JP2010524893A5 - - Google Patents
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- Publication number
- JP2010524893A5 JP2010524893A5 JP2010503510A JP2010503510A JP2010524893A5 JP 2010524893 A5 JP2010524893 A5 JP 2010524893A5 JP 2010503510 A JP2010503510 A JP 2010503510A JP 2010503510 A JP2010503510 A JP 2010503510A JP 2010524893 A5 JP2010524893 A5 JP 2010524893A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- nitrovinyl
- imidazol
- propylamino
- 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 33
- 150000001875 compounds Chemical class 0.000 claims 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000004452 carbocyclyl group Chemical group 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 239000003112 inhibitor Substances 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000003118 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
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 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
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- 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
- 239000003814 drug Substances 0.000 claims 4
- 230000001771 impaired effect Effects 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 125000000171 (C1-C6) haloalkyl 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
- 238000006243 chemical reaction Methods 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- -1 cyano, hydroxyl Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 230000002757 inflammatory effect Effects 0.000 claims 3
- 201000006417 multiple sclerosis Diseases 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- JUISCZDVYAJMBT-UHFFFAOYSA-N 1-n'-(1,3-benzodioxol-5-yl)-1-n-[3-(5-methylimidazol-1-yl)propyl]-2-nitroethene-1,1-diamine Chemical compound CC1=CN=CN1CCCNC(=C[N+]([O-])=O)NC1=CC=C(OCO2)C2=C1 JUISCZDVYAJMBT-UHFFFAOYSA-N 0.000 claims 2
- KJDYILRPNDWKLG-UHFFFAOYSA-N 1-n'-cyclohexyl-1-n-[4-(5-methylimidazol-1-yl)butyl]-2-nitroethene-1,1-diamine Chemical compound CC1=CN=CN1CCCCNC(=C[N+]([O-])=O)NC1CCCCC1 KJDYILRPNDWKLG-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
- 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
- 208000012639 Balance disease Diseases 0.000 claims 2
- 206010068597 Bulbospinal muscular atrophy congenital Diseases 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 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
- 125000003302 alkenyloxy group Chemical group 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000005133 alkynyloxy 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
- 238000000034 method Methods 0.000 claims 2
- 230000005012 migration Effects 0.000 claims 2
- 238000013508 migration Methods 0.000 claims 2
- AMQXTNLKQTXNJU-UHFFFAOYSA-N n'-[3-(5-methylimidazol-1-yl)propyl]-n-naphthalen-1-yl-2-nitroethanimidamide Chemical compound CC1=CN=CN1CCCN=C(C[N+]([O-])=O)NC1=CC=CC2=CC=CC=C12 AMQXTNLKQTXNJU-UHFFFAOYSA-N 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 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
- 150000003839 salts Chemical class 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 208000020685 sleep-wake disease Diseases 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 201000011549 stomach cancer Diseases 0.000 claims 2
