JP2010524896A5 - - Google Patents
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- Publication number
- JP2010524896A5 JP2010524896A5 JP2010503513A JP2010503513A JP2010524896A5 JP 2010524896 A5 JP2010524896 A5 JP 2010524896A5 JP 2010503513 A JP2010503513 A JP 2010503513A JP 2010503513 A JP2010503513 A JP 2010503513A JP 2010524896 A5 JP2010524896 A5 JP 2010524896A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- imidazol
- propyl
- amine
- optionally substituted
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 76
- 150000001875 compounds Chemical class 0.000 claims 35
- 125000004452 carbocyclyl group Chemical group 0.000 claims 13
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 11
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 8
- -1 cyano, hydroxyl Chemical group 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 239000003112 inhibitor Substances 0.000 claims 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000004001 thioalkyl group Chemical group 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 206010019375 Helicobacter infections Diseases 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims 4
- 230000001771 impaired effect Effects 0.000 claims 4
- 230000002757 inflammatory effect Effects 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000003107 substituted aryl group Chemical group 0.000 claims 4
- 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
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 201000006417 multiple sclerosis Diseases 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 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
- 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
- 206010003840 Autonomic nervous system imbalance 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
- 201000011510 cancer Diseases 0.000 claims 2
- 239000003795 chemical substances by application Substances 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
- 235000014632 disordered eating Nutrition 0.000 claims 2
- 201000000312 duodenum cancer Diseases 0.000 claims 2
- 230000037149 energy metabolism Effects 0.000 claims 2
- 239000012530 fluid Substances 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
- 208000027061 mild cognitive impairment Diseases 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000006473 polyradiculopathy Diseases 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
- KLNUKMASIFIMTH-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-(3-imidazol-1-ylpropyl)-6-phenylpyrimidin-4-amine Chemical compound C1=CC(Cl)=CC=C1C1=NC(NCCCN2C=NC=C2)=CC(C=2C=CC=CC=2)=N1 KLNUKMASIFIMTH-UHFFFAOYSA-N 0.000 claims 1
- UBSWNUSPOFXZAA-UHFFFAOYSA-N 2-(furan-2-yl)-n-(3-imidazol-1-ylpropyl)-6-pyrazol-1-ylpyrimidin-4-amine Chemical compound C1=CN=CN1CCCNC(N=1)=CC(N2N=CC=C2)=NC=1C1=CC=CO1 UBSWNUSPOFXZAA-UHFFFAOYSA-N 0.000 claims 1
- FRHDUYFANXEKNH-UHFFFAOYSA-N 2-methyl-n-[3-(5-methylimidazol-1-yl)propyl]-6-(3,4,5-trimethoxyphenyl)pyrimidin-4-amine Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C(C)N=C(NCCCN3C(=CN=C3)C)C=2)=C1 FRHDUYFANXEKNH-UHFFFAOYSA-N 0.000 claims 1
- CGFPKHGSCPYKMK-UHFFFAOYSA-N 6-(2,3-dihydro-1h-inden-2-yl)-n-(3-imidazol-1-ylpropyl)-2-methylpyrimidin-4-amine Chemical compound C=1C(C2CC3=CC=CC=C3C2)=NC(C)=NC=1NCCCN1C=CN=C1 CGFPKHGSCPYKMK-UHFFFAOYSA-N 0.000 claims 1
- ZWMOLIFFRPYLDS-UHFFFAOYSA-N 6-(2,3-dihydro-1h-inden-2-yl)-n-(3-imidazol-1-ylpropyl)-2-pyridin-4-ylpyrimidin-4-amine Chemical class C1=CN=CN1CCCNC(N=1)=CC(C2CC3=CC=CC=C3C2)=NC=1C1=CC=NC=C1 ZWMOLIFFRPYLDS-UHFFFAOYSA-N 0.000 claims 1
