TWI817189B - 作為fgfr4抑制劑之雙環雜環 - Google Patents

Info

Publication number

TWI817189B

TWI817189B TW110132234A TW110132234A TWI817189B TW I817189 B TWI817189 B TW I817189B TW 110132234 A TW110132234 A TW 110132234A TW 110132234 A TW110132234 A TW 110132234A TW I817189 B TWI817189 B TW I817189B

Authority

TW

Taiwan

Prior art keywords

methyl

difluoro

dimethoxyphenyl

pyrimidin

acrylamide

Prior art date

2015-02-20

Links

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• 239000003112 inhibitor Substances 0.000 title abstract description 34
• 125000002618 bicyclic heterocycle group Chemical group 0.000 title abstract description 3
• 101150082429 FGFR4 gene Proteins 0.000 title 1
• 102100027844 Fibroblast growth factor receptor 4 Human genes 0.000 claims abstract description 46
• 101000917134 Homo sapiens Fibroblast growth factor receptor 4 Proteins 0.000 claims abstract description 46
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 37
• 201000011510 cancer Diseases 0.000 claims abstract description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
• 150000001875 compounds Chemical class 0.000 claims description 216
• -1 cyanomethyl Chemical group 0.000 claims description 141
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 112
• HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 65
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
• 150000003839 salts Chemical class 0.000 claims description 46
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 19
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
• 210000004027 cell Anatomy 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 230000002401 inhibitory effect Effects 0.000 claims description 13
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
• 239000003814 drug Substances 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
• 238000002360 preparation method Methods 0.000 claims description 10
• 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 8
• 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 7
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 7
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 7
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 7
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• 206010006187 Breast cancer Diseases 0.000 claims description 7
• 208000026310 Breast neoplasm Diseases 0.000 claims description 7
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 201000009410 rhabdomyosarcoma Diseases 0.000 claims description 7
• 206010009944 Colon cancer Diseases 0.000 claims description 6
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 6
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 201000005202 lung cancer Diseases 0.000 claims description 6
• 208000020816 lung neoplasm Diseases 0.000 claims description 6
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 6
• 201000002528 pancreatic cancer Diseases 0.000 claims description 6
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 6
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 5
• 206010025323 Lymphomas Diseases 0.000 claims description 5
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 5
• 206010060862 Prostate cancer Diseases 0.000 claims description 5
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 208000005017 glioblastoma Diseases 0.000 claims description 5
• 201000001441 melanoma Diseases 0.000 claims description 5
• 238000002560 therapeutic procedure Methods 0.000 claims description 5
• 201000002510 thyroid cancer Diseases 0.000 claims description 5
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• 206010005003 Bladder cancer Diseases 0.000 claims description 4
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 4
• 230000001684 chronic effect Effects 0.000 claims description 4
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 4
• 150000004677 hydrates Chemical class 0.000 claims description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 4
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 3
• FPSLNIKJVXOHRC-UHFFFAOYSA-N 4-methyl-n-propan-2-ylpiperidine-1-carboxamide Chemical compound CC(C)NC(=O)N1CCC(C)CC1 FPSLNIKJVXOHRC-UHFFFAOYSA-N 0.000 claims description 3
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 3
• 208000009746 Adult T-Cell Leukemia-Lymphoma Diseases 0.000 claims description 3
• 208000016683 Adult T-cell leukemia/lymphoma Diseases 0.000 claims description 3
• 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 3
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 3
• 206010052178 Lymphocytic lymphoma Diseases 0.000 claims description 3
• 208000034578 Multiple myelomas Diseases 0.000 claims description 3
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 3
• 206010029260 Neuroblastoma Diseases 0.000 claims description 3
• 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 3
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 3
• 208000000453 Skin Neoplasms Diseases 0.000 claims description 3
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 3
• 208000024313 Testicular Neoplasms Diseases 0.000 claims description 3
• 206010057644 Testis cancer Diseases 0.000 claims description 3
• 208000002495 Uterine Neoplasms Diseases 0.000 claims description 3
• 201000006966 adult T-cell leukemia Diseases 0.000 claims description 3
• 229940079593 drug Drugs 0.000 claims description 3
