JP2010524895A5 - - Google Patents
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- JP2010524895A5 JP2010524895A5 JP2010503512A JP2010503512A JP2010524895A5 JP 2010524895 A5 JP2010524895 A5 JP 2010524895A5 JP 2010503512 A JP2010503512 A JP 2010503512A JP 2010503512 A JP2010503512 A JP 2010503512A JP 2010524895 A5 JP2010524895 A5 JP 2010524895A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- cyano
- imidazol
- propyl
- 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 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 19
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000004452 carbocyclyl group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 239000003112 inhibitor Substances 0.000 claims 7
- -1 cyano, hydroxyl 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
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000002950 monocyclic group Chemical group 0.000 claims 5
- 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
- 238000006243 chemical reaction Methods 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
- 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
- 239000003795 chemical substances by application Substances 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
- 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
- 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
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- UJZXBLORZDCCGM-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-3-cyano-2-[3-(5-methylimidazol-1-yl)propyl]guanidine Chemical compound CC1=CN=CN1CCCNC(=NC#N)NC1=CC=C(OCO2)C2=C1 UJZXBLORZDCCGM-UHFFFAOYSA-N 0.000 claims 1
- NFKQWGJDXPQFFM-UHFFFAOYSA-N 1-(2,1,3-benzothiadiazol-5-yl)-3-cyano-2-[3-(4-methylimidazol-1-yl)propyl]guanidine Chemical compound C1=NC(C)=CN1CCCNC(=NC#N)NC1=CC2=NSN=C2C=C1 NFKQWGJDXPQFFM-UHFFFAOYSA-N 0.000 claims 1
- DENSVTTWPDDNPB-UHFFFAOYSA-N 1-(2,1,3-benzothiadiazol-5-yl)-3-cyano-2-[3-(5-methylimidazol-1-yl)propyl]guanidine Chemical compound CC1=CN=CN1CCCNC(=NC#N)NC1=CC2=NSN=C2C=C1 DENSVTTWPDDNPB-UHFFFAOYSA-N 0.000 claims 1
- DRFWJOLELPHDTA-UHFFFAOYSA-N 1-cyano-2-[3-(4-methylimidazol-1-yl)propyl]-3-(2,4,6-trimethylphenyl)guanidine Chemical compound C1=NC(C)=CN1CCCNC(=NC#N)NC1=C(C)C=C(C)C=C1C DRFWJOLELPHDTA-UHFFFAOYSA-N 0.000 claims 1
- OPJWSTRBFRANRM-UHFFFAOYSA-N 1-cyano-2-[3-(4-methylimidazol-1-yl)propyl]-3-(3,4,5-trimethoxyphenyl)guanidine Chemical compound COC1=C(OC)C(OC)=CC(NC(NCCCN2C=C(C)N=C2)=NC#N)=C1 OPJWSTRBFRANRM-UHFFFAOYSA-N 0.000 claims 1
- VJUXEILPAVRYHL-UHFFFAOYSA-N 1-cyano-2-[3-(4-methylimidazol-1-yl)propyl]-3-(4-propan-2-ylphenyl)guanidine Chemical compound C1=CC(C(C)C)=CC=C1NC(=NC#N)NCCCN1C=C(C)N=C1 VJUXEILPAVRYHL-UHFFFAOYSA-N 0.000 claims 1
- STIHQVQNWUADQI-UHFFFAOYSA-N 1-cyano-2-[3-(4-methylimidazol-1-yl)propyl]-3-naphthalen-1-ylguanidine Chemical compound C1=NC(C)=CN1CCCNC(=NC#N)NC1=CC=CC2=CC=CC=C12 STIHQVQNWUADQI-UHFFFAOYSA-N 0.000 claims 1
