JP2012502006A5 - - Google Patents
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- Publication number
- JP2012502006A5 JP2012502006A5 JP2011525556A JP2011525556A JP2012502006A5 JP 2012502006 A5 JP2012502006 A5 JP 2012502006A5 JP 2011525556 A JP2011525556 A JP 2011525556A JP 2011525556 A JP2011525556 A JP 2011525556A JP 2012502006 A5 JP2012502006 A5 JP 2012502006A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- imidazol
- dione
- phenyl
- imidazolidine
- Prior art date
- 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
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- -1 cyano, hydroxyl Chemical group 0.000 claims description 115
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 17
- 239000003112 inhibitor Substances 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- OHGGDDBGUDKOBT-UHFFFAOYSA-N 5-(2-chlorophenyl)-1-(3-imidazol-1-ylpropyl)imidazolidine-2,4-dione Chemical compound ClC1=CC=CC=C1C1C(=O)NC(=O)N1CCCN1C=NC=C1 OHGGDDBGUDKOBT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000935 antidepressant agent Substances 0.000 claims description 2
- 229940005513 antidepressants Drugs 0.000 claims description 2
- 239000002249 anxiolytic agent Substances 0.000 claims description 2
- 230000000949 anxiolytic effect Effects 0.000 claims description 2
- 229940005530 anxiolytics Drugs 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 claims description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 14
- 125000003545 alkoxy group Chemical group 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 206010019375 Helicobacter infections Diseases 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 230000001771 impaired effect Effects 0.000 claims 4
- 230000002757 inflammatory effect Effects 0.000 claims 4
- 125000000171 (C1-C6) haloalkyl 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
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims 3
- 201000006417 multiple sclerosis Diseases 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 230000008569 process Effects 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000004001 thioalkyl group Chemical group 0.000 claims 3
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 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
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims 2
- 208000023697 ABri amyloidosis Diseases 0.000 claims 2
- 208000017227 ADan amyloidosis Diseases 0.000 claims 2
- 108010022752 Acetylcholinesterase Proteins 0.000 claims 2
- 102000012440 Acetylcholinesterase Human genes 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 claims 2
- 108010043324 Amyloid Precursor Protein Secretases Proteins 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
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 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
- 230000037424 autonomic function Effects 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 230000033228 biological regulation Effects 0.000 claims 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 210000001124 body fluid Anatomy 0.000 claims 2
