RU2518089C2 - Производные имидазопиридина в качестве ингибиторов рецепторных тирозинкиназ - Google Patents

Info

Publication number

RU2518089C2

RU2518089C2 RU2011100786/04A RU2011100786A RU2518089C2 RU 2518089 C2 RU2518089 C2 RU 2518089C2 RU 2011100786/04 A RU2011100786/04 A RU 2011100786/04A RU 2011100786 A RU2011100786 A RU 2011100786A RU 2518089 C2 RU2518089 C2 RU 2518089C2

Authority

RU

Russia

Prior art keywords

alkyl

group

groups

heterocyclic group

substituted

Prior art date

2008-06-13

Links

• Espacenet
• Global Dossier
• Discuss

• 239000003112 inhibitor Substances 0.000 title description 28
• 108091008598 receptor tyrosine kinases Proteins 0.000 title description 6
• 102000027426 receptor tyrosine kinases Human genes 0.000 title description 6
• 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 362
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 149
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 142
• 239000001257 hydrogen Substances 0.000 claims abstract description 141
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 123
• 150000002367 halogens Chemical class 0.000 claims abstract description 120
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 119
• -1 -X-R5 Chemical group 0.000 claims abstract description 118
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 113
• 108091008794 FGF receptors Proteins 0.000 claims abstract description 83
• 238000011282 treatment Methods 0.000 claims abstract description 80
• 125000003118 aryl group Chemical group 0.000 claims abstract description 71
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 63
• 201000011510 cancer Diseases 0.000 claims abstract description 54
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 51
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 42
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 39
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 37
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 31
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 25
• 230000001575 pathological effect Effects 0.000 claims abstract description 25
• 239000000126 substance Substances 0.000 claims abstract description 21
• 230000001404 mediated effect Effects 0.000 claims abstract description 18
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 18
• 230000002265 prevention Effects 0.000 claims abstract description 17
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 15
• 239000001301 oxygen Substances 0.000 claims abstract description 15
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 14
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 13
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 11
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims abstract description 10
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 6
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 472
• 238000000034 method Methods 0.000 claims description 87
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 63
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 63
• 201000010099 disease Diseases 0.000 claims description 60
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 60
• 239000003814 drug Substances 0.000 claims description 50
• 150000003839 salts Chemical class 0.000 claims description 44
• 125000002883 imidazolyl group Chemical group 0.000 claims description 35
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 30
• 125000003386 piperidinyl group Chemical group 0.000 claims description 25
• 125000004432 carbon atom Chemical group C* 0.000 claims description 24
• 125000001424 substituent group Chemical group 0.000 claims description 21
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims description 20
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 19
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
• 238000004519 manufacturing process Methods 0.000 claims description 15
• 125000001544 thienyl group Chemical group 0.000 claims description 14
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 150000002431 hydrogen Chemical class 0.000 claims description 12
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 12
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 12
• 125000000335 thiazolyl group Chemical group 0.000 claims description 11
• GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
• 125000004193 piperazinyl group Chemical group 0.000 claims description 10
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 10
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
• 229910052717 sulfur Chemical group 0.000 claims description 9
• 239000011593 sulfur Chemical group 0.000 claims description 9
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 9
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
• 230000003993 interaction Effects 0.000 claims description 7
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 6
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 6
• 125000004306 triazinyl group Chemical group 0.000 claims description 6
• KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 5
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
• 150000003053 piperidines Chemical class 0.000 claims description 4
• 102000052178 fibroblast growth factor receptor activity proteins Human genes 0.000 claims 1
• 230000000694 effects Effects 0.000 abstract description 59
• 230000002159 abnormal effect Effects 0.000 abstract description 14
• 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 8
• 239000005864 Sulphur Substances 0.000 abstract 2
• 102000044168 Fibroblast Growth Factor Receptor Human genes 0.000 description 81
• 150000007523 nucleic acids Chemical class 0.000 description 80
• 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 56
• 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 56
• 108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 55
• 230000035772 mutation Effects 0.000 description 54
• 125000003545 alkoxy group Chemical group 0.000 description 53
• 125000000392 cycloalkenyl group Chemical group 0.000 description 46
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 44
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 44
• 102100026547 Platelet-derived growth factor receptor beta Human genes 0.000 description 44
• 101000692455 Homo sapiens Platelet-derived growth factor receptor beta Proteins 0.000 description 41
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 41
• 101710182389 Fibroblast growth factor receptor 2 Proteins 0.000 description 38
• 239000000203 mixture Substances 0.000 description 38
• 102100023600 Fibroblast growth factor receptor 2 Human genes 0.000 description 37
• 102100027842 Fibroblast growth factor receptor 3 Human genes 0.000 description 36
• 101710182396 Fibroblast growth factor receptor 3 Proteins 0.000 description 36
• 230000014509 gene expression Effects 0.000 description 32
• 230000033115 angiogenesis Effects 0.000 description 30
• ZEOWTGPWHLSLOG-UHFFFAOYSA-N Cc1ccc(cc1-c1ccc2c(n[nH]c2c1)-c1cnn(c1)C1CC1)C(=O)Nc1cccc(c1)C(F)(F)F Chemical compound Cc1ccc(cc1-c1ccc2c(n[nH]c2c1)-c1cnn(c1)C1CC1)C(=O)Nc1cccc(c1)C(F)(F)F ZEOWTGPWHLSLOG-UHFFFAOYSA-N 0.000 description 29
• 102100023593 Fibroblast growth factor receptor 1 Human genes 0.000 description 29
• 101710182386 Fibroblast growth factor receptor 1 Proteins 0.000 description 29
• 230000002401 inhibitory effect Effects 0.000 description 29
• 229940079593 drug Drugs 0.000 description 28
• 102000018233 Fibroblast Growth Factor Human genes 0.000 description 27
• 108050007372 Fibroblast Growth Factor Proteins 0.000 description 27
• 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 description 27
• 238000006243 chemical reaction Methods 0.000 description 27
• 108090000623 proteins and genes Proteins 0.000 description 27
• 125000002837 carbocyclic group Chemical group 0.000 description 26
• 210000004027 cell Anatomy 0.000 description 26
• 239000012453 solvate Substances 0.000 description 26
• 108091000080 Phosphotransferase Proteins 0.000 description 25
• 102000020233 phosphotransferase Human genes 0.000 description 25
• 102100027844 Fibroblast growth factor receptor 4 Human genes 0.000 description 24
• 101000917134 Homo sapiens Fibroblast growth factor receptor 4 Proteins 0.000 description 24
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
• 125000001072 heteroaryl group Chemical group 0.000 description 23
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 23
• 229940126864 fibroblast growth factor Drugs 0.000 description 21
• 125000004076 pyridyl group Chemical group 0.000 description 21
• 230000004913 activation Effects 0.000 description 20
• 239000000460 chlorine Substances 0.000 description 20
• 239000003446 ligand Substances 0.000 description 20
• 210000001519 tissue Anatomy 0.000 description 20
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 19
• 101000851007 Homo sapiens Vascular endothelial growth factor receptor 2 Proteins 0.000 description 19
• 229910052801 chlorine Inorganic materials 0.000 description 19
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 18
• 125000004429 atom Chemical group 0.000 description 17
• 125000004122 cyclic group Chemical group 0.000 description 17
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
• 230000015572 biosynthetic process Effects 0.000 description 16
• 238000011161 development Methods 0.000 description 16
• 230000018109 developmental process Effects 0.000 description 16
• 150000002148 esters Chemical class 0.000 description 16
• 208000034578 Multiple myelomas Diseases 0.000 description 15
• 206010035226 Plasma cell myeloma Diseases 0.000 description 15
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 15
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 15
• 239000002585 base Substances 0.000 description 15
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
• 239000002253 acid Substances 0.000 description 14
• 230000000875 corresponding effect Effects 0.000 description 14
• 238000011321 prophylaxis Methods 0.000 description 14
• 230000008901 benefit Effects 0.000 description 13
• 125000002619 bicyclic group Chemical group 0.000 description 13
• 239000003054 catalyst Substances 0.000 description 13
• 229910052731 fluorine Inorganic materials 0.000 description 13
• 230000005764 inhibitory process Effects 0.000 description 13
• 230000035755 proliferation Effects 0.000 description 13
• 102000004169 proteins and genes Human genes 0.000 description 13
• 238000003786 synthesis reaction Methods 0.000 description 13
• 239000003826 tablet Substances 0.000 description 13
• 230000003827 upregulation Effects 0.000 description 13
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 12
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
• 150000001204 N-oxides Chemical class 0.000 description 12
• 239000002775 capsule Substances 0.000 description 12
• 239000011737 fluorine Substances 0.000 description 12
• 229910052763 palladium Inorganic materials 0.000 description 12
• 102000005962 receptors Human genes 0.000 description 12
• 108020003175 receptors Proteins 0.000 description 12
• 239000000243 solution Substances 0.000 description 12
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
• 208000000236 Prostatic Neoplasms Diseases 0.000 description 11
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
• 150000001412 amines Chemical class 0.000 description 11
• 230000027455 binding Effects 0.000 description 11
• 239000003153 chemical reaction reagent Substances 0.000 description 11
• 238000001802 infusion Methods 0.000 description 11
• 230000003287 optical effect Effects 0.000 description 11
• 239000002904 solvent Substances 0.000 description 11
• 230000004614 tumor growth Effects 0.000 description 11
• XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 11
• 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 description 10
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
• 125000003277 amino group Chemical group 0.000 description 10
• 239000003795 chemical substances by application Substances 0.000 description 10
• 239000002552 dosage form Substances 0.000 description 10
• 238000004949 mass spectrometry Methods 0.000 description 10
• 125000002971 oxazolyl group Chemical group 0.000 description 10
• 239000000651 prodrug Substances 0.000 description 10
• 229940002612 prodrug Drugs 0.000 description 10
• 230000001225 therapeutic effect Effects 0.000 description 10
• 238000002560 therapeutic procedure Methods 0.000 description 10
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 9
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 9
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 9
• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 description 9
• 239000004480 active ingredient Substances 0.000 description 9
• 230000010261 cell growth Effects 0.000 description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
• 125000002950 monocyclic group Chemical group 0.000 description 9
• 239000000546 pharmaceutical excipient Substances 0.000 description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
• 206010005003 Bladder cancer Diseases 0.000 description 8
• 208000026310 Breast neoplasm Diseases 0.000 description 8
• 206010060862 Prostate cancer Diseases 0.000 description 8
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 8
• 230000033228 biological regulation Effects 0.000 description 8
• 235000013877 carbamide Nutrition 0.000 description 8
• 239000011248 coating agent Substances 0.000 description 8
• 238000000576 coating method Methods 0.000 description 8
• 230000001976 improved effect Effects 0.000 description 8
• 239000000314 lubricant Substances 0.000 description 8
• 230000002018 overexpression Effects 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 230000008569 process Effects 0.000 description 8
• 230000019491 signal transduction Effects 0.000 description 8
• 208000011580 syndromic disease Diseases 0.000 description 8
• 229940124597 therapeutic agent Drugs 0.000 description 8
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
• 108090000379 Fibroblast growth factor 2 Proteins 0.000 description 7
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 7
