TW200843757A

TW200843757A - Imidazo[1,2-a]pyridine compounds as receptor tyrosine kinase inhibitors

Imidazo[1,2-a]pyridine compounds as receptor tyrosine kinase inhibitors Download PDF

Info

Publication number: TW200843757A
Authority: TW; Taiwan
Prior art keywords: alkyl; compound; mmol; formula; group
Prior art date: 2007-03-28

Application number

TW097111546A

Other languages

English (en)

Chinese (zh)

Inventor

Fredrik P Marmsater

Mark C Munson

James P Rizzi

John E Robinson

Stephen T Schlachter

George T Topalov

Qian Zhao

Joseph P Lyssikatos

Original Assignee

Array Biopharma Inc

Priority date

2007-03-28

Filing date

2008-03-28

Publication date

2008-11-16

2008-03-28 Application filed by Array Biopharma Inc filed Critical Array Biopharma Inc

2008-11-16 Publication of TW200843757A publication Critical patent/TW200843757A/zh

Links

229940127361 Receptor Tyrosine Kinase Inhibitors Drugs 0.000 title description 2
150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 154
230000001404 mediated effect Effects 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims description 222
-1 C(0)NHMe Chemical compound 0.000 claims description 155
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 120
238000000034 method Methods 0.000 claims description 51
150000003839 salts Chemical class 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
125000000753 cycloalkyl group Chemical group 0.000 claims description 26
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 23
125000004076 pyridyl group Chemical group 0.000 claims description 23
229910052731 fluorine Inorganic materials 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
150000002923 oximes Chemical class 0.000 claims description 18
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
229910003827 NRaRb Inorganic materials 0.000 claims description 15
206010028980 Neoplasm Diseases 0.000 claims description 15
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
125000004429 atom Chemical group 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 14
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
125000001424 substituent group Chemical group 0.000 claims description 14
125000003118 aryl group Chemical group 0.000 claims description 12
125000000623 heterocyclic group Chemical group 0.000 claims description 12
229910052763 palladium Inorganic materials 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 11
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 10
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
229910052707 ruthenium Inorganic materials 0.000 claims description 9
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 8
208000024891 symptom Diseases 0.000 claims description 8
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
201000011510 cancer Diseases 0.000 claims description 7
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
239000003446 ligand Substances 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
125000003554 tetrahydropyrrolyl group Chemical group 0.000 claims description 7
108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 6
102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
239000003153 chemical reaction reagent Substances 0.000 claims description 6
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
125000000468 ketone group Chemical group 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 5
239000003638 chemical reducing agent Substances 0.000 claims description 5
125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 4
230000008878 coupling Effects 0.000 claims description 4
238000010168 coupling process Methods 0.000 claims description 4
238000005859 coupling reaction Methods 0.000 claims description 4
VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 2
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 1
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
230000009615 deamination Effects 0.000 claims 1
238000006481 deamination reaction Methods 0.000 claims 1
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
239000000835 fiber Substances 0.000 claims 1
125000006239 protecting group Chemical group 0.000 claims 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 18
239000003112 inhibitor Substances 0.000 abstract description 15
108091008598 receptor tyrosine kinases Proteins 0.000 abstract description 15
102000027426 receptor tyrosine kinases Human genes 0.000 abstract description 15
201000010099 disease Diseases 0.000 abstract description 14
102000005962 receptors Human genes 0.000 abstract description 6
108020003175 receptors Proteins 0.000 abstract description 6
101001001642 Xenopus laevis Serine/threonine-protein kinase pim-3 Proteins 0.000 abstract description 5
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 abstract 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 436
238000006243 chemical reaction Methods 0.000 description 220
235000019439 ethyl acetate Nutrition 0.000 description 196
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 192
238000002360 preparation method Methods 0.000 description 182
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 171
239000000203 mixture Substances 0.000 description 133
201000006417 multiple sclerosis Diseases 0.000 description 106
239000007787 solid Substances 0.000 description 82
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 82
239000000243 solution Substances 0.000 description 76
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 74
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 73
239000011541 reaction mixture Substances 0.000 description 69
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
239000000047 product Substances 0.000 description 50
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 44
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 42
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 41
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 39
239000002585 base Substances 0.000 description 39
239000010410 layer Substances 0.000 description 39
238000010992 reflux Methods 0.000 description 39
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 38
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 38
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 38
OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 35
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 32
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
239000012044 organic layer Substances 0.000 description 29
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
238000003818 flash chromatography Methods 0.000 description 23
239000010948 rhodium Substances 0.000 description 23
239000002253 acid Substances 0.000 description 22
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 21
229910052786 argon Inorganic materials 0.000 description 21
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 20
VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 19
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 19
229910000041 hydrogen chloride Inorganic materials 0.000 description 19
239000012074 organic phase Substances 0.000 description 19
229920006395 saturated elastomer Polymers 0.000 description 19
239000007864 aqueous solution Substances 0.000 description 18
239000011521 glass Substances 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
