CA2383623A1

CA2383623A1 - 3-methylidenyl-2-indolinone modulators of protein kinase

3-methylidenyl-2-indolinone modulators of protein kinase Download PDF

Info

Publication number: CA2383623A1
Authority: CA; Canada
Prior art keywords: dihydroindol; indol; group; oxo; methoxybenzylidene
Prior art date: 1998-08-04
Legal status : Abandoned

Application number

CA002383623A

Other languages

English (en)

French (fr)

Inventor

Peng Cho Tang

Li Sun

Todd Anthony Miller

Congxin Liang

Ngoc My Tran

Anh Thi Nguyen

Asaad Nematalla

Current Assignee

Sugen LLC

Original Assignee

Individual

Priority date

1998-08-04

Filing date

1999-08-04

Publication date

2000-02-17

1999-08-04 Application filed by Individual filed Critical Individual

2000-02-17 Publication of CA2383623A1 publication Critical patent/CA2383623A1/en

Status Abandoned legal-status Critical Current

Links

102000001253 Protein Kinase Human genes 0.000 title claims abstract description 28
108060006633 protein kinase Proteins 0.000 title claims abstract description 28
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 89
150000003839 salts Chemical class 0.000 claims abstract description 54
206010028980 Neoplasm Diseases 0.000 claims abstract description 49
201000011510 cancer Diseases 0.000 claims abstract description 29
125000000217 alkyl group Chemical group 0.000 claims description 198
150000001875 compounds Chemical class 0.000 claims description 188
229910052739 hydrogen Inorganic materials 0.000 claims description 176
239000001257 hydrogen Substances 0.000 claims description 163
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 121
229910001868 water Inorganic materials 0.000 claims description 108
150000002431 hydrogen Chemical class 0.000 claims description 92
125000003118 aryl group Chemical group 0.000 claims description 87
125000003545 alkoxy group Chemical group 0.000 claims description 86
125000005843 halogen group Chemical group 0.000 claims description 82
-1 heteroalicyclic Chemical group 0.000 claims description 77
208000035475 disorder Diseases 0.000 claims description 73
238000006243 chemical reaction Methods 0.000 claims description 68
238000000034 method Methods 0.000 claims description 63
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 48
102000027426 receptor tyrosine kinases Human genes 0.000 claims description 40
108091008598 receptor tyrosine kinases Proteins 0.000 claims description 40
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 31
230000003197 catalytic effect Effects 0.000 claims description 30
239000002904 solvent Substances 0.000 claims description 29
125000001072 heteroaryl group Chemical group 0.000 claims description 28
102000009516 Protein Serine-Threonine Kinases Human genes 0.000 claims description 27
108010009341 Protein Serine-Threonine Kinases Proteins 0.000 claims description 27
125000000753 cycloalkyl group Chemical group 0.000 claims description 27
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 26
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 23
230000033115 angiogenesis Effects 0.000 claims description 19
