PT2155743E - Imidazoquinolinas com propriedades imunomoduladoras - Google Patents

Info

Publication number

PT2155743E

PT2155743E PT08737252T PT08737252T PT2155743E PT 2155743 E PT2155743 E PT 2155743E PT 08737252 T PT08737252 T PT 08737252T PT 08737252 T PT08737252 T PT 08737252T PT 2155743 E PT2155743 E PT 2155743E

Authority

PT

Portugal

Prior art keywords

methyl

amino

imidazo

propyl

quinolin

Prior art date

2007-05-08

Links

• Espacenet
• Global Dossier
• Discuss

• RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical class C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 title description 4
• 230000002519 immonomodulatory effect Effects 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims description 336
• -1 cyano, hydroxy Chemical group 0.000 claims description 226
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 133
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 129
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 107
• 238000000034 method Methods 0.000 claims description 83
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 43
• 150000003839 salts Chemical class 0.000 claims description 43
• 125000000623 heterocyclic group Chemical group 0.000 claims description 29
• 229910052757 nitrogen Inorganic materials 0.000 claims description 29
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims description 24
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
• 229910052717 sulfur Inorganic materials 0.000 claims description 22
• 239000001257 hydrogen Substances 0.000 claims description 21
• 229920006395 saturated elastomer Polymers 0.000 claims description 21
• 229910052760 oxygen Inorganic materials 0.000 claims description 19
• 238000011282 treatment Methods 0.000 claims description 19
• 229910052736 halogen Inorganic materials 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 18
• 125000006239 protecting group Chemical group 0.000 claims description 18
• 239000002253 acid Substances 0.000 claims description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
• 125000001424 substituent group Chemical group 0.000 claims description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims description 13
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• 238000002360 preparation method Methods 0.000 claims description 13
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 12
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 125000000217 alkyl group Chemical group 0.000 claims description 11
• 150000002431 hydrogen Chemical class 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• 230000008569 process Effects 0.000 claims description 11
• 239000000460 chlorine Substances 0.000 claims description 10
• 201000010099 disease Diseases 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 9
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
• 206010028980 Neoplasm Diseases 0.000 claims description 9
• 125000002947 alkylene group Chemical group 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
• 239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 9
• 238000002560 therapeutic procedure Methods 0.000 claims description 9
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 125000005843 halogen group Chemical group 0.000 claims description 8
• 239000011593 sulfur Chemical group 0.000 claims description 8
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 7
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
• 208000006673 asthma Diseases 0.000 claims description 7
• 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 6
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 6
• 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
• 125000003118 aryl group Chemical group 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 125000002619 bicyclic group Chemical group 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
• 125000002950 monocyclic group Chemical group 0.000 claims description 6
• 239000001301 oxygen Chemical group 0.000 claims description 6
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 5
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 5
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 5
• 239000002671 adjuvant Substances 0.000 claims description 5
• 125000004432 carbon atom Chemical group C* 0.000 claims description 5
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
• 125000006595 (C1-C3) alkylsulfinyl group Chemical group 0.000 claims description 4
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
• 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 230000000172 allergic effect Effects 0.000 claims description 4
• 201000010105 allergic rhinitis Diseases 0.000 claims description 4
• 208000010668 atopic eczema Diseases 0.000 claims description 4
• 201000011510 cancer Diseases 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 4
• 230000003647 oxidation Effects 0.000 claims description 4
• 238000007254 oxidation reaction Methods 0.000 claims description 4
• 230000003612 virological effect Effects 0.000 claims description 4
• 208000035143 Bacterial infection Diseases 0.000 claims description 3
• 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 3
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 3
• 208000005176 Hepatitis C Diseases 0.000 claims description 3
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
• 208000002205 allergic conjunctivitis Diseases 0.000 claims description 3
• 208000024998 atopic conjunctivitis Diseases 0.000 claims description 3
• 201000008937 atopic dermatitis Diseases 0.000 claims description 3
• 239000003638 chemical reducing agent Substances 0.000 claims description 3
• 208000002672 hepatitis B Diseases 0.000 claims description 3
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
• 230000000414 obstructive effect Effects 0.000 claims description 3
• 208000017520 skin disease Diseases 0.000 claims description 3
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
• 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 claims description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 2
• 206010048768 Dermatosis Diseases 0.000 claims description 2
• 208000022361 Human papillomavirus infectious disease Diseases 0.000 claims description 2
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 2
• NIOVKJYCMIDNPA-UHFFFAOYSA-N n-ethyl-1,4-diazepane-1-carboxamide Chemical compound CCNC(=O)N1CCCNCC1 NIOVKJYCMIDNPA-UHFFFAOYSA-N 0.000 claims description 2
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 claims description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
• 208000023504 respiratory system disease Diseases 0.000 claims description 2
