RU2644947C2 - Ингибиторы серин/треонин киназы для лечения гиперпролиферативных заболеваний - Google Patents

Info

Publication number

RU2644947C2

RU2644947C2 RU2015110985A RU2015110985A RU2644947C2 RU 2644947 C2 RU2644947 C2 RU 2644947C2 RU 2015110985 A RU2015110985 A RU 2015110985A RU 2015110985 A RU2015110985 A RU 2015110985A RU 2644947 C2 RU2644947 C2 RU 2644947C2

Authority

RU

Russia

Prior art keywords

methyl

alkyl

optionally substituted

phenyl

group

Prior art date

2012-08-27

Links

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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 42
• 201000010099 disease Diseases 0.000 title claims description 18
• 229940043355 kinase inhibitor Drugs 0.000 title description 2
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
• MTCFGRXMJLQNBG-UHFFFAOYSA-N serine Chemical compound OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 title 2
• 241001522306 Serinus serinus Species 0.000 title 1
• -1 2-oxa-bicyclo[2,2,1]heptan-5-yl Chemical group 0.000 claims abstract description 309
• 150000001875 compounds Chemical class 0.000 claims abstract description 167
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 93
• 238000000034 method Methods 0.000 claims abstract description 89
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 51
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 49
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 47
• 150000002367 halogens Chemical class 0.000 claims abstract description 46
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 39
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 35
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 27
• 239000001257 hydrogen Substances 0.000 claims abstract description 25
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
• 230000000694 effects Effects 0.000 claims abstract description 24
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 24
• 150000003839 salts Chemical class 0.000 claims abstract description 21
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 20
• 102100024193 Mitogen-activated protein kinase 1 Human genes 0.000 claims abstract description 20
• 125000003118 aryl group Chemical group 0.000 claims abstract description 19
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 19
• 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 18
• 108010007457 Extracellular Signal-Regulated MAP Kinases Proteins 0.000 claims abstract description 17
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 8
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract description 8
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract description 8
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 7
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 5
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 3
• 125000001041 indolyl group Chemical group 0.000 claims abstract description 3
• 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 3
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• 125000003545 alkoxy group Chemical group 0.000 claims description 27
• 208000035475 disorder Diseases 0.000 claims description 24
• 201000011510 cancer Diseases 0.000 claims description 21
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 17
• 238000011282 treatment Methods 0.000 claims description 17
• 239000003085 diluting agent Substances 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 16
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
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• 239000002246 antineoplastic agent Substances 0.000 claims description 9
• 239000003937 drug carrier Substances 0.000 claims description 9
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 8
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 7
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• 201000009030 Carcinoma Diseases 0.000 claims description 7
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• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 7
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• 229940127089 cytotoxic agent Drugs 0.000 claims description 7
• 201000001441 melanoma Diseases 0.000 claims description 7
• 201000002528 pancreatic cancer Diseases 0.000 claims description 7
• 201000002510 thyroid cancer Diseases 0.000 claims description 7
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 6
• 206010006187 Breast cancer Diseases 0.000 claims description 6
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 6
• 206010033128 Ovarian cancer Diseases 0.000 claims description 6
• 206010061535 Ovarian neoplasm Diseases 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
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 6
• 208000029742 colonic neoplasm Diseases 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 4
• 238000002560 therapeutic procedure Methods 0.000 claims description 4
• 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 3
• 206010005003 Bladder cancer Diseases 0.000 claims description 3
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
• 206010060862 Prostate cancer Diseases 0.000 claims description 3
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
• 206010038389 Renal cancer Diseases 0.000 claims description 3
• 206010039491 Sarcoma Diseases 0.000 claims description 3
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 3