210000004027 cell Anatomy 0.000 description 17
150000004032 porphyrins Chemical class 0.000 description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 16
150000001412 amines Chemical class 0.000 description 16
229910052805 deuterium Inorganic materials 0.000 description 16
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
238000003756 stirring Methods 0.000 description 15
244000294411 Mirabilis expansa Species 0.000 description 14
235000015429 Mirabilis expansa Nutrition 0.000 description 14
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 14
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 14
235000013536 miso Nutrition 0.000 description 14
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 14
239000003921 oil Substances 0.000 description 13
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 12
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 12
239000000706 filtrate Substances 0.000 description 12
238000001914 filtration Methods 0.000 description 12
239000002904 solvent Substances 0.000 description 12
FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 12
239000000052 vinegar Substances 0.000 description 12
235000021419 vinegar Nutrition 0.000 description 12
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical class O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
239000008367 deionised water Substances 0.000 description 11
229910021641 deionized water Inorganic materials 0.000 description 11
229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
241000894007 species Species 0.000 description 11
101150041968 CDC13 gene Proteins 0.000 description 10
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 10
101000692455 Homo sapiens Platelet-derived growth factor receptor beta Proteins 0.000 description 10
102100026547 Platelet-derived growth factor receptor beta Human genes 0.000 description 10
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
125000001153 fluoro group Chemical group F* 0.000 description 10
238000000746 purification Methods 0.000 description 10
239000000725 suspension Substances 0.000 description 10
UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 10
208000031261 Acute myeloid leukaemia Diseases 0.000 description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
229910052799 carbon Inorganic materials 0.000 description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
208000032839 leukemia Diseases 0.000 description 9
239000002609 medium Substances 0.000 description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
125000005493 quinolyl group Chemical group 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 8
208000033776 Myeloid Acute Leukemia Diseases 0.000 description 8
235000011114 ammonium hydroxide Nutrition 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 8
239000007789 gas Substances 0.000 description 8
UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical group C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 8
239000007788 liquid Substances 0.000 description 8
239000012452 mother liquor Substances 0.000 description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 7
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 7
FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 7
HBBYDTFNQNAFJA-UHFFFAOYSA-N 4-(2-methoxyethoxy)pyridin-2-amine Chemical compound COCCOC1=CC=NC(N)=C1 HBBYDTFNQNAFJA-UHFFFAOYSA-N 0.000 description 7
235000001258 Cinchona calisaya Nutrition 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
241000124008 Mammalia Species 0.000 description 7
238000005481 NMR spectroscopy Methods 0.000 description 7
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
229910000024 caesium carbonate Inorganic materials 0.000 description 7
239000000463 material Substances 0.000 description 7
239000012299 nitrogen atmosphere Substances 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
239000000843 powder Substances 0.000 description 7
229960000948 quinine Drugs 0.000 description 7
229910001961 silver nitrate Inorganic materials 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
108091000080 Phosphotransferase Proteins 0.000 description 6
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
125000004494 ethyl ester group Chemical group 0.000 description 6
239000000284 extract Substances 0.000 description 6
238000000605 extraction Methods 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
102000020233 phosphotransferase Human genes 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 6
239000002002 slurry Substances 0.000 description 6
239000011734 sodium Substances 0.000 description 6
238000000638 solvent extraction Methods 0.000 description 6
238000010792 warming Methods 0.000 description 6
239000011592 zinc chloride Substances 0.000 description 6
235000005074 zinc chloride Nutrition 0.000 description 6
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
206010016654 Fibrosis Diseases 0.000 description 5
101100335081 Mus musculus Flt3 gene Proteins 0.000 description 5
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 5
238000003556 assay Methods 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
150000007942 carboxylates Chemical class 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
239000012043 crude product Substances 0.000 description 5
239000013078 crystal Substances 0.000 description 5
230000004761 fibrosis Effects 0.000 description 5
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 5
150000004702 methyl esters Chemical class 0.000 description 5
230000035772 mutation Effects 0.000 description 5
239000011368 organic material Substances 0.000 description 5
125000002971 oxazolyl group Chemical group 0.000 description 5
BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 description 5
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 5
208000011580 syndromic disease Diseases 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
239000007832 Na2SO4 Substances 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
206010036790 Productive cough Diseases 0.000 description 4
206010039710 Scleroderma Diseases 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
230000001154 acute effect Effects 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
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 4
239000012267 brine Substances 0.000 description 4
125000001246 bromo group Chemical group Br* 0.000 description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 4
230000008859 change Effects 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
238000001035 drying Methods 0.000 description 4
238000010828 elution Methods 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
238000002309 gasification Methods 0.000 description 4
150000002431 hydrogen Chemical group 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
210000003802 sputum Anatomy 0.000 description 4
208000024794 sputum Diseases 0.000 description 4
229910021653 sulphate ion Inorganic materials 0.000 description 4
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 4
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 4
UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 4
UDVPQRRWUGKGQY-XQHVRGAUSA-N (e)-but-2-enal Chemical compound C\C=C\C=O.C\C=C\C=O UDVPQRRWUGKGQY-XQHVRGAUSA-N 0.000 description 3