- 125000004001 thioalkyl group Chemical group 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
- DRDRFTRZLLMRCL-UHFFFAOYSA-N 1-n'-(1,3-benzodioxol-5-yl)-1-n-[3-(4-methylimidazol-1-yl)propyl]-2-nitroethene-1,1-diamine Chemical compound C1=NC(C)=CN1CCCNC(=C[N+]([O-])=O)NC1=CC=C(OCO2)C2=C1 DRDRFTRZLLMRCL-UHFFFAOYSA-N 0.000 claims 1
- HJEWLERUZOGYCA-UHFFFAOYSA-N 1-n'-(2,4-dimethoxyphenyl)-1-n-[3-(4-methylimidazol-1-yl)propyl]-2-nitroethene-1,1-diamine Chemical compound COC1=CC(OC)=CC=C1NC(=C[N+]([O-])=O)NCCCN1C=C(C)N=C1 HJEWLERUZOGYCA-UHFFFAOYSA-N 0.000 claims 1
- PCLRPJYQKLMMKX-UHFFFAOYSA-N 1-n'-(2,4-dimethoxyphenyl)-1-n-[3-(5-methylimidazol-1-yl)propyl]-2-nitroethene-1,1-diamine Chemical compound COC1=CC(OC)=CC=C1NC(=C[N+]([O-])=O)NCCCN1C(C)=CN=C1 PCLRPJYQKLMMKX-UHFFFAOYSA-N 0.000 claims 1
- WEHWOHAOZUUTLE-UHFFFAOYSA-N 1-n'-(3,4-dimethoxyphenyl)-1-n-[3-(4-methylimidazol-1-yl)propyl]-2-nitroethene-1,1-diamine Chemical compound C1=C(OC)C(OC)=CC=C1NC(=C[N+]([O-])=O)NCCCN1C=C(C)N=C1 WEHWOHAOZUUTLE-UHFFFAOYSA-N 0.000 claims 1
- XGSCKLKAQKSJDK-UHFFFAOYSA-N 1-n'-(3,4-dimethoxyphenyl)-1-n-[3-(5-methylimidazol-1-yl)propyl]-2-nitroethene-1,1-diamine Chemical compound C1=C(OC)C(OC)=CC=C1NC(=C[N+]([O-])=O)NCCCN1C(C)=CN=C1 XGSCKLKAQKSJDK-UHFFFAOYSA-N 0.000 claims 1
- HYOMTYOMNXAQKB-UHFFFAOYSA-N 1-n'-(4-chlorophenyl)-1-n-[3-(4-methylimidazol-1-yl)propyl]-2-nitroethene-1,1-diamine Chemical compound C1=NC(C)=CN1CCCNC(=C[N+]([O-])=O)NC1=CC=C(Cl)C=C1 HYOMTYOMNXAQKB-UHFFFAOYSA-N 0.000 claims 1
- ZOWJSWANGDEHQV-UHFFFAOYSA-N 1-n'-cyclohexyl-1-n-[3-(5-methylimidazol-1-yl)propyl]-2-nitroethene-1,1-diamine Chemical compound CC1=CN=CN1CCCNC(=C[N+]([O-])=O)NC1CCCCC1 ZOWJSWANGDEHQV-UHFFFAOYSA-N 0.000 claims 1
- GZQGQPXNGNLMNL-UHFFFAOYSA-N 1-n-[3-(4-methylimidazol-1-yl)propyl]-1-n'-naphthalen-1-yl-2-nitroethene-1,1-diamine Chemical compound C1=NC(C)=CN1CCCNC(=C[N+]([O-])=O)NC1=CC=CC2=CC=CC=C12 GZQGQPXNGNLMNL-UHFFFAOYSA-N 0.000 claims 1
- QXWLNJOMXZMNTB-UHFFFAOYSA-N 1-n-[3-(4-methylimidazol-1-yl)propyl]-2-nitro-1-n'-(3,4,5-trimethoxyphenyl)ethene-1,1-diamine Chemical compound COC1=C(OC)C(OC)=CC(NC(NCCCN2C=C(C)N=C2)=C[N+]([O-])=O)=C1 QXWLNJOMXZMNTB-UHFFFAOYSA-N 0.000 claims 1
- XGCDJSAWMOUHID-UHFFFAOYSA-N 1-n-[3-(4-methylimidazol-1-yl)propyl]-2-nitro-1-n'-[4-(trifluoromethyl)phenyl]ethene-1,1-diamine Chemical compound C1=NC(C)=CN1CCCNC(=C[N+]([O-])=O)NC1=CC=C(C(F)(F)F)C=C1 XGCDJSAWMOUHID-UHFFFAOYSA-N 0.000 claims 1
- DRBBILLFANXMKL-UHFFFAOYSA-N 1-n-[3-(5-methylimidazol-1-yl)propyl]-2-nitro-1-n'-(3,4,5-trimethoxyphenyl)ethene-1,1-diamine Chemical compound COC1=C(OC)C(OC)=CC(NC(NCCCN2C(=CN=C2)C)=C[N+]([O-])=O)=C1 DRBBILLFANXMKL-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
- 206010003840 Autonomic nervous system imbalance 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
- 206010061218 Inflammation Diseases 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
- 229940099433 NMDA receptor antagonist 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
- 208000025865 Ulcer Diseases 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
