KR101378716B1 - Ｖｅｇｆ 수용체 및 ｈｇｆ 수용체 신호전달의 억제제 - Google Patents

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Publication number

KR101378716B1

KR101378716B1 KR1020077029798A KR20077029798A KR101378716B1 KR 101378716 B1 KR101378716 B1 KR 101378716B1 KR 1020077029798 A KR1020077029798 A KR 1020077029798A KR 20077029798 A KR20077029798 A KR 20077029798A KR 101378716 B1 KR101378716 B1 KR 101378716B1

Authority

KR

South Korea

Prior art keywords

alkyl

group

substituted

aryl

unsubstituted

Prior art date

2005-05-20

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.)

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• 230000011664 signaling Effects 0.000 title abstract description 37
• 108091008603 HGF receptors Proteins 0.000 title abstract description 21
• 108091008605 VEGF receptors Proteins 0.000 title abstract description 19
• 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 title abstract description 17
• 102000027430 HGF receptors Human genes 0.000 title abstract 3
• 239000003112 inhibitor Substances 0.000 title description 20
• 150000001875 compounds Chemical class 0.000 claims abstract description 379
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 98
• 229910052736 halogen Inorganic materials 0.000 claims description 66
• 229910052757 nitrogen Inorganic materials 0.000 claims description 65
• 150000002367 halogens Chemical class 0.000 claims description 64
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 58
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 46
• 229910052739 hydrogen Inorganic materials 0.000 claims description 42
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 36
• 229910052760 oxygen Inorganic materials 0.000 claims description 36
• 125000004429 atom Chemical group 0.000 claims description 31
• 229910052799 carbon Inorganic materials 0.000 claims description 22
• 206010028980 Neoplasm Diseases 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 239000003814 drug Substances 0.000 claims description 19
• 125000004953 trihalomethyl group Chemical group 0.000 claims description 18
• 201000011510 cancer Diseases 0.000 claims description 16
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
• 125000002883 imidazolyl group Chemical group 0.000 claims description 12
• 229940124597 therapeutic agent Drugs 0.000 claims description 12
• 125000005842 heteroatom Chemical group 0.000 claims description 11
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 11
• 239000001301 oxygen Substances 0.000 claims description 11
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
• 125000004122 cyclic group Chemical group 0.000 claims description 10
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
• 125000004076 pyridyl group Chemical group 0.000 claims description 10
• 125000002971 oxazolyl group Chemical group 0.000 claims description 9
• 150000003839 salts Chemical class 0.000 claims description 7
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 2
• 239000008194 pharmaceutical composition Substances 0.000 claims 3
• 206010005003 Bladder cancer Diseases 0.000 claims 1
• 206010006187 Breast cancer Diseases 0.000 claims 1
• 208000026310 Breast neoplasm Diseases 0.000 claims 1
• 206010009944 Colon cancer Diseases 0.000 claims 1
• 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
• 208000015634 Rectal Neoplasms Diseases 0.000 claims 1
• 206010038389 Renal cancer Diseases 0.000 claims 1
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
• 208000029742 colonic neoplasm Diseases 0.000 claims 1
• 201000010982 kidney cancer Diseases 0.000 claims 1
• 208000032839 leukemia Diseases 0.000 claims 1
• 201000005202 lung cancer Diseases 0.000 claims 1
• 208000020816 lung neoplasm Diseases 0.000 claims 1
• 206010038038 rectal cancer Diseases 0.000 claims 1
• 201000001275 rectum cancer Diseases 0.000 claims 1
• 201000005112 urinary bladder cancer Diseases 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 113
• 239000000203 mixture Substances 0.000 abstract description 93
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 28
• 201000010099 disease Diseases 0.000 abstract description 27
• 230000002401 inhibitory effect Effects 0.000 abstract description 12
• 230000005764 inhibitory process Effects 0.000 abstract description 8