- YPGXAKDORHNMEY-UHFFFAOYSA-N 6-(2-methoxyphenyl)-n-[3-(5-methylimidazol-1-yl)propyl]-2-pyridin-4-ylpyrimidin-4-amine Chemical compound COC1=CC=CC=C1C1=CC(NCCCN2C(=CN=C2)C)=NC(C=2C=CN=CC=2)=N1 YPGXAKDORHNMEY-UHFFFAOYSA-N 0.000 claims 1
- MEVYRWLBGMQJQC-UHFFFAOYSA-N 6-(furan-3-yl)-n-(3-imidazol-1-ylpropyl)-2-phenylpyrimidin-4-amine Chemical compound C1=CN=CN1CCCNC(N=1)=CC(C2=COC=C2)=NC=1C1=CC=CC=C1 MEVYRWLBGMQJQC-UHFFFAOYSA-N 0.000 claims 1
- ZDPXFNARQPFZGX-UHFFFAOYSA-N 6-(furan-3-yl)-n-(3-imidazol-1-ylpropyl)-2-pyridin-4-ylpyrimidin-4-amine Chemical compound C1=CN=CN1CCCNC(N=1)=CC(C2=COC=C2)=NC=1C1=CC=NC=C1 ZDPXFNARQPFZGX-UHFFFAOYSA-N 0.000 claims 1
- JIWPQRASWODEKU-UHFFFAOYSA-N 6-[3,5-bis(trifluoromethyl)phenyl]-n-(3-imidazol-1-ylpropyl)-2-methylpyrimidin-4-amine Chemical compound C=1C(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=NC(C)=NC=1NCCCN1C=CN=C1 JIWPQRASWODEKU-UHFFFAOYSA-N 0.000 claims 1
- JVULGDUOFGJANF-UHFFFAOYSA-N 6-[3,5-bis(trifluoromethyl)phenyl]-n-(3-imidazol-1-ylpropyl)-2-phenylpyrimidin-4-amine Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C=2N=C(N=C(NCCCN3C=NC=C3)C=2)C=2C=CC=CC=2)=C1 JVULGDUOFGJANF-UHFFFAOYSA-N 0.000 claims 1
- YNMYANMKYQHCMD-UHFFFAOYSA-N 6-[3,5-bis(trifluoromethyl)phenyl]-n-(3-imidazol-1-ylpropyl)-2-pyridin-4-ylpyrimidin-4-amine Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C=2N=C(N=C(NCCCN3C=NC=C3)C=2)C=2C=CN=CC=2)=C1 YNMYANMKYQHCMD-UHFFFAOYSA-N 0.000 claims 1
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims 1
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims 1
- 102000009091 Amyloidogenic Proteins Human genes 0.000 claims 1
- 108010048112 Amyloidogenic Proteins Proteins 0.000 claims 1
- 208000012639 Balance disease Diseases 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 229940125373 Gamma-Secretase Inhibitor Drugs 0.000 claims 1
- 101710144961 Interferon tau-1 Proteins 0.000 claims 1
- 101710144950 Interferon tau-2 Proteins 0.000 claims 1
- 101710144962 Interferon tau-3 Proteins 0.000 claims 1
- 102000004388 Interleukin-4 Human genes 0.000 claims 1
- 108090000978 Interleukin-4 Proteins 0.000 claims 1
- 229940082332 Muscarinic M1 receptor antagonist Drugs 0.000 claims 1
- 108010008881 NBI 5788 Proteins 0.000 claims 1
- 229940127523 NMDA Receptor Antagonists Drugs 0.000 claims 1
- 229930012538 Paclitaxel Natural products 0.000 claims 1
- 102100031674 Protein-L-isoaspartate(D-aspartate) O-methyltransferase Human genes 0.000 claims 1
- 102100028656 Sigma non-opioid intracellular receptor 1 Human genes 0.000 claims 1
- 101710104750 Sigma non-opioid intracellular receptor 1 Proteins 0.000 claims 1
- 229960000548 alemtuzumab Drugs 0.000 claims 1
- 229940035678 anti-parkinson drug Drugs 0.000 claims 1
- 239000000935 antidepressant agent Substances 0.000 claims 1
- 229940005513 antidepressants Drugs 0.000 claims 1
- 239000000939 antiparkinson agent Substances 0.000 claims 1
- 239000000164 antipsychotic agent Substances 0.000 claims 1
- 229940005529 antipsychotics Drugs 0.000 claims 1
- 239000002249 anxiolytic agent Substances 0.000 claims 1
- 230000000949 anxiolytic effect Effects 0.000 claims 1
- 229940005530 anxiolytics Drugs 0.000 claims 1
- 239000002439 beta secretase inhibitor Substances 0.000 claims 1
- 230000033228 biological regulation Effects 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 230000008021 deposition Effects 0.000 claims 1
- 229940002658 differin Drugs 0.000 claims 1
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- 208000035475 disorder Diseases 0.000 claims 1