239000008194 pharmaceutical composition Substances 0.000 claims description 19
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 16
230000008569 process Effects 0.000 claims description 15
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 14
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 14
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 14
229910052799 carbon Inorganic materials 0.000 claims description 13
238000010992 reflux Methods 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 12
125000004953 trihalomethyl group Chemical group 0.000 claims description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
125000003342 alkenyl group Chemical group 0.000 claims description 11
125000000304 alkynyl group Chemical group 0.000 claims description 11
239000000546 pharmaceutical excipient Substances 0.000 claims description 11
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101000692455 Homo sapiens Platelet-derived growth factor receptor beta Proteins 0.000 claims description 9
102100026547 Platelet-derived growth factor receptor beta Human genes 0.000 claims description 9
102100039688 Insulin-like growth factor 1 receptor Human genes 0.000 claims description 8
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 8
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ZGXJTSGNIOSYLO-UHFFFAOYSA-N 88755TAZ87 Chemical compound NCC(=O)CCC(O)=O ZGXJTSGNIOSYLO-UHFFFAOYSA-N 0.000 claims description 7
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HMSZUOWNDFWCOV-UHFFFAOYSA-N 1,2,3,5,6,7-hexahydroindol-4-one Chemical compound O=C1CCCC2=C1CCN2 HMSZUOWNDFWCOV-UHFFFAOYSA-N 0.000 claims description 5
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208000007766 Kaposi sarcoma Diseases 0.000 claims description 5
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 5
208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 5
125000004104 aryloxy group Chemical group 0.000 claims description 5
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239000001632 sodium acetate Substances 0.000 claims description 5
235000017281 sodium acetate Nutrition 0.000 claims description 5
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125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
DLNQZPJCLLSKPP-UHFFFAOYSA-N 3-(4-oxo-1,5,6,7-tetrahydroindol-3-yl)propanoic acid Chemical class C1CCC(=O)C2=C1NC=C2CCC(=O)O DLNQZPJCLLSKPP-UHFFFAOYSA-N 0.000 claims description 4
OOEZKKFEUCRUAH-UHFFFAOYSA-N 3-[(3-methyl-1h-indol-2-yl)methylidene]-1h-indol-2-one Chemical compound N1C2=CC=CC=C2C(C)=C1C=C1C2=CC=CC=C2NC1=O OOEZKKFEUCRUAH-UHFFFAOYSA-N 0.000 claims description 4
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
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KFGPDFWWTNSMLP-UHFFFAOYSA-N 3-(1h-indol-2-ylmethylidene)-1h-indol-2-one Chemical compound C1=CC=C2NC(C=C3C4=CC=CC=C4NC3=O)=CC2=C1 KFGPDFWWTNSMLP-UHFFFAOYSA-N 0.000 claims description 3
PTIDSPPVASCIKJ-UHFFFAOYSA-N 3-(1h-indol-2-ylmethylidene)-4-methyl-1h-indol-2-one Chemical compound C1=CC=C2NC(C=C3C(=O)NC=4C=CC=C(C3=4)C)=CC2=C1 PTIDSPPVASCIKJ-UHFFFAOYSA-N 0.000 claims description 3