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 3
FBPINGSGHKXIQA-UHFFFAOYSA-N 2-amino-3-(2-carboxyethylsulfanyl)propanoic acid Chemical compound OC(=O)C(N)CSCCC(O)=O FBPINGSGHKXIQA-UHFFFAOYSA-N 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 3
206010058314 Dysplasia Diseases 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
239000004677 Nylon Substances 0.000 description 3
240000007594 Oryza sativa Species 0.000 description 3
235000007164 Oryza sativa Nutrition 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 3
230000003213 activating effect Effects 0.000 description 3
239000000908 ammonium hydroxide Substances 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
229910002091 carbon monoxide Inorganic materials 0.000 description 3
230000001419 dependent effect Effects 0.000 description 3
238000007865 diluting Methods 0.000 description 3
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 3
238000004090 dissolution Methods 0.000 description 3
229940079593 drug Drugs 0.000 description 3
230000000694 effects Effects 0.000 description 3
108700014844 flt3 ligand Proteins 0.000 description 3
GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
238000005187 foaming Methods 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
201000011243 gastrointestinal stromal tumor Diseases 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
125000001072 heteroaryl group Chemical group 0.000 description 3
150000002460 imidazoles Chemical class 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 3
COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 3
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
102000027495 nuclear receptors type III Human genes 0.000 description 3
108091008732 nuclear receptors type III Proteins 0.000 description 3
229920001778 nylon Polymers 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 description 3
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
230000008569 process Effects 0.000 description 3
125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 3
235000009566 rice Nutrition 0.000 description 3
XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
LMJDWRWZTXQWTI-UHFFFAOYSA-N 2,3,3a,4,5,6-hexahydro-1h-indole Chemical compound C1CCC=C2NCCC21 LMJDWRWZTXQWTI-UHFFFAOYSA-N 0.000 description 2
HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 2
DPABNLZUYUAAFA-UHFFFAOYSA-N 2,8-dibromoquinoline Chemical compound C1=CC=C(Br)C2=NC(Br)=CC=C21 DPABNLZUYUAAFA-UHFFFAOYSA-N 0.000 description 2
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
LIEPVGBDUYKPLC-UHFFFAOYSA-N 2-chloro-4-nitropyridine Chemical compound [O-][N+](=O)C1=CC=NC(Cl)=C1 LIEPVGBDUYKPLC-UHFFFAOYSA-N 0.000 description 2
QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 2
FSQXULFXZKQFSU-UHFFFAOYSA-N 3,3-difluoropiperidine-4,4-diol Chemical compound OC1(O)CCNCC1(F)F FSQXULFXZKQFSU-UHFFFAOYSA-N 0.000 description 2
GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 2
BAQKUNMKVAPWGU-UHFFFAOYSA-N 4-bromopyridin-2-amine Chemical compound NC1=CC(Br)=CC=N1 BAQKUNMKVAPWGU-UHFFFAOYSA-N 0.000 description 2
MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 2
CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
125000006163 5-membered heteroaryl group Chemical group 0.000 description 2
JEHWQJWDPOQIMX-UHFFFAOYSA-N 8-bromo-5-fluoro-2-(2-methoxyethenyl)quinoline Chemical compound FC1=CC=C(Br)C2=NC(C=COC)=CC=C21 JEHWQJWDPOQIMX-UHFFFAOYSA-N 0.000 description 2
IWVKLZLPGJIBHU-UHFFFAOYSA-N 8-bromo-6-fluoroquinoline-2-carbaldehyde Chemical compound N1=C(C=O)C=CC2=CC(F)=CC(Br)=C21 IWVKLZLPGJIBHU-UHFFFAOYSA-N 0.000 description 2
208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 2
241000156724 Antirhea Species 0.000 description 2
208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 2
206010006187 Breast cancer Diseases 0.000 description 2
208000026310 Breast neoplasm Diseases 0.000 description 2
XGNMCTBRKHVXMH-UHFFFAOYSA-N C(C)(C)(C)OC(C(CCCCCCCC)NC1CCNCC1)=O Chemical compound C(C)(C)(C)OC(C(CCCCCCCC)NC1CCNCC1)=O XGNMCTBRKHVXMH-UHFFFAOYSA-N 0.000 description 2
241000283707 Capra Species 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
208000010833 Chronic myeloid leukaemia Diseases 0.000 description 2
206010009944 Colon cancer Diseases 0.000 description 2
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
239000006144 Dulbecco’s modiﬁed Eagle's medium Substances 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
206010051066 Gastrointestinal stromal tumour Diseases 0.000 description 2
206010018338 Glioma Diseases 0.000 description 2
208000002250 Hematologic Neoplasms Diseases 0.000 description 2
208000017604 Hodgkin disease Diseases 0.000 description 2
208000010747 Hodgkins lymphoma Diseases 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
239000004472 Lysine Substances 0.000 description 2
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 2
208000014767 Myeloproliferative disease Diseases 0.000 description 2
201000007224 Myeloproliferative neoplasm Diseases 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 2
YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 2
NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [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 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 2
206010060862 Prostate cancer Diseases 0.000 description 2
208000000236 Prostatic Neoplasms Diseases 0.000 description 2
206010037660 Pyrexia Diseases 0.000 description 2
241000700159 Rattus Species 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
229920004890 Triton X-100 Polymers 0.000 description 2
239000013504 Triton X-100 Substances 0.000 description 2
102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 description 2
208000027418 Wounds and injury Diseases 0.000 description 2
GJWAPAVRQYYSTK-UHFFFAOYSA-N [(dimethyl-$l^{3}-silanyl)amino]-dimethylsilicon Chemical compound C[Si](C)N[Si](C)C GJWAPAVRQYYSTK-UHFFFAOYSA-N 0.000 description 2
MCNHVBWLINLGIB-UHFFFAOYSA-N [Li].CC(CCCCCCCCCNCCCCCCCCCC(C)(C)C)(C)C Chemical compound [Li].CC(CCCCCCCCCNCCCCCCCCCC(C)(C)C)(C)C MCNHVBWLINLGIB-UHFFFAOYSA-N 0.000 description 2
AZYZJSPCUMGVDB-UHFFFAOYSA-N [N]1C2=CC=C1C=C(N1)C=C(C)C1=CC([N]1)=CC=C1C=C(N1)C=CC1=C2 Chemical compound [N]1C2=CC=C1C=C(N1)C=C(C)C1=CC([N]1)=CC=C1C=C(N1)C=CC1=C2 AZYZJSPCUMGVDB-UHFFFAOYSA-N 0.000 description 2
208000036676 acute undifferentiated leukemia Diseases 0.000 description 2
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
GUNJVIDCYZYFGV-UHFFFAOYSA-K antimony trifluoride Chemical compound F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 2
SGDSAOOGSGZQQW-UHFFFAOYSA-N benzyl n-(4-methylpiperidin-4-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1(C)CCNCC1 SGDSAOOGSGZQQW-UHFFFAOYSA-N 0.000 description 2
DWPWWTIOOLQURY-NEPJUHHUSA-N benzyl n-[(3r,4s)-3-fluoropiperidin-4-yl]carbamate Chemical compound F[C@@H]1CNCC[C@@H]1NC(=O)OCC1=CC=CC=C1 DWPWWTIOOLQURY-NEPJUHHUSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
210000000988 bone and bone Anatomy 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
FNXLCIKXHOPCKH-UHFFFAOYSA-N bromamine Chemical compound BrN FNXLCIKXHOPCKH-UHFFFAOYSA-N 0.000 description 2
125000005997 bromomethyl group Chemical group 0.000 description 2
239000000872 buffer Substances 0.000 description 2
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