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- 230000008482 dysregulation Effects 0.000 claims 1
- 239000003623 enhancer Substances 0.000 claims 1
- 239000002792 enkephalinase inhibitor Substances 0.000 claims 1
- 229940088598 enzyme Drugs 0.000 claims 1
- 239000002532 enzyme inhibitor Substances 0.000 claims 1
- 229940125532 enzyme inhibitor Drugs 0.000 claims 1
- 239000003540 gamma secretase inhibitor Substances 0.000 claims 1
- 239000003395 histamine H3 receptor antagonist Substances 0.000 claims 1
- 239000002955 immunomodulating agent Substances 0.000 claims 1
- 229940121354 immunomodulator Drugs 0.000 claims 1
- 229960003444 immunosuppressant agent Drugs 0.000 claims 1
- 239000003018 immunosuppressive agent Substances 0.000 claims 1
- 108700027921 interferon tau Proteins 0.000 claims 1
- 229940028885 interleukin-4 Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940121386 matrix metalloproteinase inhibitor Drugs 0.000 claims 1
- 239000003771 matrix metalloproteinase inhibitor Substances 0.000 claims 1
- 239000000234 muscarinic M1 receptor antagonist Substances 0.000 claims 1
- GHRVPNUEJJFASZ-UHFFFAOYSA-N n-(2-phenyl-6-quinolin-6-ylpyrimidin-4-yl)-3h-benzimidazol-5-amine Chemical compound C=1C=C2N=CNC2=CC=1NC(N=1)=CC(C=2C=C3C=CC=NC3=CC=2)=NC=1C1=CC=CC=C1 GHRVPNUEJJFASZ-UHFFFAOYSA-N 0.000 claims 1
- OXDJBYWDTCMJHW-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2,6-dimethylpyrimidin-4-amine Chemical compound CC1=NC(C)=CC(NCCCN2C=NC=C2)=N1 OXDJBYWDTCMJHW-UHFFFAOYSA-N 0.000 claims 1
- ZKJIRKYSFMMWPY-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2,6-diphenylpyrimidin-4-amine Chemical compound C1=CN=CN1CCCNC(N=1)=CC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 ZKJIRKYSFMMWPY-UHFFFAOYSA-N 0.000 claims 1
- LHUGBBATCXMIAZ-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-methyl-6-(3,4,5-trimethoxyphenyl)pyrimidin-4-amine Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C(C)N=C(NCCCN3C=NC=C3)C=2)=C1 LHUGBBATCXMIAZ-UHFFFAOYSA-N 0.000 claims 1
- IQZNYWHHEHGXJX-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-methyl-6-(4-methylphenyl)pyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1C1=CC(NCCCN2C=NC=C2)=NC(C)=N1 IQZNYWHHEHGXJX-UHFFFAOYSA-N 0.000 claims 1
- MNJKYKBTJOBIMX-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-methyl-6-phenylpyrimidin-4-amine Chemical compound C=1C(C=2C=CC=CC=2)=NC(C)=NC=1NCCCN1C=CN=C1 MNJKYKBTJOBIMX-UHFFFAOYSA-N 0.000 claims 1
- SMOBROKINILSLN-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-methyl-6-quinolin-6-ylpyrimidin-4-amine Chemical compound C=1C(C=2C=C3C=CC=NC3=CC=2)=NC(C)=NC=1NCCCN1C=CN=C1 SMOBROKINILSLN-UHFFFAOYSA-N 0.000 claims 1
- YEPGSQOAAXXYNV-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-phenyl-6-(2-phenylcyclopropyl)pyrimidin-4-amine Chemical compound C1=CN=CN1CCCNC(N=1)=CC(C2C(C2)C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 YEPGSQOAAXXYNV-UHFFFAOYSA-N 0.000 claims 1
- DGQVFUXKZIWSIV-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-phenyl-6-(3,4,5-trimethoxyphenyl)pyrimidin-4-amine Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C(N=C(NCCCN3C=NC=C3)C=2)C=2C=CC=CC=2)=C1 DGQVFUXKZIWSIV-UHFFFAOYSA-N 0.000 claims 1
- MBKUMYMDKWAWPI-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-phenyl-6-(trifluoromethyl)pyrimidin-4-amine Chemical compound N=1C(C=2C=CC=CC=2)=NC(C(F)(F)F)=CC=1NCCCN1C=CN=C1 MBKUMYMDKWAWPI-UHFFFAOYSA-N 0.000 claims 1
