JP2010524897A5 - - Google Patents

Info

Publication number

JP2010524897A5

JP2010524897A5 JP2010503514A JP2010503514A JP2010524897A5 JP 2010524897 A5 JP2010524897 A5 JP 2010524897A5 JP 2010503514 A JP2010503514 A JP 2010503514A JP 2010503514 A JP2010503514 A JP 2010503514A JP 2010524897 A5 JP2010524897 A5 JP 2010524897A5

Authority

JP

Japan

Prior art keywords

imidazol

thiourea

benzo

alkyl

methyl

Prior art date

2008-04-18

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.)

Granted

Links

• Espacenet
• Global Dossier
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• 125000000217 alkyl group Chemical group 0.000 claims 45
• 150000001875 compounds Chemical class 0.000 claims 40
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 33
• 125000001072 heteroaryl group Chemical group 0.000 claims 18
• 125000003118 aryl group Chemical group 0.000 claims 14
• 125000000623 heterocyclic group Chemical group 0.000 claims 14
• 125000004452 carbocyclyl group Chemical group 0.000 claims 10
• 125000003545 alkoxy group Chemical group 0.000 claims 9
• 229910052736 halogen Inorganic materials 0.000 claims 9
• 150000002367 halogens Chemical class 0.000 claims 9
• 125000002950 monocyclic group Chemical group 0.000 claims 9
• -1 cyano, hydroxyl Chemical group 0.000 claims 7
• 239000003112 inhibitor Substances 0.000 claims 7
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 6
• 125000002877 alkyl aryl group Chemical group 0.000 claims 6
• 201000010099 disease Diseases 0.000 claims 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
• 239000008194 pharmaceutical composition Substances 0.000 claims 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims 5
• 150000003839 salts Chemical class 0.000 claims 5
• 239000012453 solvate Substances 0.000 claims 5
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
• 206010019375 Helicobacter infections Diseases 0.000 claims 4
• 206010028980 Neoplasm Diseases 0.000 claims 4
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 4
• 238000006243 chemical reaction Methods 0.000 claims 4
• 239000003814 drug Substances 0.000 claims 4
• 230000001771 impaired effect Effects 0.000 claims 4
• 238000000034 method Methods 0.000 claims 4
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
• YVYCZILWIDAVBY-UHFFFAOYSA-N 1-(2,4-dimethoxyphenyl)-3-[3-(5-methylimidazol-1-yl)propyl]thiourea Chemical compound COC1=CC(OC)=CC=C1NC(=S)NCCCN1C(C)=CN=C1 YVYCZILWIDAVBY-UHFFFAOYSA-N 0.000 claims 3
• KBMZNLWAEWCLAY-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-[4-(5-methylimidazol-1-yl)butyl]thiourea Chemical compound C1=C(OC)C(OC)=CC=C1NC(=S)NCCCCN1C(C)=CN=C1 KBMZNLWAEWCLAY-UHFFFAOYSA-N 0.000 claims 3
• KZGHEEODIBACHZ-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-3-[3-(5-methylimidazol-1-yl)propyl]thiourea Chemical compound COC1=CC(OC)=CC(NC(=S)NCCCN2C(=CN=C2)C)=C1 KZGHEEODIBACHZ-UHFFFAOYSA-N 0.000 claims 3