- OXEBAJGFSPDZBY-UHFFFAOYSA-N 1-cyano-2-[3-(4-methylimidazol-1-yl)propyl]-3-naphthalen-2-ylguanidine Chemical compound C1=NC(C)=CN1CCCNC(=NC#N)NC1=CC=C(C=CC=C2)C2=C1 OXEBAJGFSPDZBY-UHFFFAOYSA-N 0.000 claims 1
- DLJGDMLDNKGEND-UHFFFAOYSA-N 1-cyano-2-[3-(5-methylimidazol-1-yl)propyl]-3-(2,4,6-trimethylphenyl)guanidine Chemical compound CC1=CN=CN1CCCNC(=NC#N)NC1=C(C)C=C(C)C=C1C DLJGDMLDNKGEND-UHFFFAOYSA-N 0.000 claims 1
- PGBCZFHOYGHCLS-UHFFFAOYSA-N 1-cyano-2-[3-(5-methylimidazol-1-yl)propyl]-3-(3,4,5-trimethoxyphenyl)guanidine Chemical compound COC1=C(OC)C(OC)=CC(NC(NCCCN2C(=CN=C2)C)=NC#N)=C1 PGBCZFHOYGHCLS-UHFFFAOYSA-N 0.000 claims 1
- AKIDTQDSZDLNDB-UHFFFAOYSA-N 1-cyano-2-[3-(5-methylimidazol-1-yl)propyl]-3-(4-phenylphenyl)guanidine Chemical compound CC1=CN=CN1CCCNC(=NC#N)NC1=CC=C(C=2C=CC=CC=2)C=C1 AKIDTQDSZDLNDB-UHFFFAOYSA-N 0.000 claims 1
- BNDGEQFYAIYJHX-UHFFFAOYSA-N 1-cyano-2-[3-(5-methylimidazol-1-yl)propyl]-3-(4-propan-2-ylphenyl)guanidine Chemical compound C1=CC(C(C)C)=CC=C1NC(=NC#N)NCCCN1C(C)=CN=C1 BNDGEQFYAIYJHX-UHFFFAOYSA-N 0.000 claims 1
- VFJSGVUIFPSIKM-UHFFFAOYSA-N 1-cyano-2-[3-(5-methylimidazol-1-yl)propyl]-3-naphthalen-1-ylguanidine Chemical compound CC1=CN=CN1CCCNC(=NC#N)NC1=CC=CC2=CC=CC=C12 VFJSGVUIFPSIKM-UHFFFAOYSA-N 0.000 claims 1
- LFUDVSMHWTZKGD-UHFFFAOYSA-N 1-cyano-2-[3-(5-methylimidazol-1-yl)propyl]-3-naphthalen-2-ylguanidine Chemical compound CC1=CN=CN1CCCNC(=NC#N)NC1=CC=C(C=CC=C2)C2=C1 LFUDVSMHWTZKGD-UHFFFAOYSA-N 0.000 claims 1
- AXZBOPMMEJHOFH-UHFFFAOYSA-N 1-cyano-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-[3-(4-methylimidazol-1-yl)propyl]guanidine Chemical compound C1=NC(C)=CN1CCCNC(=NC#N)NC1=CC=C(OCCO2)C2=C1 AXZBOPMMEJHOFH-UHFFFAOYSA-N 0.000 claims 1
- MTVNYDIMGJIWEF-UHFFFAOYSA-N 1-cyano-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-[3-(5-methylimidazol-1-yl)propyl]guanidine Chemical compound CC1=CN=CN1CCCNC(=NC#N)NC1=CC=C(OCCO2)C2=C1 MTVNYDIMGJIWEF-UHFFFAOYSA-N 0.000 claims 1
- UEFUBZQPRZPYKJ-UHFFFAOYSA-N 1-cyano-3-(3,4-dichlorophenyl)-2-[3-(4-methylimidazol-1-yl)propyl]guanidine Chemical compound C1=NC(C)=CN1CCCNC(=NC#N)NC1=CC=C(Cl)C(Cl)=C1 UEFUBZQPRZPYKJ-UHFFFAOYSA-N 0.000 claims 1
- FDKNRLYSKSZJND-UHFFFAOYSA-N 1-cyano-3-(3,4-dichlorophenyl)-2-[3-(5-methylimidazol-1-yl)propyl]guanidine Chemical compound CC1=CN=CN1CCCNC(=NC#N)NC1=CC=C(Cl)C(Cl)=C1 FDKNRLYSKSZJND-UHFFFAOYSA-N 0.000 claims 1
- IMSALATYMQPCJU-UHFFFAOYSA-N 1-cyano-3-(3,4-dimethylphenyl)-2-[3-(5-methylimidazol-1-yl)propyl]guanidine Chemical compound CC1=CN=CN1CCCNC(=NC#N)NC1=CC=C(C)C(C)=C1 IMSALATYMQPCJU-UHFFFAOYSA-N 0.000 claims 1
- SKJSZFSFENMTNG-UHFFFAOYSA-N 1-cyano-3-(3,5-dimethoxyphenyl)-2-[3-(4-methylimidazol-1-yl)propyl]guanidine Chemical compound COC1=CC(OC)=CC(NC(NCCCN2C=C(C)N=C2)=NC#N)=C1 SKJSZFSFENMTNG-UHFFFAOYSA-N 0.000 claims 1