150000003857 carboxamides Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
229940114081 cinnamate Drugs 0.000 description 2
208000019425 cirrhosis of liver Diseases 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
208000029742 colonic neoplasm Diseases 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
230000018109 developmental process Effects 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
DXPIZCZNFUTPEI-UHFFFAOYSA-O diphenylphosphanium;azide Chemical compound [N-]=[N+]=[N-].C=1C=CC=CC=1[PH2+]C1=CC=CC=C1 DXPIZCZNFUTPEI-UHFFFAOYSA-O 0.000 description 2
230000002500 effect on skin Effects 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
239000012458 free base Substances 0.000 description 2
230000002489 hematologic effect Effects 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002466 imines Chemical class 0.000 description 2
208000014674 injury Diseases 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
229940043355 kinase inhibitor Drugs 0.000 description 2
229910052747 lanthanoid Inorganic materials 0.000 description 2
150000002602 lanthanoids Chemical class 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
210000004072 lung Anatomy 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000008267 milk Substances 0.000 description 2
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 2
125000002757 morpholinyl group Chemical group 0.000 description 2
210000000066 myeloid cell Anatomy 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000003757 phosphotransferase inhibitor Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
229960003975 potassium Drugs 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000001508 potassium citrate Substances 0.000 description 2
229960002635 potassium citrate Drugs 0.000 description 2
QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 2
235000011082 potassium citrates Nutrition 0.000 description 2
229940002612 prodrug Drugs 0.000 description 2
239000000651 prodrug Substances 0.000 description 2
125000003226 pyrazolyl group Chemical group 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical group C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
MGCGJBXTNWUHQE-UHFFFAOYSA-N quinoline-4-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CC=NC2=C1 MGCGJBXTNWUHQE-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000007017 scission Effects 0.000 description 2
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
239000012453 solvate Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000010959 steel Substances 0.000 description 2
230000004083 survival effect Effects 0.000 description 2
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 2
DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 2
XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 description 1
XDPCNPCKDGQBAN-SCSAIBSYSA-N (3r)-oxolan-3-ol Chemical compound O[C@@H]1CCOC1 XDPCNPCKDGQBAN-SCSAIBSYSA-N 0.000 description 1
XDPCNPCKDGQBAN-BYPYZUCNSA-N (3s)-oxolan-3-ol Chemical compound O[C@H]1CCOC1 XDPCNPCKDGQBAN-BYPYZUCNSA-N 0.000 description 1
KQVLBDVPZZJAJD-UHFFFAOYSA-N (8-bromo-5-fluoroquinolin-2-yl)methanol Chemical compound FC1=CC=C(Br)C2=NC(CO)=CC=C21 KQVLBDVPZZJAJD-UHFFFAOYSA-N 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
POJYSQCMDUIYSB-UHFFFAOYSA-N (anilinoazaniumyl)formate Chemical compound OC(=O)NNC1=CC=CC=C1 POJYSQCMDUIYSB-UHFFFAOYSA-N 0.000 description 1
AEFBNJXWRHSZGO-UHFFFAOYSA-N 1,2,3,3a,4,5-hexahydropyrene Chemical compound C1=C2CCCC(CC3)C2=C2C3=CC=CC2=C1 AEFBNJXWRHSZGO-UHFFFAOYSA-N 0.000 description 1
PUNXVEAWLAVABA-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene;1,2,5,6-tetrahydroanthracene Chemical compound C1=CC=C2C=C(CCCC3)C3=CC2=C1.C1=CCCC2=C1C=C1CCC=CC1=C2 PUNXVEAWLAVABA-UHFFFAOYSA-N 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
JCMVPOVHKWWBAU-UHFFFAOYSA-N 1,2-dichlorohydrazine Chemical compound ClNNCl JCMVPOVHKWWBAU-UHFFFAOYSA-N 0.000 description 1
VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
VYYAEWBJLVAHJE-UHFFFAOYSA-N 1,3-oxazol-2-yl trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=NC=CO1 VYYAEWBJLVAHJE-UHFFFAOYSA-N 0.000 description 1
PLCMVACJJSYDFV-UHFFFAOYSA-N 1,3-oxazole-2-carboxamide Chemical compound NC(=O)C1=NC=CO1 PLCMVACJJSYDFV-UHFFFAOYSA-N 0.000 description 1
RMMKGDVKSFHHAX-UHFFFAOYSA-N 1,3-oxazole;pyridine Chemical compound C1=COC=N1.C1=CC=NC=C1 RMMKGDVKSFHHAX-UHFFFAOYSA-N 0.000 description 1
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
XNJAYQHWXYJBBD-UHFFFAOYSA-N 1,4-difluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(F)=CC=C1F XNJAYQHWXYJBBD-UHFFFAOYSA-N 0.000 description 1
OEAJNZQFAHZXAB-UHFFFAOYSA-N 1,4-dioxane;methane Chemical compound C.C1COCCO1 OEAJNZQFAHZXAB-UHFFFAOYSA-N 0.000 description 1
RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
IBXMKLPFLZYRQZ-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 IBXMKLPFLZYRQZ-UHFFFAOYSA-N 0.000 description 1
AOJIAQCJGHACCX-UHFFFAOYSA-N 1-(3,3-dimethylbut-1-ynyl)-3-methoxybenzene Chemical compound COC1=CC=CC(C#CC(C)(C)C)=C1 AOJIAQCJGHACCX-UHFFFAOYSA-N 0.000 description 1
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 description 1
JQJBQVRTSMGDJX-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxy]decane Chemical compound CCCCCCCCCCOC(C)(C)C JQJBQVRTSMGDJX-UHFFFAOYSA-N 0.000 description 1
FLTYUHLOJTZHAP-UHFFFAOYSA-N 1-aminopyrrolidine-2,5-dione Chemical compound NN1C(=O)CCC1=O FLTYUHLOJTZHAP-UHFFFAOYSA-N 0.000 description 1
GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
NZVZVGPYTICZBZ-UHFFFAOYSA-N 1-benzylpiperidine Chemical compound C=1C=CC=CC=1CN1CCCCC1 NZVZVGPYTICZBZ-UHFFFAOYSA-N 0.000 description 1
WPDRTZQNLRNDMG-UHFFFAOYSA-N 1-bromopyrrolidine Chemical compound BrN1CCCC1 WPDRTZQNLRNDMG-UHFFFAOYSA-N 0.000 description 1
MSWVMWGCNZQPIA-UHFFFAOYSA-N 1-fluoropropan-2-one Chemical compound CC(=O)CF MSWVMWGCNZQPIA-UHFFFAOYSA-N 0.000 description 1
BBYSGWAYRRMWOW-UHFFFAOYSA-N 1-hexylpiperidine Chemical compound CCCCCCN1CCCCC1 BBYSGWAYRRMWOW-UHFFFAOYSA-N 0.000 description 1
LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
IDCPFAYURAQKDZ-UHFFFAOYSA-N 1-nitroguanidine Chemical compound NC(=N)N[N+]([O-])=O IDCPFAYURAQKDZ-UHFFFAOYSA-N 0.000 description 1
PTZNCCIULVXFIJ-UHFFFAOYSA-N 1-o-tert-butyl 4-o-methyl piperidine-1,4-dicarboxylate Chemical compound COC(=O)C1CCN(C(=O)OC(C)(C)C)CC1 PTZNCCIULVXFIJ-UHFFFAOYSA-N 0.000 description 1
IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 1
AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 description 1
XVTILWLVPDMCSO-UHFFFAOYSA-N 1h-indole;piperidine Chemical compound C1CCNCC1.C1=CC=C2NC=CC2=C1 XVTILWLVPDMCSO-UHFFFAOYSA-N 0.000 description 1
HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 description 1
NMXFXOOXWOMPCX-UHFFFAOYSA-N 2,3,3a,4,5,6-hexahydroindole-1-carboxylic acid Chemical compound C1CCC=C2N(C(=O)O)CCC21 NMXFXOOXWOMPCX-UHFFFAOYSA-N 0.000 description 1
FFOVFIRMBLLEJP-UHFFFAOYSA-N 2,3,4,7-tetrahydro-1h-purine Chemical compound N1CNC=C2NC=NC21 FFOVFIRMBLLEJP-UHFFFAOYSA-N 0.000 description 1
KWVPZTJLHQKCKD-UHFFFAOYSA-N 2,3-dibromoquinoline Chemical compound C1=CC=C2N=C(Br)C(Br)=CC2=C1 KWVPZTJLHQKCKD-UHFFFAOYSA-N 0.000 description 1
QFLMSFRCLUMLIU-UHFFFAOYSA-N 2,8-dibromo-4-methylquinoline Chemical compound C1=CC=C2C(C)=CC(Br)=NC2=C1Br QFLMSFRCLUMLIU-UHFFFAOYSA-N 0.000 description 1
