 150000001335 aliphatic alkanes Chemical group 0.000 claims description 32
• 125000002541 furyl group Chemical group 0.000 claims description 31
• 125000005842 heteroatom Chemical group 0.000 claims description 31
• 125000004076 pyridyl group Chemical group 0.000 claims description 31
• 125000002619 bicyclic group Chemical group 0.000 claims description 28
• 229910052757 nitrogen Inorganic materials 0.000 claims description 28
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 28
• 125000003277 amino group Chemical group 0.000 claims description 25
• 125000002883 imidazolyl group Chemical group 0.000 claims description 24
• 229910052705 radium Inorganic materials 0.000 claims description 23
• 229910052701 rubidium Inorganic materials 0.000 claims description 23
• 125000001425 triazolyl group Chemical group 0.000 claims description 23
• 229910052799 carbon Inorganic materials 0.000 claims description 22
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 22
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 22
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 21
• 239000007789 gas Substances 0.000 claims description 21
• CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical group FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 20
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 20
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 19
• 229910052760 oxygen Inorganic materials 0.000 claims description 19
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 18
• 241000282414 Homo sapiens Species 0.000 claims description 17
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 17
• 125000001424 substituent group Chemical group 0.000 claims description 17
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 16
• 125000006239 protecting group Chemical group 0.000 claims description 15
• 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 15
• 125000004432 carbon atom Chemical group C* 0.000 claims description 14
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
• 239000000460 chlorine Substances 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 239000012948 isocyanate Substances 0.000 claims description 12
• 239000001301 oxygen Substances 0.000 claims description 12
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• 125000000335 thiazolyl group Chemical group 0.000 claims description 11
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
• 150000002513 isocyanates Chemical class 0.000 claims description 10
• 229940079593 drug Drugs 0.000 claims description 9
• 239000000126 substance Substances 0.000 claims description 9
• 125000001544 thienyl group Chemical group 0.000 claims description 9
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 9
• 150000001345 alkine derivatives Chemical class 0.000 claims description 8
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 8
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
• 229910052794 bromium Inorganic materials 0.000 claims description 7
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 6
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 229910052740 iodine Inorganic materials 0.000 claims description 5
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
• 235000015510 Cucumis melo subsp melo Nutrition 0.000 claims description 4
• 239000011630 iodine Substances 0.000 claims description 4
• 125000001725 pyrenyl group Chemical group 0.000 claims description 4
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
• JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims description 2
• YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 2
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
• FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims description 2
• 125000004104 aryloxy group Chemical group 0.000 claims description 2
• 125000003943 azolyl group Chemical group 0.000 claims description 2
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
• 125000003944 tolyl group Chemical group 0.000 claims description 2
• WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 claims description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 7
• IYMYHZHCOOWPGK-UHFFFAOYSA-N 1-chloro-n,n-dimethylmethanamine Chemical compound CN(C)CCl IYMYHZHCOOWPGK-UHFFFAOYSA-N 0.000 claims 1
• 241000219112 Cucumis Species 0.000 claims 1
• ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 1
• 125000002252 acyl group Chemical group 0.000 claims 1
• IVHKZGYFKJRXBD-UHFFFAOYSA-N amino carbamate Chemical compound NOC(N)=O IVHKZGYFKJRXBD-UHFFFAOYSA-N 0.000 claims 1
• 239000011733 molybdenum Substances 0.000 claims 1
• 229910052750 molybdenum Inorganic materials 0.000 claims 1
• 229940124617 receptor tyrosine kinase inhibitor Drugs 0.000 claims 1
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
• 241001465754 Metazoa Species 0.000 abstract description 22
• 230000008569 process Effects 0.000 abstract description 10
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 105
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 100
• 239000000543 intermediate Substances 0.000 description 74
• 239000002585 base Substances 0.000 description 65
• 239000004202 carbamide Substances 0.000 description 64
• 238000005481 NMR spectroscopy Methods 0.000 description 55
• 239000007858 starting material Substances 0.000 description 53
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 40
• 239000000243 solution Substances 0.000 description 38
• 102000005962 receptors Human genes 0.000 description 32
• 108020003175 receptors Proteins 0.000 description 32
• 210000004027 cell Anatomy 0.000 description 31
• 239000003446 ligand Substances 0.000 description 31
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 31
• 101100481408 Danio rerio tie2 gene Proteins 0.000 description 29
• 101100481410 Mus musculus Tek gene Proteins 0.000 description 29
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 28
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 26
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 26
• 206010028980 Neoplasm Diseases 0.000 description 25
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 25