- RSEUXEZFKGBVMY-UHFFFAOYSA-N 1-cyano-3-(3,5-dimethoxyphenyl)-2-[3-(5-methylimidazol-1-yl)propyl]guanidine Chemical compound COC1=CC(OC)=CC(NC(NCCCN2C(=CN=C2)C)=NC#N)=C1 RSEUXEZFKGBVMY-UHFFFAOYSA-N 0.000 claims 1
- AEBBCKBPEUPKAA-UHFFFAOYSA-N 1-cyano-3-(4-cyanophenyl)-2-[3-(4-methylimidazol-1-yl)propyl]guanidine Chemical compound C1=NC(C)=CN1CCCNC(=NC#N)NC1=CC=C(C#N)C=C1 AEBBCKBPEUPKAA-UHFFFAOYSA-N 0.000 claims 1
- KPKUOXAAFVTCCG-UHFFFAOYSA-N 1-cyano-3-(4-cyanophenyl)-2-[3-(5-methylimidazol-1-yl)propyl]guanidine Chemical compound CC1=CN=CN1CCCNC(=NC#N)NC1=CC=C(C#N)C=C1 KPKUOXAAFVTCCG-UHFFFAOYSA-N 0.000 claims 1
- DUBYSFAYIHVAIB-UHFFFAOYSA-N 1-cyano-3-(4-ethoxyphenyl)-2-[3-(4-methylimidazol-1-yl)propyl]guanidine Chemical compound C1=CC(OCC)=CC=C1NC(=NC#N)NCCCN1C=C(C)N=C1 DUBYSFAYIHVAIB-UHFFFAOYSA-N 0.000 claims 1
- CFCGYPBOSNOAKU-UHFFFAOYSA-N 1-cyano-3-(4-ethoxyphenyl)-2-[3-(5-methylimidazol-1-yl)propyl]guanidine Chemical compound C1=CC(OCC)=CC=C1NC(=NC#N)NCCCN1C(C)=CN=C1 CFCGYPBOSNOAKU-UHFFFAOYSA-N 0.000 claims 1
- VRHJIPQUYLYDMI-UHFFFAOYSA-N 1-cyano-3-(4-ethylphenyl)-2-[3-(4-methylimidazol-1-yl)propyl]guanidine Chemical compound C1=CC(CC)=CC=C1NC(=NC#N)NCCCN1C=C(C)N=C1 VRHJIPQUYLYDMI-UHFFFAOYSA-N 0.000 claims 1
- PCZNUOXJFFTMPX-UHFFFAOYSA-N 1-cyano-3-(4-ethylphenyl)-2-[3-(5-methylimidazol-1-yl)propyl]guanidine Chemical compound C1=CC(CC)=CC=C1NC(=NC#N)NCCCN1C(C)=CN=C1 PCZNUOXJFFTMPX-UHFFFAOYSA-N 0.000 claims 1
- WNWNYLJHLRRXIH-UHFFFAOYSA-N 1-cyano-3-(4-methoxyphenyl)-2-[3-(4-methylimidazol-1-yl)propyl]guanidine Chemical compound C1=CC(OC)=CC=C1NC(=NC#N)NCCCN1C=C(C)N=C1 WNWNYLJHLRRXIH-UHFFFAOYSA-N 0.000 claims 1
- CHUPRJAOUKAMEC-UHFFFAOYSA-N 1-cyano-3-(4-methoxyphenyl)-2-[3-(5-methylimidazol-1-yl)propyl]guanidine Chemical compound C1=CC(OC)=CC=C1NC(=NC#N)NCCCN1C(C)=CN=C1 CHUPRJAOUKAMEC-UHFFFAOYSA-N 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 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
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- 229930012538 Paclitaxel Natural products 0.000 claims 1
- 102100031674 Protein-L-isoaspartate(D-aspartate) O-methyltransferase Human genes 0.000 claims 1
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- 229940005513 antidepressants Drugs 0.000 claims 1
- 239000000939 antiparkinson agent Substances 0.000 claims 1
- 239000000164 antipsychotic agent Substances 0.000 claims 1
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- 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
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- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
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- 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
- 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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=*)=C=N Chemical compound BN(*)C(N=*)=C=N 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91252807P | 2007-04-18 | 2007-04-18 | |