DMHROXAXOCSHHR-UHFFFAOYSA-N 3-[[3-(3-morpholin-4-yl-3-oxopropyl)-4,5,6,7-tetrahydro-1h-indol-2-yl]methylidene]-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2C1=CC=1NC=2CCCCC=2C=1CCC(=O)N1CCOCC1 DMHROXAXOCSHHR-UHFFFAOYSA-N 0.000 claims description 3
UKYGUPWSIOWZHO-UHFFFAOYSA-N 5-acetyl-3-(1h-indol-2-ylmethylidene)-1h-indol-2-one Chemical compound C1=CC=C2NC(C=C3C(=O)NC4=CC=C(C=C43)C(=O)C)=CC2=C1 UKYGUPWSIOWZHO-UHFFFAOYSA-N 0.000 claims description 3
DEAUIKKPCUHQEU-UHFFFAOYSA-N 5-amino-3-(1h-indol-2-ylmethylidene)-1h-indol-2-one Chemical compound C1=CC=C2NC(C=C3C(=O)NC4=CC=C(C=C43)N)=CC2=C1 DEAUIKKPCUHQEU-UHFFFAOYSA-N 0.000 claims description 3
RIDQKNFSZKZGMG-UHFFFAOYSA-N 5-bromo-3-(1h-indol-2-ylmethylidene)-1h-indol-2-one Chemical compound C1=CC=C2NC(C=C3C(=O)NC4=CC=C(C=C43)Br)=CC2=C1 RIDQKNFSZKZGMG-UHFFFAOYSA-N 0.000 claims description 3
ZLNUFZMRSPBKNV-UHFFFAOYSA-N 6-chloro-3-(1h-indol-2-ylmethylidene)-1h-indol-2-one Chemical compound C1=CC=C2NC(C=C3C4=CC=C(C=C4NC3=O)Cl)=CC2=C1 ZLNUFZMRSPBKNV-UHFFFAOYSA-N 0.000 claims description 3
208000001333 Colorectal Neoplasms Diseases 0.000 claims description 3
206010018338 Glioma Diseases 0.000 claims description 3
208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
239000003638 chemical reducing agent Substances 0.000 claims description 3
208000027866 inflammatory disease Diseases 0.000 claims description 3
239000012280 lithium aluminium hydride Substances 0.000 claims description 3
108091008046 non-receptor tyrosine kinases Proteins 0.000 claims description 3
102000037979 non-receptor tyrosine kinases Human genes 0.000 claims description 3
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208000006542 von Hippel-Lindau disease Diseases 0.000 claims description 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
ZMWDREZMPWLMLN-UHFFFAOYSA-N 3-(1H-indol-2-ylmethylidene)-5-(1H-indol-2-ylmethylideneamino)-1H-indol-2-one Chemical compound C1=CC=C2NC(C=NC3=CC=C4NC(C(C4=C3)=CC=3NC4=CC=CC=C4C=3)=O)=CC2=C1 ZMWDREZMPWLMLN-UHFFFAOYSA-N 0.000 claims description 2
MTKVRHKXTYDALL-UHFFFAOYSA-N 3-(1h-indol-2-ylmethylidene)-2-oxo-1h-indole-5-carboxylic acid Chemical compound C1=CC=C2NC(C=C3C(=O)NC4=CC=C(C=C43)C(=O)O)=CC2=C1 MTKVRHKXTYDALL-UHFFFAOYSA-N 0.000 claims description 2
QKAGVJCEMCSNJW-UHFFFAOYSA-N 3-(1h-indol-2-ylmethylidene)-2-oxo-1h-indole-5-sulfonamide Chemical compound C1=CC=C2NC(C=C3C(=O)NC4=CC=C(C=C43)S(=O)(=O)N)=CC2=C1 QKAGVJCEMCSNJW-UHFFFAOYSA-N 0.000 claims description 2
BHAXPJSCKCQZCC-UHFFFAOYSA-N 3-[(2,2-dimethyl-3,4-dihydrochromen-6-yl)methylidene]-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2C1=CC1=CC=C(OC(C)(C)CC2)C2=C1 BHAXPJSCKCQZCC-UHFFFAOYSA-N 0.000 claims description 2
NZLBRXWPCCBUHP-UHFFFAOYSA-N 3-[(3-methyl-1h-indol-2-yl)methylidene]-2-oxo-1h-indole-5-carboxylic acid Chemical compound N1C2=CC=CC=C2C(C)=C1C=C1C2=CC(C(O)=O)=CC=C2NC1=O NZLBRXWPCCBUHP-UHFFFAOYSA-N 0.000 claims description 2
JVGSSAXQAJNKKH-UHFFFAOYSA-N 3-[(3-methyl-1h-indol-2-yl)methylidene]-2-oxo-1h-indole-5-sulfonamide Chemical compound N1C2=CC=CC=C2C(C)=C1C=C1C2=CC(S(N)(=O)=O)=CC=C2NC1=O JVGSSAXQAJNKKH-UHFFFAOYSA-N 0.000 claims description 2