• 102000001253 Protein Kinase Human genes 0.000 description 7
• 102000004278 Receptor Protein-Tyrosine Kinases Human genes 0.000 description 7
• 108090000873 Receptor Protein-Tyrosine Kinases Proteins 0.000 description 7
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 7
• 230000003321 amplification Effects 0.000 description 7
• 210000004204 blood vessel Anatomy 0.000 description 7
• 238000002405 diagnostic procedure Methods 0.000 description 7
• 230000012010 growth Effects 0.000 description 7
• 239000003102 growth factor Substances 0.000 description 7
• 238000009396 hybridization Methods 0.000 description 7
• 238000002347 injection Methods 0.000 description 7
• 239000007924 injection Substances 0.000 description 7
• 208000032839 leukemia Diseases 0.000 description 7
• 230000007246 mechanism Effects 0.000 description 7
• 238000003199 nucleic acid amplification method Methods 0.000 description 7
• 239000012071 phase Substances 0.000 description 7
• 108060006633 protein kinase Proteins 0.000 description 7
• 238000000746 purification Methods 0.000 description 7
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 7
• 238000011160 research Methods 0.000 description 7
• 239000007787 solid Substances 0.000 description 7
• 201000005112 urinary bladder cancer Diseases 0.000 description 7
• 230000002792 vascular Effects 0.000 description 7
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
• 125000001963 4 membered heterocyclic group Chemical group 0.000 description 6
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 6
• 206010006187 Breast cancer Diseases 0.000 description 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• 102000004190 Enzymes Human genes 0.000 description 6
• 108090000790 Enzymes Proteins 0.000 description 6
• 206010016654 Fibrosis Diseases 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 6
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 6
• 230000001594 aberrant effect Effects 0.000 description 6
• 230000003213 activating effect Effects 0.000 description 6
• 230000002491 angiogenic effect Effects 0.000 description 6
• 125000002393 azetidinyl group Chemical group 0.000 description 6
• 230000004071 biological effect Effects 0.000 description 6
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical class OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 6
• 239000000872 buffer Substances 0.000 description 6
• 150000001721 carbon Chemical group 0.000 description 6
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
• 210000001072 colon Anatomy 0.000 description 6
• 239000002299 complementary DNA Substances 0.000 description 6
• 230000007423 decrease Effects 0.000 description 6
• 230000004069 differentiation Effects 0.000 description 6
• 125000000524 functional group Chemical group 0.000 description 6
• 230000004077 genetic alteration Effects 0.000 description 6
• 150000002430 hydrocarbons Chemical group 0.000 description 6
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
• 238000007901 in situ hybridization Methods 0.000 description 6
• 238000000338 in vitro Methods 0.000 description 6
• 239000000543 intermediate Substances 0.000 description 6
• 238000001990 intravenous administration Methods 0.000 description 6
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 6
• 239000002502 liposome Substances 0.000 description 6
• 238000004811 liquid chromatography Methods 0.000 description 6
• 210000004072 lung Anatomy 0.000 description 6
• 238000002595 magnetic resonance imaging Methods 0.000 description 6
• 239000000463 material Substances 0.000 description 6
• 108020004999 messenger RNA Proteins 0.000 description 6
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 6
• 229920000642 polymer Polymers 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 238000002360 preparation method Methods 0.000 description 6
• 238000012545 processing Methods 0.000 description 6
• 125000006239 protecting group Chemical group 0.000 description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 description 6
• 230000002829 reductive effect Effects 0.000 description 6
• 239000000523 sample Substances 0.000 description 6
• 238000012216 screening Methods 0.000 description 6
• 239000006104 solid solution Substances 0.000 description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 6
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 6
• 230000005747 tumor angiogenesis Effects 0.000 description 6
• 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 6
• BJHCYTJNPVGSBZ-YXSASFKJSA-N 1-[4-[6-amino-5-[(Z)-methoxyiminomethyl]pyrimidin-4-yl]oxy-2-chlorophenyl]-3-ethylurea Chemical compound CCNC(=O)Nc1ccc(Oc2ncnc(N)c2\C=N/OC)cc1Cl BJHCYTJNPVGSBZ-YXSASFKJSA-N 0.000 description 5
• 201000010028 Acrocephalosyndactylia Diseases 0.000 description 5
• 208000031261 Acute myeloid leukaemia Diseases 0.000 description 5
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 5
• 206010008342 Cervix carcinoma Diseases 0.000 description 5
• 108091006146 Channels Proteins 0.000 description 5
• 102000003974 Fibroblast growth factor 2 Human genes 0.000 description 5
• 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 description 5
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 5
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
• 206010033128 Ovarian cancer Diseases 0.000 description 5
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
• 238000006069 Suzuki reaction reaction Methods 0.000 description 5
• 230000009471 action Effects 0.000 description 5
• 239000002870 angiogenesis inducing agent Substances 0.000 description 5
• 230000006907 apoptotic process Effects 0.000 description 5
• 230000000903 blocking effect Effects 0.000 description 5
• 210000004369 blood Anatomy 0.000 description 5
• 239000008280 blood Substances 0.000 description 5
• 239000004202 carbamide Substances 0.000 description 5
• 125000002843 carboxylic acid group Chemical group 0.000 description 5
• 230000004663 cell proliferation Effects 0.000 description 5
• 201000010881 cervical cancer Diseases 0.000 description 5
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 description 5
• 238000005859 coupling reaction Methods 0.000 description 5
• 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 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
• 238000003745 diagnosis Methods 0.000 description 5
• 239000003085 diluting agent Substances 0.000 description 5
• 239000007884 disintegrant Substances 0.000 description 5
• 238000001035 drying Methods 0.000 description 5
• 210000002889 endothelial cell Anatomy 0.000 description 5
• 230000004761 fibrosis Effects 0.000 description 5
• 238000004108 freeze drying Methods 0.000 description 5
• 210000001035 gastrointestinal tract Anatomy 0.000 description 5
• 208000036971 interstitial lung disease 2 Diseases 0.000 description 5
• 210000004185 liver Anatomy 0.000 description 5
• 239000003550 marker Substances 0.000 description 5
• 125000006574 non-aromatic ring group Chemical group 0.000 description 5
• 238000010606 normalization Methods 0.000 description 5
• 108020004707 nucleic acids Proteins 0.000 description 5
• 102000039446 nucleic acids Human genes 0.000 description 5
• 239000002243 precursor Substances 0.000 description 5
• 230000001023 pro-angiogenic effect Effects 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• 230000002062 proliferating effect Effects 0.000 description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
• 125000000168 pyrrolyl group Chemical group 0.000 description 5
• 230000001105 regulatory effect Effects 0.000 description 5
• 229920006395 saturated elastomer Polymers 0.000 description 5
• 230000011664 signaling Effects 0.000 description 5
• 238000010561 standard procedure Methods 0.000 description 5
• 238000013518 transcription Methods 0.000 description 5
• 230000035897 transcription Effects 0.000 description 5
• 210000004881 tumor cell Anatomy 0.000 description 5
• 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 4
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
• 208000025490 Apert syndrome Diseases 0.000 description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
• 206010014759 Endometrial neoplasm Diseases 0.000 description 4
• 108090000386 Fibroblast Growth Factor 1 Proteins 0.000 description 4
• 108010010803 Gelatin Proteins 0.000 description 4
• 208000032612 Glial tumor Diseases 0.000 description 4
• 206010018338 Glioma Diseases 0.000 description 4
• 206010018364 Glomerulonephritis Diseases 0.000 description 4
• 206010021143 Hypoxia Diseases 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
• 208000008839 Kidney Neoplasms Diseases 0.000 description 4
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
• 208000033833 Myelomonocytic Chronic Leukemia Diseases 0.000 description 4
• 108020005497 Nuclear hormone receptor Proteins 0.000 description 4
• 102000007399 Nuclear hormone receptor Human genes 0.000 description 4
• 108700020796 Oncogene Proteins 0.000 description 4
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 4
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
• 102000004257 Potassium Channel Human genes 0.000 description 4
• 102000001708 Protein Isoforms Human genes 0.000 description 4
• 108010029485 Protein Isoforms Proteins 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 4
• 208000005718 Stomach Neoplasms Diseases 0.000 description 4
• 208000024770 Thyroid neoplasm Diseases 0.000 description 4
• 150000001345 alkine derivatives Chemical class 0.000 description 4
• 150000001413 amino acids Chemical class 0.000 description 4
• 238000001574 biopsy Methods 0.000 description 4
• 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 4
• 210000000481 breast Anatomy 0.000 description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
• 238000004587 chromatography analysis Methods 0.000 description 4
• 230000001684 chronic effect Effects 0.000 description 4
• 201000010902 chronic myelomonocytic leukemia Diseases 0.000 description 4
• 208000029742 colonic neoplasm Diseases 0.000 description 4
• 238000002648 combination therapy Methods 0.000 description 4
• 230000002354 daily effect Effects 0.000 description 4
• 239000006185 dispersion Substances 0.000 description 4
• 239000000945 filler Substances 0.000 description 4
• 239000012634 fragment Substances 0.000 description 4
• 230000006870 function Effects 0.000 description 4
• JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 4
• 239000008273 gelatin Substances 0.000 description 4
• 229920000159 gelatin Polymers 0.000 description 4
• 235000019322 gelatine Nutrition 0.000 description 4
• 235000011852 gelatine desserts Nutrition 0.000 description 4
• UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 4
• 230000007954 hypoxia Effects 0.000 description 4
• 238000001727 in vivo Methods 0.000 description 4
• 230000003834 intracellular effect Effects 0.000 description 4
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 4
• 125000000468 ketone group Chemical group 0.000 description 4
• 239000008101 lactose Substances 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• 208000020816 lung neoplasm Diseases 0.000 description 4
• 230000003211 malignant effect Effects 0.000 description 4
• 239000012528 membrane Substances 0.000 description 4
• 229910052751 metal Inorganic materials 0.000 description 4
• 239000002184 metal Substances 0.000 description 4
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 4
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 4
• 238000002156 mixing Methods 0.000 description 4
• 208000015122 neurodegenerative disease Diseases 0.000 description 4
• 239000003960 organic solvent Substances 0.000 description 4
• 230000011164 ossification Effects 0.000 description 4
• CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical compound C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 description 4
• 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 4
• 238000007911 parenteral administration Methods 0.000 description 4
• 230000026731 phosphorylation Effects 0.000 description 4
• 238000006366 phosphorylation reaction Methods 0.000 description 4
• 230000035790 physiological processes and functions Effects 0.000 description 4
• 239000002798 polar solvent Substances 0.000 description 4
• 125000003367 polycyclic group Chemical group 0.000 description 4
• 108020001213 potassium channel Proteins 0.000 description 4
• 208000005069 pulmonary fibrosis Diseases 0.000 description 4
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 4
• 238000006722 reduction reaction Methods 0.000 description 4
• 238000003757 reverse transcription PCR Methods 0.000 description 4
• 230000002441 reversible effect Effects 0.000 description 4
• 201000009410 rhabdomyosarcoma Diseases 0.000 description 4
• 206010039073 rheumatoid arthritis Diseases 0.000 description 4
• 102200143304 rs351855 Human genes 0.000 description 4
• 239000007858 starting material Substances 0.000 description 4
• 210000002784 stomach Anatomy 0.000 description 4
• 238000007920 subcutaneous administration Methods 0.000 description 4
• 235000000346 sugar Nutrition 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• 150000003536 tetrazoles Chemical class 0.000 description 4
• 150000003852 triazoles Chemical class 0.000 description 4
• 239000003643 water by type Substances 0.000 description 4
• CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 3
• 108091032973 (ribonucleotides)n+m Proteins 0.000 description 3
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 3
• XXJWYDDUDKYVKI-UHFFFAOYSA-N 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-[3-(1-pyrrolidinyl)propoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C(=C4C=C(C)NC4=CC=3)F)N=CN=C2C=C1OCCCN1CCCC1 XXJWYDDUDKYVKI-UHFFFAOYSA-N 0.000 description 3
• 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 3
• 201000001320 Atherosclerosis Diseases 0.000 description 3
• COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 3
• 206010049889 Craniosynostosis Diseases 0.000 description 3
• 102000004127 Cytokines Human genes 0.000 description 3
• 108090000695 Cytokines Proteins 0.000 description 3
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
