JP2007519753A - 化合物 - Google Patents

Info

Publication number

JP2007519753A

JP2007519753A JP2006551625A JP2006551625A JP2007519753A JP 2007519753 A JP2007519753 A JP 2007519753A JP 2006551625 A JP2006551625 A JP 2006551625A JP 2006551625 A JP2006551625 A JP 2006551625A JP 2007519753 A JP2007519753 A JP 2007519753A

Authority

JP

Japan

Prior art keywords

pyridinyl

thiophenecarboxamide

ethyl

alkyl

pyrimidinyl

Prior art date

2004-01-30

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Pending

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 112
• 150000003839 salts Chemical class 0.000 claims abstract description 29
• 239000012453 solvate Substances 0.000 claims abstract description 16
• -1 NH 2 Chemical group 0.000 claims description 131
• 125000000217 alkyl group Chemical group 0.000 claims description 72
• 238000000034 method Methods 0.000 claims description 40
• 125000003118 aryl group Chemical group 0.000 claims description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• 239000001257 hydrogen Substances 0.000 claims description 26
• 125000003545 alkoxy group Chemical group 0.000 claims description 22
• 230000000694 effects Effects 0.000 claims description 18
• 125000005843 halogen group Chemical group 0.000 claims description 18
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 150000002367 halogens Chemical group 0.000 claims description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
• 238000004519 manufacturing process Methods 0.000 claims description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 14
• 201000010099 disease Diseases 0.000 claims description 14
• 125000001072 heteroaryl group Chemical group 0.000 claims description 14
• 125000000623 heterocyclic group Chemical group 0.000 claims description 14
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 14
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
• 125000004104 aryloxy group Chemical group 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• 230000001404 mediated effect Effects 0.000 claims description 10
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 241000124008 Mammalia Species 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 150000002431 hydrogen Chemical class 0.000 claims description 5
• LJPDISQCQVBIIX-UHFFFAOYSA-N n-[(3-methoxyphenyl)methyl]-4,5-dipyridin-4-ylthiophene-2-carboxamide Chemical compound COC1=CC=CC(CNC(=O)C=2SC(=C(C=2)C=2C=CN=CC=2)C=2C=CN=CC=2)=C1 LJPDISQCQVBIIX-UHFFFAOYSA-N 0.000 claims description 5
• AAWNVQYZVTTYED-UHFFFAOYSA-N n-[2-(4-fluorophenyl)ethyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound C1=CC(F)=CC=C1CCNC(=O)C1=CC=C(C=2C=CN=CC=2)S1 AAWNVQYZVTTYED-UHFFFAOYSA-N 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
• FLWREGAOVVKATM-UHFFFAOYSA-N 5-pyridin-4-yl-n-[[3-(trifluoromethyl)phenyl]methyl]thiophene-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC(CNC(=O)C=2SC(=CC=2)C=2C=CN=CC=2)=C1 FLWREGAOVVKATM-UHFFFAOYSA-N 0.000 claims description 4
• UFYSIIQSAOSPRP-UHFFFAOYSA-N 5-pyridin-4-yl-n-[[4-(thiadiazol-4-yl)phenyl]methyl]thiophene-2-carboxamide Chemical compound C=1C=C(C=2C=CN=CC=2)SC=1C(=O)NCC(C=C1)=CC=C1C1=CSN=N1 UFYSIIQSAOSPRP-UHFFFAOYSA-N 0.000 claims description 4
• UTGLLPISBOSSSP-UHFFFAOYSA-N n-(2-phenoxyethyl)-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound C=1C=C(C=2C=CN=CC=2)SC=1C(=O)NCCOC1=CC=CC=C1 UTGLLPISBOSSSP-UHFFFAOYSA-N 0.000 claims description 4
• OLKJZIBVEBBCCE-UHFFFAOYSA-N n-[(3-fluorophenyl)methyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound FC1=CC=CC(CNC(=O)C=2SC(=CC=2)C=2C=CN=CC=2)=C1 OLKJZIBVEBBCCE-UHFFFAOYSA-N 0.000 claims description 4