CNIIGCLFLJGOGP-UHFFFAOYSA-N 2-(1-naphthalenylmethyl)-4,5-dihydro-1H-imidazole Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 CNIIGCLFLJGOGP-UHFFFAOYSA-N 0.000 description 1
NPAWEUITWXWQGK-UHFFFAOYSA-N 2-(2-aminopyridin-4-yl)oxyethanol Chemical compound NC1=NC=CC(=C1)OCCO NPAWEUITWXWQGK-UHFFFAOYSA-N 0.000 description 1
RGUFZILIVUBHAE-UHFFFAOYSA-N 2-(2-decoxy-2-oxoethyl)-2-hydroxybutanedioic acid Chemical compound CCCCCCCCCCOC(=O)CC(O)(C(O)=O)CC(O)=O RGUFZILIVUBHAE-UHFFFAOYSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
BHUPIKYIGMWGAD-UHFFFAOYSA-N 2-amino-9-(hydroxymethyl)-3-oxophenoxazine-1-carboxylic acid Chemical class C1=CC=C2OC3=CC(=O)C(N)=C(C(O)=O)C3=NC2=C1CO BHUPIKYIGMWGAD-UHFFFAOYSA-N 0.000 description 1
YLMFXCIATJJKQL-UHFFFAOYSA-N 2-bromo-4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1Br YLMFXCIATJJKQL-UHFFFAOYSA-N 0.000 description 1
FWTXFEKVHSFTDQ-UHFFFAOYSA-N 2-bromo-5-fluoroaniline Chemical compound NC1=CC(F)=CC=C1Br FWTXFEKVHSFTDQ-UHFFFAOYSA-N 0.000 description 1
AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 1
MTDOAXRREVUUAU-UHFFFAOYSA-N 2-chloro-4-(2-methoxyethoxy)pyridine Chemical compound COCCOC1=CC=NC(Cl)=C1 MTDOAXRREVUUAU-UHFFFAOYSA-N 0.000 description 1
CBVDPTYIDMQDEO-UHFFFAOYSA-N 2-decoxyethanol Chemical compound CCCCCCCCCCOCCO CBVDPTYIDMQDEO-UHFFFAOYSA-N 0.000 description 1
XUGNJOCQALIQFG-UHFFFAOYSA-N 2-ethenylquinoline Chemical compound C1=CC=CC2=NC(C=C)=CC=C21 XUGNJOCQALIQFG-UHFFFAOYSA-N 0.000 description 1
ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 description 1
125000004918 2-methyl-2-pentyl group Chemical group CC(C)(CCC)* 0.000 description 1
125000004922 2-methyl-3-pentyl group Chemical group CC(C)C(CC)* 0.000 description 1
JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 description 1
SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
HLTDBMHJSBSAOM-UHFFFAOYSA-N 2-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CC=N1 HLTDBMHJSBSAOM-UHFFFAOYSA-N 0.000 description 1
CZMRCDWAGMRECN-UHFFFAOYSA-N 2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound OCC1OC(CO)(OC2OC(CO)C(O)C(O)C2O)C(O)C1O CZMRCDWAGMRECN-UHFFFAOYSA-N 0.000 description 1
GSXRIAKWODYOEN-UHFFFAOYSA-N 3,7-diphenylimidazo[1,2-a]pyridine Chemical compound C=1N=C2C=C(C=3C=CC=CC=3)C=CN2C=1C1=CC=CC=C1 GSXRIAKWODYOEN-UHFFFAOYSA-N 0.000 description 1
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
YIBCUMYEGNESAP-UHFFFAOYSA-N 3-bromo-5-fluoro-2-methyl-1h-indole Chemical compound C1=C(F)C=C2C(Br)=C(C)NC2=C1 YIBCUMYEGNESAP-UHFFFAOYSA-N 0.000 description 1
DEVLCRJHRJHMCX-UHFFFAOYSA-N 3-fluoropiperidin-4-amine Chemical compound NC1CCNCC1F DEVLCRJHRJHMCX-UHFFFAOYSA-N 0.000 description 1
102100040842 3-galactosyl-N-acetylglucosaminide 4-alpha-L-fucosyltransferase FUT3 Human genes 0.000 description 1
125000004919 3-methyl-2-pentyl group Chemical group CC(C(C)*)CC 0.000 description 1
125000004921 3-methyl-3-pentyl group Chemical group CC(CC)(CC)* 0.000 description 1
KCHQXPGUJBVNTN-UHFFFAOYSA-N 4,4-diphenylbut-3-en-2-one Chemical compound C=1C=CC=CC=1C(=CC(=O)C)C1=CC=CC=C1 KCHQXPGUJBVNTN-UHFFFAOYSA-N 0.000 description 1
WVYVRKDALUNYQY-UHFFFAOYSA-N 4-(2-methoxyethoxy)-1H-pyridin-2-one Chemical compound COCCOC=1C=CNC(C=1)=O WVYVRKDALUNYQY-UHFFFAOYSA-N 0.000 description 1
BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
DZQLQEYLEYWJIB-UHFFFAOYSA-N 4-aminobutanal Chemical compound NCCCC=O DZQLQEYLEYWJIB-UHFFFAOYSA-N 0.000 description 1
NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 1
DZGGGLJOCYPKHN-UHFFFAOYSA-N 4-ethenylquinoline Chemical compound C1=CC=C2C(C=C)=CC=NC2=C1 DZGGGLJOCYPKHN-UHFFFAOYSA-N 0.000 description 1
AZRRZGIBBLWSSQ-UHFFFAOYSA-N 4-ethyl-7-phenyl-3,5-diazabicyclo[2.2.2]octane-2,6-dione Chemical compound N1C(=O)C2C(=O)NC1(CC)CC2C1=CC=CC=C1 AZRRZGIBBLWSSQ-UHFFFAOYSA-N 0.000 description 1
125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 1
VZSPRDGYHFGDAY-UHFFFAOYSA-N 4-pyridin-3-ylpyridin-2-amine Chemical compound C1=NC(N)=CC(C=2C=NC=CC=2)=C1 VZSPRDGYHFGDAY-UHFFFAOYSA-N 0.000 description 1
RGNFIXBEYXCOLV-UHFFFAOYSA-N 4-sulfanylpiperidine-4-carboxylic acid Chemical compound SC1(CCNCC1)C(=O)O RGNFIXBEYXCOLV-UHFFFAOYSA-N 0.000 description 1
WMFXCDGQRHJFKL-UHFFFAOYSA-N 5-fluoroquinoline Chemical compound C1=CC=C2C(F)=CC=CC2=N1 WMFXCDGQRHJFKL-UHFFFAOYSA-N 0.000 description 1
RTVUNKIAMQMWTL-UHFFFAOYSA-N 5-fluoroquinoline-2-carboxylic acid Chemical compound FC1=CC=CC2=NC(C(=O)O)=CC=C21 RTVUNKIAMQMWTL-UHFFFAOYSA-N 0.000 description 1
HZGQCCSFFAPMKJ-UHFFFAOYSA-N 6-fluoroquinoline Chemical compound N1=C=CC=C2[CH]C(F)=CC=C21 HZGQCCSFFAPMKJ-UHFFFAOYSA-N 0.000 description 1
125000006164 6-membered heteroaryl group Chemical group 0.000 description 1
AZDWSVWOEDWZSN-UHFFFAOYSA-N 7-pyridin-2-ylimidazo[1,2-a]pyridine Chemical compound C=1C2=NC=CN2C=CC=1C1=CC=CC=N1 AZDWSVWOEDWZSN-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
DXSVIVLMRAWPIM-UHFFFAOYSA-N 8-azaspiro[4.5]decane-1,4-dione Chemical compound O=C1CCC(=O)C11CCNCC1 DXSVIVLMRAWPIM-UHFFFAOYSA-N 0.000 description 1
CAJIAUQJSMUVHH-UHFFFAOYSA-N 8-bromo-2-(2-methoxyethenyl)-6-(trifluoromethyl)quinoline Chemical compound C1=C(C(F)(F)F)C=C(Br)C2=NC(C=COC)=CC=C21 CAJIAUQJSMUVHH-UHFFFAOYSA-N 0.000 description 1
WNCMKCYNUDBQQO-UHFFFAOYSA-N 8-bromo-2-(dibromomethyl)-5-fluoroquinoline Chemical compound BrC(Br)C1=CC=C2C(F)=CC=C(Br)C2=N1 WNCMKCYNUDBQQO-UHFFFAOYSA-N 0.000 description 1
SKYJNBNYCRKOPC-UHFFFAOYSA-N 8-bromo-5-fluoro-2-methylquinoline Chemical compound FC1=CC=C(Br)C2=NC(C)=CC=C21 SKYJNBNYCRKOPC-UHFFFAOYSA-N 0.000 description 1
OUZLPGJFGCOKJJ-UHFFFAOYSA-N 8-bromo-5-fluoroquinoline Chemical compound C1=CC=C2C(F)=CC=C(Br)C2=N1 OUZLPGJFGCOKJJ-UHFFFAOYSA-N 0.000 description 1
MJWZFQJNGFPWGE-UHFFFAOYSA-N 8-bromo-5-fluoroquinoline-2-carbaldehyde Chemical compound O=CC1=CC=C2C(F)=CC=C(Br)C2=N1 MJWZFQJNGFPWGE-UHFFFAOYSA-N 0.000 description 1
NWPHMULLPITJJY-UHFFFAOYSA-N 8-bromo-5-fluoroquinoline-2-carboxylic acid Chemical compound FC1=CC=C(Br)C2=NC(C(=O)O)=CC=C21 NWPHMULLPITJJY-UHFFFAOYSA-N 0.000 description 1
HYNGTUOHHRSCMG-UHFFFAOYSA-N 8-bromo-6-fluoro-2-(2-methoxyethenyl)quinoline Chemical compound C1=C(F)C=C(Br)C2=NC(C=COC)=CC=C21 HYNGTUOHHRSCMG-UHFFFAOYSA-N 0.000 description 1
MHOZAOOOCGCDQS-UHFFFAOYSA-N 8-bromo-6-fluoro-2-methylquinoline Chemical compound C1=C(F)C=C(Br)C2=NC(C)=CC=C21 MHOZAOOOCGCDQS-UHFFFAOYSA-N 0.000 description 1
CLFPSUQMEIZXHS-UHFFFAOYSA-N 8-bromo-6-fluoroquinoline-2-carboxylic acid Chemical compound C1=C(F)C=C(Br)C2=NC(C(=O)O)=CC=C21 CLFPSUQMEIZXHS-UHFFFAOYSA-N 0.000 description 1
GZSUIHUAFPHZSU-UHFFFAOYSA-N 9-ethyl-2,3-dihydro-1h-carbazol-4-one Chemical compound C12=CC=CC=C2N(CC)C2=C1C(=O)CCC2 GZSUIHUAFPHZSU-UHFFFAOYSA-N 0.000 description 1
102100037651 AP-2 complex subunit sigma Human genes 0.000 description 1
241000238876 Acari Species 0.000 description 1
241000254032 Acrididae Species 0.000 description 1
206010000830 Acute leukaemia Diseases 0.000 description 1
208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
239000012116 Alexa Fluor 680 Substances 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
206010073478 Anaplastic large-cell lymphoma Diseases 0.000 description 1
208000032467 Aplastic anaemia Diseases 0.000 description 1
235000003911 Arachis Nutrition 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
241000972773 Aulopiformes Species 0.000 description 1