• 206010014733 Endometrial cancer Diseases 0.000 description 3
• 102000003971 Fibroblast Growth Factor 1 Human genes 0.000 description 3
• 206010051066 Gastrointestinal stromal tumour Diseases 0.000 description 3
• 208000034951 Genetic Translocation Diseases 0.000 description 3
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
• 101000617130 Homo sapiens Stromal cell-derived factor 1 Proteins 0.000 description 3
• 239000005517 L01XE01 - Imatinib Substances 0.000 description 3
• 239000000232 Lipid Bilayer Substances 0.000 description 3
• 208000000265 Lobular Carcinoma Diseases 0.000 description 3
• 206010027476 Metastases Diseases 0.000 description 3
• 241001465754 Metazoa Species 0.000 description 3
• 201000003793 Myelodysplastic syndrome Diseases 0.000 description 3
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 3
• 208000014767 Myeloproliferative disease Diseases 0.000 description 3
• 206010061535 Ovarian neoplasm Diseases 0.000 description 3
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
• 108010051742 Platelet-Derived Growth Factor beta Receptor Proteins 0.000 description 3
• 238000010240 RT-PCR analysis Methods 0.000 description 3
• 206010038389 Renal cancer Diseases 0.000 description 3
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
• 206010041857 Squamous cell carcinoma of the oral cavity Diseases 0.000 description 3
• 102100021669 Stromal cell-derived factor 1 Human genes 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 229940091171 VEGFR-2 tyrosine kinase inhibitor Drugs 0.000 description 3
• 102100033178 Vascular endothelial growth factor receptor 1 Human genes 0.000 description 3
• 230000005856 abnormality Effects 0.000 description 3
• 238000010521 absorption reaction Methods 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
• 125000004423 acyloxy group Chemical group 0.000 description 3
• 150000001408 amides Chemical class 0.000 description 3
• 238000004458 analytical method Methods 0.000 description 3
• 239000004037 angiogenesis inhibitor Substances 0.000 description 3
• 239000003963 antioxidant agent Substances 0.000 description 3
• 206010003119 arrhythmia Diseases 0.000 description 3
• 206010003246 arthritis Diseases 0.000 description 3
• 150000001502 aryl halides Chemical class 0.000 description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
• 239000012472 biological sample Substances 0.000 description 3
• 239000000090 biomarker Substances 0.000 description 3
• 230000037396 body weight Effects 0.000 description 3
• 125000005621 boronate group Chemical class 0.000 description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
• 229960002412 cediranib Drugs 0.000 description 3
• 230000032823 cell division Effects 0.000 description 3
• 230000033077 cellular process Effects 0.000 description 3
• 230000008859 change Effects 0.000 description 3
• 230000002596 correlated effect Effects 0.000 description 3
• 125000000753 cycloalkyl group Chemical group 0.000 description 3
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
• 230000001419 dependent effect Effects 0.000 description 3
• 230000008021 deposition Effects 0.000 description 3
• 238000001514 detection method Methods 0.000 description 3
• 230000002255 enzymatic effect Effects 0.000 description 3
• JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 3
• 230000008014 freezing Effects 0.000 description 3
• 238000007710 freezing Methods 0.000 description 3
• 206010017758 gastric cancer Diseases 0.000 description 3
• 230000002496 gastric effect Effects 0.000 description 3
• 201000011243 gastrointestinal stromal tumor Diseases 0.000 description 3
• 230000002068 genetic effect Effects 0.000 description 3
• 208000005017 glioblastoma Diseases 0.000 description 3
• 150000004820 halides Chemical class 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• 208000014951 hematologic disease Diseases 0.000 description 3
• 208000016356 hereditary diffuse gastric adenocarcinoma Diseases 0.000 description 3
• 229940088597 hormone Drugs 0.000 description 3
• 239000005556 hormone Substances 0.000 description 3
• 150000004677 hydrates Chemical class 0.000 description 3
• 230000002209 hydrophobic effect Effects 0.000 description 3
• KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 description 3
• 229960002411 imatinib Drugs 0.000 description 3
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
• 239000004615 ingredient Substances 0.000 description 3
• 230000000977 initiatory effect Effects 0.000 description 3
• 238000002955 isolation Methods 0.000 description 3
• 201000010982 kidney cancer Diseases 0.000 description 3
• 229940043355 kinase inhibitor Drugs 0.000 description 3
• 208000014018 liver neoplasm Diseases 0.000 description 3
• 239000011159 matrix material Substances 0.000 description 3
• 230000004060 metabolic process Effects 0.000 description 3
• 230000009401 metastasis Effects 0.000 description 3
• 239000008267 milk Substances 0.000 description 3
• 230000004770 neurodegeneration Effects 0.000 description 3
• 208000010655 oral cavity squamous cell carcinoma Diseases 0.000 description 3
• MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 3
• 230000007170 pathology Effects 0.000 description 3
• 230000037361 pathway Effects 0.000 description 3
• 239000003757 phosphotransferase inhibitor Substances 0.000 description 3
• 229910000027 potassium carbonate Inorganic materials 0.000 description 3
• 239000003755 preservative agent Substances 0.000 description 3
• 230000000069 prophylactic effect Effects 0.000 description 3
• 201000001514 prostate carcinoma Diseases 0.000 description 3
• 125000002577 pseudohalo group Chemical group 0.000 description 3
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 3
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 3
• 230000002285 radioactive effect Effects 0.000 description 3
• 230000009467 reduction Effects 0.000 description 3
• 230000004044 response Effects 0.000 description 3
• 230000000250 revascularization Effects 0.000 description 3
• 238000012552 review Methods 0.000 description 3
• 238000000926 separation method Methods 0.000 description 3
• 239000007962 solid dispersion Substances 0.000 description 3
• 239000007909 solid dosage form Substances 0.000 description 3
• 201000011549 stomach cancer Diseases 0.000 description 3
• 239000004094 surface-active agent Substances 0.000 description 3
• 208000024891 symptom Diseases 0.000 description 3
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 3
• 229930192474 thiophene Natural products 0.000 description 3
• 201000002510 thyroid cancer Diseases 0.000 description 3
• 210000001685 thyroid gland Anatomy 0.000 description 3
• 230000002588 toxic effect Effects 0.000 description 3
• 231100000419 toxicity Toxicity 0.000 description 3
• 230000001988 toxicity Effects 0.000 description 3
• 230000009466 transformation Effects 0.000 description 3
• 230000005945 translocation Effects 0.000 description 3
• UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 3
• 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 3
• 239000005483 tyrosine kinase inhibitor Substances 0.000 description 3
• 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 description 3
• 150000003672 ureas Chemical class 0.000 description 3
• 239000008215 water for injection Substances 0.000 description 3
• 230000029663 wound healing Effects 0.000 description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
• UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
• LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
• CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 2
• KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 2
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 2
• LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 2
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
• 101150028074 2 gene Proteins 0.000 description 2
• OYJGEOAXBALSMM-UHFFFAOYSA-N 2,3-dihydro-1,3-thiazole Chemical compound C1NC=CS1 OYJGEOAXBALSMM-UHFFFAOYSA-N 0.000 description 2
• KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical compound C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 description 2
• HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
• MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 description 2
• YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
• VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 description 2
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
• 208000024827 Alzheimer disease Diseases 0.000 description 2
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
• 108010031480 Artificial Receptors Proteins 0.000 description 2
• 208000023275 Autoimmune disease Diseases 0.000 description 2
• 208000003950 B-cell lymphoma Diseases 0.000 description 2
• MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 description 2
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
• 208000024172 Cardiovascular disease Diseases 0.000 description 2
• 208000001333 Colorectal Neoplasms Diseases 0.000 description 2
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
• 208000009283 Craniosynostoses Diseases 0.000 description 2
• 229920000858 Cyclodextrin Polymers 0.000 description 2
• 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 2
• 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 2
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
• 108020004414 DNA Proteins 0.000 description 2
• 208000008334 Dermatofibrosarcoma Diseases 0.000 description 2
• 206010057070 Dermatofibrosarcoma protuberans Diseases 0.000 description 2
• 208000012239 Developmental disease Diseases 0.000 description 2
• 102000003951 Erythropoietin Human genes 0.000 description 2
• 108090000394 Erythropoietin Proteins 0.000 description 2
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
• 101150025764 FGFR3 gene Proteins 0.000 description 2
• 102100024785 Fibroblast growth factor 2 Human genes 0.000 description 2
• 206010016935 Follicular thyroid cancer Diseases 0.000 description 2
• 108010017080 Granulocyte Colony-Stimulating Factor Proteins 0.000 description 2
• 102000004269 Granulocyte Colony-Stimulating Factor Human genes 0.000 description 2
• 102000009465 Growth Factor Receptors Human genes 0.000 description 2
• 108010009202 Growth Factor Receptors Proteins 0.000 description 2
• 101001047090 Homo sapiens Potassium voltage-gated channel subfamily H member 2 Proteins 0.000 description 2
• 101000851018 Homo sapiens Vascular endothelial growth factor receptor 1 Proteins 0.000 description 2
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
• 206010048643 Hypereosinophilic syndrome Diseases 0.000 description 2
• 102100034343 Integrase Human genes 0.000 description 2
• 102000004310 Ion Channels Human genes 0.000 description 2
• 108090000862 Ion Channels Proteins 0.000 description 2
• 229930194542 Keto Natural products 0.000 description 2
• 206010058467 Lung neoplasm malignant Diseases 0.000 description 2
• 206010025323 Lymphomas Diseases 0.000 description 2
• 229930195725 Mannitol Natural products 0.000 description 2
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
• LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 2
• 238000005481 NMR spectroscopy Methods 0.000 description 2
• 206010029098 Neoplasm skin Diseases 0.000 description 2
• 206010030113 Oedema Diseases 0.000 description 2
• 102000043276 Oncogene Human genes 0.000 description 2
• 208000007571 Ovarian Epithelial Carcinoma Diseases 0.000 description 2
• 229910019142 PO4 Inorganic materials 0.000 description 2
• 201000004014 Pfeiffer syndrome Diseases 0.000 description 2
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
• 208000007913 Pituitary Neoplasms Diseases 0.000 description 2
• 102100022807 Potassium voltage-gated channel subfamily H member 2 Human genes 0.000 description 2
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
• 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 2
• 229940124639 Selective inhibitor Drugs 0.000 description 2
• 208000000453 Skin Neoplasms Diseases 0.000 description 2
• 102000005157 Somatostatin Human genes 0.000 description 2
• 108010056088 Somatostatin Proteins 0.000 description 2
• 208000006011 Stroke Diseases 0.000 description 2
• 102000004887 Transforming Growth Factor beta Human genes 0.000 description 2
• 108090001012 Transforming Growth Factor beta Proteins 0.000 description 2
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
• 108010053100 Vascular Endothelial Growth Factor Receptor-3 Proteins 0.000 description 2
• 206010052428 Wound Diseases 0.000 description 2
• 208000027418 Wounds and injury Diseases 0.000 description 2
• 230000002378 acidificating effect Effects 0.000 description 2
• 230000001154 acute effect Effects 0.000 description 2
• ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
• 206010064930 age-related macular degeneration Diseases 0.000 description 2
• 150000001299 aldehydes Chemical class 0.000 description 2
• 150000001336 alkenes Chemical class 0.000 description 2
• 150000005215 alkyl ethers Chemical class 0.000 description 2
• 150000001409 amidines Chemical class 0.000 description 2
• 125000000539 amino acid group Chemical group 0.000 description 2
• 229940121369 angiogenesis inhibitor Drugs 0.000 description 2
• 125000000129 anionic group Chemical group 0.000 description 2
• 238000011319 anticancer therapy Methods 0.000 description 2
• 239000002246 antineoplastic agent Substances 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 230000006793 arrhythmia Effects 0.000 description 2
• 125000005015 aryl alkynyl group Chemical group 0.000 description 2
• 230000003305 autocrine Effects 0.000 description 2
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
• BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 description 2
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
• LUFPJJNWMYZRQE-UHFFFAOYSA-N benzylsulfanylmethylbenzene Chemical compound C=1C=CC=CC=1CSCC1=CC=CC=C1 LUFPJJNWMYZRQE-UHFFFAOYSA-N 0.000 description 2
• DKDXHNMKTYUOOT-UHFFFAOYSA-N bis(4-bicyclo[2.2.1]heptanyl)phosphane Chemical compound C1CC(C2)CCC12PC1(C2)CCC2CC1 DKDXHNMKTYUOOT-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 210000000988 bone and bone Anatomy 0.000 description 2