• 201000004101 esophageal cancer Diseases 0.000 claims description 3
• 206010017758 gastric cancer Diseases 0.000 claims description 3
• 201000000849 skin cancer Diseases 0.000 claims description 3
• 206010041823 squamous cell carcinoma Diseases 0.000 claims description 3
• 201000011549 stomach cancer Diseases 0.000 claims description 3
• 201000003120 testicular cancer Diseases 0.000 claims description 3
• 229940124597 therapeutic agent Drugs 0.000 claims description 3
• 206010046766 uterine cancer Diseases 0.000 claims description 3
• 208000003950 B-cell lymphoma Diseases 0.000 claims description 2
• 206010008342 Cervix carcinoma Diseases 0.000 claims description 2
• 206010014733 Endometrial cancer Diseases 0.000 claims description 2
• 206010014759 Endometrial neoplasm Diseases 0.000 claims description 2
• 208000022072 Gallbladder Neoplasms Diseases 0.000 claims description 2
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 2
• 206010027406 Mesothelioma Diseases 0.000 claims description 2
• 206010033128 Ovarian cancer Diseases 0.000 claims description 2
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
• 206010038389 Renal cancer Diseases 0.000 claims description 2
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 2
• 208000033559 Waldenström macroglobulinemia Diseases 0.000 claims description 2
• 201000010881 cervical cancer Diseases 0.000 claims description 2
• 201000010175 gallbladder cancer Diseases 0.000 claims description 2
• 201000010536 head and neck cancer Diseases 0.000 claims description 2
• 201000010982 kidney cancer Diseases 0.000 claims description 2
• 208000032839 leukemia Diseases 0.000 claims description 2
• 201000007270 liver cancer Diseases 0.000 claims description 2
• 208000014018 liver neoplasm Diseases 0.000 claims description 2
• JNRLEMMIVRBKJE-UHFFFAOYSA-N 4,4'-Methylenebis(N,N-dimethylaniline) Chemical compound C1=CC(N(C)C)=CC=C1CC1=CC=C(N(C)C)C=C1 JNRLEMMIVRBKJE-UHFFFAOYSA-N 0.000 claims 1
• 208000017604 Hodgkin disease Diseases 0.000 claims 1
• 208000021519 Hodgkin lymphoma Diseases 0.000 claims 1
• 208000010747 Hodgkins lymphoma Diseases 0.000 claims 1
• 239000003560 cancer drug Substances 0.000 claims 1
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 35
• 201000010099 disease Diseases 0.000 abstract description 26
• 238000011282 treatment Methods 0.000 abstract description 14
• 229910052799 carbon Inorganic materials 0.000 description 139
• 125000000217 alkyl group Chemical group 0.000 description 133
• 125000000592 heterocycloalkyl group Chemical group 0.000 description 94
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 86
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 85
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 82
• 238000000034 method Methods 0.000 description 77
• 125000005842 heteroatom Chemical group 0.000 description 66
• 229910052760 oxygen Inorganic materials 0.000 description 60
• 229910052717 sulfur Inorganic materials 0.000 description 58
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 56
• 239000000203 mixture Substances 0.000 description 55
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 48
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 45
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 44
• 239000000243 solution Substances 0.000 description 42
• 125000005843 halogen group Chemical group 0.000 description 41
• 229910052739 hydrogen Inorganic materials 0.000 description 41
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 40
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 40
• 235000019439 ethyl acetate Nutrition 0.000 description 36
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 35
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 35
• 150000001721 carbon Chemical group 0.000 description 35
• 125000000753 cycloalkyl group Chemical group 0.000 description 33
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 31
• 125000003118 aryl group Chemical group 0.000 description 30
• 239000000047 product Substances 0.000 description 29
• 125000001424 substituent group Chemical group 0.000 description 28
• 108091008794 FGF receptors Proteins 0.000 description 27
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 27
• 102000044168 Fibroblast Growth Factor Receptor Human genes 0.000 description 26
• 125000001072 heteroaryl group Chemical group 0.000 description 25
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
• 125000004432 carbon atom Chemical group C* 0.000 description 24
• 238000006243 chemical reaction Methods 0.000 description 24
• 239000012044 organic layer Substances 0.000 description 24
• 239000011541 reaction mixture Substances 0.000 description 24
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
• 125000003342 alkenyl group Chemical group 0.000 description 23
• 239000002585 base Substances 0.000 description 23
• 230000002829 reductive effect Effects 0.000 description 23
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 22
• 229920006395 saturated elastomer Polymers 0.000 description 22
• 125000000304 alkynyl group Chemical group 0.000 description 21
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 18
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 17
• 239000003795 chemical substances by application Substances 0.000 description 17
