EA011890B1 - Замещённые бензазолы и их применение в качестве ингибиторов raf-киназы - Google Patents

Info

Publication number

EA011890B1

EA011890B1 EA200600689A EA200600689A EA011890B1 EA 011890 B1 EA011890 B1 EA 011890B1 EA 200600689 A EA200600689 A EA 200600689A EA 200600689 A EA200600689 A EA 200600689A EA 011890 B1 EA011890 B1 EA 011890B1

Authority

EA

Eurasian Patent Office

Prior art keywords

amino

methyl

oxy

carboxamide

phenyl

Prior art date

2003-09-29

Links

• Espacenet
• Global Dossier
• Discuss

• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title abstract description 12
• 102000009929 raf Kinases Human genes 0.000 title abstract 3
• 108010077182 raf Kinases Proteins 0.000 title abstract 3
• 239000003112 inhibitor Substances 0.000 title description 6
• 239000000203 mixture Substances 0.000 claims abstract description 187
• 150000001875 compounds Chemical class 0.000 claims abstract description 107
• 238000000034 method Methods 0.000 claims abstract description 52
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 45
• 201000011510 cancer Diseases 0.000 claims abstract description 33
• 241001465754 Metazoa Species 0.000 claims abstract description 27
• 230000000694 effects Effects 0.000 claims abstract description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
• 230000001404 mediated effect Effects 0.000 claims abstract description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 610
• -1 nitro, amino, imino Chemical group 0.000 claims description 562
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 206
• 125000000217 alkyl group Chemical group 0.000 claims description 75
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 59
• 229910052739 hydrogen Inorganic materials 0.000 claims description 54
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 48
• 239000001257 hydrogen Substances 0.000 claims description 40
• 125000003118 aryl group Chemical group 0.000 claims description 39
• 108091000080 Phosphotransferase Proteins 0.000 claims description 30
• 102000020233 phosphotransferase Human genes 0.000 claims description 30
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
• 125000001072 heteroaryl group Chemical group 0.000 claims description 27
• 150000003839 salts Chemical class 0.000 claims description 24
• 239000003795 chemical substances by application Substances 0.000 claims description 21
• 108091054455 MAP kinase family Proteins 0.000 claims description 19
• 102000043136 MAP kinase family Human genes 0.000 claims description 19
• 150000002148 esters Chemical class 0.000 claims description 19
• 239000000651 prodrug Substances 0.000 claims description 18
• 229940002612 prodrug Drugs 0.000 claims description 18
• 125000000623 heterocyclic group Chemical group 0.000 claims description 15
• 125000001424 substituent group Chemical group 0.000 claims description 15
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 12
• 125000005842 heteroatom Chemical group 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 10
• 150000002367 halogens Chemical class 0.000 claims description 10
• 238000002360 preparation method Methods 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 230000019491 signal transduction Effects 0.000 claims description 8
• 230000002401 inhibitory effect Effects 0.000 claims description 7
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
• 239000005517 L01XE01 - Imatinib Substances 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 6
• 229940088597 hormone Drugs 0.000 claims description 6
• 239000005556 hormone Substances 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 6
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 5
• 206010006187 Breast cancer Diseases 0.000 claims description 5
• 208000026310 Breast neoplasm Diseases 0.000 claims description 5
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 5
• 125000000068 chlorophenyl group Chemical group 0.000 claims description 5
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 5
• 229960004316 cisplatin Drugs 0.000 claims description 5
• 230000001419 dependent effect Effects 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims description 5
• 229960004768 irinotecan Drugs 0.000 claims description 5
• 229910052700 potassium Inorganic materials 0.000 claims description 5
• 229960004641 rituximab Drugs 0.000 claims description 5
• VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 claims description 4
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 4
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 4
• 229940123237 Taxane Drugs 0.000 claims description 4
• 125000002252 acyl group Chemical group 0.000 claims description 4
• 229940045799 anthracyclines and related substance Drugs 0.000 claims description 4
• VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims description 4
• 229960004562 carboplatin Drugs 0.000 claims description 4
• 229960004397 cyclophosphamide Drugs 0.000 claims description 4
• 229960002949 fluorouracil Drugs 0.000 claims description 4
• VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 claims description 4
• 235000008191 folinic acid Nutrition 0.000 claims description 4
• 239000011672 folinic acid Substances 0.000 claims description 4
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
• SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims description 4
• 229960005277 gemcitabine Drugs 0.000 claims description 4
• KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 claims description 4
• 229960002411 imatinib Drugs 0.000 claims description 4
• 229960001691 leucovorin Drugs 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 229950006410 tezacitabine Drugs 0.000 claims description 4
• GFFXZLZWLOBBLO-ASKVSEFXSA-N tezacitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 GFFXZLZWLOBBLO-ASKVSEFXSA-N 0.000 claims description 4
• UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims description 4
• 229960000303 topotecan Drugs 0.000 claims description 4
• 229960000575 trastuzumab Drugs 0.000 claims description 4
• 206010060862 Prostate cancer Diseases 0.000 claims description 3
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
• 229910052796 boron Inorganic materials 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 229940122803 Vinca alkaloid Drugs 0.000 claims description 2
• 229930013930 alkaloid Natural products 0.000 claims description 2
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
• 230000002489 hematologic effect Effects 0.000 claims 2
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
• YTGJWQPHMWSCST-UHFFFAOYSA-N Tiopronin Chemical class CC(S)C(=O)NCC(O)=O YTGJWQPHMWSCST-UHFFFAOYSA-N 0.000 claims 1
• 241000863480 Vinca Species 0.000 claims 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
• 125000003368 amide group Chemical group 0.000 claims 1
• 239000000919 ceramic Substances 0.000 claims 1
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
• 239000011701 zinc Substances 0.000 claims 1
• 229910052725 zinc Inorganic materials 0.000 claims 1
• 230000005764 inhibitory process Effects 0.000 abstract description 7
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 255
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 231
• IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 227
• 230000015572 biosynthetic process Effects 0.000 description 209