• 125000005620 boronic acid group Chemical class 0.000 description 2
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
• 238000002045 capillary electrochromatography Methods 0.000 description 2
• 239000000969 carrier Substances 0.000 description 2
• 238000006555 catalytic reaction Methods 0.000 description 2
• 150000001768 cations Chemical class 0.000 description 2
• 230000003915 cell function Effects 0.000 description 2
• 210000000170 cell membrane Anatomy 0.000 description 2
• 230000001413 cellular effect Effects 0.000 description 2
• 230000036755 cellular response Effects 0.000 description 2
• 210000003679 cervix uteri Anatomy 0.000 description 2
• 238000002512 chemotherapy Methods 0.000 description 2
• 239000007910 chewable tablet Substances 0.000 description 2
• OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
• VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 2
• 210000000349 chromosome Anatomy 0.000 description 2
• 208000019425 cirrhosis of liver Diseases 0.000 description 2
• 229910052802 copper Inorganic materials 0.000 description 2
• 239000010949 copper Substances 0.000 description 2
• 239000006184 cosolvent Substances 0.000 description 2
• 239000013078 crystal Substances 0.000 description 2
• 150000003950 cyclic amides Chemical group 0.000 description 2
• 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 2
• HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
• 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 2
• 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 2
• LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
• 230000002074 deregulated effect Effects 0.000 description 2
• AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 2
• 208000035475 disorder Diseases 0.000 description 2
• 238000004090 dissolution Methods 0.000 description 2
• 239000008298 dragée Substances 0.000 description 2
• 239000003937 drug carrier Substances 0.000 description 2
• 239000003480 eluent Substances 0.000 description 2
• 239000003995 emulsifying agent Substances 0.000 description 2
• 239000000839 emulsion Substances 0.000 description 2
• 238000003821 enantio-separation Methods 0.000 description 2
• 208000023965 endometrium neoplasm Diseases 0.000 description 2
• 150000002085 enols Chemical class 0.000 description 2
• 229940105423 erythropoietin Drugs 0.000 description 2
• 210000003238 esophagus Anatomy 0.000 description 2
• 125000004185 ester group Chemical group 0.000 description 2
• 150000002170 ethers Chemical class 0.000 description 2
• 235000019439 ethyl acetate Nutrition 0.000 description 2
• 208000030533 eye disease Diseases 0.000 description 2
• 210000002950 fibroblast Anatomy 0.000 description 2
• 238000011049 filling Methods 0.000 description 2
• 239000007888 film coating Substances 0.000 description 2
• 238000009501 film coating Methods 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
• VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 description 2
• 235000008191 folinic acid Nutrition 0.000 description 2
• 239000011672 folinic acid Substances 0.000 description 2
• 239000000499 gel Substances 0.000 description 2
• 239000008187 granular material Substances 0.000 description 2
• 230000035876 healing Effects 0.000 description 2
• 201000011066 hemangioma Diseases 0.000 description 2
• 208000019691 hematopoietic and lymphoid cell neoplasm Diseases 0.000 description 2
• 208000018706 hematopoietic system disease Diseases 0.000 description 2
• 206010073071 hepatocellular carcinoma Diseases 0.000 description 2
• 238000004128 high performance liquid chromatography Methods 0.000 description 2
• 238000005984 hydrogenation reaction Methods 0.000 description 2
• 230000007062 hydrolysis Effects 0.000 description 2
• 238000006460 hydrolysis reaction Methods 0.000 description 2
• 208000013403 hyperactivity Diseases 0.000 description 2
• 229960003685 imatinib mesylate Drugs 0.000 description 2
• YLMAHDNUQAMNNX-UHFFFAOYSA-N imatinib methanesulfonate Chemical compound CS(O)(=O)=O.C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 YLMAHDNUQAMNNX-UHFFFAOYSA-N 0.000 description 2
• YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 2
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 2
• 230000001771 impaired effect Effects 0.000 description 2
• 238000011065 in-situ storage Methods 0.000 description 2
• PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
• 230000006698 induction Effects 0.000 description 2
• 230000001939 inductive effect Effects 0.000 description 2
• 238000007918 intramuscular administration Methods 0.000 description 2
• 239000012948 isocyanate Substances 0.000 description 2
• 150000002513 isocyanates Chemical class 0.000 description 2
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
• 125000000842 isoxazolyl group Chemical group 0.000 description 2
• 229960001691 leucovorin Drugs 0.000 description 2
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
• 201000007270 liver cancer Diseases 0.000 description 2
• 210000001853 liver microsome Anatomy 0.000 description 2
• 230000007774 longterm Effects 0.000 description 2
• 201000005202 lung cancer Diseases 0.000 description 2
• 208000002780 macular degeneration Diseases 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• 239000000594 mannitol Substances 0.000 description 2
• 235000010355 mannitol Nutrition 0.000 description 2
• 230000002503 metabolic effect Effects 0.000 description 2
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 2
• 235000013336 milk Nutrition 0.000 description 2
• 210000004080 milk Anatomy 0.000 description 2
• 239000003607 modifier Substances 0.000 description 2
• 238000010172 mouse model Methods 0.000 description 2
• 230000002071 myeloproliferative effect Effects 0.000 description 2
• 239000002773 nucleotide Substances 0.000 description 2
• 125000003729 nucleotide group Chemical group 0.000 description 2
• 230000000771 oncological effect Effects 0.000 description 2
• 231100000822 oral exposure Toxicity 0.000 description 2
• 210000000056 organ Anatomy 0.000 description 2
• 210000001672 ovary Anatomy 0.000 description 2
• 210000000496 pancreas Anatomy 0.000 description 2
• 239000000825 pharmaceutical preparation Substances 0.000 description 2
• 230000000144 pharmacologic effect Effects 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
• 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
• 239000000049 pigment Substances 0.000 description 2
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
• XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 2
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 2
• 238000003752 polymerase chain reaction Methods 0.000 description 2
• 229920005862 polyol Polymers 0.000 description 2
• 150000003077 polyols Chemical class 0.000 description 2
• 238000010837 poor prognosis Methods 0.000 description 2
• OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 2
• XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 2
• 229960004618 prednisone Drugs 0.000 description 2
• 238000004262 preparative liquid chromatography Methods 0.000 description 2
• 108090000765 processed proteins & peptides Proteins 0.000 description 2
• 230000000750 progressive effect Effects 0.000 description 2
• 210000002307 prostate Anatomy 0.000 description 2
• 230000001681 protective effect Effects 0.000 description 2
• 238000001959 radiotherapy Methods 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• 230000007420 reactivation Effects 0.000 description 2
• 210000000664 rectum Anatomy 0.000 description 2
• 102200126674 rs121913478 Human genes 0.000 description 2
• 230000028327 secretion Effects 0.000 description 2
• 238000012163 sequencing technique Methods 0.000 description 2
• 210000003491 skin Anatomy 0.000 description 2
• 210000003625 skull Anatomy 0.000 description 2
• 229910000029 sodium carbonate Inorganic materials 0.000 description 2
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
• 238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 2
• NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 description 2
• 229960000553 somatostatin Drugs 0.000 description 2
• 239000003381 stabilizer Substances 0.000 description 2
• 230000004936 stimulating effect Effects 0.000 description 2
• 239000000829 suppository Substances 0.000 description 2
• 230000001629 suppression Effects 0.000 description 2
• 238000001308 synthesis method Methods 0.000 description 2
• 238000010189 synthetic method Methods 0.000 description 2
• 230000009885 systemic effect Effects 0.000 description 2
• 239000007916 tablet composition Substances 0.000 description 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 2
• 238000002411 thermogravimetry Methods 0.000 description 2
• 150000004867 thiadiazoles Chemical class 0.000 description 2
• 125000005996 thiadiazolopyrimidinyl group Chemical group 0.000 description 2
• 208000030901 thyroid gland follicular carcinoma Diseases 0.000 description 2
• 231100000331 toxic Toxicity 0.000 description 2
• 230000002103 transcriptional effect Effects 0.000 description 2
• 238000000844 transformation Methods 0.000 description 2
• 206010044412 transitional cell carcinoma Diseases 0.000 description 2
• 125000001425 triazolyl group Chemical group 0.000 description 2
• WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 2
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
• 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 2
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
• COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
• BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
• 230000005748 tumor development Effects 0.000 description 2
• 102000003390 tumor necrosis factor Human genes 0.000 description 2
• 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
• 208000023747 urothelial carcinoma Diseases 0.000 description 2
• 230000008728 vascular permeability Effects 0.000 description 2
• 238000002424 x-ray crystallography Methods 0.000 description 2
• SYSFTTYJTWPOOR-UHFFFAOYSA-N (2-diphenylphosphanyl-1-naphthalen-1-yl-3h-naphthalen-2-yl)-diphenylphosphane Chemical group C1C=C2C=CC=CC2=C(C=2C3=CC=CC=C3C=CC=2)C1(P(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 SYSFTTYJTWPOOR-UHFFFAOYSA-N 0.000 description 1
• LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
• NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 1
• DEQANNDTNATYII-OULOTJBUSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-19-[[(2r)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-n-[(2r,3r)-1,3-dihydroxybutan-2-yl]-7-[(1r)-1-hydroxyethyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxa Chemical compound C([C@@H](N)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)C1=CC=CC=C1 DEQANNDTNATYII-OULOTJBUSA-N 0.000 description 1
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
• DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
• 229930007886 (R)-camphor Natural products 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
• QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 1
• XGYCWCIGCYGQFU-UHFFFAOYSA-N 1,2-thiazolidine 1,1-dioxide Chemical compound O=S1(=O)CCCN1 XGYCWCIGCYGQFU-UHFFFAOYSA-N 0.000 description 1
• BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
• YUIOPHXTILULQC-UHFFFAOYSA-N 1,4-Dithiane-2,5-diol Chemical compound OC1CSC(O)CS1 YUIOPHXTILULQC-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
• FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
• HUIPNSHEKKIBLB-UHFFFAOYSA-N 1-[3-(7-chloroimidazo[1,2-a]pyridin-3-yl)phenyl]-3-cyclopropylurea Chemical compound C=1N=C2C=C(Cl)C=CN2C=1C(C=1)=CC=CC=1NC(=O)NC1CC1 HUIPNSHEKKIBLB-UHFFFAOYSA-N 0.000 description 1
• ROYBINRYZOWKLS-UHFFFAOYSA-N 1-[5-(7-chloroimidazo[1,2-a]pyridin-3-yl)-1,3-thiazol-2-yl]-3-ethylurea;hydrochloride Chemical compound Cl.S1C(NC(=O)NCC)=NC=C1C1=CN=C2N1C=CC(Cl)=C2 ROYBINRYZOWKLS-UHFFFAOYSA-N 0.000 description 1
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
• UIMPAOAAAYDUKQ-UHFFFAOYSA-N 1-methoxy-4-(4-methoxyphenyl)benzene Chemical group C1=CC(OC)=CC=C1C1=CC=C(OC)C=C1 UIMPAOAAAYDUKQ-UHFFFAOYSA-N 0.000 description 1
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
• MFJCPDOGFAYSTF-UHFFFAOYSA-N 1H-isochromene Chemical compound C1=CC=C2COC=CC2=C1 MFJCPDOGFAYSTF-UHFFFAOYSA-N 0.000 description 1
• VLJMOPCEBPOBBD-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyridine-2-carbaldehyde Chemical compound C1=CC=C2NC(C=O)=NC2=N1 VLJMOPCEBPOBBD-UHFFFAOYSA-N 0.000 description 1
• AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 description 1
• KIPSRYDSZQRPEA-UHFFFAOYSA-N 2,2,2-trifluoroethanamine Chemical compound NCC(F)(F)F KIPSRYDSZQRPEA-UHFFFAOYSA-N 0.000 description 1
• MXILHVKNAYIRPJ-UHFFFAOYSA-N 2,3,7,7a-tetrahydro-1h-triazolo[4,5-b]pyrazine Chemical compound N1C=CN=C2NNNC21 MXILHVKNAYIRPJ-UHFFFAOYSA-N 0.000 description 1
• OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 1
• JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 1
• ZEMZPXWZVTUONV-UHFFFAOYSA-N 2-(2-dicyclohexylphosphanylphenyl)-n,n-dimethylaniline Chemical group CN(C)C1=CC=CC=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 ZEMZPXWZVTUONV-UHFFFAOYSA-N 0.000 description 1
• HXMBAEKXJMPQAA-UHFFFAOYSA-N 2-(3-methoxy-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound [O-][N+](=O)C1=CC(OC)=CC(B2OC(C)(C)C(C)(C)O2)=C1 HXMBAEKXJMPQAA-UHFFFAOYSA-N 0.000 description 1
• IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
• UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
• SIRRAQQGGCNHQB-UHFFFAOYSA-N 2-chloro-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC=C2NC(Cl)=NC2=N1 SIRRAQQGGCNHQB-UHFFFAOYSA-N 0.000 description 1
• QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 1
• CMRFJAMFEWYMKE-UHFFFAOYSA-N 2-oxaadamantane Chemical compound C1C(O2)CC3CC1CC2C3 CMRFJAMFEWYMKE-UHFFFAOYSA-N 0.000 description 1
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
• CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 1
• UMZCLZPXPCNKML-UHFFFAOYSA-N 2h-imidazo[4,5-d][1,3]thiazole Chemical compound C1=NC2=NCSC2=N1 UMZCLZPXPCNKML-UHFFFAOYSA-N 0.000 description 1