- 239000010839 body fluid Substances 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 230000003210 demyelinating effect Effects 0.000 claims 2
- 208000035475 disorder Diseases 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
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 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
- 229910052739 hydrogen Inorganic materials 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
- 230000021633 leukocyte mediated immunity 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
- 238000004519 manufacturing process Methods 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
- 208000027061 mild cognitive impairment Diseases 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 230000001717 pathogenic effect Effects 0.000 claims 2
- 230000004044 response Effects 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
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 2
- 201000011549 stomach cancer Diseases 0.000 claims 2
- 229910052717 sulfur Inorganic materials 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
- SOCSUCKHKHAOMU-UHFFFAOYSA-N 1'-(3h-benzimidazol-5-yl)spiro[1,3-dihydroindene-2,5'-imidazolidine]-2',4'-dione Chemical compound C1=C2NC=NC2=CC(N2C3(CC4=CC=CC=C4C3)C(=O)NC2=O)=C1 SOCSUCKHKHAOMU-UHFFFAOYSA-N 0.000 claims 1
- HQTRUHWLKNRAGK-UHFFFAOYSA-N 1-(3-imidazol-1-ylpropyl)-5-(4-propoxyphenyl)imidazolidine-2,4-dione Chemical compound C1=CC(OCCC)=CC=C1C1C(=O)NC(=O)N1CCCN1C=NC=C1 HQTRUHWLKNRAGK-UHFFFAOYSA-N 0.000 claims 1
- XXVJUOMHONVAEU-UHFFFAOYSA-N 1-(3-imidazol-1-ylpropyl)-5-phenylimidazolidine-2,4-dione Chemical compound C=1C=CC=CC=1C1C(=O)NC(=O)N1CCCN1C=CN=C1 XXVJUOMHONVAEU-UHFFFAOYSA-N 0.000 claims 1
- BFAULAUMYNQZCW-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-methyl-5-phenylimidazolidine-2,4-dione Chemical compound C=1C=C2N=CNC2=CC=1N1C(=O)N(C)C(=O)C1C1=CC=CC=C1 BFAULAUMYNQZCW-UHFFFAOYSA-N 0.000 claims 1
- NGJZDGZTGWZQHU-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-4-sulfanylidene-5-(2,3,4-trifluorophenyl)imidazolidin-2-one Chemical compound FC1=C(F)C(F)=CC=C1C1C(=S)NC(=O)N1C1=CC=C(NC=N2)C2=C1 NGJZDGZTGWZQHU-UHFFFAOYSA-N 0.000 claims 1
- BYZXAUWCXPMPDK-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-(2,1,3-benzothiadiazol-5-yl)-2-sulfanylideneimidazolidin-4-one Chemical compound C1=C2NC=NC2=CC(N2C(=S)NC(C2C2=CC3=NSN=C3C=C2)=O)=C1 BYZXAUWCXPMPDK-UHFFFAOYSA-N 0.000 claims 1
- QNIMPEFZOBTPAU-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-(2,1,3-benzothiadiazol-5-yl)imidazolidine-2,4-dione Chemical compound C1=C2NC=NC2=CC(N2C(=O)NC(C2C2=CC3=NSN=C3C=C2)=O)=C1 QNIMPEFZOBTPAU-UHFFFAOYSA-N 0.000 claims 1
- AZZFRDKXGUGTRC-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-(2,3-difluoro-4-methylphenyl)-4-sulfanylideneimidazolidin-2-one Chemical compound FC1=C(F)C(C)=CC=C1C1C(=S)NC(=O)N1C1=CC=C(NC=N2)C2=C1 AZZFRDKXGUGTRC-UHFFFAOYSA-N 0.000 claims 1
- AJUGSLXCFBLQHE-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-(2,3-dihydro-1,4-benzodioxin-6-yl)imidazolidine-2,4-dione Chemical compound C1=C2NC=NC2=CC(N2C(=O)NC(C2C=2C=C3OCCOC3=CC=2)=O)=C1 AJUGSLXCFBLQHE-UHFFFAOYSA-N 0.000 claims 1