• FPSGEHYIQQFWOG-UHFFFAOYSA-N 1-(4-ethoxyphenyl)-3-[3-(5-methylimidazol-1-yl)propyl]thiourea Chemical compound C1=CC(OCC)=CC=C1NC(=S)NCCCN1C(C)=CN=C1 FPSGEHYIQQFWOG-UHFFFAOYSA-N 0.000 claims 3
• IBAVDZGHMDWZIA-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-[3-(5-methylimidazol-1-yl)propyl]thiourea Chemical compound C1=CC(OC)=CC=C1NC(=S)NCCCN1C(C)=CN=C1 IBAVDZGHMDWZIA-UHFFFAOYSA-N 0.000 claims 3
• OFJXVHVIXDRBQN-UHFFFAOYSA-N 1-[3-(5-methylimidazol-1-yl)propyl]-3-(3,4,5-trimethoxyphenyl)thiourea Chemical compound COC1=C(OC)C(OC)=CC(NC(=S)NCCCN2C(=CN=C2)C)=C1 OFJXVHVIXDRBQN-UHFFFAOYSA-N 0.000 claims 3
• KLDSMUQVSXMITG-UHFFFAOYSA-N 1-[3-(5-methylimidazol-1-yl)propyl]-3-[4-(1,3-oxazol-5-yl)phenyl]thiourea Chemical compound CC1=CN=CN1CCCNC(=S)NC1=CC=C(C=2OC=NC=2)C=C1 KLDSMUQVSXMITG-UHFFFAOYSA-N 0.000 claims 3
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
• LZCDAPDGXCYOEH-UHFFFAOYSA-N adapalene Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=CC=C21 LZCDAPDGXCYOEH-UHFFFAOYSA-N 0.000 claims 3
• 125000003302 alkenyloxy group Chemical group 0.000 claims 3
• 125000002947 alkylene group Chemical group 0.000 claims 3
• 125000005133 alkynyloxy group Chemical group 0.000 claims 3
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 3
• 239000003795 chemical substances by application Substances 0.000 claims 3
• 230000002757 inflammatory effect Effects 0.000 claims 3
• 238000004519 manufacturing process Methods 0.000 claims 3
• 201000006417 multiple sclerosis Diseases 0.000 claims 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
• 125000001424 substituent group Chemical group 0.000 claims 3
• 125000004001 thioalkyl group Chemical group 0.000 claims 3
• AYTMAWUKURFAAB-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-[3-(5-methylimidazol-1-yl)propyl]thiourea Chemical compound C1=C(OC)C(OC)=CC=C1NC(=S)NCCCN1C(C)=CN=C1 AYTMAWUKURFAAB-UHFFFAOYSA-N 0.000 claims 2
• RLKRNEFSDSGCSZ-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-[(2,4-dimethoxyphenyl)methyl]thiourea Chemical compound COC1=CC(OC)=CC=C1CNC(=S)NC1=CC=C(NC=N2)C2=C1 RLKRNEFSDSGCSZ-UHFFFAOYSA-N 0.000 claims 2
• GVRHCRQDLQLLDH-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-[(3,4-dimethoxyphenyl)methyl]thiourea Chemical compound C1=C(OC)C(OC)=CC=C1CNC(=S)NC1=CC=C(NC=N2)C2=C1 GVRHCRQDLQLLDH-UHFFFAOYSA-N 0.000 claims 2
• MHMZFLWGVRUZQM-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-[(4-fluorophenyl)methyl]thiourea Chemical compound C1=CC(F)=CC=C1CNC(=S)NC1=CC=C(NC=N2)C2=C1 MHMZFLWGVRUZQM-UHFFFAOYSA-N 0.000 claims 2
• ONCNFWMRDXZIJU-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]thiourea Chemical compound C1=C(O)C(OC)=CC(CNC(=S)NC=2C=C3N=CNC3=CC=2)=C1 ONCNFWMRDXZIJU-UHFFFAOYSA-N 0.000 claims 2