• 125000003396 thiol group Chemical class [H]S* 0.000 claims 2
• MITQPGKTRNEULN-UHFFFAOYSA-N CCCCC1=NC2=C(N1CCCN(CC3=CC(=CC=C3)OC(=O)C)C(=O)CN4CC(C4)O)C5=CC=CC=C5N=C2N Chemical compound CCCCC1=NC2=C(N1CCCN(CC3=CC(=CC=C3)OC(=O)C)C(=O)CN4CC(C4)O)C5=CC=CC=C5N=C2N MITQPGKTRNEULN-UHFFFAOYSA-N 0.000 claims 1
• NKRDSOWWBRATKT-UHFFFAOYSA-N S1(=O)(=O)NC(=O)C2=CC=CC=C12.S1(=O)(=O)NC(=O)C2=CC=CC=C12.C(C)(=O)O Chemical compound S1(=O)(=O)NC(=O)C2=CC=CC=C12.S1(=O)(=O)NC(=O)C2=CC=CC=C12.C(C)(=O)O NKRDSOWWBRATKT-UHFFFAOYSA-N 0.000 claims 1
• NFDBDIZWMPMJPK-UHFFFAOYSA-N [4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(dimethylamino)ethyl]amino]methyl]phenyl] acetate Chemical compound C(C)(=O)OC1=CC=C(C=C1)CN(CCN(C)C)CCCN1C(=NC=2C(=NC=3C=CC=CC=3C=21)N)CCCC NFDBDIZWMPMJPK-UHFFFAOYSA-N 0.000 claims 1
• QZFADOOSKOLOCQ-UHFFFAOYSA-N acetic acid benzenesulfonic acid Chemical compound C1(=CC=CC=C1)S(=O)(=O)O.C1(=CC=CC=C1)S(=O)(=O)O.C(C)(=O)O QZFADOOSKOLOCQ-UHFFFAOYSA-N 0.000 claims 1
• IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims 1
• SYGWYBOJXOGMRU-UHFFFAOYSA-N chembl233051 Chemical compound C1=CC=C2C3=CC(C(N(CCN(C)C)C4=O)=O)=C5C4=CC=CC5=C3SC2=C1 SYGWYBOJXOGMRU-UHFFFAOYSA-N 0.000 claims 1
• 125000001188 haloalkyl group Chemical group 0.000 claims 1
• 229940049953 phenylacetate Drugs 0.000 claims 1
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 1
• 125000003944 tolyl group Chemical group 0.000 claims 1
• 239000000047 product Substances 0.000 description 126
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 111
• 239000007787 solid Substances 0.000 description 66
• 238000005481 NMR spectroscopy Methods 0.000 description 61
• 239000000203 mixture Substances 0.000 description 58
• 239000000243 solution Substances 0.000 description 57
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 47
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 46
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 37
• 238000006243 chemical reaction Methods 0.000 description 36
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 32
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
• 239000002904 solvent Substances 0.000 description 32
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
• 239000003112 inhibitor Substances 0.000 description 29
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
• 239000011541 reaction mixture Substances 0.000 description 24
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 24
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
• 235000019439 ethyl acetate Nutrition 0.000 description 21
• 238000005160 1H NMR spectroscopy Methods 0.000 description 20
• 238000013459 approach Methods 0.000 description 20
• 238000000634 powder X-ray diffraction Methods 0.000 description 18
• 239000003960 organic solvent Substances 0.000 description 17
• AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 15
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
• 239000012043 crude product Substances 0.000 description 14
• 229960005419 nitrogen Drugs 0.000 description 14
• 239000002585 base Substances 0.000 description 13
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
• 239000003795 chemical substances by application Substances 0.000 description 11
• 239000003814 drug Substances 0.000 description 11
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 10
• 102000004127 Cytokines Human genes 0.000 description 10
• 108090000695 Cytokines Proteins 0.000 description 10
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
• 230000006870 function Effects 0.000 description 10
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
• 239000000725 suspension Substances 0.000 description 9
• AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 8
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 8
• QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• 125000001309 chloro group Chemical group Cl* 0.000 description 8
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
• 102000002689 Toll-like receptor Human genes 0.000 description 7
• 108020000411 Toll-like receptor Proteins 0.000 description 7
• 125000004429 atom Chemical group 0.000 description 7
• 239000003054 catalyst Substances 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 125000001153 fluoro group Chemical group F* 0.000 description 7
• 239000003102 growth factor Substances 0.000 description 7
• 208000015181 infectious disease Diseases 0.000 description 7
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• 101000669402 Homo sapiens Toll-like receptor 7 Proteins 0.000 description 6
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
• 108010058846 Ovalbumin Proteins 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• 230000001594 aberrant effect Effects 0.000 description 6
• 239000012267 brine Substances 0.000 description 6
• 229940079593 drug Drugs 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
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
• WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
• 229940092253 ovalbumin Drugs 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 5
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
• VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 5
• 239000007821 HATU Substances 0.000 description 5
• 230000001154 acute effect Effects 0.000 description 5
• 210000004027 cell Anatomy 0.000 description 5
• 238000010511 deprotection reaction Methods 0.000 description 5
• 238000001914 filtration Methods 0.000 description 5
• 238000009472 formulation Methods 0.000 description 5
• 239000012458 free base Substances 0.000 description 5
• YPJYQGMVBYQTTA-UHFFFAOYSA-N methyl 2-(4-formylphenyl)acetate Chemical compound COC(=O)CC1=CC=C(C=O)C=C1 YPJYQGMVBYQTTA-UHFFFAOYSA-N 0.000 description 5
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
• 235000019204 saccharin Nutrition 0.000 description 5
• CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 5
• 229940081974 saccharin Drugs 0.000 description 5
• 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 5
• 239000000377 silicon dioxide Substances 0.000 description 5
• 210000003491 skin Anatomy 0.000 description 5
• 239000003826 tablet Substances 0.000 description 5
• 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 5
• 239000005483 tyrosine kinase inhibitor Substances 0.000 description 5
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• BMEMBBFDTYHTLH-UHFFFAOYSA-N 1-(2-methoxyethyl)piperazine Chemical compound COCCN1CCNCC1 BMEMBBFDTYHTLH-UHFFFAOYSA-N 0.000 description 4
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
• NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 4
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