• 229910052757 nitrogen Inorganic materials 0.000 description 17
• 150000001412 amines Chemical class 0.000 description 16
• 239000000741 silica gel Substances 0.000 description 16
• 229910002027 silica gel Inorganic materials 0.000 description 16
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 description 15
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 15
• ZEOWTGPWHLSLOG-UHFFFAOYSA-N Cc1ccc(cc1-c1ccc2c(n[nH]c2c1)-c1cnn(c1)C1CC1)C(=O)Nc1cccc(c1)C(F)(F)F Chemical compound Cc1ccc(cc1-c1ccc2c(n[nH]c2c1)-c1cnn(c1)C1CC1)C(=O)Nc1cccc(c1)C(F)(F)F ZEOWTGPWHLSLOG-UHFFFAOYSA-N 0.000 description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 125000003545 alkoxy group Chemical group 0.000 description 15
• CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 14
• 238000000746 purification Methods 0.000 description 13
• 235000017557 sodium bicarbonate Nutrition 0.000 description 13
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 239000002253 acid Substances 0.000 description 12
• 239000012267 brine Substances 0.000 description 12
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
• 235000019341 magnesium sulphate Nutrition 0.000 description 12
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
• 150000001336 alkenes Chemical class 0.000 description 11
• 229910052938 sodium sulfate Inorganic materials 0.000 description 11
• 235000011152 sodium sulphate Nutrition 0.000 description 11
• 239000007832 Na2SO4 Substances 0.000 description 10
• 239000002552 dosage form Substances 0.000 description 10
• 239000007787 solid Substances 0.000 description 10
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 239000004480 active ingredient Substances 0.000 description 9
• 125000004429 atom Chemical group 0.000 description 9
• 229940127089 cytotoxic agent Drugs 0.000 description 9
• 208000035475 disorder Diseases 0.000 description 9
• 239000003446 ligand Substances 0.000 description 9
• 125000002950 monocyclic group Chemical group 0.000 description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 description 9
• 238000004007 reversed phase HPLC Methods 0.000 description 9
• 239000002904 solvent Substances 0.000 description 9
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 8
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
• RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 8
• LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 8
• 102000004190 Enzymes Human genes 0.000 description 8
• 108090000790 Enzymes Proteins 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
• XEXMHFAYNZWPMJ-UHFFFAOYSA-N N-[(4,6-dichloropyridin-3-yl)methyl]-2,6-difluoro-3,5-dimethoxyaniline Chemical compound COc1cc(OC)c(F)c(NCc2cnc(Cl)cc2Cl)c1F XEXMHFAYNZWPMJ-UHFFFAOYSA-N 0.000 description 8
• 238000005481 NMR spectroscopy Methods 0.000 description 8
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 8
• 229960004316 cisplatin Drugs 0.000 description 8
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 8
• 229940088598 enzyme Drugs 0.000 description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
• 230000008685 targeting Effects 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
• 102100023593 Fibroblast growth factor receptor 1 Human genes 0.000 description 7
• 101710182386 Fibroblast growth factor receptor 1 Proteins 0.000 description 7
• 230000015572 biosynthetic process Effects 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 238000009472 formulation Methods 0.000 description 7
• 238000005457 optimization Methods 0.000 description 7
• 229940127084 other anti-cancer agent Drugs 0.000 description 7
• 229910000104 sodium hydride Inorganic materials 0.000 description 7
• 208000024891 symptom Diseases 0.000 description 7
• 238000003786 synthesis reaction Methods 0.000 description 7
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 6
• IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 6
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
• 108050007372 Fibroblast Growth Factor Proteins 0.000 description 6
• 102100023600 Fibroblast growth factor receptor 2 Human genes 0.000 description 6
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• 101710182396 Fibroblast growth factor receptor 3 Proteins 0.000 description 6
• 235000019270 ammonium chloride Nutrition 0.000 description 6
• 239000007864 aqueous solution Substances 0.000 description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 229940126864 fibroblast growth factor Drugs 0.000 description 6
• 239000000706 filtrate Substances 0.000 description 6
• 229910052731 fluorine Inorganic materials 0.000 description 6
• 125000001153 fluoro group Chemical group F* 0.000 description 6
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
• 239000002245 particle Substances 0.000 description 6
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 6
• 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 description 5
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
• 229930012538 Paclitaxel Natural products 0.000 description 5
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
• 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 description 5
• 230000004913 activation Effects 0.000 description 5
• 238000004458 analytical method Methods 0.000 description 5
• 239000002246 antineoplastic agent Substances 0.000 description 5
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