- 210000000467 autonomic pathway Anatomy 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 239000002439 beta secretase inhibitor Substances 0.000 claims 1
- 210000001124 body fluid Anatomy 0.000 claims 1
- 239000010839 body fluid Substances 0.000 claims 1
- 208000035269 cancer or benign tumor Diseases 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 230000008021 deposition Effects 0.000 claims 1
- 229940002658 differin Drugs 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 230000004064 dysfunction 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
- 239000012530 fluid Substances 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
- 230000002584 immunomodulator Effects 0.000 claims 1
- 229960003444 immunosuppressant agent Drugs 0.000 claims 1
- 230000001861 immunosuppressant effect Effects 0.000 claims 1
- 239000003018 immunosuppressive agent Substances 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 108700027921 interferon tau Proteins 0.000 claims 1
- 229940028885 interleukin-4 Drugs 0.000 claims 1
- 229940121386 matrix metalloproteinase inhibitor Drugs 0.000 claims 1
- 239000003771 matrix metalloproteinase inhibitor Substances 0.000 claims 1
- 208000027061 mild cognitive impairment Diseases 0.000 claims 1
- 239000000234 muscarinic M1 receptor antagonist Substances 0.000 claims 1
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims 1
- GPQHOIQTHKOAGY-UHFFFAOYSA-N n'-[3-(5-methylimidazol-1-yl)propyl]-2-nitro-n-[4-(trifluoromethyl)phenyl]ethanimidamide Chemical compound CC1=CN=CN1CCCN=C(C[N+]([O-])=O)NC1=CC=C(C(F)(F)F)C=C1 GPQHOIQTHKOAGY-UHFFFAOYSA-N 0.000 claims 1
- KJIVXLFFKWSWIW-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-6-yl)-n'-[3-(4-methylimidazol-1-yl)propyl]-2-nitroethanimidamide Chemical compound C1=NC(C)=CN1CCCN=C(C[N+]([O-])=O)NC1=CC=C(OCCO2)C2=C1 KJIVXLFFKWSWIW-UHFFFAOYSA-N 0.000 claims 1
- MZYLSVFGZFWYEJ-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-6-yl)-n'-[3-(5-methylimidazol-1-yl)propyl]-2-nitroethanimidamide Chemical compound CC1=CN=CN1CCCN=C(C[N+]([O-])=O)NC1=CC=C(OCCO2)C2=C1 MZYLSVFGZFWYEJ-UHFFFAOYSA-N 0.000 claims 1
- OVKWACFPXWSZFC-UHFFFAOYSA-N n-(4-chlorophenyl)-n'-[3-(5-methylimidazol-1-yl)propyl]-2-nitroethanimidamide Chemical compound CC1=CN=CN1CCCN=C(C[N+]([O-])=O)NC1=CC=C(Cl)C=C1 OVKWACFPXWSZFC-UHFFFAOYSA-N 0.000 claims 1
- 229960005027 natalizumab Drugs 0.000 claims 1
- 230000009826 neoplastic cell growth Effects 0.000 claims 1
- 239000004090 neuroprotective agent Substances 0.000 claims 1
- 229960001592 paclitaxel Drugs 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 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 1
- 108010018276 trimethylguanosine synthase Proteins 0.000 claims 1
- 229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 claims 1
- 239000002452 tumor necrosis factor alpha inhibitor Substances 0.000 claims 1
- 0 BN(*)C(N*)=* Chemical compound BN(*)C(N*)=* 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91253707P | 2007-04-18 | 2007-04-18 | |
| US60/912,537 | 2007-04-18 | ||
| PCT/EP2008/054710 WO2008128981A1 (en) | 2007-04-18 | 2008-04-18 | Nitrovinyl-diamine derivatives as glutaminyl cyclase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010524893A JP2010524893A (ja) | 2010-07-22 |