• BBCIWLQKHLTFCS-UHFFFAOYSA-N 1-[3-(5-methylimidazol-1-yl)propyl]-3-(2,4,6-trimethylphenyl)thiourea Chemical compound CC1=CN=CN1CCCNC(=S)NC1=C(C)C=C(C)C=C1C BBCIWLQKHLTFCS-UHFFFAOYSA-N 0.000 claims 2
• JJLCUXAOBHRORK-UHFFFAOYSA-N 1-[3-(5-methylimidazol-1-yl)propyl]-3-(4-phenylmethoxyphenyl)thiourea Chemical compound CC1=CN=CN1CCCNC(=S)NC(C=C1)=CC=C1OCC1=CC=CC=C1 JJLCUXAOBHRORK-UHFFFAOYSA-N 0.000 claims 2
• MSYGAHOHLUJIKV-UHFFFAOYSA-N 3,5-dimethyl-1-(3-nitrophenyl)-1h-pyrazole-4-carboxylic acid ethyl ester Chemical compound CC1=C(C(=O)OCC)C(C)=NN1C1=CC=CC([N+]([O-])=O)=C1 MSYGAHOHLUJIKV-UHFFFAOYSA-N 0.000 claims 2
• 208000023697 ABri amyloidosis Diseases 0.000 claims 2
• 208000017227 ADan amyloidosis Diseases 0.000 claims 2
• 102000012440 Acetylcholinesterase Human genes 0.000 claims 2
• 108010022752 Acetylcholinesterase Proteins 0.000 claims 2
• 208000024827 Alzheimer disease Diseases 0.000 claims 2
• 201000001320 Atherosclerosis Diseases 0.000 claims 2
• 208000012639 Balance disease Diseases 0.000 claims 2
• 206010068597 Bulbospinal muscular atrophy congenital Diseases 0.000 claims 2
• 206010009944 Colon cancer Diseases 0.000 claims 2
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims 2
• 201000010374 Down Syndrome Diseases 0.000 claims 2
• 206010061825 Duodenal neoplasm Diseases 0.000 claims 2
• 208000030814 Eating disease Diseases 0.000 claims 2
• 208000019454 Feeding and Eating disease Diseases 0.000 claims 2
• 208000035895 Guillain-Barré syndrome Diseases 0.000 claims 2
• 208000023105 Huntington disease Diseases 0.000 claims 2
• 201000000162 ITM2B-related cerebral amyloid angiopathy 1 Diseases 0.000 claims 2
• 201000000194 ITM2B-related cerebral amyloid angiopathy 2 Diseases 0.000 claims 2
• 208000027747 Kennedy disease Diseases 0.000 claims 2
• 206010027476 Metastases Diseases 0.000 claims 2
• 206010049567 Miller Fisher syndrome Diseases 0.000 claims 2
• 206010033645 Pancreatitis Diseases 0.000 claims 2
• 208000018737 Parkinson disease Diseases 0.000 claims 2
• 201000004681 Psoriasis Diseases 0.000 claims 2
• 206010037779 Radiculopathy Diseases 0.000 claims 2
• 206010054184 Small intestine carcinoma Diseases 0.000 claims 2
• 208000005718 Stomach Neoplasms Diseases 0.000 claims 2
• 230000024932 T cell mediated immunity Effects 0.000 claims 2
• 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims 2
• 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims 2
• 208000006269 X-Linked Bulbo-Spinal Atrophy Diseases 0.000 claims 2
• 201000008629 Zollinger-Ellison syndrome Diseases 0.000 claims 2
• 229940022698 acetylcholinesterase Drugs 0.000 claims 2
• 125000003342 alkenyl group Chemical group 0.000 claims 2
• 230000033228 biological regulation Effects 0.000 claims 2
• 230000015572 biosynthetic process Effects 0.000 claims 2
• 201000011510 cancer Diseases 0.000 claims 2
• 230000001684 chronic effect Effects 0.000 claims 2
• 230000003210 demyelinating effect Effects 0.000 claims 2
