JP2009510162A5 - - Google Patents
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- Publication number
- JP2009510162A5 JP2009510162A5 JP2008534485A JP2008534485A JP2009510162A5 JP 2009510162 A5 JP2009510162 A5 JP 2009510162A5 JP 2008534485 A JP2008534485 A JP 2008534485A JP 2008534485 A JP2008534485 A JP 2008534485A JP 2009510162 A5 JP2009510162 A5 JP 2009510162A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- haloalkyl
- imidazo
- optionally
- hydrogen
- 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.)
- Pending
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- 229910052739 hydrogen Inorganic materials 0.000 claims 43
- 239000001257 hydrogen Substances 0.000 claims 43
- 150000002431 hydrogen Chemical class 0.000 claims 37
- 125000005843 halogen group Chemical group 0.000 claims 32
- 125000000623 heterocyclic group Chemical group 0.000 claims 24
- 125000001072 heteroaryl group Chemical group 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000003118 aryl group Chemical group 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 16
- 239000012453 solvate Substances 0.000 claims 16
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 15
- 125000004429 atom Chemical group 0.000 claims 15
- 125000005842 heteroatom Chemical group 0.000 claims 14
- 229910052760 oxygen Inorganic materials 0.000 claims 13
- 229910052717 sulfur Inorganic materials 0.000 claims 13
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 208000010877 cognitive disease Diseases 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 239000012458 free base Substances 0.000 claims 6
- 206010012289 Dementia Diseases 0.000 claims 5
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 208000028698 Cognitive impairment Diseases 0.000 claims 3
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- 201000004384 Alopecia Diseases 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 230000006999 cognitive decline Effects 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 206010027175 memory impairment Diseases 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 229940095102 methyl benzoate Drugs 0.000 claims 2
- GPUXGTQTRDHLOM-UHFFFAOYSA-N 2-[3-fluoro-4-(morpholin-4-ylmethyl)phenyl]-n-(3-methoxypropyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide;hydrochloride Chemical compound Cl.N=1C=2C(C(=O)NCCCOC)=CC=NC=2NC=1C(C=C1F)=CC=C1CN1CCOCC1 GPUXGTQTRDHLOM-UHFFFAOYSA-N 0.000 claims 1
- UIKBJDZPWDXMJS-UHFFFAOYSA-N 2-[3-methoxy-4-(morpholin-4-ylmethyl)phenyl]-n-(3-methoxypropyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide;hydrochloride Chemical compound Cl.N=1C=2C(C(=O)NCCCOC)=CC=NC=2NC=1C(C=C1OC)=CC=C1CN1CCOCC1 UIKBJDZPWDXMJS-UHFFFAOYSA-N 0.000 claims 1
- FITNLIOHKLUSOC-UHFFFAOYSA-N 2-[4-(dipropylsulfamoyl)phenyl]-n-(3-methoxypropyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide;hydrochloride Chemical compound Cl.C1=CC(S(=O)(=O)N(CCC)CCC)=CC=C1C1=NC2=C(C(=O)NCCCOC)C=CN=C2N1 FITNLIOHKLUSOC-UHFFFAOYSA-N 0.000 claims 1
- OXALLHVVTPDYOM-UHFFFAOYSA-N 2-[4-(morpholin-4-ylmethyl)phenyl]-n-pyridin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3C=CC(CN4CCOCC4)=CC=3)=NC=2C=1C(=O)NC1=CC=CN=C1 OXALLHVVTPDYOM-UHFFFAOYSA-N 0.000 claims 1