• 208000005017 glioblastoma Diseases 0.000 claims description 3
• 201000010536 head and neck cancer Diseases 0.000 claims description 3
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 3
• 201000010982 kidney cancer Diseases 0.000 claims description 3
• 208000032839 leukemia Diseases 0.000 claims description 3
• 201000005249 lung adenocarcinoma Diseases 0.000 claims description 3
• 208000010576 undifferentiated carcinoma Diseases 0.000 claims description 3
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 3
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 2
• 208000003200 Adenoma Diseases 0.000 claims description 2
• 206010001233 Adenoma benign Diseases 0.000 claims description 2
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 2
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 2
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 2
• 208000034578 Multiple myelomas Diseases 0.000 claims description 2
• 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 2
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 2
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 2
• 208000033833 Myelomonocytic Chronic Leukemia Diseases 0.000 claims description 2
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 2
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
• 208000024313 Testicular Neoplasms Diseases 0.000 claims description 2
• 206010057644 Testis cancer Diseases 0.000 claims description 2
• 201000010902 chronic myelomonocytic leukemia Diseases 0.000 claims description 2
• 210000001072 colon Anatomy 0.000 claims description 2
• 208000003849 large cell carcinoma Diseases 0.000 claims description 2
• 208000025113 myeloid leukemia Diseases 0.000 claims description 2
• 201000010198 papillary carcinoma Diseases 0.000 claims description 2
• 208000000649 small cell carcinoma Diseases 0.000 claims description 2
• 201000003120 testicular cancer Diseases 0.000 claims description 2
• 208000030901 thyroid gland follicular carcinoma Diseases 0.000 claims description 2
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
• 208000015634 Rectal Neoplasms Diseases 0.000 claims 1
• 208000008385 Urogenital Neoplasms Diseases 0.000 claims 1
• 206010038038 rectal cancer Diseases 0.000 claims 1
• 201000001275 rectum cancer Diseases 0.000 claims 1
• 201000000849 skin cancer Diseases 0.000 claims 1
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract description 12
• 239000000126 substance Substances 0.000 abstract description 6
• 125000005843 halogen group Chemical group 0.000 abstract description 3
• 125000004438 haloalkoxy group Chemical group 0.000 abstract description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 abstract 2
• 150000002391 heterocyclic compounds Chemical class 0.000 abstract 2
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 212
• 239000000203 mixture Substances 0.000 description 167
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 150
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 144
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 127
• 239000000243 solution Substances 0.000 description 123
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 108
• 235000019439 ethyl acetate Nutrition 0.000 description 105
• 239000007787 solid Substances 0.000 description 92
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 90
• 239000002904 solvent Substances 0.000 description 86
• 239000011541 reaction mixture Substances 0.000 description 68
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 67
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 66
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 65
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 63
• QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 57
• 229910004298 SiO 2 Inorganic materials 0.000 description 49
• 238000004587 chromatography analysis Methods 0.000 description 49
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 48
• 238000000132 electrospray ionisation Methods 0.000 description 45
• 239000011734 sodium Substances 0.000 description 41
• BKMMTJMQCTUHRP-VKHMYHEASA-N (S)-2-aminopropan-1-ol Chemical compound C[C@H](N)CO BKMMTJMQCTUHRP-VKHMYHEASA-N 0.000 description 39
• MBJVWMQHKCGMLZ-UHFFFAOYSA-N isoquinoline-6-carboxamide Chemical compound C1=NC=CC2=CC(C(=O)N)=CC=C21 MBJVWMQHKCGMLZ-UHFFFAOYSA-N 0.000 description 32
• 238000003756 stirring Methods 0.000 description 30
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
• 239000003208 petroleum Substances 0.000 description 27
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 25
• 238000006243 chemical reaction Methods 0.000 description 24
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 24
• 239000012267 brine Substances 0.000 description 23
• 210000004027 cell Anatomy 0.000 description 23
• 239000000706 filtrate Substances 0.000 description 21
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
• 238000000746 purification Methods 0.000 description 19
• 239000012043 crude product Substances 0.000 description 18
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• 125000004432 carbon atom Chemical group C* 0.000 description 17
• 238000002360 preparation method Methods 0.000 description 17
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• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
• 150000001412 amines Chemical class 0.000 description 15
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