• 235000014632 disordered eating Nutrition 0.000 claims 2
• 201000000312 duodenum cancer Diseases 0.000 claims 2
• 230000008482 dysregulation Effects 0.000 claims 2
• 230000037149 energy metabolism Effects 0.000 claims 2
• 206010017758 gastric cancer Diseases 0.000 claims 2
• 201000000052 gastrinoma Diseases 0.000 claims 2
• 230000013632 homeostatic process Effects 0.000 claims 2
• 230000003054 hormonal effect Effects 0.000 claims 2
• 230000028996 humoral immune response Effects 0.000 claims 2
• 208000000509 infertility Diseases 0.000 claims 2
• 230000036512 infertility Effects 0.000 claims 2
• 231100000535 infertility Toxicity 0.000 claims 2
• 230000023404 leukocyte cell-cell adhesion Effects 0.000 claims 2
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims 2
• 230000003211 malignant effect Effects 0.000 claims 2
• 201000001441 melanoma Diseases 0.000 claims 2
• 230000009401 metastasis Effects 0.000 claims 2
• 230000005012 migration Effects 0.000 claims 2
• 238000013508 migration Methods 0.000 claims 2
• 230000004770 neurodegeneration Effects 0.000 claims 2
• 229910052757 nitrogen Inorganic materials 0.000 claims 2
• 208000006473 polyradiculopathy Diseases 0.000 claims 2
• 238000002360 preparation method Methods 0.000 claims 2
• 208000037803 restenosis Diseases 0.000 claims 2
• 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
• 201000000980 schizophrenia Diseases 0.000 claims 2
• 208000020685 sleep-wake disease Diseases 0.000 claims 2
• 201000011549 stomach cancer Diseases 0.000 claims 2
• NITUEMISTORFON-PPFXTMJRSA-N (2S)-1-[(2S,3R)-2-[[(2S)-2-[[(2S)-1-[(2S,3R)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2R)-2-aminopropanoyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-3-methylbutanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-4-methylpentanoyl]amino]-3-phenylpropanoyl]amino]propanoyl]amino]-4-oxobutanoyl]amino]-3-methylpentanoyl]amino]-3-methylbutanoyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carboxylic acid Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@@H](C)N)C(C)C)C(C)C)C1=CC=CC=C1 NITUEMISTORFON-PPFXTMJRSA-N 0.000 claims 1
• NDHNTISUGBRYFU-UHFFFAOYSA-N 1-(2,4-dimethoxyphenyl)-3-[3-(4-methylimidazol-1-yl)propyl]thiourea Chemical compound COC1=CC(OC)=CC=C1NC(=S)NCCCN1C=C(C)N=C1 NDHNTISUGBRYFU-UHFFFAOYSA-N 0.000 claims 1
• WBMNLCQLBFBMPR-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-[3-(4-methylimidazol-1-yl)propyl]thiourea Chemical compound C1=C(OC)C(OC)=CC=C1NC(=S)NCCCN1C=C(C)N=C1 WBMNLCQLBFBMPR-UHFFFAOYSA-N 0.000 claims 1
• IBEGQMNZBWUKCD-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-3-[3-(4-methylimidazol-1-yl)propyl]thiourea Chemical compound COC1=CC(OC)=CC(NC(=S)NCCCN2C=C(C)N=C2)=C1 IBEGQMNZBWUKCD-UHFFFAOYSA-N 0.000 claims 1