- TXBCOCGENUWIHP-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-(2-bromo-5-fluorophenyl)imidazolidine-2,4-dione Chemical compound FC1=CC=C(Br)C(C2C(NC(=O)N2C=2C=C3N=CNC3=CC=2)=O)=C1 TXBCOCGENUWIHP-UHFFFAOYSA-N 0.000 claims 1
- PHTVQKCBKDWZBY-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-(2-chlorophenyl)imidazolidine-2,4-dione Chemical compound ClC1=CC=CC=C1C1C(=O)NC(=O)N1C1=CC=C(NC=N2)C2=C1 PHTVQKCBKDWZBY-UHFFFAOYSA-N 0.000 claims 1
- VNSPICHGRNGTIL-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-(2-hydroxy-3-methoxyphenyl)imidazolidine-2,4-dione Chemical compound COC1=CC=CC(C2C(NC(=O)N2C=2C=C3N=CNC3=CC=2)=O)=C1O VNSPICHGRNGTIL-UHFFFAOYSA-N 0.000 claims 1
- NTNRIUAFBHODRG-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-(2-hydroxy-5-methylphenyl)imidazolidine-2,4-dione Chemical compound CC1=CC=C(O)C(C2C(NC(=O)N2C=2C=C3N=CNC3=CC=2)=O)=C1 NTNRIUAFBHODRG-UHFFFAOYSA-N 0.000 claims 1
- WADYLOHJJCSTAF-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-(3-chlorophenyl)imidazolidine-2,4-dione Chemical compound ClC1=CC=CC(C2C(NC(=O)N2C=2C=C3N=CNC3=CC=2)=O)=C1 WADYLOHJJCSTAF-UHFFFAOYSA-N 0.000 claims 1
- PDLPFLLSLKPGSQ-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-(3-hydroxy-4-methoxyphenyl)-2-sulfanylideneimidazolidin-4-one Chemical compound C1=C(O)C(OC)=CC=C1C1C(=O)NC(=S)N1C1=CC=C(NC=N2)C2=C1 PDLPFLLSLKPGSQ-UHFFFAOYSA-N 0.000 claims 1
- JWLPLQZPWGTGDM-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-(3-hydroxy-4-methoxyphenyl)imidazolidine-2,4-dione Chemical compound C1=C(O)C(OC)=CC=C1C1C(=O)NC(=O)N1C1=CC=C(NC=N2)C2=C1 JWLPLQZPWGTGDM-UHFFFAOYSA-N 0.000 claims 1
- CVLWWSXQLNSNGF-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-(4-bromo-2-fluorophenyl)-4-sulfanylideneimidazolidin-2-one Chemical compound FC1=CC(Br)=CC=C1C1C(=S)NC(=O)N1C1=CC=C(N=CN2)C2=C1 CVLWWSXQLNSNGF-UHFFFAOYSA-N 0.000 claims 1
- JIVXZMFLCFNNBY-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-(4-chloro-3-methylphenyl)-4-sulfanylideneimidazolidin-2-one Chemical compound C1=C(Cl)C(C)=CC(C2C(NC(=O)N2C=2C=C3N=CNC3=CC=2)=S)=C1 JIVXZMFLCFNNBY-UHFFFAOYSA-N 0.000 claims 1
- XPTXSMOWEGMJQC-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-(4-chlorophenyl)-4-sulfanylideneimidazolidin-2-one Chemical compound C1=CC(Cl)=CC=C1C1C(=S)NC(=O)N1C1=CC=C(NC=N2)C2=C1 XPTXSMOWEGMJQC-UHFFFAOYSA-N 0.000 claims 1
- ROKHRVRZZBNKGJ-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-(4-chlorophenyl)imidazolidine-2,4-dione Chemical compound C1=CC(Cl)=CC=C1C1C(=O)NC(=O)N1C1=CC=C(NC=N2)C2=C1 ROKHRVRZZBNKGJ-UHFFFAOYSA-N 0.000 claims 1
- CEZNAXCARYIAEU-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-(4-fluorophenyl)imidazolidine-2,4-dione Chemical compound C1=CC(F)=CC=C1C1C(=O)NC(=O)N1C1=CC=C(NC=N2)C2=C1 CEZNAXCARYIAEU-UHFFFAOYSA-N 0.000 claims 1
- JABHGIDIXZRVDN-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-(4-phenylphenyl)-2-sulfanylideneimidazolidin-4-one Chemical compound O=C1NC(=S)N(C=2C=C3N=CNC3=CC=2)C1C(C=C1)=CC=C1C1=CC=CC=C1 JABHGIDIXZRVDN-UHFFFAOYSA-N 0.000 claims 1
