MX2011002106A - Inhibidores novedosos. - Google Patents
Inhibidores novedosos.Info
- Publication number
- MX2011002106A MX2011002106A MX2011002106A MX2011002106A MX2011002106A MX 2011002106 A MX2011002106 A MX 2011002106A MX 2011002106 A MX2011002106 A MX 2011002106A MX 2011002106 A MX2011002106 A MX 2011002106A MX 2011002106 A MX2011002106 A MX 2011002106A
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- imidazol
- dione
- phenyl
- benzo
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title claims abstract description 185
- 150000001875 compounds Chemical class 0.000 claims abstract description 250
- -1 cyano, hydroxyl Chemical group 0.000 claims description 244
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 102
- 238000000034 method Methods 0.000 claims description 91
- 125000001072 heteroaryl group Chemical group 0.000 claims description 65
- 239000003814 drug Substances 0.000 claims description 55
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 50
- 239000003795 chemical substances by application Substances 0.000 claims description 39
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 230000002265 prevention Effects 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 26
- 230000015572 biosynthetic process Effects 0.000 claims description 24
- 201000010099 disease Diseases 0.000 claims description 23
- 102000004190 Enzymes Human genes 0.000 claims description 21
- 108090000790 Enzymes Proteins 0.000 claims description 21
- 229940088598 enzyme Drugs 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 21
- 230000033228 biological regulation Effects 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims description 18
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims description 18
- 206010012289 Dementia Diseases 0.000 claims description 18
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
- 125000002950 monocyclic group Chemical group 0.000 claims description 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 208000024827 Alzheimer disease Diseases 0.000 claims description 15
- 201000006417 multiple sclerosis Diseases 0.000 claims description 15
- 201000001320 Atherosclerosis Diseases 0.000 claims description 14
- 210000004027 cell Anatomy 0.000 claims description 14
- 229940079593 drug Drugs 0.000 claims description 14
- 102000005962 receptors Human genes 0.000 claims description 14
- 108020003175 receptors Proteins 0.000 claims description 14
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- 230000004770 neurodegeneration Effects 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 230000006870 function Effects 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 208000037803 restenosis Diseases 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 238000003786 synthesis reaction Methods 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 125000002619 bicyclic group Chemical group 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 11
- 229910052979 sodium sulfide Inorganic materials 0.000 claims description 11
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 11
- 239000002439 beta secretase inhibitor Substances 0.000 claims description 10
- 230000001771 impaired effect Effects 0.000 claims description 10
- 239000000969 carrier Substances 0.000 claims description 9
- 208000010877 cognitive disease Diseases 0.000 claims description 9
- 239000003540 gamma secretase inhibitor Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 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 description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
- 230000003284 homeostatic effect Effects 0.000 claims description 8
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims description 8
- 208000027061 mild cognitive impairment Diseases 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 206010033645 Pancreatitis Diseases 0.000 claims description 7
- 125000005605 benzo group Chemical group 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 230000005012 migration Effects 0.000 claims description 7
- 238000013508 migration Methods 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 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 description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims description 6
- 206010019375 Helicobacter infections Diseases 0.000 claims description 6
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims description 6
- 229930012538 Paclitaxel Natural products 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims description 6
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims description 6
- 239000000164 antipsychotic agent Substances 0.000 claims description 6
- 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 description 6
- 210000003038 endothelium Anatomy 0.000 claims description 6
- 230000037149 energy metabolism Effects 0.000 claims description 6
- 230000037406 food intake Effects 0.000 claims description 6
- 235000012631 food intake Nutrition 0.000 claims description 6
- 230000003054 hormonal effect Effects 0.000 claims description 6
- 230000002757 inflammatory effect Effects 0.000 claims description 6
- 230000009826 neoplastic cell growth Effects 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 229960001592 paclitaxel Drugs 0.000 claims description 6
- 230000004044 response Effects 0.000 claims description 6
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims description 5
- 102000009091 Amyloidogenic Proteins Human genes 0.000 claims description 5
- 108010048112 Amyloidogenic Proteins Proteins 0.000 claims description 5
- 206010009944 Colon cancer Diseases 0.000 claims description 5
- 208000023105 Huntington disease Diseases 0.000 claims description 5
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 206010017758 gastric cancer Diseases 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 239000011159 matrix material Substances 0.000 claims description 5
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- 230000009467 reduction Effects 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- 201000011549 stomach cancer Diseases 0.000 claims description 5
- 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 description 4
- 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 description 4
- 102000012440 Acetylcholinesterase Human genes 0.000 claims description 4
- 108010022752 Acetylcholinesterase Proteins 0.000 claims description 4
- 206010057645 Chronic Inflammatory Demyelinating Polyradiculoneuropathy Diseases 0.000 claims description 4
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- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 4
- 206010061825 Duodenal neoplasm Diseases 0.000 claims description 4
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- 229940127523 NMDA Receptor Antagonists Drugs 0.000 claims description 4
- 206010062519 Poor quality sleep Diseases 0.000 claims description 4
- 102100031674 Protein-L-isoaspartate(D-aspartate) O-methyltransferase Human genes 0.000 claims description 4
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- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
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- 210000000265 leukocyte Anatomy 0.000 claims description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 4
- 230000003211 malignant effect Effects 0.000 claims description 4
- 230000009401 metastasis Effects 0.000 claims description 4
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- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 108010018276 trimethylguanosine synthase Proteins 0.000 claims description 4
- 239000002452 tumor necrosis factor alpha inhibitor Substances 0.000 claims description 4
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- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 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 3
- OTCASTOVNBEOFF-UHFFFAOYSA-N 5-(3-chlorophenyl)-1-(3-imidazol-1-ylpropyl)imidazolidine-2,4-dione Chemical compound ClC1=CC=CC(C2C(NC(=O)N2CCCN2C=NC=C2)=O)=C1 OTCASTOVNBEOFF-UHFFFAOYSA-N 0.000 claims description 3
- FPHHWBQEXLHUNV-UHFFFAOYSA-N 5-[3-fluoro-4-(trifluoromethyl)phenyl]-1-(3-imidazol-1-ylpropyl)imidazolidine-2,4-dione Chemical compound C1=C(C(F)(F)F)C(F)=CC(C2C(NC(=O)N2CCCN2C=NC=C2)=O)=C1 FPHHWBQEXLHUNV-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
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- 239000003395 histamine H3 receptor antagonist Substances 0.000 claims description 3
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
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- NDFPNCHSKYNNSQ-UHFFFAOYSA-N spiro[imidazolidine-5,2'-indene]-2,4-dione Chemical compound N1C(=O)NC(=O)C21C=C1C=CC=CC1=C2 NDFPNCHSKYNNSQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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| PL2475428T3 (pl) | 2009-09-11 | 2015-12-31 | Probiodrug Ag | Pochodne heterocykliczne jako inhibitory cyklazy glutaminowej |
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| KR20210091830A (ko) | 2013-03-15 | 2021-07-22 | 비보리온 테라퓨틱스 아게 | 신규한 억제제 |
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| 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 |
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| 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 |
| JP7301862B2 (ja) * | 2018-02-23 | 2023-07-03 | フラウンホーファー－ゲゼルシャフト ツル フェルデルング デル アンゲヴァンテン フォルシュング エー ファウ | 歯周病及び関連疾患の治療に用いる細菌性グルタミニルシクラーゼの新規阻害剤 |
| 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 |
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| WO2025021012A1 (en) * | 2023-07-21 | 2025-01-30 | Insilico Medicine Ip Limited | Crystalline beta-lactam derivatives and uses thereof |
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| EP2344157A1 (en) | 2011-07-20 |
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