- GWCIZWFQLMKPQX-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-pyridin-4-yl-6-(3,4,5-trimethoxyphenyl)pyrimidin-4-amine Chemical compound COC1=C(OC)C(OC)=CC(C=2N=C(N=C(NCCCN3C=NC=C3)C=2)C=2C=CN=CC=2)=C1 GWCIZWFQLMKPQX-UHFFFAOYSA-N 0.000 claims 1
- BCJFFAJBTSTZNX-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-2-pyridin-4-yl-6-(trifluoromethyl)pyrimidin-4-amine Chemical compound N=1C(C=2C=CN=CC=2)=NC(C(F)(F)F)=CC=1NCCCN1C=CN=C1 BCJFFAJBTSTZNX-UHFFFAOYSA-N 0.000 claims 1
- RCMSWBFZWRTJOY-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-6-(2-methoxyphenyl)-2-methylpyrimidin-4-amine Chemical compound COC1=CC=CC=C1C1=CC(NCCCN2C=NC=C2)=NC(C)=N1 RCMSWBFZWRTJOY-UHFFFAOYSA-N 0.000 claims 1
- RXIHHUJNCHZXQB-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-6-(2-methoxyphenyl)-2-phenylpyrimidin-4-amine Chemical compound COC1=CC=CC=C1C1=CC(NCCCN2C=NC=C2)=NC(C=2C=CC=CC=2)=N1 RXIHHUJNCHZXQB-UHFFFAOYSA-N 0.000 claims 1
- SRKXUDWQCUODPB-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-6-(2-methoxyphenyl)-2-pyridin-4-ylpyrimidin-4-amine Chemical compound COC1=CC=CC=C1C1=CC(NCCCN2C=NC=C2)=NC(C=2C=CN=CC=2)=N1 SRKXUDWQCUODPB-UHFFFAOYSA-N 0.000 claims 1
- GVBYDYMSDOYAIA-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-6-(2-phenylcyclopropyl)-2-pyridin-4-ylpyrimidin-4-amine Chemical compound C1=CN=CN1CCCNC(N=1)=CC(C2C(C2)C=2C=CC=CC=2)=NC=1C1=CC=NC=C1 GVBYDYMSDOYAIA-UHFFFAOYSA-N 0.000 claims 1
- WNARQUVJVHGVAL-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-6-(3-methoxyphenyl)-2-methylpyrimidin-4-amine Chemical compound COC1=CC=CC(C=2N=C(C)N=C(NCCCN3C=NC=C3)C=2)=C1 WNARQUVJVHGVAL-UHFFFAOYSA-N 0.000 claims 1
- LZQVXUHKUQIMHX-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-6-(3-methoxyphenyl)-2-phenylpyrimidin-4-amine Chemical compound COC1=CC=CC(C=2N=C(N=C(NCCCN3C=NC=C3)C=2)C=2C=CC=CC=2)=C1 LZQVXUHKUQIMHX-UHFFFAOYSA-N 0.000 claims 1
- ZLGRWKXTEWISOQ-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-6-(3-methoxyphenyl)-2-pyridin-4-ylpyrimidin-4-amine Chemical compound COC1=CC=CC(C=2N=C(N=C(NCCCN3C=NC=C3)C=2)C=2C=CN=CC=2)=C1 ZLGRWKXTEWISOQ-UHFFFAOYSA-N 0.000 claims 1
- GXQQRDMRVLEGDC-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-6-(4-methoxyphenyl)-2-methylpyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C1=CC(NCCCN2C=NC=C2)=NC(C)=N1 GXQQRDMRVLEGDC-UHFFFAOYSA-N 0.000 claims 1
- PRAXDOWVRMEBDF-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-6-(4-methylphenyl)-2-phenylpyrimidin-4-amine Chemical compound C1=CC(C)=CC=C1C1=CC(NCCCN2C=NC=C2)=NC(C=2C=CC=CC=2)=N1 PRAXDOWVRMEBDF-UHFFFAOYSA-N 0.000 claims 1
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- LIAUJJATPRPDPX-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-6-(4-nitrophenyl)-2-phenylpyrimidin-4-amine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CC(NCCCN2C=NC=C2)=NC(C=2C=CC=CC=2)=N1 LIAUJJATPRPDPX-UHFFFAOYSA-N 0.000 claims 1
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| US7732162B2 (en) * | 2003-05-05 | 2010-06-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase for treating neurodegenerative diseases |
| US8889709B2 (en) * | 2006-09-21 | 2014-11-18 | Probiodrug Ag | Use of isoQC inhibitors in the treatment and prevention of inflammatory diseases or conditions |
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| CN102947705A (zh) | 2010-02-18 | 2013-02-27 | 前体生物药物股份公司 | 通过确定焦谷氨酸修饰的mcp-1诊断炎性疾病的方法和谷氨酰胺酰基环化酶抑制剂的筛选方法 |
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| WO2012149528A1 (en) * | 2011-04-29 | 2012-11-01 | Exelixis, Inc. | Inhibitors of inducible form of 6-phosphofructose-2-kinase |