| US60/912,528 | 2007-04-18 | ||
| PCT/EP2008/054712 WO2008128983A1 (en) | 2007-04-18 | 2008-04-18 | Cyano-guanidine derivatives as glutaminyl cyclase inhibitors |
Publications (3)
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| JP2010524895A JP2010524895A (ja) | 2010-07-22 |
| JP2010524895A5 true JP2010524895A5 (OSRAM) | 2011-05-26 |
| JP5675342B2 JP5675342B2 (ja) | 2015-02-25 |
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| EP (1) | EP2160380B1 (OSRAM) |
| JP (1) | JP5675342B2 (OSRAM) |
| DK (1) | DK2160380T3 (OSRAM) |
| ES (1) | ES2474693T3 (OSRAM) |
| WO (1) | WO2008128983A1 (OSRAM) |
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| US7732162B2 (en) * | 2003-05-05 | 2010-06-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase for treating neurodegenerative diseases |
| JP5676249B2 (ja) * | 2007-04-20 | 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アミノピリジン誘導体 |
| EP2195336B1 (en) * | 2007-09-12 | 2015-01-21 | Probiodrug AG | Transgenic mice |
| EP2238252B1 (en) * | 2008-01-14 | 2013-07-31 | Probiodrug AG | Mouse models carrying a knock-out mutation of the glutaminyl cyclase gene |
| JP5828762B2 (ja) | 2008-07-21 | 2015-12-09 | プロビオドルグ エージー | 診断用抗体アッセイ |
| ES2548913T3 (es) | 2009-09-11 | 2015-10-21 | Probiodrug Ag | Derivados heterocíclicos como inhibidores de glutaminil ciclasa |
| WO2011076854A1 (en) | 2009-12-22 | 2011-06-30 | Probiodrug Ag | CLEAVAGE OF β-AMYLOID PRECURSOR PROTEIN |
| SG182615A1 (en) | 2010-02-18 | 2012-08-30 | Probiodrug Ag | Methods of diagnosing inflammatory diseases by determining pyroglutamate-modified mcp-1 and screening methods for inhibitors of glutaminyl cyclase |
| BR112013023211B1 (pt) | 2011-03-16 | 2022-11-08 | Vivoryon Therapeutics N.V. | Anticorpo monoclonal, seu uso, composição, linhagem celular, método diagnóstico in vitro e kit |
| US20130052203A1 (en) * | 2011-08-12 | 2013-02-28 | Probiodrug Ag | In vivo screening models for treatment of qc-related disorders |
| EP2874997A4 (en) | 2012-07-19 | 2016-01-06 | Univ Drexel | NEW SIGMA RECEPTOR LIGANDS AND METHOD FOR REGULATING CELLULAR PROTEIN HOMEOSTASIS THEREWITH |
| EP3234611A1 (en) | 2014-12-19 | 2017-10-25 | Probiodrug AG | Novel method for the detection of pglu-abeta peptides |
| PL3658141T3 (pl) | 2017-07-24 | 2023-06-12 | Stichting Het Nederlands Kanker Instituut-Antoni van Leeuwenhoek Ziekenhuis | Leczenie stanów patologicznych przez bezpośrednie i pośrednie celowanie w oddziaływanie sirpalfa - cd47 |
| EP3461819B1 (en) | 2017-09-29 | 2020-05-27 | Probiodrug AG | Inhibitors of glutaminyl cyclase |
| US11117870B2 (en) | 2017-11-01 | 2021-09-14 | Drexel University | Compounds, compositions, and methods for treating diseases |
| EP3521308B1 (en) | 2018-01-31 | 2024-03-13 | Vivoryon Therapeutics N.V. | Humanized and de-immunized antibodies |