• UHTMAZNMIBNNJH-UHFFFAOYSA-N n-[(3-iodophenyl)methyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound IC1=CC=CC(CNC(=O)C=2SC(=CC=2)C=2C=CN=CC=2)=C1 UHTMAZNMIBNNJH-UHFFFAOYSA-N 0.000 claims description 4
• NYXQARDWNLVKEO-UHFFFAOYSA-N n-[(4-iodophenyl)methyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound C1=CC(I)=CC=C1CNC(=O)C1=CC=C(C=2C=CN=CC=2)S1 NYXQARDWNLVKEO-UHFFFAOYSA-N 0.000 claims description 4
• VCISBEJCMXTRJZ-UHFFFAOYSA-N n-[2-(2-bromophenyl)ethyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound BrC1=CC=CC=C1CCNC(=O)C1=CC=C(C=2C=CN=CC=2)S1 VCISBEJCMXTRJZ-UHFFFAOYSA-N 0.000 claims description 4
• HXVGIXBNUXGSLV-UHFFFAOYSA-N n-[2-(2-chlorophenyl)ethyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound ClC1=CC=CC=C1CCNC(=O)C1=CC=C(C=2C=CN=CC=2)S1 HXVGIXBNUXGSLV-UHFFFAOYSA-N 0.000 claims description 4
• FTEIRLNYDJAAMY-UHFFFAOYSA-N n-[2-(2-ethoxyphenyl)ethyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound CCOC1=CC=CC=C1CCNC(=O)C1=CC=C(C=2C=CN=CC=2)S1 FTEIRLNYDJAAMY-UHFFFAOYSA-N 0.000 claims description 4
• KIRWVCOBPRINSB-UHFFFAOYSA-N n-[2-(2-fluorophenyl)ethyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound FC1=CC=CC=C1CCNC(=O)C1=CC=C(C=2C=CN=CC=2)S1 KIRWVCOBPRINSB-UHFFFAOYSA-N 0.000 claims description 4
• QBTINFUQRCIFPN-UHFFFAOYSA-N n-[2-(2-methoxyphenyl)ethyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound COC1=CC=CC=C1CCNC(=O)C1=CC=C(C=2C=CN=CC=2)S1 QBTINFUQRCIFPN-UHFFFAOYSA-N 0.000 claims description 4
• LDGMNZADCZUNOC-UHFFFAOYSA-N n-[2-(2-methylphenyl)ethyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound CC1=CC=CC=C1CCNC(=O)C1=CC=C(C=2C=CN=CC=2)S1 LDGMNZADCZUNOC-UHFFFAOYSA-N 0.000 claims description 4
• KNHHWBDGXMIZKY-UHFFFAOYSA-N n-[2-(3-bromophenyl)ethyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound BrC1=CC=CC(CCNC(=O)C=2SC(=CC=2)C=2C=CN=CC=2)=C1 KNHHWBDGXMIZKY-UHFFFAOYSA-N 0.000 claims description 4
• ZCNGUPCJOGKIMC-UHFFFAOYSA-N n-[2-(3-chlorophenyl)ethyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound ClC1=CC=CC(CCNC(=O)C=2SC(=CC=2)C=2C=CN=CC=2)=C1 ZCNGUPCJOGKIMC-UHFFFAOYSA-N 0.000 claims description 4
• KADPJLAZRJJBLZ-UHFFFAOYSA-N n-[2-(3-fluorophenyl)ethyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound FC1=CC=CC(CCNC(=O)C=2SC(=CC=2)C=2C=CN=CC=2)=C1 KADPJLAZRJJBLZ-UHFFFAOYSA-N 0.000 claims description 4
• IERMUUYUZYNTNV-UHFFFAOYSA-N n-[2-(3-methoxyphenyl)ethyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound COC1=CC=CC(CCNC(=O)C=2SC(=CC=2)C=2C=CN=CC=2)=C1 IERMUUYUZYNTNV-UHFFFAOYSA-N 0.000 claims description 4
• YEARVZRDAHCEKE-UHFFFAOYSA-N n-[2-(3-methylphenyl)ethyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound CC1=CC=CC(CCNC(=O)C=2SC(=CC=2)C=2C=CN=CC=2)=C1 YEARVZRDAHCEKE-UHFFFAOYSA-N 0.000 claims description 4
• ZWHNPJHDIQXJKC-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1CCNC(=O)C1=CC=C(C=2C=CN=CC=2)S1 ZWHNPJHDIQXJKC-UHFFFAOYSA-N 0.000 claims description 4
• ONMNVQFYJSDTSK-UHFFFAOYSA-N n-[2-(4-ethoxyphenyl)ethyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound C1=CC(OCC)=CC=C1CCNC(=O)C1=CC=C(C=2C=CN=CC=2)S1 ONMNVQFYJSDTSK-UHFFFAOYSA-N 0.000 claims description 4
• GLXDXPJVBQNVCW-UHFFFAOYSA-N n-[2-(4-methoxyphenyl)ethyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound C1=CC(OC)=CC=C1CCNC(=O)C1=CC=C(C=2C=CN=CC=2)S1 GLXDXPJVBQNVCW-UHFFFAOYSA-N 0.000 claims description 4