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 24
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
• 108010090091 TIE-2 Receptor Proteins 0.000 description 21
• 239000007787 solid Substances 0.000 description 19
• 238000012360 testing method Methods 0.000 description 19
• 230000000694 effects Effects 0.000 description 18
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 18
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
• 238000010561 standard procedure Methods 0.000 description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
• 201000011510 cancer Diseases 0.000 description 16
• 239000003112 inhibitor Substances 0.000 description 15
• 239000011541 reaction mixture Substances 0.000 description 15
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 15
• 229910001868 water Inorganic materials 0.000 description 15
• 150000001721 carbon Chemical group 0.000 description 14
• 239000000203 mixture Substances 0.000 description 14
• 239000000047 product Substances 0.000 description 14
• 102000012753 TIE-2 Receptor Human genes 0.000 description 13
• 125000000168 pyrrolyl group Chemical group 0.000 description 13
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
• 108091000080 Phosphotransferase Proteins 0.000 description 12
• 230000033115 angiogenesis Effects 0.000 description 12
• 238000003556 assay Methods 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
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
• 230000002401 inhibitory effect Effects 0.000 description 12
• 102000020233 phosphotransferase Human genes 0.000 description 12
• 238000011282 treatment Methods 0.000 description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
• 150000003973 alkyl amines Chemical class 0.000 description 11
• 125000000304 alkynyl group Chemical group 0.000 description 11
• 230000035578 autophosphorylation Effects 0.000 description 11
• 210000004204 blood vessel Anatomy 0.000 description 11
• 150000002148 esters Chemical class 0.000 description 11
• 108090000623 proteins and genes Proteins 0.000 description 11
• 230000015572 biosynthetic process Effects 0.000 description 10
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• 239000003480 eluent Substances 0.000 description 10
• 235000019439 ethyl acetate Nutrition 0.000 description 10
• 238000003818 flash chromatography Methods 0.000 description 10
• 230000005764 inhibitory process Effects 0.000 description 10
• 125000004149 thio group Chemical group *S* 0.000 description 10
• 230000002792 vascular Effects 0.000 description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 238000004458 analytical method Methods 0.000 description 9
• LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 9
• 201000010099 disease Diseases 0.000 description 9
• 210000002889 endothelial cell Anatomy 0.000 description 9
• 238000001727 in vivo Methods 0.000 description 9
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• 239000006166 lysate Substances 0.000 description 9
• 238000006366 phosphorylation reaction Methods 0.000 description 9
• 125000005630 sialyl group Chemical group 0.000 description 9
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
• 239000002253 acid Substances 0.000 description 8
• 230000012010 growth Effects 0.000 description 8
• 239000003701 inert diluent Substances 0.000 description 8
• 108090000765 processed proteins & peptides Proteins 0.000 description 8
• 238000000746 purification Methods 0.000 description 8
• MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical compound NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 description 8
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 7
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 7
• 101100323232 Mus musculus Ang3 gene Proteins 0.000 description 7
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 7
• 125000004122 cyclic group Chemical group 0.000 description 7
• 230000026731 phosphorylation Effects 0.000 description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 7
• 230000019491 signal transduction Effects 0.000 description 7
• 239000000741 silica gel Substances 0.000 description 7
• 229910002027 silica gel Inorganic materials 0.000 description 7
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• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 7
• AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 6
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 6
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 6
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• 238000007792 addition Methods 0.000 description 6
• 229910021529 ammonia Inorganic materials 0.000 description 6
• 235000010290 biphenyl Nutrition 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• 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 6
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 6
• 238000005516 engineering process Methods 0.000 description 6
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• 229910000069 nitrogen hydride Inorganic materials 0.000 description 6
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• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 5
• 241000282412 Homo Species 0.000 description 5
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
• 208000034038 Pathologic Neovascularization Diseases 0.000 description 5
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
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• 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 5
• 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 5
• ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 description 5
• 230000002159 abnormal effect Effects 0.000 description 5
• 235000001014 amino acid Nutrition 0.000 description 5
• 239000000010 aprotic solvent Substances 0.000 description 5
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• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
• 230000018109 developmental process Effects 0.000 description 5
• 150000002170 ethers Chemical class 0.000 description 5
• 239000000796 flavoring agent Substances 0.000 description 5
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