- JPGWSJPHNNPVIP-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-(4-phenylphenyl)-4-sulfanylideneimidazolidin-2-one Chemical compound C=1C=C2NC=NC2=CC=1N1C(=O)NC(=S)C1C(C=C1)=CC=C1C1=CC=CC=C1 JPGWSJPHNNPVIP-UHFFFAOYSA-N 0.000 claims 1
- HEXVNBQITIFOKU-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-(4-phenylphenyl)imidazolidine-2,4-dione Chemical compound O=C1NC(=O)N(C=2C=C3N=CNC3=CC=2)C1C(C=C1)=CC=C1C1=CC=CC=C1 HEXVNBQITIFOKU-UHFFFAOYSA-N 0.000 claims 1
- GTFPAKYEYXNXOT-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-(4-propoxyphenyl)imidazolidine-2,4-dione Chemical compound C1=CC(OCCC)=CC=C1C1C(=O)NC(=O)N1C1=CC=C(NC=N2)C2=C1 GTFPAKYEYXNXOT-UHFFFAOYSA-N 0.000 claims 1
- SJNCPVKBIRFHDW-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-[3-fluoro-4-(trifluoromethyl)phenyl]imidazolidine-2,4-dione Chemical compound C1=C(C(F)(F)F)C(F)=CC(C2C(NC(=O)N2C=2C=C3N=CNC3=CC=2)=O)=C1 SJNCPVKBIRFHDW-UHFFFAOYSA-N 0.000 claims 1
- RERCJFJTRNJPCK-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-phenyl-2-sulfanylideneimidazolidin-4-one Chemical compound O=C1NC(=S)N(C=2C=C3N=CNC3=CC=2)C1C1=CC=CC=C1 RERCJFJTRNJPCK-UHFFFAOYSA-N 0.000 claims 1
- OBUJIRSEIQGFOA-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-phenyl-4-sulfanylideneimidazolidin-2-one Chemical compound C=1C=C2NC=NC2=CC=1N1C(=O)NC(=S)C1C1=CC=CC=C1 OBUJIRSEIQGFOA-UHFFFAOYSA-N 0.000 claims 1
- HZEIAWPYZBVCBW-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-5-phenylimidazolidine-2,4-dione Chemical compound O=C1NC(=O)N(C=2C=C3N=CNC3=CC=2)C1C1=CC=CC=C1 HZEIAWPYZBVCBW-UHFFFAOYSA-N 0.000 claims 1
- CTQKNEDJEFNYQB-UHFFFAOYSA-N 1-[3-(4-methylimidazol-1-yl)propyl]-5-phenylimidazolidine-2,4-dione Chemical compound C1=NC(C)=CN1CCCN1C(=O)NC(=O)C1C1=CC=CC=C1 CTQKNEDJEFNYQB-UHFFFAOYSA-N 0.000 claims 1
- AZUMTGCYMDJDNF-UHFFFAOYSA-N 1-[3-(5-methylimidazol-1-yl)propyl]-5-(4-phenylphenyl)imidazolidine-2,4-dione Chemical compound CC1=CN=CN1CCCN1C(=O)NC(=O)C1C1=CC=C(C=2C=CC=CC=2)C=C1 AZUMTGCYMDJDNF-UHFFFAOYSA-N 0.000 claims 1
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| US20110152341A1 (en) | 2009-12-22 | 2011-06-23 | Probiodrug Ag | Cleavage of b-amyloid precursor protein |
| EP2686313B1 (en) * | 2011-03-16 | 2016-02-03 | Probiodrug AG | Benzimidazole derivatives as inhibitors of glutaminyl cyclase |
| CN103561776B (zh) | 2011-05-27 | 2016-08-31 | 前体生物药物股份公司 | 放射性标记的谷氨酰胺酰环化酶抑制剂 |
| CA2904465C (en) | 2013-03-15 | 2021-07-13 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| US20170363645A1 (en) | 2014-12-19 | 2017-12-21 | Probiodrug Ag | Novel Method for the Detection of pGlu-Abeta Peptides |
| CN108658869A (zh) * | 2017-03-29 | 2018-10-16 | 复旦大学 | 具有抗肿瘤活性的化合物及其制备方法和在制药中的用途 |
| GB201705263D0 (en) * | 2017-03-31 | 2017-05-17 | Probiodrug Ag | Novel inhibitors |
| RU2665633C1 (ru) * | 2017-05-26 | 2018-09-03 | Общество С Ограниченной Ответственностью "Фарминтерпрайсез" | Новый ингибитор глутаминилциклаз и его применение |