• ZUMNEEQNJOUTEQ-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-(1,2-diphenylethyl)thiourea Chemical compound C=1C=C2NC=NC2=CC=1NC(=S)NC(C=1C=CC=CC=1)CC1=CC=CC=C1 ZUMNEEQNJOUTEQ-UHFFFAOYSA-N 0.000 claims 1
• ZUUKOFVVNXMKSQ-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-(1,3-benzodioxol-5-yl)thiourea Chemical compound C1=C2NC=NC2=CC(NC(NC=2C=C3OCOC3=CC=2)=S)=C1 ZUUKOFVVNXMKSQ-UHFFFAOYSA-N 0.000 claims 1
• PUZWIEPWWZTJCZ-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-(1,3-benzodioxol-5-ylmethyl)thiourea Chemical compound C1=C2NC=NC2=CC(NC(NCC=2C=C3OCOC3=CC=2)=S)=C1 PUZWIEPWWZTJCZ-UHFFFAOYSA-N 0.000 claims 1
• LZCWJHPODVGSDT-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-(1-phenylethyl)thiourea Chemical compound C=1C=C2NC=NC2=CC=1NC(=S)NC(C)C1=CC=CC=C1 LZCWJHPODVGSDT-UHFFFAOYSA-N 0.000 claims 1
• OTCCXULJKWMXTH-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-(2,1,3-benzothiadiazol-4-yl)thiourea Chemical compound C1=CC2=NSN=C2C(NC(NC=2C=C3N=CNC3=CC=2)=S)=C1 OTCCXULJKWMXTH-UHFFFAOYSA-N 0.000 claims 1
• OUIZUDZKLFGCEN-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-(2,1,3-benzothiadiazol-5-yl)thiourea Chemical compound C1=CC2=NSN=C2C=C1NC(=S)NC1=CC=C(NC=N2)C2=C1 OUIZUDZKLFGCEN-UHFFFAOYSA-N 0.000 claims 1
• QRIHHWOOTBRDLE-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-(2,4-dimethoxyphenyl)thiourea Chemical compound COC1=CC(OC)=CC=C1NC(=S)NC1=CC=C(NC=N2)C2=C1 QRIHHWOOTBRDLE-UHFFFAOYSA-N 0.000 claims 1
• DRGMBJLGHQTFGL-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-(2-phenylethyl)thiourea Chemical compound C=1C=C2NC=NC2=CC=1NC(=S)NCCC1=CC=CC=C1 DRGMBJLGHQTFGL-UHFFFAOYSA-N 0.000 claims 1
• YIWWFEWFVCKFNY-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-(3,5-dimethoxyphenyl)thiourea Chemical compound COC1=CC(OC)=CC(NC(=S)NC=2C=C3N=CNC3=CC=2)=C1 YIWWFEWFVCKFNY-UHFFFAOYSA-N 0.000 claims 1
• RXIUIAGVQGJWSX-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-(3-methoxyphenyl)thiourea Chemical compound COC1=CC=CC(NC(=S)NC=2C=C3N=CNC3=CC=2)=C1 RXIUIAGVQGJWSX-UHFFFAOYSA-N 0.000 claims 1
• MEAUCDLOUYRETL-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-(4-bromophenyl)thiourea Chemical compound C1=CC(Br)=CC=C1NC(=S)NC1=CC=C(NC=N2)C2=C1 MEAUCDLOUYRETL-UHFFFAOYSA-N 0.000 claims 1
• JVEJUXQNKGSXAM-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-(4-fluorophenyl)thiourea Chemical compound C1=CC(F)=CC=C1NC(=S)NC1=CC=C(NC=N2)C2=C1 JVEJUXQNKGSXAM-UHFFFAOYSA-N 0.000 claims 1
• KTRKKRAUDHELSP-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-(4-iodophenyl)thiourea Chemical compound C1=CC(I)=CC=C1NC(=S)NC1=CC=C(NC=N2)C2=C1 KTRKKRAUDHELSP-UHFFFAOYSA-N 0.000 claims 1
• QBLBFLGUNAHQDI-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-(4-methoxyphenyl)thiourea Chemical compound C1=CC(OC)=CC=C1NC(=S)NC1=CC=C(NC=N2)C2=C1 QBLBFLGUNAHQDI-UHFFFAOYSA-N 0.000 claims 1