• 230000002062 proliferating effect Effects 0.000 abstract description 6
• -1 CH 3 -CH 2- ) Chemical class 0.000 description 312
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 283
• 125000000623 heterocyclic group Chemical group 0.000 description 229
• 125000003118 aryl group Chemical group 0.000 description 179
• 239000000243 solution Substances 0.000 description 145
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 144
• 235000019439 ethyl acetate Nutrition 0.000 description 137
• 239000011541 reaction mixture Substances 0.000 description 131
• 239000007787 solid Substances 0.000 description 123
• 125000001072 heteroaryl group Chemical group 0.000 description 120
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 113
• 125000000217 alkyl group Chemical group 0.000 description 108
• 125000001424 substituent group Chemical group 0.000 description 104
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 89
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 86
• 150000001412 amines Chemical class 0.000 description 85
• 125000005843 halogen group Chemical group 0.000 description 79
• 239000002253 acid Substances 0.000 description 78
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 73
• 125000004432 carbon atom Chemical group C* 0.000 description 66
• YWIZJSODCFXCBY-UHFFFAOYSA-N 7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine Chemical compound FC1=CC([N+](=O)[O-])=CC=C1OC1=CC=NC2=C1SC=C2 YWIZJSODCFXCBY-UHFFFAOYSA-N 0.000 description 63
• 230000002829 reductive effect Effects 0.000 description 63
• 229920006395 saturated elastomer Polymers 0.000 description 59
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 58
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 48
• 239000012074 organic phase Substances 0.000 description 48
• 230000015572 biosynthetic process Effects 0.000 description 44
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 43
• 238000003786 synthesis reaction Methods 0.000 description 43
• 238000004440 column chromatography Methods 0.000 description 40
• 239000003480 eluent Substances 0.000 description 39
• 125000003710 aryl alkyl group Chemical group 0.000 description 38
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 38
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 36
• 239000011734 sodium Substances 0.000 description 36
• 238000000746 purification Methods 0.000 description 34
• 239000002904 solvent Substances 0.000 description 33
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 28
• 238000003818 flash chromatography Methods 0.000 description 27
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 24
• 125000004433 nitrogen atom Chemical group N* 0.000 description 24
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 23
• 125000003386 piperidinyl group Chemical group 0.000 description 23
• 125000003627 8 membered carbocyclic group Chemical group 0.000 description 22
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 22
• 125000003545 alkoxy group Chemical group 0.000 description 22
• 150000002828 nitro derivatives Chemical class 0.000 description 22
• 239000000725 suspension Substances 0.000 description 22
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 21
• 239000012267 brine Substances 0.000 description 21
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 21
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 21
• 229910052717 sulfur Inorganic materials 0.000 description 20
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 19
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
• 239000000284 extract Substances 0.000 description 19
• 102100022623 Hepatocyte growth factor receptor Human genes 0.000 description 18
• 125000002393 azetidinyl group Chemical group 0.000 description 18
• 239000003795 chemical substances by application Substances 0.000 description 18
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 18
• 125000002757 morpholinyl group Chemical group 0.000 description 18
• 125000004193 piperazinyl group Chemical group 0.000 description 18
• JERACDZUEXGNSE-UHFFFAOYSA-N 7-chloro-2-(1-ethylimidazol-4-yl)thieno[3,2-b]pyridine Chemical compound CCN1C=NC(C=2SC3=C(Cl)C=CN=C3C=2)=C1 JERACDZUEXGNSE-UHFFFAOYSA-N 0.000 description 17
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 16