| JP7751894B2 (ja) * | 2021-03-30 | 2025-10-09 | ナミックス株式会社 | 硬化触媒、樹脂組成物、封止材、接着剤、及び硬化物 |
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| DE3044566A1 (de) * | 1980-11-26 | 1982-07-15 | Basf Ag, 6700 Ludwigshafen | N-substituierte imidazol-derivate, ihre herstellung, diese enthaltende arzneimittel und ihre verwendung |
| AU7331098A (en) | 1997-05-07 | 1998-11-27 | Novo Nordisk A/S | Substituted 3,3-diamino-2-propenenitriles, their preparation and use |
| US6948038B2 (en) * | 2001-07-24 | 2005-09-20 | Microsoft Corporation | System and method for backing up and restoring data |
| US7371871B2 (en) | 2003-05-05 | 2008-05-13 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| US8338120B2 (en) | 2003-05-05 | 2012-12-25 | Probiodrug Ag | Method of treating inflammation with glutaminyl cyclase inhibitors |
| NZ572274A (en) | 2003-05-05 | 2009-06-26 | Probiodrug Ag | Use of effectors of glutaminyl and glutamate cyclases |
| US7732162B2 (en) | 2003-05-05 | 2010-06-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase for treating neurodegenerative diseases |
| EA010108B1 (ru) | 2003-10-15 | 2008-06-30 | Пробиодруг Аг | Применение эффекторов глутаминил- и глутаматциклаз |
| CA2544573A1 (en) | 2003-11-03 | 2005-06-02 | Probiodrug Ag | Combinations useful for the treatment of neuronal disorders |
| US7667044B2 (en) | 2003-11-03 | 2010-02-23 | Probiodrug Ag | Compounds for the treatment of neurological disorders |
| US20050171112A1 (en) | 2003-11-03 | 2005-08-04 | Probiodrug Ag | Combinations useful for the treatment of neuronal disorders |
| KR101099206B1 (ko) | 2004-02-05 | 2011-12-27 | 프로비오드룩 아게 | 신규한 글루타미닐 시클라제 저해제 |
| US20080249083A1 (en) | 2006-09-21 | 2008-10-09 | Probiodrug Ag | Novel genes related to glutaminyl cyclase |
| US8420684B2 (en) | 2006-11-09 | 2013-04-16 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| US7741354B2 (en) | 2006-11-09 | 2010-06-22 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| EP2091948B1 (en) | 2006-11-30 | 2012-04-18 | Probiodrug AG | Novel inhibitors of glutaminyl cyclase |
| HRP20110651T1 (hr) | 2007-01-19 | 2011-10-31 | Probiodrug Ag | Modeli pretraživanja in vivo radi liječenja alzheimerove bolesti i drugih poremećaja povezanih s qpct |
| US7803810B2 (en) | 2007-03-09 | 2010-09-28 | Probiodrug Ag | Inhibitors |
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2008
- 2008-04-18 DK DK08736361.0T patent/DK2160380T3/da active
- 2008-04-18 US US12/105,874 patent/US8227498B2/en not_active Expired - Fee Related
- 2008-04-18 JP JP2010503512A patent/JP5675342B2/ja not_active Expired - Fee Related
- 2008-04-18 ES ES08736361.0T patent/ES2474693T3/es active Active
- 2008-04-18 EP EP08736361.0A patent/EP2160380B1/en active Active
- 2008-04-18 WO PCT/EP2008/054712 patent/WO2008128983A1/en not_active Ceased
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