• WNZGPQPQIWEJNR-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-(4-methylphenyl)thiourea Chemical compound C1=CC(C)=CC=C1NC(=S)NC1=CC=C(NC=N2)C2=C1 WNZGPQPQIWEJNR-UHFFFAOYSA-N 0.000 claims 1
• QRCZJFXYOSNPGJ-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-(furan-2-ylmethyl)thiourea Chemical compound C=1C=C2NC=NC2=CC=1NC(=S)NCC1=CC=CO1 QRCZJFXYOSNPGJ-UHFFFAOYSA-N 0.000 claims 1
• IJGAFGWXCLNZSZ-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-(oxolan-2-ylmethyl)thiourea Chemical compound C=1C=C2NC=NC2=CC=1NC(=S)NCC1CCCO1 IJGAFGWXCLNZSZ-UHFFFAOYSA-N 0.000 claims 1
• ANWPWXBSYOVVBP-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-(pyridin-2-ylmethyl)thiourea Chemical compound C=1C=C2NC=NC2=CC=1NC(=S)NCC1=CC=CC=N1 ANWPWXBSYOVVBP-UHFFFAOYSA-N 0.000 claims 1
• BGDPLMXMUSEZNY-LLVKDONJSA-N 1-(3h-benzimidazol-5-yl)-3-[(1r)-1-(4-methoxyphenyl)ethyl]thiourea Chemical compound C1=CC(OC)=CC=C1[C@@H](C)NC(=S)NC1=CC=C(NC=N2)C2=C1 BGDPLMXMUSEZNY-LLVKDONJSA-N 0.000 claims 1
• JSDOUDLSZZNCLW-CQSZACIVSA-N 1-(3h-benzimidazol-5-yl)-3-[(1r)-1-phenylpropyl]thiourea Chemical compound C1([C@H](NC(=S)NC=2C=C3N=CNC3=CC=2)CC)=CC=CC=C1 JSDOUDLSZZNCLW-CQSZACIVSA-N 0.000 claims 1
• BGDPLMXMUSEZNY-NSHDSACASA-N 1-(3h-benzimidazol-5-yl)-3-[(1s)-1-(4-methoxyphenyl)ethyl]thiourea Chemical compound C1=CC(OC)=CC=C1[C@H](C)NC(=S)NC1=CC=C(NC=N2)C2=C1 BGDPLMXMUSEZNY-NSHDSACASA-N 0.000 claims 1
• JSDOUDLSZZNCLW-AWEZNQCLSA-N 1-(3h-benzimidazol-5-yl)-3-[(1s)-1-phenylpropyl]thiourea Chemical compound C1([C@@H](NC(=S)NC=2C=C3N=CNC3=CC=2)CC)=CC=CC=C1 JSDOUDLSZZNCLW-AWEZNQCLSA-N 0.000 claims 1
• XWBPNYYGPBJYPT-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-[(2,3-dimethoxyphenyl)methyl]thiourea Chemical compound COC1=CC=CC(CNC(=S)NC=2C=C3N=CNC3=CC=2)=C1OC XWBPNYYGPBJYPT-UHFFFAOYSA-N 0.000 claims 1
• AJBNFRFYWBBRMS-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-[(2,4-dichlorophenyl)methyl]thiourea Chemical compound ClC1=CC(Cl)=CC=C1CNC(=S)NC1=CC=C(NC=N2)C2=C1 AJBNFRFYWBBRMS-UHFFFAOYSA-N 0.000 claims 1
• MHPYYRGAKSYFRC-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-[(2,5-dimethoxyphenyl)methyl]thiourea Chemical compound COC1=CC=C(OC)C(CNC(=S)NC=2C=C3N=CNC3=CC=2)=C1 MHPYYRGAKSYFRC-UHFFFAOYSA-N 0.000 claims 1
• PGOQNHPKVGBXFR-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-[(2-chlorophenyl)methyl]thiourea Chemical compound ClC1=CC=CC=C1CNC(=S)NC1=CC=C(NC=N2)C2=C1 PGOQNHPKVGBXFR-UHFFFAOYSA-N 0.000 claims 1
• QIYUFEGQFBUVGG-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-[(2-methoxyphenyl)methyl]thiourea Chemical compound COC1=CC=CC=C1CNC(=S)NC1=CC=C(NC=N2)C2=C1 QIYUFEGQFBUVGG-UHFFFAOYSA-N 0.000 claims 1
• VRCGXEZJKJJCBJ-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-[(3,4,5-trimethoxyphenyl)methyl]thiourea Chemical compound COC1=C(OC)C(OC)=CC(CNC(=S)NC=2C=C3N=CNC3=CC=2)=C1 VRCGXEZJKJJCBJ-UHFFFAOYSA-N 0.000 claims 1
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