208000023275 Autoimmune disease Diseases 0.000 description 1
208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 1
229910015845 BBr3 Inorganic materials 0.000 description 1
241000884302 Baicaloides Species 0.000 description 1
208000023328 Basedow disease Diseases 0.000 description 1
108010081589 Becaplermin Proteins 0.000 description 1
208000009137 Behcet syndrome Diseases 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
208000020084 Bone disease Diseases 0.000 description 1
206010048396 Bone marrow transplant rejection Diseases 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
QSLNMZJKLARNOB-UHFFFAOYSA-N BrC1=C2NC(=C1)C=C1C=C(C(=N1)C=C1C=CC(N1)=CC=1C=CC(N1)=C2)Br Chemical compound BrC1=C2NC(=C1)C=C1C=C(C(=N1)C=C1C=CC(N1)=CC=1C=CC(N1)=C2)Br QSLNMZJKLARNOB-UHFFFAOYSA-N 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
DGSQFZLPROJXNI-UHFFFAOYSA-N C(C=1C(C(=O)O)=CC=CC1)(=O)O.FC(F)F Chemical compound C(C=1C(C(=O)O)=CC=CC1)(=O)O.FC(F)F DGSQFZLPROJXNI-UHFFFAOYSA-N 0.000 description 1
VPXYTOUYEPRUIY-UHFFFAOYSA-N C(CCC)OC(=O)C1NCC(NC1C(=O)OCCCC)C(=O)OCCCC Chemical compound C(CCC)OC(=O)C1NCC(NC1C(=O)OCCCC)C(=O)OCCCC VPXYTOUYEPRUIY-UHFFFAOYSA-N 0.000 description 1
GSNHMMZJWBEFNQ-UHFFFAOYSA-N C(CCCCCCCCC)OCCOC1=CC(=NC=C1)N Chemical compound C(CCCCCCCCC)OCCOC1=CC(=NC=C1)N GSNHMMZJWBEFNQ-UHFFFAOYSA-N 0.000 description 1
RENMTPBWXSDLGR-UHFFFAOYSA-N C(CO)(=O)O.SC=CC Chemical compound C(CO)(=O)O.SC=CC RENMTPBWXSDLGR-UHFFFAOYSA-N 0.000 description 1
VBFYGPFWNLACDS-UHFFFAOYSA-M C(N)([O-])=O.[Cs+] Chemical compound C(N)([O-])=O.[Cs+] VBFYGPFWNLACDS-UHFFFAOYSA-M 0.000 description 1
BKKPBJXJRGPXSG-UHFFFAOYSA-N C1(CCCC2NC3=CC=CC=C3C=C12)O Chemical compound C1(CCCC2NC3=CC=CC=C3C=C12)O BKKPBJXJRGPXSG-UHFFFAOYSA-N 0.000 description 1
QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 1
WSCDCBOHVINCDP-UHFFFAOYSA-N CCCCCCCCCCC1(C=CC=CN1)CCCCCCCCCC Chemical compound CCCCCCCCCCC1(C=CC=CN1)CCCCCCCCCC WSCDCBOHVINCDP-UHFFFAOYSA-N 0.000 description 1
PJHVJLZUWCPSKD-UHFFFAOYSA-N CN1CCC2C(CCC=C12)N Chemical compound CN1CCC2C(CCC=C12)N PJHVJLZUWCPSKD-UHFFFAOYSA-N 0.000 description 1
HVNJRMREZFDHSD-UHFFFAOYSA-N CN1CCCCC1.NN Chemical compound CN1CCCCC1.NN HVNJRMREZFDHSD-UHFFFAOYSA-N 0.000 description 1
102000055006 Calcitonin Human genes 0.000 description 1
108060001064 Calcitonin Proteins 0.000 description 1
102100022789 Calcium/calmodulin-dependent protein kinase type IV Human genes 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
IECDQFTWLJHUJV-UHFFFAOYSA-N ClC1=NC=CC(=C1)OCCOC.[N] Chemical compound ClC1=NC=CC(=C1)OCCOC.[N] IECDQFTWLJHUJV-UHFFFAOYSA-N 0.000 description 1
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
244000241257 Cucumis melo Species 0.000 description 1
235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
102000054300 EC 2.7.11.- Human genes 0.000 description 1
108700035490 EC 2.7.11.- Proteins 0.000 description 1
238000002965 ELISA Methods 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical group CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
201000008808 Fibrosarcoma Diseases 0.000 description 1
101150072536 Flt3 gene Proteins 0.000 description 1
241001536352 Fraxinus americana Species 0.000 description 1
206010017993 Gastrointestinal neoplasms Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
208000032612 Glial tumor Diseases 0.000 description 1
108030001320 Glutamine kinases Proteins 0.000 description 1
208000015023 Graves' disease Diseases 0.000 description 1
239000007821 HATU Substances 0.000 description 1
229910004373 HOAc Inorganic materials 0.000 description 1
208000021519 Hodgkin lymphoma Diseases 0.000 description 1
241000282412 Homo Species 0.000 description 1
101000893701 Homo sapiens 3-galactosyl-N-acetylglucosaminide 4-alpha-L-fucosyltransferase FUT3 Proteins 0.000 description 1
101000806914 Homo sapiens AP-2 complex subunit sigma Proteins 0.000 description 1
101100287682 Homo sapiens CAMK2G gene Proteins 0.000 description 1
101100126883 Homo sapiens CAMK4 gene Proteins 0.000 description 1
206010020880 Hypertrophy Diseases 0.000 description 1
206010058031 Joint adhesion Diseases 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
206010023421 Kidney fibrosis Diseases 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
229910010084 LiAlH4 Inorganic materials 0.000 description 1
208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
206010025323 Lymphomas Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
RZMWRIGBZCLMQB-UHFFFAOYSA-N N1CCC(CC1)NC(C(=O)O)CCCCCCCC Chemical compound N1CCC(CC1)NC(C(=O)O)CCCCCCCC RZMWRIGBZCLMQB-UHFFFAOYSA-N 0.000 description 1
OYIGRHWUVWIXOQ-UHFFFAOYSA-N N1CCC(CC1)NNC(O)=O Chemical compound N1CCC(CC1)NNC(O)=O OYIGRHWUVWIXOQ-UHFFFAOYSA-N 0.000 description 1
229910017974 NH40H Inorganic materials 0.000 description 1
208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
206010031149 Osteitis Diseases 0.000 description 1
244000131316 Panax pseudoginseng Species 0.000 description 1
235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
235000003140 Panax quinquefolius Nutrition 0.000 description 1
206010061902 Pancreatic neoplasm Diseases 0.000 description 1
241000282320 Panthera leo Species 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
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 1
241000288906 Primates Species 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
102000001253 Protein Kinase Human genes 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
206010037180 Psychiatric symptoms Diseases 0.000 description 1
208000015634 Rectal Neoplasms Diseases 0.000 description 1
208000006265 Renal cell carcinoma Diseases 0.000 description 1
239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 1
208000034189 Sclerosis Diseases 0.000 description 1
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
201000002661 Spondylitis Diseases 0.000 description 1
208000005718 Stomach Neoplasms Diseases 0.000 description 1
208000029052 T-cell acute lymphoblastic leukemia Diseases 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 1
206010043561 Thrombocytopenic purpura Diseases 0.000 description 1
206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
108091008605 VEGF receptors Proteins 0.000 description 1
102000016548 Vascular Endothelial Growth Factor Receptor-1 Human genes 0.000 description 1
108010053096 Vascular Endothelial Growth Factor Receptor-1 Proteins 0.000 description 1
241000251539 Vertebrata <Metazoa> Species 0.000 description 1
FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
DQZACHDJIOHKBU-UHFFFAOYSA-N [K].C(C(=C)C)(=O)OC Chemical compound [K].C(C(=C)C)(=O)OC DQZACHDJIOHKBU-UHFFFAOYSA-N 0.000 description 1
UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 1
125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
230000009471 action Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
238000004220 aggregation Methods 0.000 description 1
125000006241 alcohol protecting group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
OGVYUYRVZAMBRJ-UHFFFAOYSA-N amino(butyl)carbamic acid Chemical compound CCCCN(N)C(O)=O OGVYUYRVZAMBRJ-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000033115 angiogenesis Effects 0.000 description 1
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
150000004056 anthraquinones Chemical class 0.000 description 1