• LSJKTQNRBPFHOI-UHFFFAOYSA-N n-[2-(4-methylphenyl)ethyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound C1=CC(C)=CC=C1CCNC(=O)C1=CC=C(C=2C=CN=CC=2)S1 LSJKTQNRBPFHOI-UHFFFAOYSA-N 0.000 claims description 4
• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 3
• 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 3
• XNKDJYWEHKDRKM-UHFFFAOYSA-N n-[2-(4-phenoxyphenyl)ethyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound C=1C=C(C=2C=CN=CC=2)SC=1C(=O)NCCC(C=C1)=CC=C1OC1=CC=CC=C1 XNKDJYWEHKDRKM-UHFFFAOYSA-N 0.000 claims description 3
• NKQBYWBQSXGNSU-UHFFFAOYSA-N n-benzyl-5-(1h-pyrazol-4-yl)thiophene-2-carboxamide Chemical compound C=1C=C(C2=CNN=C2)SC=1C(=O)NCC1=CC=CC=C1 NKQBYWBQSXGNSU-UHFFFAOYSA-N 0.000 claims description 3
• 238000002560 therapeutic procedure Methods 0.000 claims description 3
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 2
• FEMAMSZDYMIFHO-UHFFFAOYSA-N BrC1=C(CNC(=O)C=2SC(=CC2)C2=CC=NC=C2)C=CC=C1.C(C)OC1=C(CNC(=O)C=2SC(=CC2)C2=CC=NC=C2)C=CC=C1.C1(=CC=CC2=CC=CC=C12)CNC(=O)C=1SC(=CC1)C1=CC=NC=C1 Chemical compound BrC1=C(CNC(=O)C=2SC(=CC2)C2=CC=NC=C2)C=CC=C1.C(C)OC1=C(CNC(=O)C=2SC(=CC2)C2=CC=NC=C2)C=CC=C1.C1(=CC=CC2=CC=CC=C12)CNC(=O)C=1SC(=CC1)C1=CC=NC=C1 FEMAMSZDYMIFHO-UHFFFAOYSA-N 0.000 claims description 2
• GIXCKNDPNJZTBV-UHFFFAOYSA-N N1=CC=C(C=C1)C1=CC=C(S1)C(=O)NCC1=NC=CC=C1.COC=1C=C(CNC(=O)C=2SC(=CC2)C2=CC=NC=C2)C=CC1.C1(=CC=CC=C1)CCNC(=O)C=1SC(=CC1)C1=CC=NC=C1 Chemical compound N1=CC=C(C=C1)C1=CC=C(S1)C(=O)NCC1=NC=CC=C1.COC=1C=C(CNC(=O)C=2SC(=CC2)C2=CC=NC=C2)C=CC1.C1(=CC=CC=C1)CCNC(=O)C=1SC(=CC1)C1=CC=NC=C1 GIXCKNDPNJZTBV-UHFFFAOYSA-N 0.000 claims description 2
• 229910052799 carbon Inorganic materials 0.000 claims description 2
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
• 125000004043 oxo group Chemical group O=* 0.000 claims description 2
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• YNSCKPCDFIDINW-UHFFFAOYSA-N 3-[[2-[[1-[2-(dimethylamino)acetyl]-6-methoxy-4,4-dimethyl-2,3-dihydroquinolin-7-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]thiophene-2-carboxamide Chemical compound COC1=CC(C(CCN2C(=O)CN(C)C)(C)C)=C2C=C1NC(N=C1NC=CC1=1)=NC=1NC=1C=CSC=1C(N)=O YNSCKPCDFIDINW-UHFFFAOYSA-N 0.000 claims 1
• 125000006574 non-aromatic ring group Chemical group 0.000 claims 1
• 238000001819 mass spectrum Methods 0.000 description 163
• 239000007787 solid Substances 0.000 description 122
• OJOWGMLSJKRJNV-UHFFFAOYSA-N 5-pyridin-4-ylthiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=NC=C1 OJOWGMLSJKRJNV-UHFFFAOYSA-N 0.000 description 75
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 56
• 239000000203 mixture Substances 0.000 description 47
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
• 239000002904 solvent Substances 0.000 description 32
• 238000005160 1H NMR spectroscopy Methods 0.000 description 29
• 235000002639 sodium chloride Nutrition 0.000 description 29
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
• 239000000243 solution Substances 0.000 description 25
• 239000011435 rock Substances 0.000 description 23
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
• 238000006243 chemical reaction Methods 0.000 description 21
• YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 20
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
• 239000002585 base Substances 0.000 description 17
• 238000002360 preparation method Methods 0.000 description 17
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
• 239000003054 catalyst Substances 0.000 description 16
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 14
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