| RU2662559C1 (ru) * | 2017-10-27 | 2018-07-26 | Общество С Ограниченной Ответственностью "Фарминтерпрайсез" | Новый ингибитор глутаминилциклаз и его применение для лечения заболеваний легких и дыхательных путей |
| PL3461819T3 (pl) * | 2017-09-29 | 2020-11-30 | Probiodrug Ag | Inhibitory cyklazy glutaminylowej |
| EP3521308B1 (en) | 2018-01-31 | 2024-03-13 | Vivoryon Therapeutics N.V. | Humanized and de-immunized antibodies |
| KR102743609B1 (ko) * | 2018-02-23 | 2024-12-16 | 프라운호퍼-게젤샤프트 츄어 푀르더룽 데어 안게반텐 포르슝에.파우. | 치주 및 관련 질환의 치료에 사용하기 위한 박테리아 글루타미닐 사이클라제에 대한 새로운 저해제 |
| TWI715156B (zh) | 2018-08-31 | 2021-01-01 | 財團法人國家衛生研究院 | 苯并咪唑化合物及其用於治療阿茲海默症或亨丁頓氏症之用途 |
| WO2020242933A1 (en) * | 2019-05-24 | 2020-12-03 | Emory University | Asparagine endopeptidase (aep) inhibitors, compositions, and uses related thereto |
| WO2021009068A1 (en) * | 2019-07-12 | 2021-01-21 | Scenic Immunology B.V. | N-substituted-3,4-(fused 5-ring)-5-phenyl-pyrrolidine-2-one compounds as inhibitors of isoqc and/or qc enzyme |
| JP2024523552A (ja) | 2021-06-24 | 2024-06-28 | インシリコ メディシン アイピー リミテッド | 疾患の処置のためのベータ－ラクタム誘導体 |
| WO2025021012A1 (en) * | 2023-07-21 | 2025-01-30 | Insilico Medicine Ip Limited | Crystalline beta-lactam derivatives and uses thereof |
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| DD293584A5 (de) * | 1990-03-23 | 1991-09-05 | Adw,Zi Fuer Organische Chemie,De | Verfahren zur herstellung von neuen 3,5,5-trisubstituierten 1-(benzimidazol-2-yl)-imidazolidin-2,4-dionen bzw. -4-on-2-thionen |
| DE4320432A1 (de) * | 1993-06-21 | 1994-12-22 | Bayer Ag | Substituierte Mono- und Bipyridylmethylderivate |
| US20040006011A1 (en) * | 1996-07-12 | 2004-01-08 | Gour Barbara J. | Peptidomimetic modulators of cell adhesion |
| HUP0002037A3 (en) | 1997-07-31 | 2001-07-30 | Abbott Lab | Hydroximic acid derivatives, use of them for producing pharmaceutical compositions suitable for inhibiting matrix metalloproteinas and pharmaceutical compositions containing the compounds |
| US6235786B1 (en) * | 1997-08-06 | 2001-05-22 | Abbott Laboratories | Reverse hydroxamate inhibitors of matrix metalloproteinases |
| DE602004026289D1 (de) * | 2003-05-05 | 2010-05-12 | Probiodrug Ag | Glutaminylcyclase-hemmer |
| AU2005210004B2 (en) * | 2004-02-05 | 2010-10-28 | Probiodrug Ag | Novel inhibitors of glutaminyl cyclase |
| US7795287B2 (en) | 2006-09-01 | 2010-09-14 | Allergan, Inc. | Therapeutic substituted hydantoins and related compounds |
| MX2009003090A (es) * | 2006-09-21 | 2009-04-02 | Probiodrug Ag | Genes novedosos relacionados con ciclasa de glutaminilo. |
| WO2008055947A1 (en) * | 2006-11-09 | 2008-05-15 | Probiodrug Ag | Novel inhibitors of glutaminyl cyclase |
| TW200831080A (en) | 2006-12-15 | 2008-08-01 | Irm Llc | Compounds and compositions as inhibitors of cannabinoid receptor 1 activity |
| CN101519376B (zh) * | 2008-02-27 | 2012-10-10 | 上海药明康德新药开发有限公司 | 一种芳香环双酰胺螺环类药物模板的合成方法 |
| WO2010026209A1 (en) | 2008-09-04 | 2010-03-11 | Probiodrug Ag | Use of isoQC inhibitors |
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