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| CN105384692B (zh) * | 2015-10-26 | 2018-06-29 | 深圳大学 | 一种谷氨酰胺酰基环化酶抑制剂 |
| CN105384691B (zh) * | 2015-10-26 | 2018-06-29 | 深圳大学 | 一种谷氨酰胺酰基环化酶抑制剂的制备方法及应用 |
| CN106831713B (zh) * | 2017-01-13 | 2019-04-02 | 深圳大学 | 一种多靶点Aβ寡聚化抑制剂的合成方法及应用 |
| CN106831712B (zh) * | 2017-01-13 | 2019-04-02 | 深圳大学 | 一种多靶点Aβ寡聚化抑制剂 |
| 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 |
| CN108912051B (zh) * | 2018-08-23 | 2022-04-15 | 深圳大学 | 一种含有4-咪唑基的谷氨酰胺酰基环化酶抑制剂 |
| CN109305942B (zh) * | 2018-08-23 | 2022-04-22 | 深圳大学 | 一种含有4-咪唑基的谷氨酰胺酰基环化酶抑制剂的制备方法及应用 |
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| JPH0710870A (ja) | 1993-06-23 | 1995-01-13 | Asahi Glass Co Ltd | 新規アミノピリジン誘導体およびその塩 |
| DE19836697A1 (de) | 1998-08-13 | 2000-02-17 | Hoechst Marion Roussel De Gmbh | Substituierte 4-Amino-2-aryl-pyrimidine, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
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| WO2003026661A1 (fr) | 2001-09-14 | 2003-04-03 | Yamanouchi Pharmaceutical Co., Ltd. | Accelerateur de secretion de l'insuline et nouveau derive de pyrimidine |
| WO2004041814A1 (en) | 2002-11-04 | 2004-05-21 | Vertex Pharmaceuticals Incorporated | Heteroaryl-pyramidine derivatives as jak inhibitors |
| CA2507100C (en) * | 2002-11-21 | 2012-10-09 | Chiron Corporation | 2,4,6-trisubstituted pyrimidines as phosphotidylinositol (pi) 3-kinase inhibitors and their use in the treatment of cancer |
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| US7732162B2 (en) | 2003-05-05 | 2010-06-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase for treating neurodegenerative diseases |
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| DE602004026289D1 (de) * | 2003-05-05 | 2010-05-12 | Probiodrug Ag | Glutaminylcyclase-hemmer |
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| JO2660B1 (en) * | 2006-01-20 | 2012-06-17 | نوفارتيس ايه جي | Pi-3 inhibitors and methods of use |
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| US8420684B2 (en) | 2006-11-09 | 2013-04-16 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| ES2481442T3 (es) | 2006-11-09 | 2014-07-30 | Probiodrug Ag | Inhibidores novedosos de glutaminil ciclasa |
| SI2091948T1 (sl) | 2006-11-30 | 2012-07-31 | Probiodrug Ag | Novi inhibitorji glutaminil ciklaze |
| AU2008206936B2 (en) | 2007-01-19 | 2013-03-14 | Probiodrug Ag | In vivo screening models for treatment of Alzheimer's disease and other Qpct-related disorders |
| JP5612860B2 (ja) | 2007-03-09 | 2014-10-22 | プロビオドルグ エージー | グルタミニルシクラーゼ阻害剤としてのイミダゾ［１，５−ａ］ピリジン誘導体 |
| WO2008128986A1 (en) | 2007-04-18 | 2008-10-30 | Probiodrug Ag | Urea derivatives as glutaminyl cyclase inhibitors |
| ES2473621T3 (es) | 2007-04-18 | 2014-07-07 | Probiodrug Ag | Derivados de nitrovinil-diamina como inhibidores de glutaminil ciclasa |
| WO2008128983A1 (en) | 2007-04-18 | 2008-10-30 | Probiodrug Ag | Cyano-guanidine derivatives as glutaminyl cyclase inhibitors |
| JP5675341B2 (ja) | 2007-04-18 | 2015-02-25 | プロビオドルグ エージー | グルタミニルシクラーゼ阻害剤としてのチオキソキナゾリノン誘導体 |
| DK2142514T3 (da) | 2007-04-18 | 2015-03-23 | Probiodrug Ag | Thioureaderivater som glutaminylcyclase-inhibitorer |
| JP5675340B2 (ja) | 2007-04-18 | 2015-02-25 | プロビオドルグ エージー | 新規阻害剤 |
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2008
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- 2008-04-18 US US12/105,832 patent/US8188094B2/en not_active Expired - Fee Related
- 2008-04-18 JP JP2010503513A patent/JP5676249B2/ja not_active Expired - Fee Related
- 2008-04-18 EP EP08736363.6A patent/EP2142536B1/en active Active