• MESFXNGUDNODTJ-UHFFFAOYSA-N 2h-thiazine 1,1-dioxide Chemical compound O=S1(=O)NC=CC=C1 MESFXNGUDNODTJ-UHFFFAOYSA-N 0.000 description 1
• WPWNEKFMGCWNPR-UHFFFAOYSA-N 3,4-dihydro-2h-thiochromene Chemical compound C1=CC=C2CCCSC2=C1 WPWNEKFMGCWNPR-UHFFFAOYSA-N 0.000 description 1
• WEVYNIUIFUYDGI-UHFFFAOYSA-N 3-[6-[4-(trifluoromethoxy)anilino]-4-pyrimidinyl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N=CN=C(NC=3C=CC(OC(F)(F)F)=CC=3)C=2)=C1 WEVYNIUIFUYDGI-UHFFFAOYSA-N 0.000 description 1
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• XDADYJOYIMVXTH-UHFFFAOYSA-N 3h-imidazo[1,2-a]imidazole Chemical compound C1=CN2CC=NC2=N1 XDADYJOYIMVXTH-UHFFFAOYSA-N 0.000 description 1
• YCVAGNVTZICLNM-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1-benzofuran Chemical compound C1CCCC2=C1C=CO2 YCVAGNVTZICLNM-UHFFFAOYSA-N 0.000 description 1
• GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
• BAQKUNMKVAPWGU-UHFFFAOYSA-N 4-bromopyridin-2-amine Chemical compound NC1=CC(Br)=CC=N1 BAQKUNMKVAPWGU-UHFFFAOYSA-N 0.000 description 1
• RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical compound NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 description 1
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• OURXRFYZEOUCRM-UHFFFAOYSA-N 4-hydroxymorpholine Chemical class ON1CCOCC1 OURXRFYZEOUCRM-UHFFFAOYSA-N 0.000 description 1
• 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• MRUWJENAYHTDQG-UHFFFAOYSA-N 4H-pyran Chemical compound C1C=COC=C1 MRUWJENAYHTDQG-UHFFFAOYSA-N 0.000 description 1
• GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 description 1
• UMEIYBJBGZKZOS-UHFFFAOYSA-N 5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine Chemical compound C1NCCN2C=NN=C21 UMEIYBJBGZKZOS-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
• 125000004008 6 membered carbocyclic group Chemical group 0.000 description 1
• BMZKZBWPMWEQAY-UHFFFAOYSA-N 6h-1,2,5-thiadiazine Chemical compound C1SN=CC=N1 BMZKZBWPMWEQAY-UHFFFAOYSA-N 0.000 description 1
• NGHRUBVFDAKWBC-UHFFFAOYSA-N 7-chloroimidazo[1,2-a]pyridine Chemical compound C1=C(Cl)C=CN2C=CN=C21 NGHRUBVFDAKWBC-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• 206010065040 AIDS dementia complex Diseases 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• 206010000599 Acromegaly Diseases 0.000 description 1
• 206010000830 Acute leukaemia Diseases 0.000 description 1
• 208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 1
• 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
• 208000036762 Acute promyelocytic leukaemia Diseases 0.000 description 1
• GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
• 229930024421 Adenine Natural products 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
• 102100022987 Angiogenin Human genes 0.000 description 1
• 102000009088 Angiopoietin-1 Human genes 0.000 description 1
• 108010048154 Angiopoietin-1 Proteins 0.000 description 1
• 102400000068 Angiostatin Human genes 0.000 description 1
• 108010079709 Angiostatins Proteins 0.000 description 1
• 208000032467 Aplastic anaemia Diseases 0.000 description 1
• BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
• 241000238017 Astacoidea Species 0.000 description 1
• 206010003571 Astrocytoma Diseases 0.000 description 1
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
• 229940122361 Bisphosphonate Drugs 0.000 description 1
• 201000004569 Blindness Diseases 0.000 description 1
• 102000004506 Blood Proteins Human genes 0.000 description 1
• 108010017384 Blood Proteins Proteins 0.000 description 1
• 208000006386 Bone Resorption Diseases 0.000 description 1
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
• 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
• ORHOWDMVPOGXDV-UHFFFAOYSA-N C1CC=[C-]C1 Chemical compound C1CC=[C-]C1 ORHOWDMVPOGXDV-UHFFFAOYSA-N 0.000 description 1
• RZYKUPXRYIOEME-UHFFFAOYSA-N CCCCCCCCCCCC[S] Chemical compound CCCCCCCCCCCC[S] RZYKUPXRYIOEME-UHFFFAOYSA-N 0.000 description 1
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
• 101100381481 Caenorhabditis elegans baz-2 gene Proteins 0.000 description 1
• 206010058019 Cancer Pain Diseases 0.000 description 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
• 206010007572 Cardiac hypertrophy Diseases 0.000 description 1
• 208000006029 Cardiomegaly Diseases 0.000 description 1
• 102100025064 Cellular tumor antigen p53 Human genes 0.000 description 1
• 206010008479 Chest Pain Diseases 0.000 description 1
• 206010008723 Chondrodystrophy Diseases 0.000 description 1
• 108010077544 Chromatin Proteins 0.000 description 1
• 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
• 235000005979 Citrus limon Nutrition 0.000 description 1
• 244000131522 Citrus pyriformis Species 0.000 description 1
• 102000008186 Collagen Human genes 0.000 description 1
• 108010035532 Collagen Proteins 0.000 description 1
• 206010048832 Colon adenoma Diseases 0.000 description 1
• 206010009944 Colon cancer Diseases 0.000 description 1
• 102000007644 Colony-Stimulating Factors Human genes 0.000 description 1
• 108010071942 Colony-Stimulating Factors Proteins 0.000 description 1
• 229920002261 Corn starch Polymers 0.000 description 1
• 208000011990 Corticobasal Degeneration Diseases 0.000 description 1
• 206010011224 Cough Diseases 0.000 description 1
• 108091029523 CpG island Proteins 0.000 description 1
• 229920002785 Croscarmellose sodium Polymers 0.000 description 1
• VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
• HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
• 201000003883 Cystic fibrosis Diseases 0.000 description 1
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
• 230000004544 DNA amplification Effects 0.000 description 1
• 229940123780 DNA topoisomerase I inhibitor Drugs 0.000 description 1
• 229940124087 DNA topoisomerase II inhibitor Drugs 0.000 description 1
• 206010011953 Decreased activity Diseases 0.000 description 1
• 206010012434 Dermatitis allergic Diseases 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 206010012689 Diabetic retinopathy Diseases 0.000 description 1
• XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
• BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
• 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 1
• 241000255601 Drosophila melanogaster Species 0.000 description 1
• 206010013883 Dwarfism Diseases 0.000 description 1
• 206010058314 Dysplasia Diseases 0.000 description 1
• 208000000059 Dyspnea Diseases 0.000 description 1
• 206010013975 Dyspnoeas Diseases 0.000 description 1
• 238000002965 ELISA Methods 0.000 description 1
• 101150029707 ERBB2 gene Proteins 0.000 description 1
• LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
• 241000196324 Embryophyta Species 0.000 description 1
• 102100037241 Endoglin Human genes 0.000 description 1
• 102400001047 Endostatin Human genes 0.000 description 1
• 108010079505 Endostatins Proteins 0.000 description 1
• 208000032027 Essential Thrombocythemia Diseases 0.000 description 1
• 239000001856 Ethyl cellulose Substances 0.000 description 1
• ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• 229920003134 Eudragit® polymer Polymers 0.000 description 1
• 208000006168 Ewing Sarcoma Diseases 0.000 description 1
• 108050001049 Extracellular proteins Proteins 0.000 description 1
• 101150081124 FGFR gene Proteins 0.000 description 1
• 101150082429 FGFR4 gene Proteins 0.000 description 1
• 102100031706 Fibroblast growth factor 1 Human genes 0.000 description 1
• 102100028412 Fibroblast growth factor 10 Human genes 0.000 description 1
• 102100028043 Fibroblast growth factor 3 Human genes 0.000 description 1
• 102000003972 Fibroblast growth factor 7 Human genes 0.000 description 1
• 108090000385 Fibroblast growth factor 7 Proteins 0.000 description 1
• 102100028071 Fibroblast growth factor 7 Human genes 0.000 description 1
• 102100037362 Fibronectin Human genes 0.000 description 1
• 108010067306 Fibronectins Proteins 0.000 description 1
• 201000008808 Fibrosarcoma Diseases 0.000 description 1
• MPJKWIXIYCLVCU-UHFFFAOYSA-N Folinic acid Natural products NC1=NC2=C(N(C=O)C(CNc3ccc(cc3)C(=O)NC(CCC(=O)O)CC(=O)O)CN2)C(=O)N1 MPJKWIXIYCLVCU-UHFFFAOYSA-N 0.000 description 1
• 206010017993 Gastrointestinal neoplasms Diseases 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• 102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 1
• 108010051696 Growth Hormone Proteins 0.000 description 1
• 206010019196 Head injury Diseases 0.000 description 1
• 102100031573 Hematopoietic progenitor cell antigen CD34 Human genes 0.000 description 1
• 208000017604 Hodgkin disease Diseases 0.000 description 1
• 208000021519 Hodgkin lymphoma Diseases 0.000 description 1
• 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
• 101000762379 Homo sapiens Bone morphogenetic protein 4 Proteins 0.000 description 1
• 101000917237 Homo sapiens Fibroblast growth factor 10 Proteins 0.000 description 1
• 101001060280 Homo sapiens Fibroblast growth factor 3 Proteins 0.000 description 1
• 101001060261 Homo sapiens Fibroblast growth factor 7 Proteins 0.000 description 1
• 101000777663 Homo sapiens Hematopoietic progenitor cell antigen CD34 Proteins 0.000 description 1
• 101000604123 Homo sapiens Noggin Proteins 0.000 description 1
• 101000779418 Homo sapiens RAC-alpha serine/threonine-protein kinase Proteins 0.000 description 1
• 206010020751 Hypersensitivity Diseases 0.000 description 1
• 206010020772 Hypertension Diseases 0.000 description 1
• MPBVHIBUJCELCL-UHFFFAOYSA-N Ibandronate Chemical compound CCCCCN(C)CCC(O)(P(O)(O)=O)P(O)(O)=O MPBVHIBUJCELCL-UHFFFAOYSA-N 0.000 description 1
• 206010061218 Inflammation Diseases 0.000 description 1
• 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
• 108090000723 Insulin-Like Growth Factor I Proteins 0.000 description 1
• 102000004218 Insulin-Like Growth Factor I Human genes 0.000 description 1
• 208000009289 Jackson-Weiss syndrome Diseases 0.000 description 1
• 208000007766 Kaposi sarcoma Diseases 0.000 description 1
• 206010023347 Keratoacanthoma Diseases 0.000 description 1
• 102000003855 L-lactate dehydrogenase Human genes 0.000 description 1
• 108700023483 L-lactate dehydrogenases Proteins 0.000 description 1
• FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
• KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
• 239000005511 L01XE05 - Sorafenib Substances 0.000 description 1
• 208000019693 Lung disease Diseases 0.000 description 1
• 208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
• 208000030289 Lymphoproliferative disease Diseases 0.000 description 1
• 239000004472 Lysine Substances 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• 102000019149 MAP kinase activity proteins Human genes 0.000 description 1
• 108040008097 MAP kinase activity proteins Proteins 0.000 description 1
• 238000005004 MAS NMR spectroscopy Methods 0.000 description 1
• 206010025421 Macule Diseases 0.000 description 1
• 206010064912 Malignant transformation Diseases 0.000 description 1
• VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
• 108060004795 Methyltransferase Proteins 0.000 description 1
• 102000016397 Methyltransferase Human genes 0.000 description 1
• 208000003445 Mouth Neoplasms Diseases 0.000 description 1
• 206010028289 Muscle atrophy Diseases 0.000 description 1
• 201000007224 Myeloproliferative neoplasm Diseases 0.000 description 1
• OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
• 206010029260 Neuroblastoma Diseases 0.000 description 1
• 102100038454 Noggin Human genes 0.000 description 1
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
• 229920002292 Nylon 6 Polymers 0.000 description 1
• VYEAHXRPWKOEMY-UHFFFAOYSA-N O-(9H-fluoren-9-ylmethyl)hydroxylamine Chemical compound C1=CC=C2C(CON)C3=CC=CC=C3C2=C1 VYEAHXRPWKOEMY-UHFFFAOYSA-N 0.000 description 1
• BHVRCUAHXVLSNX-UHFFFAOYSA-N O-[(4,5-dimethoxy-2-nitrophenyl)methyl]hydroxylamine Chemical compound COC1=CC(CON)=C([N+]([O-])=O)C=C1OC BHVRCUAHXVLSNX-UHFFFAOYSA-N 0.000 description 1
• 108010016076 Octreotide Proteins 0.000 description 1
• 208000022873 Ocular disease Diseases 0.000 description 1
• 108091034117 Oligonucleotide Proteins 0.000 description 1
• 208000001132 Osteoporosis Diseases 0.000 description 1
• 101150053185 P450 gene Proteins 0.000 description 1
• 238000012408 PCR amplification Methods 0.000 description 1
• 108091008606 PDGF receptors Proteins 0.000 description 1
• 241000381142 Pachydermia Species 0.000 description 1
• 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
• 208000018737 Parkinson disease Diseases 0.000 description 1
• 101150003085 Pdcl gene Proteins 0.000 description 1
• SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 1
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
• 244000203593 Piper nigrum Species 0.000 description 1
• 102100024616 Platelet endothelial cell adhesion molecule Human genes 0.000 description 1
• 102000011653 Platelet-Derived Growth Factor Receptors Human genes 0.000 description 1
• 102100030485 Platelet-derived growth factor receptor alpha Human genes 0.000 description 1
• 101710148465 Platelet-derived growth factor receptor alpha Proteins 0.000 description 1
• 241000276498 Pollachius virens Species 0.000 description 1
• 208000008601 Polycythemia Diseases 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 1
• 229940079156 Proteasome inhibitor Drugs 0.000 description 1
• 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 description 1
• 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 description 1
• 201000004681 Psoriasis Diseases 0.000 description 1
• 102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 description 1
• 239000007868 Raney catalyst Substances 0.000 description 1
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
• 229910000564 Raney nickel Inorganic materials 0.000 description 1
• 101100372762 Rattus norvegicus Flt1 gene Proteins 0.000 description 1
• 206010063837 Reperfusion injury Diseases 0.000 description 1
• 208000017442 Retinal disease Diseases 0.000 description 1
• 206010038923 Retinopathy Diseases 0.000 description 1
• 206010038933 Retinopathy of prematurity Diseases 0.000 description 1
• 206010038934 Retinopathy proliferative Diseases 0.000 description 1