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
• 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 16
• KNCCWVJEKOKTHK-UHFFFAOYSA-N n'-(2-fluorophenyl)propanediamide Chemical compound NC(=O)CC(=O)NC1=CC=CC=C1F KNCCWVJEKOKTHK-UHFFFAOYSA-N 0.000 description 16
• YUZHVIIXJVNLKI-UHFFFAOYSA-N n'-(2-methoxyphenyl)propanediamide Chemical compound COC1=CC=CC=C1NC(=O)CC(N)=O YUZHVIIXJVNLKI-UHFFFAOYSA-N 0.000 description 16
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• 238000010992 reflux Methods 0.000 description 16
• DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 16
• 125000004568 thiomorpholinyl group Chemical group 0.000 description 16
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 15
• NOJXRHBIVBIMQY-UHFFFAOYSA-N 3-anilino-3-oxopropanoic acid Chemical compound OC(=O)CC(=O)NC1=CC=CC=C1 NOJXRHBIVBIMQY-UHFFFAOYSA-N 0.000 description 15
• BINMGRBJWNEAJX-UHFFFAOYSA-N 3-fluoro-4-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxyaniline Chemical compound CN1C=CN=C1C1=CC2=NC=CC(OC=3C(=CC(N)=CC=3)F)=C2S1 BINMGRBJWNEAJX-UHFFFAOYSA-N 0.000 description 15
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
• 102000003745 Hepatocyte Growth Factor Human genes 0.000 description 15
• 108090000100 Hepatocyte Growth Factor Proteins 0.000 description 15
• 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 15
• 238000006243 chemical reaction Methods 0.000 description 15
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 15
• GXDLBQIVQXLQCY-UHFFFAOYSA-N n-[3-fluoro-4-[2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-n'-(2-methoxyphenyl)propanediamide Chemical compound COC1=CC=CC=C1NC(=O)CC(=O)NC(C=C1F)=CC=C1OC1=CC=NC2=C1SC(C=1N(C=CN=1)C)=C2 GXDLBQIVQXLQCY-UHFFFAOYSA-N 0.000 description 15
• NSMUQEBVZYHOBF-UHFFFAOYSA-N n-[3-fluoro-4-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]-n'-(2-methoxyphenyl)propanediamide Chemical compound COC1=CC=CC=C1NC(=O)CC(=O)NC(C=C1F)=CC=C1OC1=CC=NC2=C1SC(C=1C=CC(CN3CCCC3)=CC=1)=C2 NSMUQEBVZYHOBF-UHFFFAOYSA-N 0.000 description 15
• YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 14
• 125000002947 alkylene group Chemical group 0.000 description 14
• 125000004069 aziridinyl group Chemical group 0.000 description 14
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 14
• 125000006413 ring segment Chemical group 0.000 description 14
• ORPHLVJBJOCHBR-UHFFFAOYSA-N 403-19-0 Chemical compound OC1=CC=C([N+]([O-])=O)C=C1F ORPHLVJBJOCHBR-UHFFFAOYSA-N 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 13
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 13
• 229910052731 fluorine Inorganic materials 0.000 description 13
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 13
• 238000011282 treatment Methods 0.000 description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 13
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 125000003342 alkenyl group Chemical group 0.000 description 12
• 125000000304 alkynyl group Chemical group 0.000 description 12
• 239000008346 aqueous phase Substances 0.000 description 12
• 125000000392 cycloalkenyl group Chemical group 0.000 description 12
• 125000004475 heteroaralkyl group Chemical group 0.000 description 12
• 229910052938 sodium sulfate Inorganic materials 0.000 description 12
• 235000011152 sodium sulphate Nutrition 0.000 description 12
• 125000000335 thiazolyl group Chemical group 0.000 description 12
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 11
• 235000019270 ammonium chloride Nutrition 0.000 description 11
• 125000004415 heterocyclylalkyl group Chemical group 0.000 description 11
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 11
• WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 description 11
• 239000003921 oil Substances 0.000 description 11
• 235000019198 oils Nutrition 0.000 description 11
• 238000003756 stirring Methods 0.000 description 11
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 10
• TZCCKCLHNUSAMQ-DUGSHLAESA-N NC(=O)C[C@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](Cc2ccc(F)cc2)NC(=O)[C@H](Cc3c[nH]c4ccccc34)NC(=O)Cc5cccs5)C(=O)N Chemical compound NC(=O)C[C@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](Cc2ccc(F)cc2)NC(=O)[C@H](Cc3c[nH]c4ccccc34)NC(=O)Cc5cccs5)C(=O)N TZCCKCLHNUSAMQ-DUGSHLAESA-N 0.000 description 10