IYDNWSXTRGNJFM-UHFFFAOYSA-N 3-[2-[(2-oxo-1h-indol-3-ylidene)methyl]-4,5,6,7-tetrahydro-1h-indol-3-yl]propanamide Chemical compound C1CCCC2=C1NC(C=C1C3=CC=CC=C3NC1=O)=C2CCC(=O)N IYDNWSXTRGNJFM-UHFFFAOYSA-N 0.000 claims description 2
SDQYBRYUJUZOBP-UHFFFAOYSA-N 3-[2-[(2-oxo-1h-indol-3-ylidene)methyl]phenyl]propanoic acid Chemical compound OC(=O)CCC1=CC=CC=C1C=C1C2=CC=CC=C2NC1=O SDQYBRYUJUZOBP-UHFFFAOYSA-N 0.000 claims description 2
AENZRBDTEWXNFM-UHFFFAOYSA-N 3-[2-[(4-methyl-2-oxo-1h-indol-3-ylidene)methyl]-4,5,6,7-tetrahydro-1h-indol-3-yl]propanoic acid Chemical compound C1CCCC2=C1NC(C=C1C(=O)NC=3C=CC=C(C1=3)C)=C2CCC(O)=O AENZRBDTEWXNFM-UHFFFAOYSA-N 0.000 claims description 2
LJLQADXSGCVLNW-UHFFFAOYSA-N 3-[2-[(5-bromo-2-oxo-1h-indol-3-ylidene)methyl]-4,5,6,7-tetrahydro-1h-indol-3-yl]-n-(2-morpholin-4-ylethyl)propanamide Chemical compound C12=CC(Br)=CC=C2NC(=O)C1=CC=1NC=2CCCCC=2C=1CCC(=O)NCCN1CCOCC1 LJLQADXSGCVLNW-UHFFFAOYSA-N 0.000 claims description 2
YSXXXUUPXLNFMQ-UHFFFAOYSA-N 3-[2-[(5-bromo-4-methyl-2-oxo-1h-indol-3-ylidene)methyl]-4,5,6,7-tetrahydro-1h-indol-3-yl]propanoic acid Chemical compound C1CCCC2=C1NC(C=C1C3=C(C(=CC=C3NC1=O)Br)C)=C2CCC(O)=O YSXXXUUPXLNFMQ-UHFFFAOYSA-N 0.000 claims description 2
BWGQGBFWXFRHSU-UHFFFAOYSA-N 3-[2-[(5-chloro-2-oxo-1h-indol-3-ylidene)methyl]-4,5,6,7-tetrahydro-1h-indol-3-yl]-n-(2-morpholin-4-ylethyl)propanamide Chemical compound C12=CC(Cl)=CC=C2NC(=O)C1=CC=1NC=2CCCCC=2C=1CCC(=O)NCCN1CCOCC1 BWGQGBFWXFRHSU-UHFFFAOYSA-N 0.000 claims description 2
NTBZETWHTDHTJG-UHFFFAOYSA-N 3-[2-[(5-chloro-2-oxo-1h-indol-3-ylidene)methyl]-4,5,6,7-tetrahydro-1h-indol-3-yl]propanoic acid Chemical compound C1CCCC2=C1NC(C=C1C3=CC(Cl)=CC=C3NC1=O)=C2CCC(=O)O NTBZETWHTDHTJG-UHFFFAOYSA-N 0.000 claims description 2
GQHRTHFDNYRJMA-UHFFFAOYSA-N 3-[2-[(5-chloro-4-methyl-2-oxo-1h-indol-3-ylidene)methyl]-4,5,6,7-tetrahydro-1h-indol-3-yl]propanoic acid Chemical compound C1CCCC2=C1NC(C=C1C3=C(C(=CC=C3NC1=O)Cl)C)=C2CCC(O)=O GQHRTHFDNYRJMA-UHFFFAOYSA-N 0.000 claims description 2
OWPKTCUCUHPOTI-UHFFFAOYSA-N 3-[2-[(5-methyl-2-oxo-1h-indol-3-ylidene)methyl]-4,5,6,7-tetrahydro-1h-indol-3-yl]propanoic acid Chemical compound C1CCCC2=C1NC(C=C1C(=O)NC3=CC=C(C=C31)C)=C2CCC(O)=O OWPKTCUCUHPOTI-UHFFFAOYSA-N 0.000 claims description 2
YTTUVDIJINNTEQ-UHFFFAOYSA-N 3-[2-[(6-chloro-2-oxo-1h-indol-3-ylidene)methyl]-4,5,6,7-tetrahydro-1h-indol-3-yl]propanoic acid Chemical compound C1CCCC2=C1NC(C=C1C3=CC=C(Cl)C=C3NC1=O)=C2CCC(=O)O YTTUVDIJINNTEQ-UHFFFAOYSA-N 0.000 claims description 2
QKVUBIOLQLJVKI-UHFFFAOYSA-N 3-[2-[(6-methoxy-2-oxo-1h-indol-3-ylidene)methyl]-4,5,6,7-tetrahydro-1h-indol-3-yl]propanoic acid Chemical compound C1CCCC2=C1NC(C=C1C3=CC=C(C=C3NC1=O)OC)=C2CCC(O)=O QKVUBIOLQLJVKI-UHFFFAOYSA-N 0.000 claims description 2
ROMVYKQLLKDRKN-UHFFFAOYSA-N 3-[2-[(6-morpholin-4-yl-2-oxo-1h-indol-3-ylidene)methyl]-4,5,6,7-tetrahydro-1h-indol-3-yl]propanoic acid Chemical compound OC(=O)CCC=1C=2CCCCC=2NC=1C=C(C1=CC=2)C(=O)NC1=CC=2N1CCOCC1 ROMVYKQLLKDRKN-UHFFFAOYSA-N 0.000 claims description 2