| JP2010524893A5 true JP2010524893A5 (enExample) | 2011-05-19 |
| JP5675340B2 JP5675340B2 (ja) | 2015-02-25 |
Family
ID=39639570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010503510A Expired - Fee Related JP5675340B2 (ja) | 2007-04-18 | 2008-04-18 | 新規阻害剤 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8772508B2 (enExample) |
| EP (1) | EP2142513B1 (enExample) |
| JP (1) | JP5675340B2 (enExample) |
| DK (1) | DK2142513T3 (enExample) |
| ES (1) | ES2468551T3 (enExample) |
| WO (1) | WO2008128981A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7732162B2 (en) * | 2003-05-05 | 2010-06-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase for treating neurodegenerative diseases |
| EP2142536B1 (en) * | 2007-04-20 | 2015-10-21 | Probiodrug AG | Aminopyrimidine derivatives as glutaminyl cyclase inhibitors |
| EP2195336B1 (en) * | 2007-09-12 | 2015-01-21 | Probiodrug AG | Transgenic mice |
| WO2009090190A1 (en) * | 2008-01-14 | 2009-07-23 | Probiodrug Ag | Mouse models carrying a knock-out mutation of the glutaminyl cyclase gene |
| EP3338796A1 (en) | 2008-07-21 | 2018-06-27 | Probiodrug AG | Diagnostic antibody assay |
| US9925282B2 (en) | 2009-01-29 | 2018-03-27 | The General Hospital Corporation | Cromolyn derivatives and related methods of imaging and treatment |
| WO2011029920A1 (en) | 2009-09-11 | 2011-03-17 | Probiodrug Ag | Heterocylcic derivatives as inhibitors of glutaminyl cyclase |
| US20110152341A1 (en) | 2009-12-22 | 2011-06-23 | Probiodrug Ag | Cleavage of b-amyloid precursor protein |
| EP2533651A1 (en) | 2010-02-08 | 2012-12-19 | The Coca-Cola Company | Solubility enhanced terpene glycoside(s) |
| JP2013519891A (ja) | 2010-02-18 | 2013-05-30 | プロビオドルグ エージー | ピログルタミン酸修飾ｍｃｐ−１を決定することにより炎症性疾患を診断する方法及びグルタミニルシクラーゼの阻害剤のスクリーニング方法 |
| SG192805A1 (en) | 2011-03-16 | 2013-09-30 | Probiodrug Ag | Diagnostic antibody assay |
| CA2889446C (en) | 2012-10-25 | 2021-05-11 | The General Hospital Corporation | Combination therapies for the treatment of alzheimer's disease and related disorders |
| US10525005B2 (en) | 2013-05-23 | 2020-01-07 | The General Hospital Corporation | Cromolyn compositions and methods thereof |
| AU2014340182B2 (en) | 2013-10-22 | 2019-05-23 | The General Hospital Corporation | Cromolyn derivatives and related methods of imaging and treatment |
| JP2018501482A (ja) | 2014-12-19 | 2018-01-18 | プロビオドルグ エージー | ｐＧｌｕ−Ａｂｅｔａペプチドの検出のための新規の方法 |
| WO2017064302A1 (en) * | 2015-10-16 | 2017-04-20 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of autoimmune inflammatory diseases |
| JP2019524865A (ja) | 2016-08-31 | 2019-09-05 | ザ ジェネラル ホスピタル コーポレイション | 神経変性疾患と関連する神経炎症におけるマクロファージ／ミクログリア |
| KR20210070232A (ko) | 2017-07-20 | 2021-06-14 | 아즈테라피즈 인코포레이티드 | 크로몰린 나트륨 및 이부프로펜의 분말화된 제형 |
| EP3461819B1 (en) | 2017-09-29 | 2020-05-27 | Probiodrug AG | Inhibitors of glutaminyl cyclase |
| EP3521308B1 (en) | 2018-01-31 | 2024-03-13 | Vivoryon Therapeutics N.V. | Humanized and de-immunized antibodies |
| CN113038944A (zh) | 2018-07-02 | 2021-06-25 | 通用医疗公司 | 色甘酸钠和α-乳糖的粉末化制剂 |
| AU2019397436A1 (en) | 2018-12-10 | 2021-07-22 | The General Hospital Corporation | Cromolyn esters and uses thereof |