• BNQDGHGZPVUAAC-YDALLXLXSA-N (s)-(3-fluoro-4-methoxyphenyl)-(1-methylpyrazol-4-yl)methanamine;hydrochloride Chemical compound Cl.C1=C(F)C(OC)=CC=C1[C@H](N)C1=CN(C)N=C1 BNQDGHGZPVUAAC-YDALLXLXSA-N 0.000 description 14
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• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 14
• 239000012298 atmosphere Substances 0.000 description 14
• 238000002474 experimental method Methods 0.000 description 14
• 239000000460 chlorine Substances 0.000 description 13
• 238000004128 high performance liquid chromatography Methods 0.000 description 13
• MIPHRQMEIYLZFZ-UHFFFAOYSA-N oxolan-3-amine Chemical compound NC1CCOC1 MIPHRQMEIYLZFZ-UHFFFAOYSA-N 0.000 description 13
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 12
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 11
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
• 239000002253 acid Substances 0.000 description 11
• 239000012223 aqueous fraction Substances 0.000 description 11
• 229940079593 drug Drugs 0.000 description 11
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• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 11
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• 239000002244 precipitate Substances 0.000 description 11
• 238000004007 reversed phase HPLC Methods 0.000 description 11
• QDFKKJYEIFBEFC-UHFFFAOYSA-N 1-bromo-3-fluorobenzene Chemical compound FC1=CC=CC(Br)=C1 QDFKKJYEIFBEFC-UHFFFAOYSA-N 0.000 description 10
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• 239000000463 material Substances 0.000 description 10
• 229920006395 saturated elastomer Polymers 0.000 description 10
• 230000019491 signal transduction Effects 0.000 description 10
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 238000001816 cooling Methods 0.000 description 9
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• 238000003786 synthesis reaction Methods 0.000 description 9
• RTWSYKYQHQVELW-UHNVWZDZSA-N (3s,4s)-3-fluorooxan-4-amine Chemical compound N[C@H]1CCOC[C@H]1F RTWSYKYQHQVELW-UHNVWZDZSA-N 0.000 description 8
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 8
• 229910052757 nitrogen Inorganic materials 0.000 description 8
• 239000012299 nitrogen atmosphere Substances 0.000 description 8
• AHVQYHFYQWKUKB-UHFFFAOYSA-N oxan-4-amine Chemical group NC1CCOCC1 AHVQYHFYQWKUKB-UHFFFAOYSA-N 0.000 description 8
• 239000000825 pharmaceutical preparation Substances 0.000 description 8
• 239000007858 starting material Substances 0.000 description 8
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• KCQBJCDRFDNGKM-DDWIOCJRSA-N (2s)-2-amino-2-(3-fluoro-4-methoxyphenyl)ethanol;hydrochloride Chemical compound Cl.COC1=CC=C([C@H](N)CO)C=C1F KCQBJCDRFDNGKM-DDWIOCJRSA-N 0.000 description 7
• OCXUHTGTHKUEES-YDALLXLXSA-N (s)-(3-fluoro-4-methoxyphenyl)-(1-methylpyrazol-3-yl)methanamine;hydrochloride Chemical compound Cl.C1=C(F)C(OC)=CC=C1[C@H](N)C1=NN(C)C=C1 OCXUHTGTHKUEES-YDALLXLXSA-N 0.000 description 7
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 7
• 238000004458 analytical method Methods 0.000 description 7
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• 239000003795 chemical substances by application Substances 0.000 description 7
• LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 7
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• 125000001424 substituent group Chemical group 0.000 description 7
• 239000003826 tablet Substances 0.000 description 7
• FEFLEQVGCBGMTC-SECBINFHSA-N (3r)-3-amino-3-(4-chloro-3-fluorophenyl)propan-1-ol Chemical compound OCC[C@@H](N)C1=CC=C(Cl)C(F)=C1 FEFLEQVGCBGMTC-SECBINFHSA-N 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
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• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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• 239000003153 chemical reaction reagent Substances 0.000 description 6
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• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
• 230000014509 gene expression Effects 0.000 description 6
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
• 239000011780 sodium chloride Substances 0.000 description 6
• 239000010936 titanium Substances 0.000 description 6
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• OQUHYNMITHDQLD-UHFFFAOYSA-N (5-bromopyridin-3-yl)methanamine Chemical compound NCC1=CN=CC(Br)=C1 OQUHYNMITHDQLD-UHFFFAOYSA-N 0.000 description 5
• AGYWDGVTLKNTBS-UHFFFAOYSA-N 4-bromo-1-chloro-2-fluorobenzene Chemical compound FC1=CC(Br)=CC=C1Cl AGYWDGVTLKNTBS-UHFFFAOYSA-N 0.000 description 5
• DWNXGZBXFDNKOR-UHFFFAOYSA-N 4-bromo-2-fluoro-1-methoxybenzene Chemical compound COC1=CC=C(Br)C=C1F DWNXGZBXFDNKOR-UHFFFAOYSA-N 0.000 description 5
• 239000004215 Carbon black (E152) Substances 0.000 description 5
• PHEDXBVPIONUQT-UHFFFAOYSA-N Cocarcinogen A1 Natural products CCCCCCCCCCCCCC(=O)OC1C(C)C2(O)C3C=C(C)C(=O)C3(O)CC(CO)=CC2C2C1(OC(C)=O)C2(C)C PHEDXBVPIONUQT-UHFFFAOYSA-N 0.000 description 5
• 108040008097 MAP kinase activity proteins Proteins 0.000 description 5
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• 125000004414 alkyl thio group Chemical group 0.000 description 5
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• WUUOEJJGRCQGBQ-UHFFFAOYSA-N oxan-3-amine Chemical group NC1CCCOC1 WUUOEJJGRCQGBQ-UHFFFAOYSA-N 0.000 description 5
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