NPNOMACTPXEJJY-PTNGSMBKSA-N 3-[2-[(z)-(2-oxo-1h-indol-3-ylidene)methyl]-4,5,6,7-tetrahydro-1h-indol-3-yl]propanoic acid Chemical compound C1CCCC2=C1NC(\C=C/1C3=CC=CC=C3NC\1=O)=C2CCC(=O)O NPNOMACTPXEJJY-PTNGSMBKSA-N 0.000 claims description 2
NQIZOXPPUYQOQV-QNGOZBTKSA-N 3-[2-[(z)-(2-oxo-6-phenyl-1h-indol-3-ylidene)methyl]-4,5,6,7-tetrahydro-1h-indol-3-yl]propanoic acid Chemical compound N1C=2CCCCC=2C(CCC(=O)O)=C1\C=C(C1=CC=2)/C(=O)NC1=CC=2C1=CC=CC=C1 NQIZOXPPUYQOQV-QNGOZBTKSA-N 0.000 claims description 2
FUXHNAHZJZOIIP-JCMHNJIXSA-N 3-[2-[(z)-[6-(3-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-4,5,6,7-tetrahydro-1h-indol-3-yl]propanoic acid Chemical compound COC1=CC=CC(C=2C=C3NC(=O)C(=C\C4=C(C=5CCCCC=5N4)CCC(O)=O)/C3=CC=2)=C1 FUXHNAHZJZOIIP-JCMHNJIXSA-N 0.000 claims description 2
IEDHIXOGGAHSLI-JCMHNJIXSA-N 3-[2-[(z)-[6-(4-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-4,5,6,7-tetrahydro-1h-indol-3-yl]propanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(\C(=C\C2=C(C=3CCCCC=3N2)CCC(O)=O)C(=O)N2)C2=C1 IEDHIXOGGAHSLI-JCMHNJIXSA-N 0.000 claims description 2
VWFMZAIPTVJFHG-UHFFFAOYSA-N 3-[2-[[2-oxo-5-(propan-2-ylsulfamoyl)-1h-indol-3-ylidene]methyl]-4,5,6,7-tetrahydro-1h-indol-3-yl]propanoic acid Chemical compound C1CCCC2=C1NC(C=C1C(=O)NC3=CC=C(C=C31)S(=O)(=O)NC(C)C)=C2CCC(O)=O VWFMZAIPTVJFHG-UHFFFAOYSA-N 0.000 claims description 2
JROBWQZZQGDCLF-UHFFFAOYSA-N 3-[2-[[6-(2-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-4,5,6,7-tetrahydro-1h-indol-3-yl]propanoic acid Chemical compound COC1=CC=CC=C1C1=CC=C(C(=CC2=C(C=3CCCCC=3N2)CCC(O)=O)C(=O)N2)C2=C1 JROBWQZZQGDCLF-UHFFFAOYSA-N 0.000 claims description 2
FWTOUWIXFUMZEK-UHFFFAOYSA-N 3-[[3-[3-(dimethylamino)propyl]-4,5,6,7-tetrahydro-1h-indol-2-yl]methylidene]-1h-indol-2-one Chemical compound C1CCCC2=C1NC(C=C1C3=CC=CC=C3NC1=O)=C2CCCN(C)C FWTOUWIXFUMZEK-UHFFFAOYSA-N 0.000 claims description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
XOXACDNRLJMVTM-UHFFFAOYSA-N 4-methyl-3-[(3-methyl-1h-indol-2-yl)methylidene]-1h-indol-2-one Chemical compound N1C2=CC=CC=C2C(C)=C1C=C1C2=C(C)C=CC=C2NC1=O XOXACDNRLJMVTM-UHFFFAOYSA-N 0.000 claims description 2
FUPOUVHSQOHDBU-UHFFFAOYSA-N 5-acetyl-3-[(3-methyl-1h-indol-2-yl)methylidene]-1h-indol-2-one Chemical compound N1C2=CC=CC=C2C(C)=C1C=C1C(=O)NC2=CC=C(C(=O)C)C=C21 FUPOUVHSQOHDBU-UHFFFAOYSA-N 0.000 claims description 2
QIIVFQXIPFYVIQ-UHFFFAOYSA-N 5-acetyl-3-[[4-methoxy-3,5-di(propan-2-yl)phenyl]methylidene]-1h-indol-2-one;methyl 3-[[4-methoxy-3,5-di(propan-2-yl)phenyl]methylidene]-2-oxo-1h-indole-5-carboxylate Chemical compound C1=C(C(C)C)C(OC)=C(C(C)C)C=C1C=C1C2=CC(C(C)=O)=CC=C2NC1=O.C12=CC(C(=O)OC)=CC=C2NC(=O)C1=CC1=CC(C(C)C)=C(OC)C(C(C)C)=C1 QIIVFQXIPFYVIQ-UHFFFAOYSA-N 0.000 claims description 2
CHDKFTZZLNOGHE-UHFFFAOYSA-N 5-bromo-3-[(3-methyl-1h-indol-2-yl)methylidene]-1h-indol-2-one Chemical compound N1C2=CC=CC=C2C(C)=C1C=C1C2=CC(Br)=CC=C2NC1=O CHDKFTZZLNOGHE-UHFFFAOYSA-N 0.000 claims description 2
RBQPBXNTRIMSNP-UHFFFAOYSA-N 5-chloro-3-(1h-indol-2-ylmethylidene)-1h-indol-2-one Chemical compound C1=CC=C2NC(C=C3C(=O)NC4=CC=C(C=C43)Cl)=CC2=C1 RBQPBXNTRIMSNP-UHFFFAOYSA-N 0.000 claims description 2
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