• 238000009472 formulation Methods 0.000 description 14
• 239000000843 powder Substances 0.000 description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
• 239000003112 inhibitor Substances 0.000 description 13
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 12
• 108091000080 Phosphotransferase Proteins 0.000 description 11
• 102000020233 phosphotransferase Human genes 0.000 description 11
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 10
• 239000010410 layer Substances 0.000 description 10
• QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 10
• ORIONTBOMZNQIE-UHFFFAOYSA-N 5-bromothiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=C(Br)S1 ORIONTBOMZNQIE-UHFFFAOYSA-N 0.000 description 9
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
• 102000001253 Protein Kinase Human genes 0.000 description 9
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 238000006069 Suzuki reaction reaction Methods 0.000 description 9
• 239000004480 active ingredient Substances 0.000 description 9
• 150000001543 aryl boronic acids Chemical class 0.000 description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
• 108060006633 protein kinase Proteins 0.000 description 9
• 229910000029 sodium carbonate Inorganic materials 0.000 description 9
• 238000003786 synthesis reaction Methods 0.000 description 9
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 8
• 239000002253 acid Substances 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• 238000010438 heat treatment Methods 0.000 description 8
• 239000011541 reaction mixture Substances 0.000 description 8
• 239000003826 tablet Substances 0.000 description 8
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
• 239000003921 oil Substances 0.000 description 7
• 229910052763 palladium Inorganic materials 0.000 description 7
• 230000008569 process Effects 0.000 description 7
• 238000010992 reflux Methods 0.000 description 7
• 239000003039 volatile agent Substances 0.000 description 7
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• 101100356682 Caenorhabditis elegans rho-1 gene Proteins 0.000 description 6
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 6
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 6
• 101150111584 RHOA gene Proteins 0.000 description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• 150000001408 amides Chemical class 0.000 description 6
• 150000001502 aryl halides Chemical class 0.000 description 6
• 238000003556 assay Methods 0.000 description 6
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• 238000005859 coupling reaction Methods 0.000 description 6
• 238000004128 high performance liquid chromatography Methods 0.000 description 6
• 239000007788 liquid Substances 0.000 description 6
• VUXRAYUNCGJZHX-UHFFFAOYSA-N n-(2-phenylethyl)-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound C=1C=C(C=2C=CN=CC=2)SC=1C(=O)NCCC1=CC=CC=C1 VUXRAYUNCGJZHX-UHFFFAOYSA-N 0.000 description 6
• 239000012044 organic layer Substances 0.000 description 6
• 230000026731 phosphorylation Effects 0.000 description 6
• 238000006366 phosphorylation reaction Methods 0.000 description 6
• 239000000741 silica gel Substances 0.000 description 6
• 229910002027 silica gel Inorganic materials 0.000 description 6
• 239000011734 sodium Substances 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• GRRIMVWABNHKBX-UHFFFAOYSA-N (3-methoxyphenyl)methanamine Chemical compound COC1=CC=CC(CN)=C1 GRRIMVWABNHKBX-UHFFFAOYSA-N 0.000 description 5
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