• 108091028664 Ribonucleotide Proteins 0.000 description 1
• 206010039491 Sarcoma Diseases 0.000 description 1
• 201000010208 Seminoma Diseases 0.000 description 1
• 206010070834 Sensitisation Diseases 0.000 description 1
• 206010041067 Small cell lung cancer Diseases 0.000 description 1
• 208000021712 Soft tissue sarcoma Diseases 0.000 description 1
• 102100038803 Somatotropin Human genes 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
• 229930006000 Sucrose Natural products 0.000 description 1
• 101100482220 Sulfurisphaera tokodaii (strain DSM 16993 / JCM 10545 / NBRC 100140 / 7) triC gene Proteins 0.000 description 1
• 206010042971 T-cell lymphoma Diseases 0.000 description 1
• 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 description 1
• 210000001744 T-lymphocyte Anatomy 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• 241000255588 Tephritidae Species 0.000 description 1
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
• 102000002938 Thrombospondin Human genes 0.000 description 1
• 108060008245 Thrombospondin Proteins 0.000 description 1
• 239000000365 Topoisomerase I Inhibitor Substances 0.000 description 1
• 239000000317 Topoisomerase II Inhibitor Substances 0.000 description 1
• 108091023040 Transcription factor Proteins 0.000 description 1
• 102000040945 Transcription factor Human genes 0.000 description 1
• 239000007983 Tris buffer Substances 0.000 description 1
• 102000004243 Tubulin Human genes 0.000 description 1
• 108090000704 Tubulin Proteins 0.000 description 1
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
• KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
• 108010053096 Vascular Endothelial Growth Factor Receptor-1 Proteins 0.000 description 1
• 102000016549 Vascular Endothelial Growth Factor Receptor-2 Human genes 0.000 description 1
• 102000016663 Vascular Endothelial Growth Factor Receptor-3 Human genes 0.000 description 1
• 102100033179 Vascular endothelial growth factor receptor 3 Human genes 0.000 description 1
• 102000003734 Voltage-Gated Potassium Channels Human genes 0.000 description 1
• 108090000013 Voltage-Gated Potassium Channels Proteins 0.000 description 1
• 238000007239 Wittig reaction Methods 0.000 description 1
• 206010048218 Xeroderma Diseases 0.000 description 1
• SRNKZYRMFBGSGE-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CN=C21 SRNKZYRMFBGSGE-UHFFFAOYSA-N 0.000 description 1
• MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
• POIOOCHMXHKUHV-UHFFFAOYSA-N [nitro-[nitro(phenyl)methoxy]methyl]benzene Chemical compound C=1C=CC=CC=1C([N+](=O)[O-])OC([N+]([O-])=O)C1=CC=CC=C1 POIOOCHMXHKUHV-UHFFFAOYSA-N 0.000 description 1
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
• 150000001241 acetals Chemical class 0.000 description 1
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
• 229960001138 acetylsalicylic acid Drugs 0.000 description 1
• 208000008919 achondroplasia Diseases 0.000 description 1
• ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 1
• 125000005042 acyloxymethyl group Chemical group 0.000 description 1
• 229960000643 adenine Drugs 0.000 description 1
• 208000009956 adenocarcinoma Diseases 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• 150000001335 aliphatic alkanes Chemical class 0.000 description 1
• 150000001337 aliphatic alkines Chemical group 0.000 description 1
• 229910001413 alkali metal ion Inorganic materials 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 125000005907 alkyl ester group Chemical group 0.000 description 1
• 239000002168 alkylating agent Substances 0.000 description 1
• 229940100198 alkylating agent Drugs 0.000 description 1
• 230000002152 alkylating effect Effects 0.000 description 1
• 125000000304 alkynyl group Chemical group 0.000 description 1
• 208000030961 allergic reaction Diseases 0.000 description 1
• 125000003275 alpha amino acid group Chemical group 0.000 description 1
• 102000013529 alpha-Fetoproteins Human genes 0.000 description 1
• 108010026331 alpha-Fetoproteins Proteins 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• 125000004103 aminoalkyl group Chemical group 0.000 description 1
• 150000005018 aminopurines Chemical class 0.000 description 1
• 150000003927 aminopyridines Chemical class 0.000 description 1
• 239000003708 ampul Substances 0.000 description 1
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
• 208000007502 anemia Diseases 0.000 description 1
• 230000006427 angiogenic response Effects 0.000 description 1
• 108010072788 angiogenin Proteins 0.000 description 1
• 239000005557 antagonist Substances 0.000 description 1
• 239000003242 anti bacterial agent Substances 0.000 description 1
• 230000001772 anti-angiogenic effect Effects 0.000 description 1
• 230000000844 anti-bacterial effect Effects 0.000 description 1
• 230000001093 anti-cancer Effects 0.000 description 1
• 230000003474 anti-emetic effect Effects 0.000 description 1
• 230000003388 anti-hormonal effect Effects 0.000 description 1
• 230000000340 anti-metabolite Effects 0.000 description 1
• 239000000729 antidote Substances 0.000 description 1
• 239000002111 antiemetic agent Substances 0.000 description 1
• 229940125683 antiemetic agent Drugs 0.000 description 1
• 239000003429 antifungal agent Substances 0.000 description 1
• 229940121375 antifungal agent Drugs 0.000 description 1
• 229940100197 antimetabolite Drugs 0.000 description 1
• 239000002256 antimetabolite Substances 0.000 description 1
• 229940041181 antineoplastic drug Drugs 0.000 description 1
• 210000000436 anus Anatomy 0.000 description 1
• 230000005775 apoptotic pathway Effects 0.000 description 1
• 230000004596 appetite loss Effects 0.000 description 1
• 238000013459 approach Methods 0.000 description 1
• 239000012736 aqueous medium Substances 0.000 description 1
• 239000003125 aqueous solvent Substances 0.000 description 1
• 239000008135 aqueous vehicle Substances 0.000 description 1
• 150000004982 aromatic amines Chemical class 0.000 description 1
• 239000008122 artificial sweetener Substances 0.000 description 1
• 235000021311 artificial sweeteners Nutrition 0.000 description 1
• 210000003567 ascitic fluid Anatomy 0.000 description 1
• FZCSTZYAHCUGEM-UHFFFAOYSA-N aspergillomarasmine B Natural products OC(=O)CNC(C(O)=O)CNC(C(O)=O)CC(O)=O FZCSTZYAHCUGEM-UHFFFAOYSA-N 0.000 description 1
• 208000006673 asthma Diseases 0.000 description 1
• 239000012298 atmosphere Substances 0.000 description 1
• 230000001363 autoimmune Effects 0.000 description 1
• 230000035578 autophosphorylation Effects 0.000 description 1
• 229940120638 avastin Drugs 0.000 description 1
• JPNZKPRONVOMLL-UHFFFAOYSA-N azane;octadecanoic acid Chemical class [NH4+].CCCCCCCCCCCCCCCCCC([O-])=O JPNZKPRONVOMLL-UHFFFAOYSA-N 0.000 description 1
• 230000009286 beneficial effect Effects 0.000 description 1
• OJCKJHHYVUPUSJ-UHFFFAOYSA-N benzamide;methanesulfonic acid Chemical compound CS(O)(=O)=O.NC(=O)C1=CC=CC=C1 OJCKJHHYVUPUSJ-UHFFFAOYSA-N 0.000 description 1
• RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000004602 benzodiazinyl group Chemical group N1=NC(=CC2=C1C=CC=C2)* 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 1
• 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 229960004217 benzyl alcohol Drugs 0.000 description 1
• 210000000941 bile Anatomy 0.000 description 1
• MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 230000008238 biochemical pathway Effects 0.000 description 1
• 230000005540 biological transmission Effects 0.000 description 1
• 150000004663 bisphosphonates Chemical class 0.000 description 1
• 201000006598 bladder squamous cell carcinoma Diseases 0.000 description 1
• 230000036770 blood supply Effects 0.000 description 1
• 210000001185 bone marrow Anatomy 0.000 description 1
• 208000015322 bone marrow disease Diseases 0.000 description 1
• 230000024279 bone resorption Effects 0.000 description 1
• 229910052796 boron Inorganic materials 0.000 description 1
• 150000001639 boron compounds Chemical class 0.000 description 1
• WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical class FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
• 150000001642 boronic acid derivatives Chemical class 0.000 description 1
• GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 description 1
• 229960001467 bortezomib Drugs 0.000 description 1
• 210000004556 brain Anatomy 0.000 description 1
• 201000003714 breast lobular carcinoma Diseases 0.000 description 1
• 229930188620 butyrolactone Natural products 0.000 description 1
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
• 229910000024 caesium carbonate Inorganic materials 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910000019 calcium carbonate Inorganic materials 0.000 description 1
• 239000001506 calcium phosphate Substances 0.000 description 1
• 229910000389 calcium phosphate Inorganic materials 0.000 description 1
• 235000011010 calcium phosphates Nutrition 0.000 description 1
• MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
• 239000007894 caplet Substances 0.000 description 1
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical group C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
• SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical compound SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 description 1
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
• 239000001768 carboxy methyl cellulose Substances 0.000 description 1
• 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
• 150000007942 carboxylates Chemical class 0.000 description 1
• 150000001733 carboxylic acid esters Chemical class 0.000 description 1
• 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
• 210000000845 cartilage Anatomy 0.000 description 1
• 230000015556 catabolic process Effects 0.000 description 1
• 239000003729 cation exchange resin Substances 0.000 description 1
• 229940023913 cation exchange resins Drugs 0.000 description 1
• 150000001767 cationic compounds Chemical class 0.000 description 1
• 230000024245 cell differentiation Effects 0.000 description 1
• 238000002701 cell growth assay Methods 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 210000003169 central nervous system Anatomy 0.000 description 1
• 208000025434 cerebellar degeneration Diseases 0.000 description 1
• OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 230000000973 chemotherapeutic effect Effects 0.000 description 1
• 229940068682 chewable tablet Drugs 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• 229960004926 chlorobutanol Drugs 0.000 description 1
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
• 229960001231 choline Drugs 0.000 description 1
• 210000003483 chromatin Anatomy 0.000 description 1
• 238000013375 chromatographic separation Methods 0.000 description 1
• 238000011097 chromatography purification Methods 0.000 description 1
• QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 1
• 208000037976 chronic inflammation Diseases 0.000 description 1
• 208000037893 chronic inflammatory disorder Diseases 0.000 description 1
• 235000017803 cinnamon Nutrition 0.000 description 1
• WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• 210000003040 circulating cell Anatomy 0.000 description 1
• 230000004087 circulation Effects 0.000 description 1
• 230000007882 cirrhosis Effects 0.000 description 1
• 239000007979 citrate buffer Substances 0.000 description 1
• 230000007012 clinical effect Effects 0.000 description 1
• 230000003021 clonogenic effect Effects 0.000 description 1
• 229920001436 collagen Polymers 0.000 description 1
• 201000010897 colon adenocarcinoma Diseases 0.000 description 1
• 239000008139 complexing agent Substances 0.000 description 1
• 230000006552 constitutive activation Effects 0.000 description 1
• 238000013270 controlled release Methods 0.000 description 1
• 230000001276 controlling effect Effects 0.000 description 1
• GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
• 239000002285 corn oil Substances 0.000 description 1
• 235000005687 corn oil Nutrition 0.000 description 1
• 239000008120 corn starch Substances 0.000 description 1
• 230000008878 coupling Effects 0.000 description 1
• 238000010168 coupling process Methods 0.000 description 1
• 210000004714 cranial suture Anatomy 0.000 description 1
• 239000006071 cream Substances 0.000 description 1
• 229920006037 cross link polymer Polymers 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• MAEBCGDGGATMSC-OSHGGGOQSA-N cyclamine Chemical compound O([C@H]1CO[C@H]([C@@H]([C@H]1O[C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O[C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@H]1CC[C@]2(C)[C@H]3CCC45OCC6([C@@H](C[C@@]4(C)[C@]3(C)CCC2C1(C)C)O)CC[C@@](C[C@@H]65)(C)C=O)[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O MAEBCGDGGATMSC-OSHGGGOQSA-N 0.000 description 1
• 150000004292 cyclic ethers Chemical group 0.000 description 1
• 150000004294 cyclic thioethers Chemical group 0.000 description 1
• CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 description 1
• 229940097362 cyclodextrins Drugs 0.000 description 1
• ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
• KDUIUFJBNGTBMD-UHFFFAOYSA-N cyclooctatetraene Chemical compound C1=CC=CC=CC=C1 KDUIUFJBNGTBMD-UHFFFAOYSA-N 0.000 description 1
• URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
• 239000004913 cyclooctene Substances 0.000 description 1
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
• OOXWYYGXTJLWHA-UHFFFAOYSA-N cyclopropene Chemical compound C1C=C1 OOXWYYGXTJLWHA-UHFFFAOYSA-N 0.000 description 1
• 230000001086 cytosolic effect Effects 0.000 description 1
• 229940127089 cytotoxic agent Drugs 0.000 description 1
• 235000013365 dairy product Nutrition 0.000 description 1
• 230000034994 death Effects 0.000 description 1
• 231100000517 death Toxicity 0.000 description 1
• 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 229920006237 degradable polymer Polymers 0.000 description 1
• 230000018044 dehydration Effects 0.000 description 1
• 238000006297 dehydration reaction Methods 0.000 description 1
• 238000012217 deletion Methods 0.000 description 1
• 230000037430 deletion Effects 0.000 description 1