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
• 150000001263 acyl chlorides Chemical class 0.000 description 10
• 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 description 10
• USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 239000000463 material Substances 0.000 description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 10
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
• 102000005962 receptors Human genes 0.000 description 10
• 108020003175 receptors Proteins 0.000 description 10
• XMZQZXNHMUDHNZ-UHFFFAOYSA-N 2-bromo-7-chlorothieno[3,2-b]pyridine Chemical compound ClC1=CC=NC2=C1SC(Br)=C2 XMZQZXNHMUDHNZ-UHFFFAOYSA-N 0.000 description 9
• LJYQFQKUXOCPNI-UHFFFAOYSA-N 7-chloro-2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridine Chemical compound CN1C=CN=C1C1=CC2=NC=CC(Cl)=C2S1 LJYQFQKUXOCPNI-UHFFFAOYSA-N 0.000 description 9
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
• 125000003277 amino group Chemical group 0.000 description 9
• 239000002246 antineoplastic agent Substances 0.000 description 9
• 239000000460 chlorine Substances 0.000 description 9
• WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 9
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
• 238000001914 filtration Methods 0.000 description 9
• 238000002953 preparative HPLC Methods 0.000 description 9
• 125000004434 sulfur atom Chemical group 0.000 description 9
• KDXROTVXLGAFGW-UHFFFAOYSA-N 1-(phenylcarbamoyl)cyclopropane-1-carboxylic acid Chemical compound C=1C=CC=CC=1NC(=O)C1(C(=O)O)CC1 KDXROTVXLGAFGW-UHFFFAOYSA-N 0.000 description 8
• 125000001960 7 membered carbocyclic group Chemical group 0.000 description 8
• KMFQJCZBJFJJAV-UHFFFAOYSA-N 7-(2-fluoro-4-nitrophenoxy)-2-(1-methylimidazol-4-yl)thieno[3,2-b]pyridine Chemical compound CN1C=NC(C=2SC3=C(OC=4C(=CC(=CC=4)[N+]([O-])=O)F)C=CN=C3C=2)=C1 KMFQJCZBJFJJAV-UHFFFAOYSA-N 0.000 description 8
• GYQUXKQLCNFKQT-UHFFFAOYSA-N 7-chlorothieno[3,2-b]pyridine Chemical compound ClC1=CC=NC2=C1SC=C2 GYQUXKQLCNFKQT-UHFFFAOYSA-N 0.000 description 8
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
• 239000000908 ammonium hydroxide Substances 0.000 description 8
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 8
• 239000007864 aqueous solution Substances 0.000 description 8
• 239000012043 crude product Substances 0.000 description 8
• 239000001257 hydrogen Substances 0.000 description 8
• DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 8
• GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical compound CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 description 8
• 229910000027 potassium carbonate Inorganic materials 0.000 description 8
• OKCMGTGQOJQMOW-UHFFFAOYSA-N (7-chlorothieno[3,2-b]pyridin-2-yl)-pyrrolidin-1-ylmethanone Chemical compound S1C=2C(Cl)=CC=NC=2C=C1C(=O)N1CCCC1 OKCMGTGQOJQMOW-UHFFFAOYSA-N 0.000 description 7
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 description 7
• ZZKMDRAVIPHGJV-UHFFFAOYSA-N 2,4,5-triiodo-1-(2-pyrrolidin-1-ylethyl)imidazole Chemical compound IC1=C(I)N=C(I)N1CCN1CCCC1 ZZKMDRAVIPHGJV-UHFFFAOYSA-N 0.000 description 7
• ZTUKRGQWDZCKQG-UHFFFAOYSA-N 2-bromo-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine Chemical compound FC1=CC([N+](=O)[O-])=CC=C1OC1=CC=NC2=C1SC(Br)=C2 ZTUKRGQWDZCKQG-UHFFFAOYSA-N 0.000 description 7
• XKNFEJCGPIJXKT-UHFFFAOYSA-N 3-(2-fluoroanilino)-3-oxopropanoic acid Chemical compound OC(=O)CC(=O)NC1=CC=CC=C1F XKNFEJCGPIJXKT-UHFFFAOYSA-N 0.000 description 7
• AAQSCQXXRMZCDK-UHFFFAOYSA-N 3-(2-methoxyanilino)-3-oxopropanoic acid Chemical compound COC1=CC=CC=C1NC(=O)CC(O)=O AAQSCQXXRMZCDK-UHFFFAOYSA-N 0.000 description 7
• ZJZIXJISOLMKBB-UHFFFAOYSA-N 4-[2-(1-ethylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]oxy-3-fluoroaniline Chemical compound CCN1C=NC(C=2SC3=C(OC=4C(=CC(N)=CC=4)F)C=CN=C3C=2)=C1 ZJZIXJISOLMKBB-UHFFFAOYSA-N 0.000 description 7
• NWWZZZKKPMRZJB-UHFFFAOYSA-N 7-(2-fluoro-4-nitrophenoxy)-2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridine Chemical compound CN1C=CN=C1C1=CC2=NC=CC(OC=3C(=CC(=CC=3)[N+]([O-])=O)F)=C2S1 NWWZZZKKPMRZJB-UHFFFAOYSA-N 0.000 description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
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