230000003510 anti-fibrotic effect Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
230000003305 autocrine Effects 0.000 description 1
210000003719 b-lymphocyte Anatomy 0.000 description 1
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
229960004217 benzyl alcohol Drugs 0.000 description 1
ZSAYVPCIKVBDRI-UHFFFAOYSA-N benzyl decanoate Chemical compound CCCCCCCCCC(=O)OCC1=CC=CC=C1 ZSAYVPCIKVBDRI-UHFFFAOYSA-N 0.000 description 1
DWPWWTIOOLQURY-VXGBXAGGSA-N benzyl n-[(3r,4r)-3-fluoropiperidin-4-yl]carbamate Chemical compound F[C@@H]1CNCC[C@H]1NC(=O)OCC1=CC=CC=C1 DWPWWTIOOLQURY-VXGBXAGGSA-N 0.000 description 1
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
239000000090 biomarker Substances 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
125000004799 bromophenyl group Chemical group 0.000 description 1
239000004067 bulking agent Substances 0.000 description 1
OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
LYQFWZFBNBDLEO-UHFFFAOYSA-M caesium bromide Chemical compound [Br-].[Cs+] LYQFWZFBNBDLEO-UHFFFAOYSA-M 0.000 description 1
BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 1
229960004015 calcitonin Drugs 0.000 description 1
BKRRPNHAJPONSH-UHFFFAOYSA-N carbazole Chemical compound C1=CC=C2[C]3C=CC=CC3=NC2=C1 BKRRPNHAJPONSH-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
201000002797 childhood leukemia Diseases 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
201000010902 chronic myelomonocytic leukemia Diseases 0.000 description 1
210000001072 colon Anatomy 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
239000013058 crude material Substances 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
230000001186 cumulative effect Effects 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000004980 cyclopropylene group Chemical group 0.000 description 1
GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
230000006378 damage Effects 0.000 description 1
DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
230000006837 decompression Effects 0.000 description 1
125000002704 decyl group Chemical group [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])* 0.000 description 1
230000017858 demethylation Effects 0.000 description 1
238000010520 demethylation reaction Methods 0.000 description 1
210000004443 dendritic cell Anatomy 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
125000000950 dibromo group Chemical group Br* 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
125000005594 diketone group Chemical group 0.000 description 1
IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
229910001882 dioxygen Inorganic materials 0.000 description 1
230000006806 disease prevention Effects 0.000 description 1
238000009826 distribution Methods 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
230000002327 eosinophilic effect Effects 0.000 description 1
210000002919 epithelial cell Anatomy 0.000 description 1
ZRSDQBKGDNPFLT-UHFFFAOYSA-N ethanol;oxolane Chemical compound CCO.C1CCOC1 ZRSDQBKGDNPFLT-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
XAHXFLGTAKROPJ-UHFFFAOYSA-N ethyl 8-bromo-5-fluoroquinoline-2-carboxylate Chemical compound FC1=CC=C(Br)C2=NC(C(=O)OCC)=CC=C21 XAHXFLGTAKROPJ-UHFFFAOYSA-N 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
238000004880 explosion Methods 0.000 description 1
229960004979 fampridine Drugs 0.000 description 1
239000012091 fetal bovine serum Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
206010017758 gastric cancer Diseases 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000000499 gel Substances 0.000 description 1
238000005227 gel permeation chromatography Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
235000008434 ginseng Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
201000005787 hematologic cancer Diseases 0.000 description 1
208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 1
210000000777 hematopoietic system Anatomy 0.000 description 1
208000007475 hemolytic anemia Diseases 0.000 description 1
125000005842 heteroatom Chemical group 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
238000004128 high performance liquid chromatography Methods 0.000 description 1
210000003630 histaminocyte Anatomy 0.000 description 1
ATBKVKDEMSGMTQ-UHFFFAOYSA-N hydrazine triphenylphosphane Chemical compound NN.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 ATBKVKDEMSGMTQ-UHFFFAOYSA-N 0.000 description 1
GSEPHVGFSQHACX-UHFFFAOYSA-N hydrazine;pyridine Chemical compound NN.C1=CC=NC=C1 GSEPHVGFSQHACX-UHFFFAOYSA-N 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000004693 imidazolium salts Chemical group 0.000 description 1
125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
ZSKVGTPCRGIANV-ZXFLCMHBSA-N imipenem Chemical compound C1C(SCC\N=C\N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 ZSKVGTPCRGIANV-ZXFLCMHBSA-N 0.000 description 1
229960002182 imipenem Drugs 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011534 incubation Methods 0.000 description 1
125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 description 1
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
238000003331 infrared imaging Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000002346 iodo group Chemical group I* 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
MQUPWTBHHPUUMC-UHFFFAOYSA-N isoindole Chemical compound C1=CC=C[C]2C=NC=C21 MQUPWTBHHPUUMC-UHFFFAOYSA-N 0.000 description 1
230000000155 isotopic effect Effects 0.000 description 1
230000000366 juvenile effect Effects 0.000 description 1
201000005992 juvenile myelomonocytic leukemia Diseases 0.000 description 1
238000002386 leaching Methods 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
229930013686 lignan Natural products 0.000 description 1
150000005692 lignans Chemical class 0.000 description 1
235000009408 lignans Nutrition 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
238000011068 loading method Methods 0.000 description 1
210000002751 lymph Anatomy 0.000 description 1
230000000527 lymphocytic effect Effects 0.000 description 1
208000003747 lymphoid leukemia Diseases 0.000 description 1
239000006166 lysate Substances 0.000 description 1
239000012139 lysis buffer Substances 0.000 description 1
208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
SCDXZWQMCDSDCA-UHFFFAOYSA-N methyl 4-(phenylmethoxycarbonylamino)piperidine-4-carboxylate Chemical compound C=1C=CC=CC=1COC(=O)NC1(C(=O)OC)CCNCC1 SCDXZWQMCDSDCA-UHFFFAOYSA-N 0.000 description 1
RZVWBASHHLFBJF-UHFFFAOYSA-N methyl piperidine-4-carboxylate Chemical compound COC(=O)C1CCNCC1 RZVWBASHHLFBJF-UHFFFAOYSA-N 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
RRIWSQXXBIFKQM-UHFFFAOYSA-N monomeric N-benzylcarbamic acid Natural products OC(=O)NCC1=CC=CC=C1 RRIWSQXXBIFKQM-UHFFFAOYSA-N 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
206010028417 myasthenia gravis Diseases 0.000 description 1
208000025113 myeloid leukemia Diseases 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
VUTALNKXTAWHTC-UHFFFAOYSA-N n-benzyl-3,3-difluoropiperidin-4-amine Chemical compound FC1(F)CNCCC1NCC1=CC=CC=C1 VUTALNKXTAWHTC-UHFFFAOYSA-N 0.000 description 1
FUTZDFOAPDCBHZ-UHFFFAOYSA-N n-bromo-3-fluoroaniline Chemical compound FC1=CC=CC(NBr)=C1 FUTZDFOAPDCBHZ-UHFFFAOYSA-N 0.000 description 1
DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 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
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
210000004498 neuroglial cell Anatomy 0.000 description 1
229960002715 nicotine Drugs 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
210000001331 nose Anatomy 0.000 description 1
229920006284 nylon film Polymers 0.000 description 1
125000002347 octyl 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])[H] 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000005416 organic matter Substances 0.000 description 1
230000002611 ovarian Effects 0.000 description 1
230000002018 overexpression Effects 0.000 description 1
125000003544 oxime group Chemical group 0.000 description 1
125000005825 oxyethoxy group Chemical group [H]C([H])(O[*:1])C([H])([H])O[*:2] 0.000 description 1
PVSCLHDHWOAWGV-UHFFFAOYSA-N oxygen;toluene Chemical compound [O].CC1=CC=CC=C1 PVSCLHDHWOAWGV-UHFFFAOYSA-N 0.000 description 1
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 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
201000002528 pancreatic cancer Diseases 0.000 description 1
208000008443 pancreatic carcinoma Diseases 0.000 description 1
230000003076 paracrine Effects 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 1
RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
230000026731 phosphorylation Effects 0.000 description 1
238000006366 phosphorylation reaction Methods 0.000 description 1
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
QHDUBNMGSDGCKZ-UHFFFAOYSA-N piperidin-1-ium;propanoate Chemical compound CCC(O)=O.C1CCNCC1 QHDUBNMGSDGCKZ-UHFFFAOYSA-N 0.000 description 1
LEGMHPGYPXPXKB-UHFFFAOYSA-N piperidin-2-ol Chemical compound OC1CCCCN1 LEGMHPGYPXPXKB-UHFFFAOYSA-N 0.000 description 1
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
IIKFXOLJMNWWCH-UHFFFAOYSA-N piperidine-1,4-dicarboxylic acid Chemical compound OC(=O)C1CCN(C(O)=O)CC1 IIKFXOLJMNWWCH-UHFFFAOYSA-N 0.000 description 1
238000010837 poor prognosis Methods 0.000 description 1
239000011148 porous material Substances 0.000 description 1
LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
208000023958 prostate neoplasm Diseases 0.000 description 1
108060006633 protein kinase Proteins 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
208000005069 pulmonary fibrosis Diseases 0.000 description 1
PNNRZXFUPQQZSO-UHFFFAOYSA-N pyran Chemical compound [CH]1OC=CC=C1 PNNRZXFUPQQZSO-UHFFFAOYSA-N 0.000 description 1
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
ZRNDSLLIAOLRJS-UHFFFAOYSA-N pyridin-3-yl trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=CN=C1 ZRNDSLLIAOLRJS-UHFFFAOYSA-N 0.000 description 1
125000005554 pyridyloxy group Chemical group 0.000 description 1
229960001404 quinidine Drugs 0.000 description 1
125000003410 quininyl group Chemical group 0.000 description 1
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
ZXZKYYHTWHJHFT-UHFFFAOYSA-N quinoline-2,8-diol Chemical compound C1=CC(=O)NC2=C1C=CC=C2O ZXZKYYHTWHJHFT-UHFFFAOYSA-N 0.000 description 1
BTUQCUPQFZHMNS-UHFFFAOYSA-N quinoline;dihydrochloride Chemical compound Cl.Cl.N1=CC=CC2=CC=CC=C21 BTUQCUPQFZHMNS-UHFFFAOYSA-N 0.000 description 1
150000004060 quinone imines Chemical class 0.000 description 1
206010038038 rectal cancer Diseases 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
201000001275 rectum cancer Diseases 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000008439 repair process Effects 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
201000006845 reticulosarcoma Diseases 0.000 description 1
208000029922 reticulum cell sarcoma Diseases 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
PESCJSXFKGVICJ-UHFFFAOYSA-N ruthenium(3+) ruthenium(4+) Chemical compound [Ru+3].[Ru+4] PESCJSXFKGVICJ-UHFFFAOYSA-N 0.000 description 1
210000003296 saliva Anatomy 0.000 description 1
235000019515 salmon Nutrition 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
229910052711 selenium Inorganic materials 0.000 description 1
239000011669 selenium Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000011664 signaling Effects 0.000 description 1
210000000329 smooth muscle myocyte Anatomy 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
235000011006 sodium potassium tartrate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
210000000278 spinal cord Anatomy 0.000 description 1
230000007839 spinal cord development Effects 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
210000000130 stem cell Anatomy 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
201000011549 stomach cancer Diseases 0.000 description 1
XXCMBPUMZXRBTN-UHFFFAOYSA-N strontium sulfide Chemical compound [Sr]=S XXCMBPUMZXRBTN-UHFFFAOYSA-N 0.000 description 1
239000000758 substrate Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000013589 supplement Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
LCZVKKUAUWQDPX-UHFFFAOYSA-N tert-butyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]ethyl]amino]acetate Chemical compound CC(=O)OC1=CC=CC=C1CN(CC(=O)OC(C)(C)C)CCN(CC(=O)OC(C)(C)C)CC1=CC=CC=C1OC(C)=O LCZVKKUAUWQDPX-UHFFFAOYSA-N 0.000 description 1
DHJKRRZIUOQEFW-UHFFFAOYSA-N tert-butyl 2-methylpiperidine-1-carboxylate Chemical compound CC1CCCCN1C(=O)OC(C)(C)C DHJKRRZIUOQEFW-UHFFFAOYSA-N 0.000 description 1
XTDXZSGSIMLARD-UHFFFAOYSA-N tert-butyl 2h-pyridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC=CC=C1 XTDXZSGSIMLARD-UHFFFAOYSA-N 0.000 description 1
WPWXYQIMXTUMJB-UHFFFAOYSA-N tert-butyl 3-(aminomethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC(CN)C1 WPWXYQIMXTUMJB-UHFFFAOYSA-N 0.000 description 1
IZUZIVIUDTZPFE-UHFFFAOYSA-N tert-butyl decanoate Chemical compound CCCCCCCCCC(=O)OC(C)(C)C IZUZIVIUDTZPFE-UHFFFAOYSA-N 0.000 description 1
RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical compound CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
BHUKKFNQXNWGFW-UHFFFAOYSA-N tert-butyl n-(2-ethynyl-6-methoxyphenyl)carbamate Chemical compound COC1=CC=CC(C#C)=C1NC(=O)OC(C)(C)C BHUKKFNQXNWGFW-UHFFFAOYSA-N 0.000 description 1
MXMNIQCGKFKLPN-UHFFFAOYSA-N tert-butyl n-(piperidin-4-ylamino)carbamate Chemical compound CC(C)(C)OC(=O)NNC1CCNCC1 MXMNIQCGKFKLPN-UHFFFAOYSA-N 0.000 description 1
FRHOQDDDDFBHGW-UHFFFAOYSA-N tert-butyl n-piperidin-1-ylcarbamate Chemical compound CC(C)(C)OC(=O)NN1CCCCC1 FRHOQDDDDFBHGW-UHFFFAOYSA-N 0.000 description 1
CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
RQCNHUCCQJMSRG-UHFFFAOYSA-N tert-butyl piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1 RQCNHUCCQJMSRG-UHFFFAOYSA-N 0.000 description 1
239000012085 test solution Substances 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
229940098465 tincture Drugs 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
BHAROVLESINHSM-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1.CC1=CC=CC=C1 BHAROVLESINHSM-UHFFFAOYSA-N 0.000 description 1
TXXHDPDFNKHHGW-ZPUQHVIOSA-N trans,trans-muconic acid Chemical compound OC(=O)\C=C\C=C\C(O)=O TXXHDPDFNKHHGW-ZPUQHVIOSA-N 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-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
238000001665 trituration Methods 0.000 description 1
230000005740 tumor formation Effects 0.000 description 1
229960003732 tyramine Drugs 0.000 description 1
229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1