• 238000003786 synthesis reaction Methods 0.000 description 177
• 150000003857 carboxamides Chemical class 0.000 description 170
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 168
• 239000000243 solution Substances 0.000 description 129
• 238000001819 mass spectrum Methods 0.000 description 128
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 114
• 239000011541 reaction mixture Substances 0.000 description 112
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 98
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 93
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 76
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 76
• 239000012044 organic layer Substances 0.000 description 72
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 65
• 239000007787 solid Substances 0.000 description 63
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 62
• 238000002514 liquid chromatography mass spectrum Methods 0.000 description 58
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 54
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 54
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 54
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 47
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 46
• 229910052757 nitrogen Inorganic materials 0.000 description 46
• 239000000047 product Substances 0.000 description 41
• 239000012267 brine Substances 0.000 description 40
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 40
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 39
• 238000006243 chemical reaction Methods 0.000 description 37
• 238000004237 preparative chromatography Methods 0.000 description 35
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 35
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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 32
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 32
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 32
• 238000004811 liquid chromatography Methods 0.000 description 31
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 29
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 29
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 28
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 28
• 238000004949 mass spectrometry Methods 0.000 description 28
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
• 238000000746 purification Methods 0.000 description 28
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 27
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 27
• 239000000725 suspension Substances 0.000 description 27
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 26
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 25
• 125000003710 aryl alkyl group Chemical group 0.000 description 25
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 24
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 24
• 230000002829 reductive effect Effects 0.000 description 24
• 238000004128 high performance liquid chromatography Methods 0.000 description 22
• 239000010410 layer Substances 0.000 description 22
• 239000000741 silica gel Substances 0.000 description 22
• 229910002027 silica gel Inorganic materials 0.000 description 22
• 229910052938 sodium sulfate Inorganic materials 0.000 description 21
• 235000011152 sodium sulphate Nutrition 0.000 description 21
• 238000003756 stirring Methods 0.000 description 21
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 21
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 20
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 20
• 239000010802 sludge Substances 0.000 description 20
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 19
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 19
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 18
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
• 239000002904 solvent Substances 0.000 description 17
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 16
• 239000012298 atmosphere Substances 0.000 description 16
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 16
• 150000004985 diamines Chemical class 0.000 description 15
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 14
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
• 239000008346 aqueous phase Substances 0.000 description 14
• 229910000027 potassium carbonate Inorganic materials 0.000 description 14
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
• 150000001412 amines Chemical class 0.000 description 13
• 229910052799 carbon Inorganic materials 0.000 description 13
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 13
• IVWFPGYPIXURMK-UHFFFAOYSA-N 3,4-dimethylpyridine-2-carboxamide Chemical compound CC1=CC=NC(C(N)=O)=C1C IVWFPGYPIXURMK-UHFFFAOYSA-N 0.000 description 12
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 11
• 125000004432 carbon atom Chemical group C* 0.000 description 11
• 150000002431 hydrogen Chemical class 0.000 description 11
• 239000012299 nitrogen atmosphere Substances 0.000 description 11
• 238000004007 reversed phase HPLC Methods 0.000 description 11
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
• 235000017557 sodium bicarbonate Nutrition 0.000 description 11
• HZBPBLHQOUNXFS-UHFFFAOYSA-N tert-butyl 4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylate Chemical compound C1=C(N)C(NC)=CC=C1OC1=CC=NC(C(=O)OC(C)(C)C)=C1 HZBPBLHQOUNXFS-UHFFFAOYSA-N 0.000 description 11
• ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 11
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
• 230000003197 catalytic effect Effects 0.000 description 10
• 125000000753 cycloalkyl group Chemical group 0.000 description 10
• 229910052745 lead Inorganic materials 0.000 description 10
• 239000012074 organic phase Substances 0.000 description 10
• SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 10
• WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 description 9
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 9
• 239000012043 crude product Substances 0.000 description 9
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 9
• HXXAUIXTYRHFNO-UHFFFAOYSA-N n-methylpyridine-2-carboxamide Chemical compound CNC(=O)C1=CC=CC=N1 HXXAUIXTYRHFNO-UHFFFAOYSA-N 0.000 description 9
• 230000037361 pathway Effects 0.000 description 9
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 9
• XQACWEBGSZBLRG-UHFFFAOYSA-N 1-bromo-4-isothiocyanatobenzene Chemical compound BrC1=CC=C(N=C=S)C=C1 XQACWEBGSZBLRG-UHFFFAOYSA-N 0.000 description 8
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
• 239000002253 acid Substances 0.000 description 8
• 125000003282 alkyl amino group Chemical group 0.000 description 8
• 208000035475 disorder Diseases 0.000 description 8
• 229940043355 kinase inhibitor Drugs 0.000 description 8
• 239000003757 phosphotransferase inhibitor Substances 0.000 description 8
• IQXUIDYRTHQTET-UHFFFAOYSA-N 4-amino-3-nitrophenol Chemical compound NC1=CC=C(O)C=C1[N+]([O-])=O IQXUIDYRTHQTET-UHFFFAOYSA-N 0.000 description 7
• 239000005711 Benzoic acid Substances 0.000 description 7
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
• 239000002246 antineoplastic agent Substances 0.000 description 7
• 235000010233 benzoic acid Nutrition 0.000 description 7
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