• 238000002716 delivery method Methods 0.000 description 1
• 238000001739 density measurement Methods 0.000 description 1
• 238000010511 deprotection reaction Methods 0.000 description 1
• 230000001066 destructive effect Effects 0.000 description 1
• UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
• 229960003957 dexamethasone Drugs 0.000 description 1
• 239000008121 dextrose Substances 0.000 description 1
• 206010012601 diabetes mellitus Diseases 0.000 description 1
• 238000010586 diagram Methods 0.000 description 1
• MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
• WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
• LCSNDSFWVKMJCT-UHFFFAOYSA-N dicyclohexyl-(2-phenylphenyl)phosphane Chemical group C1CCCCC1P(C=1C(=CC=CC=1)C=1C=CC=CC=1)C1CCCCC1 LCSNDSFWVKMJCT-UHFFFAOYSA-N 0.000 description 1
• 150000005690 diesters Chemical class 0.000 description 1
• 235000005911 diet Nutrition 0.000 description 1
• 230000037213 diet Effects 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• 238000000113 differential scanning calorimetry Methods 0.000 description 1
• 238000002050 diffraction method Methods 0.000 description 1
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
• 238000006471 dimerization reaction Methods 0.000 description 1
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
• 230000006806 disease prevention Effects 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 238000010494 dissociation reaction Methods 0.000 description 1
• 230000005593 dissociations Effects 0.000 description 1
• 238000009826 distribution Methods 0.000 description 1
• CNXMDTWQWLGCPE-UHFFFAOYSA-N ditert-butyl-(2-phenylphenyl)phosphane Chemical group CC(C)(C)P(C(C)(C)C)C1=CC=CC=C1C1=CC=CC=C1 CNXMDTWQWLGCPE-UHFFFAOYSA-N 0.000 description 1
• LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 1
• 238000002651 drug therapy Methods 0.000 description 1
• 208000017574 dry cough Diseases 0.000 description 1
• 210000001198 duodenum Anatomy 0.000 description 1
• 235000013399 edible fruits Nutrition 0.000 description 1
• 239000012636 effector Substances 0.000 description 1
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
• 230000008030 elimination Effects 0.000 description 1
• 238000003379 elimination reaction Methods 0.000 description 1
• 150000002081 enamines Chemical class 0.000 description 1
• 230000010595 endothelial cell migration Effects 0.000 description 1
• 238000005516 engineering process Methods 0.000 description 1
• 239000002532 enzyme inhibitor Substances 0.000 description 1
• 229940125532 enzyme inhibitor Drugs 0.000 description 1
• 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 description 1
• 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 description 1
• 210000002615 epidermis Anatomy 0.000 description 1
• 206010015037 epilepsy Diseases 0.000 description 1
• 210000003743 erythrocyte Anatomy 0.000 description 1
• 102000015694 estrogen receptors Human genes 0.000 description 1
• 108010038795 estrogen receptors Proteins 0.000 description 1
• BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
• 125000001033 ether group Chemical group 0.000 description 1
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
• 235000019325 ethyl cellulose Nutrition 0.000 description 1
• 229920001249 ethyl cellulose Polymers 0.000 description 1
• LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
• 229940093471 ethyl oleate Drugs 0.000 description 1
• 230000003203 everyday effect Effects 0.000 description 1
• 230000029142 excretion Effects 0.000 description 1
• 208000021045 exocrine pancreatic carcinoma Diseases 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 230000008622 extracellular signaling Effects 0.000 description 1
• 206010016256 fatigue Diseases 0.000 description 1
• 230000002349 favourable effect Effects 0.000 description 1
• 210000003608 fece Anatomy 0.000 description 1
• 230000003352 fibrogenic effect Effects 0.000 description 1
• 230000003176 fibrotic effect Effects 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 235000019634 flavors Nutrition 0.000 description 1
• 238000000684 flow cytometry Methods 0.000 description 1
• 238000002509 fluorescent in situ hybridization Methods 0.000 description 1
• 125000001153 fluoro group Chemical group F* 0.000 description 1
• 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
• 235000019152 folic acid Nutrition 0.000 description 1
• 239000011724 folic acid Substances 0.000 description 1
• 229960000304 folic acid Drugs 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• 238000009472 formulation Methods 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• 230000005714 functional activity Effects 0.000 description 1
• 238000007306 functionalization reaction Methods 0.000 description 1
• 125000003838 furazanyl group Chemical group 0.000 description 1
• 210000000232 gallbladder Anatomy 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 238000001415 gene therapy Methods 0.000 description 1
• XOXYHGOIRWABTC-UHFFFAOYSA-N gentisin Chemical compound C1=C(O)C=C2C(=O)C3=C(O)C=C(OC)C=C3OC2=C1 XOXYHGOIRWABTC-UHFFFAOYSA-N 0.000 description 1
• 210000004602 germ cell Anatomy 0.000 description 1
• 239000003979 granulating agent Substances 0.000 description 1
• 150000004795 grignard reagents Chemical class 0.000 description 1
• 239000000122 growth hormone Substances 0.000 description 1
• 125000005843 halogen group Chemical group 0.000 description 1
• 210000002064 heart cell Anatomy 0.000 description 1
• 150000002391 heterocyclic compounds Chemical class 0.000 description 1
• UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
• 230000003054 hormonal effect Effects 0.000 description 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
• 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
• 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
• UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
• 235000013828 hydroxypropyl starch Nutrition 0.000 description 1
• 230000001631 hypertensive effect Effects 0.000 description 1
• 229940015872 ibandronate Drugs 0.000 description 1
• 206010021198 ichthyosis Diseases 0.000 description 1
• 210000003405 ileum Anatomy 0.000 description 1
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical group C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 1
• 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 description 1
• UFBBWLWUIISIPW-UHFFFAOYSA-N imidazo[2,1-b][1,3]thiazole Chemical compound C1=CSC2=NC=CN21 UFBBWLWUIISIPW-UHFFFAOYSA-N 0.000 description 1
• CQQJSOXDEFZGFG-UHFFFAOYSA-N imidazo[4,5-d]imidazole Chemical compound C1=NC2=NC=NC2=N1 CQQJSOXDEFZGFG-UHFFFAOYSA-N 0.000 description 1
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
• 150000002466 imines Chemical class 0.000 description 1
• 230000001900 immune effect Effects 0.000 description 1
• 238000002991 immunohistochemical analysis Methods 0.000 description 1
• 230000002779 inactivation Effects 0.000 description 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 230000006882 induction of apoptosis Effects 0.000 description 1
• 239000003701 inert diluent Substances 0.000 description 1
• 239000012442 inert solvent Substances 0.000 description 1
• 208000027866 inflammatory disease Diseases 0.000 description 1
• 230000002757 inflammatory effect Effects 0.000 description 1
• 230000004054 inflammatory process Effects 0.000 description 1
• 239000007972 injectable composition Substances 0.000 description 1
• 150000007529 inorganic bases Chemical class 0.000 description 1
• 229910001411 inorganic cation Inorganic materials 0.000 description 1
• 210000000936 intestine Anatomy 0.000 description 1
• 230000035987 intoxication Effects 0.000 description 1
• 231100000566 intoxication Toxicity 0.000 description 1
• 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
• 238000007912 intraperitoneal administration Methods 0.000 description 1
• 230000002601 intratumoral effect Effects 0.000 description 1
• 238000010253 intravenous injection Methods 0.000 description 1
• 206010073096 invasive lobular breast carcinoma Diseases 0.000 description 1
• 238000011835 investigation Methods 0.000 description 1
• 150000002500 ions Chemical class 0.000 description 1
• 230000002427 irreversible effect Effects 0.000 description 1
• 230000007794 irritation Effects 0.000 description 1
• 208000037906 ischaemic injury Diseases 0.000 description 1
• 230000000302 ischemic effect Effects 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• HEBMCVBCEDMUOF-UHFFFAOYSA-N isochromane Chemical compound C1=CC=C2COCCC2=C1 HEBMCVBCEDMUOF-UHFFFAOYSA-N 0.000 description 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 239000007951 isotonicity adjuster Substances 0.000 description 1
• 230000000155 isotopic effect Effects 0.000 description 1
• 210000003734 kidney Anatomy 0.000 description 1
• 208000017169 kidney disease Diseases 0.000 description 1
• 239000000787 lecithin Substances 0.000 description 1
• 235000010445 lecithin Nutrition 0.000 description 1
• 229940067606 lecithin Drugs 0.000 description 1
• 231100001231 less toxic Toxicity 0.000 description 1
• 231100000518 lethal Toxicity 0.000 description 1
• 230000001665 lethal effect Effects 0.000 description 1
• 210000000265 leukocyte Anatomy 0.000 description 1
• 108020001756 ligand binding domains Proteins 0.000 description 1
• 208000012987 lip and oral cavity carcinoma Diseases 0.000 description 1
• 150000002632 lipids Chemical group 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 208000019423 liver disease Diseases 0.000 description 1
• 208000019017 loss of appetite Diseases 0.000 description 1
• 235000021266 loss of appetite Nutrition 0.000 description 1
• 210000001165 lymph node Anatomy 0.000 description 1
• 208000003747 lymphoid leukemia Diseases 0.000 description 1
• 238000012792 lyophilization process Methods 0.000 description 1
• 239000006166 lysate Substances 0.000 description 1
• JMZFEHDNIAQMNB-UHFFFAOYSA-N m-aminophenylboronic acid Chemical compound NC1=CC=CC(B(O)O)=C1 JMZFEHDNIAQMNB-UHFFFAOYSA-N 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 230000036212 malign transformation Effects 0.000 description 1
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
• 210000001161 mammalian embryo Anatomy 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
• 238000005259 measurement Methods 0.000 description 1
• 229940126601 medicinal product Drugs 0.000 description 1
• 239000002609 medium Substances 0.000 description 1
• 229960004296 megestrol acetate Drugs 0.000 description 1
• RQZAXGRLVPAYTJ-GQFGMJRRSA-N megestrol acetate Chemical compound C1=C(C)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RQZAXGRLVPAYTJ-GQFGMJRRSA-N 0.000 description 1
• 229960003194 meglumine Drugs 0.000 description 1
• 201000001441 melanoma Diseases 0.000 description 1
• 230000005906 menstruation Effects 0.000 description 1
• MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
• 229930182817 methionine Natural products 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 235000010981 methylcellulose Nutrition 0.000 description 1
• 238000010208 microarray analysis Methods 0.000 description 1
• 244000005700 microbiome Species 0.000 description 1
• 210000004088 microvessel Anatomy 0.000 description 1
• 230000002297 mitogenic effect Effects 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 238000010369 molecular cloning Methods 0.000 description 1
• 210000000214 mouth Anatomy 0.000 description 1
• 210000004877 mucosa Anatomy 0.000 description 1
• 201000006417 multiple sclerosis Diseases 0.000 description 1
• 230000020763 muscle atrophy Effects 0.000 description 1
• 201000000585 muscular atrophy Diseases 0.000 description 1
• 210000002346 musculoskeletal system Anatomy 0.000 description 1
• 239000003471 mutagenic agent Substances 0.000 description 1
• 231100000707 mutagenic chemical Toxicity 0.000 description 1
• 230000003505 mutagenic effect Effects 0.000 description 1
• 206010028537 myelofibrosis Diseases 0.000 description 1
• 201000000050 myeloid neoplasm Diseases 0.000 description 1
• 208000010125 myocardial infarction Diseases 0.000 description 1
• APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
• MRHQBBSKCLIMRH-UHFFFAOYSA-N n-(acetamidomethoxymethyl)acetamide Chemical compound CC(=O)NCOCNC(C)=O MRHQBBSKCLIMRH-UHFFFAOYSA-N 0.000 description 1
• YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 description 1
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
• KOIYCZMWZNWMML-UHFFFAOYSA-N n-[5-(7-chloroimidazo[1,2-a]pyridin-3-yl)-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC=C1C1=CN=C2N1C=CC(Cl)=C2 KOIYCZMWZNWMML-UHFFFAOYSA-N 0.000 description 1
• GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• SJWPLOQINHZILX-UHFFFAOYSA-N n-ethoxybenzenesulfonamide Chemical compound CCONS(=O)(=O)C1=CC=CC=C1 SJWPLOQINHZILX-UHFFFAOYSA-N 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
• 230000009707 neogenesis Effects 0.000 description 1
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 230000009826 neoplastic cell growth Effects 0.000 description 1
• 208000007538 neurilemmoma Diseases 0.000 description 1
• 210000002569 neuron Anatomy 0.000 description 1
• 208000004235 neutropenia Diseases 0.000 description 1
• 239000002547 new drug Substances 0.000 description 1
• YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
• 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
• 208000002154 non-small cell lung carcinoma Diseases 0.000 description 1
• 239000012457 nonaqueous media Substances 0.000 description 1
• 239000002687 nonaqueous vehicle Substances 0.000 description 1
• 230000009871 nonspecific binding Effects 0.000 description 1
• 231100000252 nontoxic Toxicity 0.000 description 1
• 230000003000 nontoxic effect Effects 0.000 description 1
• 238000001216 nucleic acid method Methods 0.000 description 1
• 239000012038 nucleophile Substances 0.000 description 1
• LUHFJLLCZSYACL-UHFFFAOYSA-N o-(2,2,2-trichloroethyl)hydroxylamine Chemical compound NOCC(Cl)(Cl)Cl LUHFJLLCZSYACL-UHFFFAOYSA-N 0.000 description 1
• GWCBVFMHGHMALR-UHFFFAOYSA-N o-(2-trimethylsilylethyl)hydroxylamine Chemical compound C[Si](C)(C)CCON GWCBVFMHGHMALR-UHFFFAOYSA-N 0.000 description 1
• XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 1
• KKVUFSINQFSJNK-UHFFFAOYSA-N o-tert-butylhydroxylamine Chemical compound CC(C)(C)ON KKVUFSINQFSJNK-UHFFFAOYSA-N 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• OIPZNTLJVJGRCI-UHFFFAOYSA-M octadecanoyloxyaluminum;dihydrate Chemical compound O.O.CCCCCCCCCCCCCCCCCC(=O)O[Al] OIPZNTLJVJGRCI-UHFFFAOYSA-M 0.000 description 1
• WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
• 229960001494 octreotide acetate Drugs 0.000 description 1
• 239000003921 oil Substances 0.000 description 1
• 235000019198 oils Nutrition 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 239000004006 olive oil Substances 0.000 description 1
• 235000008390 olive oil Nutrition 0.000 description 1
• 102000027450 oncoproteins Human genes 0.000 description 1
• 108091008819 oncoproteins Proteins 0.000 description 1
• 238000005457 optimization Methods 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 150000002892 organic cations Chemical class 0.000 description 1
• 150000002895 organic esters Chemical class 0.000 description 1
• 239000003791 organic solvent mixture Substances 0.000 description 1
• 230000003204 osmotic effect Effects 0.000 description 1
• 210000000963 osteoblast Anatomy 0.000 description 1
• 230000002188 osteogenic effect Effects 0.000 description 1
• 201000008968 osteosarcoma Diseases 0.000 description 1
• 229940127084 other anti-cancer agent Drugs 0.000 description 1
• 230000016087 ovulation Effects 0.000 description 1
• 239000007800 oxidant agent Substances 0.000 description 1
• 230000003647 oxidation Effects 0.000 description 1
• 238000007254 oxidation reaction Methods 0.000 description 1
• 150000002923 oximes Chemical class 0.000 description 1
• 238000006213 oxygenation reaction Methods 0.000 description 1
• MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
• LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
• JGBZTJWQMWZVNX-UHFFFAOYSA-N palladium;tricyclohexylphosphane Chemical compound [Pd].C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 JGBZTJWQMWZVNX-UHFFFAOYSA-N 0.000 description 1
• IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
• WRUUGTRCQOWXEG-UHFFFAOYSA-N pamidronate Chemical compound NCCC(O)(P(O)(O)=O)P(O)(O)=O WRUUGTRCQOWXEG-UHFFFAOYSA-N 0.000 description 1
• 229940046231 pamidronate Drugs 0.000 description 1
• 201000002528 pancreatic cancer Diseases 0.000 description 1
• 208000008443 pancreatic carcinoma Diseases 0.000 description 1
• 230000003076 paracrine Effects 0.000 description 1
• 239000002245 particle Substances 0.000 description 1
• 230000001991 pathophysiological effect Effects 0.000 description 1
• 230000007310 pathophysiology Effects 0.000 description 1
• 244000144985 peep Species 0.000 description 1
• RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
• 210000001428 peripheral nervous system Anatomy 0.000 description 1
• 210000004786 perivascular cell Anatomy 0.000 description 1
• 230000035699 permeability Effects 0.000 description 1
• 150000004965 peroxy acids Chemical class 0.000 description 1
• 229960003742 phenol Drugs 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• 239000008363 phosphate buffer Substances 0.000 description 1
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
• 229910052698 phosphorus Inorganic materials 0.000 description 1
• 239000011574 phosphorus Substances 0.000 description 1
• 238000002428 photodynamic therapy Methods 0.000 description 1
• LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
• 230000004962 physiological condition Effects 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 description 1
• 229960003073 pirfenidone Drugs 0.000 description 1
• 201000002511 pituitary cancer Diseases 0.000 description 1
• 229920003023 plastic Polymers 0.000 description 1
• 239000004033 plastic Substances 0.000 description 1
• 239000004014 plasticizer Substances 0.000 description 1
• 210000004910 pleural fluid Anatomy 0.000 description 1
• 231100000614 poison Toxicity 0.000 description 1
• 239000003880 polar aprotic solvent Substances 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 229920005596 polymer binder Polymers 0.000 description 1
• 239000002491 polymer binding agent Substances 0.000 description 1
• 229920001184 polypeptide Polymers 0.000 description 1
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• 230000004481 post-translational protein modification Effects 0.000 description 1
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
• 229910000160 potassium phosphate Inorganic materials 0.000 description 1
• 235000011009 potassium phosphates Nutrition 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 229940098458 powder spray Drugs 0.000 description 1
• 230000002028 premature Effects 0.000 description 1
• 238000002953 preparative HPLC Methods 0.000 description 1
• 238000004237 preparative chromatography Methods 0.000 description 1
• 239000000955 prescription drug Substances 0.000 description 1
• 150000003138 primary alcohols Chemical class 0.000 description 1
• 150000003141 primary amines Chemical class 0.000 description 1
• 208000003476 primary myelofibrosis Diseases 0.000 description 1
• 102000004196 processed proteins & peptides Human genes 0.000 description 1
• 201000002212 progressive supranuclear palsy Diseases 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• 239000003207 proteasome inhibitor Substances 0.000 description 1
• CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
• 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
• USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
• 150000003219 pyrazolines Chemical class 0.000 description 1
• DVUBDHRTVYLIPA-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine Chemical compound C1=CC=CN2N=CC=C21 DVUBDHRTVYLIPA-UHFFFAOYSA-N 0.000 description 1
• LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 description 1
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
• ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
• 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
• 125000001453 quaternary ammonium group Chemical group 0.000 description 1
• 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• 230000005855 radiation Effects 0.000 description 1
• 238000007154 radical cyclization reaction Methods 0.000 description 1
• 208000020615 rectal carcinoma Diseases 0.000 description 1
• 230000000306 recurrent effect Effects 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 208000037803 restenosis Diseases 0.000 description 1
• 201000006845 reticulosarcoma Diseases 0.000 description 1
• 208000029922 reticulum cell sarcoma Diseases 0.000 description 1
• 210000001525 retina Anatomy 0.000 description 1
• 239000000790 retinal pigment Substances 0.000 description 1
• 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
• 206010039083 rhinitis Diseases 0.000 description 1
• 239000002336 ribonucleotide Substances 0.000 description 1
• 125000002652 ribonucleotide group Chemical group 0.000 description 1
• 238000007363 ring formation reaction Methods 0.000 description 1
• 125000006413 ring segment Chemical group 0.000 description 1
• 102200126698 rs1057519045 Human genes 0.000 description 1
• 102200126694 rs1057519047 Human genes 0.000 description 1
• 102200158153 rs11057353 Human genes 0.000 description 1
• 102200126858 rs121918488 Human genes 0.000 description 1
• 102200126859 rs121918488 Human genes 0.000 description 1
• 102200126856 rs121918496 Human genes 0.000 description 1
• 102200126968 rs121918499 Human genes 0.000 description 1
• 102200126971 rs121918510 Human genes 0.000 description 1
• 102200126834 rs1554928884 Human genes 0.000 description 1
• 210000003296 saliva Anatomy 0.000 description 1
• 229930195734 saturated hydrocarbon Natural products 0.000 description 1
• 230000037390 scarring Effects 0.000 description 1
• HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
• 206010039667 schwannoma Diseases 0.000 description 1
• 238000007790 scraping Methods 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 150000003335 secondary amines Chemical class 0.000 description 1
• 238000010956 selective crystallization Methods 0.000 description 1
• 230000008313 sensitization Effects 0.000 description 1
• 230000001235 sensitizing effect Effects 0.000 description 1
• 230000009919 sequestration Effects 0.000 description 1
• 210000002966 serum Anatomy 0.000 description 1
• 208000013220 shortness of breath Diseases 0.000 description 1
• 230000008054 signal transmission Effects 0.000 description 1
• 201000009890 sinusitis Diseases 0.000 description 1
• 230000022379 skeletal muscle tissue development Effects 0.000 description 1
• 239000010802 sludge Substances 0.000 description 1
• 208000000587 small cell lung carcinoma Diseases 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• 238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 1
• 239000007790 solid phase Substances 0.000 description 1
• 230000003381 solubilizing effect Effects 0.000 description 1
• 229960003787 sorafenib Drugs 0.000 description 1
• IVDHYUQIDRJSTI-UHFFFAOYSA-N sorafenib tosylate Chemical compound [H+].CC1=CC=C(S([O-])(=O)=O)C=C1.C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 IVDHYUQIDRJSTI-UHFFFAOYSA-N 0.000 description 1
• 239000004334 sorbic acid Substances 0.000 description 1
• 235000010199 sorbic acid Nutrition 0.000 description 1
• 229940075582 sorbic acid Drugs 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 238000011895 specific detection Methods 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 206010041823 squamous cell carcinoma Diseases 0.000 description 1
• 230000006641 stabilisation Effects 0.000 description 1
• 238000011105 stabilization Methods 0.000 description 1
• 230000000087 stabilizing effect Effects 0.000 description 1
• KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical class [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 210000000130 stem cell Anatomy 0.000 description 1
• 230000001954 sterilising effect Effects 0.000 description 1
• 239000003270 steroid hormone Substances 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 201000000498 stomach carcinoma Diseases 0.000 description 1
• 238000003860 storage Methods 0.000 description 1
• 239000006190 sub-lingual tablet Substances 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• 239000000758 substrate Substances 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• 150000005846 sugar alcohols Chemical class 0.000 description 1
• 150000008163 sugars Chemical class 0.000 description 1
• MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical compound O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 description 1
• 229940124530 sulfonamide Drugs 0.000 description 1
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
• 238000001356 surgical procedure Methods 0.000 description 1
• 230000004083 survival effect Effects 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 230000002459 sustained effect Effects 0.000 description 1
• 239000012730 sustained-release form Substances 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 208000018015 syndromic craniosynostosis Diseases 0.000 description 1
• 230000002195 synergetic effect Effects 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 230000001839 systemic circulation Effects 0.000 description 1
• 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
• 208000001608 teratocarcinoma Diseases 0.000 description 1
• FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 1
• 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
• ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 1
• NFRGCMIFZVPLSJ-UHFFFAOYSA-N thiazepane 1,1-dioxide Chemical compound O=S1(=O)CCCCCN1 NFRGCMIFZVPLSJ-UHFFFAOYSA-N 0.000 description 1
• CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
• 239000002562 thickening agent Substances 0.000 description 1
• 150000003568 thioethers Chemical class 0.000 description 1
• 125000003396 thiol group Chemical group [H]S* 0.000 description 1
• 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
• 230000009424 thromboembolic effect Effects 0.000 description 1
• 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
• 125000005490 tosylate group Chemical class 0.000 description 1
• 231100000563 toxic property Toxicity 0.000 description 1
• 239000003440 toxic substance Substances 0.000 description 1
• 238000012546 transfer Methods 0.000 description 1
• 238000013519 translation Methods 0.000 description 1
• YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
• QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
• 150000008648 triflates Chemical class 0.000 description 1
• PBIMIGNDTBRRPI-UHFFFAOYSA-N trifluoro borate Chemical compound FOB(OF)OF PBIMIGNDTBRRPI-UHFFFAOYSA-N 0.000 description 1
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical compound C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
• DLQYXUGCCKQSRJ-UHFFFAOYSA-N tris(furan-2-yl)phosphane Chemical compound C1=COC(P(C=2OC=CC=2)C=2OC=CC=2)=C1 DLQYXUGCCKQSRJ-UHFFFAOYSA-N 0.000 description 1
• 229960000281 trometamol Drugs 0.000 description 1
• 150000003668 tyrosines Chemical class 0.000 description 1
• 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 241000701161 unidentified adenovirus Species 0.000 description 1
• 208000011479 upper respiratory tract disease Diseases 0.000 description 1
• 210000002700 urine Anatomy 0.000 description 1
• 239000004474 valine Substances 0.000 description 1
• 239000002966 varnish Substances 0.000 description 1
• 235000015112 vegetable and seed oil Nutrition 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1
• 230000007998 vessel formation Effects 0.000 description 1
• 235000012431 wafers Nutrition 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 230000004580 weight loss Effects 0.000 description 1
• 238000001262 western blot Methods 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 1
• UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical group CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 1
• 229960004276 zoledronic acid Drugs 0.000 description 1
• XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 description 1