| IL297023A (en) | 2020-04-06 | 2022-12-01 | Massachusetts Gen Hospital | Methods for treating inflammatory conditions caused by the corona virus |
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| US4277485A (en) * | 1973-05-17 | 1981-07-07 | Smith Kline & French Laboratories Limited | Oxazole or isoxazole alkylamino ethylene compounds as inhibitors of H-2 histamine receptors |
| DE3044566A1 (de) * | 1980-11-26 | 1982-07-15 | Basf Ag, 6700 Ludwigshafen | N-substituierte imidazol-derivate, ihre herstellung, diese enthaltende arzneimittel und ihre verwendung |
| AU2001241194A1 (en) | 2000-03-21 | 2001-10-03 | Ishihara Sangyo Kaisha Ltd. | Nitroethenamine derivatives or salts thereof and pharmaceutical compositions containing the derivatives or the salts |
| US6948038B2 (en) | 2001-07-24 | 2005-09-20 | Microsoft Corporation | System and method for backing up and restoring data |
| KR20110059664A (ko) | 2003-05-05 | 2011-06-02 | 프로비오드룩 아게 | 글루타미닐 및 글루타메이트 사이클라제의 이펙터의 용도 |
| US8338120B2 (en) | 2003-05-05 | 2012-12-25 | Probiodrug Ag | Method of treating inflammation with glutaminyl cyclase inhibitors |
| WO2004098591A2 (en) * | 2003-05-05 | 2004-11-18 | Probiodrug Ag | Inhibitors of glutaminyl cyclase and their use in the treatment of neurological diseases |
| US7732162B2 (en) | 2003-05-05 | 2010-06-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase for treating neurodegenerative diseases |
| EP2289498A1 (en) | 2003-10-15 | 2011-03-02 | Probiodrug AG | Use of inhibitors of glutaminyl clyclase |
| US7667044B2 (en) | 2003-11-03 | 2010-02-23 | Probiodrug Ag | Compounds for the treatment of neurological disorders |
| EP1680120A2 (en) | 2003-11-03 | 2006-07-19 | Probiodrug AG | Combinations useful for the treatment of neuronal disorders |
| US20050171112A1 (en) | 2003-11-03 | 2005-08-04 | Probiodrug Ag | Combinations useful for the treatment of neuronal disorders |
| EP1713780B1 (en) | 2004-02-05 | 2012-01-18 | Probiodrug AG | Novel inhibitors of glutaminyl cyclase |
| EP2581449B1 (en) | 2006-09-21 | 2016-09-14 | Probiodrug AG | Novel genes related to glutaminyl cyclase |
| WO2008055950A1 (en) | 2006-11-09 | 2008-05-15 | Probiodrug Ag | Novel inhibitors of glutaminyl cyclase |
| US8420684B2 (en) | 2006-11-09 | 2013-04-16 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| EP2091948B1 (en) | 2006-11-30 | 2012-04-18 | Probiodrug AG | Novel inhibitors of glutaminyl cyclase |
| JP2010516235A (ja) | 2007-01-19 | 2010-05-20 | プロビオドルグ エージー | アルツハイマー病及び他のｑｐｃｔ関連障害の治療のためのインビボスクリーニングモデル |
| DK2118101T3 (da) | 2007-03-09 | 2013-01-02 | Probiodrug Ag | IMIDAZO (1,5-A)-PYRIDinderivater som glutaminylcyclaseinhibitorer |
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2008
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- 2008-04-18 WO PCT/EP2008/054710 patent/WO2008128981A1/en not_active Ceased
- 2008-04-18 EP EP08736360.2A patent/EP2142513B1/en active Active
- 2008-04-18 US US12/105,730 patent/US8772508B2/en active Active
- 2008-04-18 JP JP2010503510A patent/JP5675340B2/ja not_active Expired - Fee Related
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