- IGHXERWKFVYLDK-UHFFFAOYSA-N 3-[4-[2-[4-(morpholin-4-ylmethyl)phenyl]-1h-imidazo[4,5-b]pyridine-7-carbonyl]piperazin-1-yl]propanenitrile Chemical compound C=1C=NC=2NC(C=3C=CC(CN4CCOCC4)=CC=3)=NC=2C=1C(=O)N1CCN(CCC#N)CC1 IGHXERWKFVYLDK-UHFFFAOYSA-N 0.000 claims 1
- KSSRXIATALCOIA-UHFFFAOYSA-N 4-(7-chloro-1h-imidazo[4,5-b]pyridin-2-yl)-n,n-dipropylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(CCC)CCC)=CC=C1C1=NC2=C(Cl)C=CN=C2N1 KSSRXIATALCOIA-UHFFFAOYSA-N 0.000 claims 1
- UGEUOTKVTBSELL-UHFFFAOYSA-N 4-(7-chloro-1h-imidazo[4,5-b]pyridin-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC2=C(Cl)C=CN=C2N1 UGEUOTKVTBSELL-UHFFFAOYSA-N 0.000 claims 1
- XHYPOLPWZMNGGI-UHFFFAOYSA-N 4-[[3-(7-chloro-1h-imidazo[4,5-b]pyridin-2-yl)phenyl]methyl]morpholine Chemical compound N=1C=2C(Cl)=CC=NC=2NC=1C(C=1)=CC=CC=1CN1CCOCC1 XHYPOLPWZMNGGI-UHFFFAOYSA-N 0.000 claims 1
- YSUWVLSXEJRSCJ-UHFFFAOYSA-N 4-[[4-(7-chloro-1h-imidazo[4,5-b]pyridin-2-yl)-2-(trifluoromethyl)phenyl]methyl]morpholine Chemical compound FC(F)(F)C1=CC(C=2NC3=NC=CC(Cl)=C3N=2)=CC=C1CN1CCOCC1 YSUWVLSXEJRSCJ-UHFFFAOYSA-N 0.000 claims 1
- ARFASBZXPARXPJ-UHFFFAOYSA-N 4-[[4-(7-chloro-1h-imidazo[4,5-b]pyridin-2-yl)-2-fluorophenyl]methyl]morpholine Chemical compound FC1=CC(C=2NC3=NC=CC(Cl)=C3N=2)=CC=C1CN1CCOCC1 ARFASBZXPARXPJ-UHFFFAOYSA-N 0.000 claims 1
- TZURWQDHFPMICJ-UHFFFAOYSA-N 4-[[4-(7-chloro-1h-imidazo[4,5-b]pyridin-2-yl)-2-methoxyphenyl]methyl]morpholine Chemical compound COC1=CC(C=2NC3=NC=CC(Cl)=C3N=2)=CC=C1CN1CCOCC1 TZURWQDHFPMICJ-UHFFFAOYSA-N 0.000 claims 1
- PAAJESGBRNIYKE-UHFFFAOYSA-N 4-[[4-(7-chloro-1h-imidazo[4,5-b]pyridin-2-yl)phenyl]methyl]morpholine Chemical compound N=1C=2C(Cl)=CC=NC=2NC=1C(C=C1)=CC=C1CN1CCOCC1 PAAJESGBRNIYKE-UHFFFAOYSA-N 0.000 claims 1
- QIIOUULEPKIONV-UHFFFAOYSA-N 4-[[4-(7-iodo-1h-imidazo[4,5-b]pyridin-2-yl)phenyl]methyl]morpholine Chemical compound N=1C=2C(I)=CC=NC=2NC=1C(C=C1)=CC=C1CN1CCOCC1 QIIOUULEPKIONV-UHFFFAOYSA-N 0.000 claims 1
- JAVVBPBDSPVAOJ-UHFFFAOYSA-N 7-chloro-2-(3-methylsulfonylphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound CS(=O)(=O)C1=CC=CC(C=2NC3=NC=CC(Cl)=C3N=2)=C1 JAVVBPBDSPVAOJ-UHFFFAOYSA-N 0.000 claims 1
- QSMNDCHFVFRFHN-UHFFFAOYSA-N 7-chloro-2-(4-methylsulfonylphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=NC2=C(Cl)C=CN=C2N1 QSMNDCHFVFRFHN-UHFFFAOYSA-N 0.000 claims 1
- KEKRVZJPBQWIMT-UHFFFAOYSA-N 7-chloro-2-(4-pyrrolidin-1-ylsulfonylphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound N=1C=2C(Cl)=CC=NC=2NC=1C(C=C1)=CC=C1S(=O)(=O)N1CCCC1 KEKRVZJPBQWIMT-UHFFFAOYSA-N 0.000 claims 1
- NVVZAKSOQZCEKH-UHFFFAOYSA-N 7-chloro-2-[2-(trifluoromethyl)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound FC(F)(F)C1=CC=CC=C1C1=NC2=C(Cl)C=CN=C2N1 NVVZAKSOQZCEKH-UHFFFAOYSA-N 0.000 claims 1
- LQOOJHIVPHSUMA-UHFFFAOYSA-N 7-chloro-2-[3-(2,2,3,3-tetrafluoropropoxymethyl)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound FC(F)C(F)(F)COCC1=CC=CC(C=2NC3=NC=CC(Cl)=C3N=2)=C1 LQOOJHIVPHSUMA-UHFFFAOYSA-N 0.000 claims 1
- QELLNVILFUXQKO-UHFFFAOYSA-N 7-chloro-2-[3-(trifluoromethyl)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2NC3=NC=CC(Cl)=C3N=2)=C1 QELLNVILFUXQKO-UHFFFAOYSA-N 0.000 claims 1
- CTAFXHISAWHZSA-UHFFFAOYSA-N 7-chloro-2-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C1CN(C)CCN1CC1=CC=CC(C=2NC3=NC=CC(Cl)=C3N=2)=C1 CTAFXHISAWHZSA-UHFFFAOYSA-N 0.000 claims 1
- KZJDYFKBRIBSEN-UHFFFAOYSA-N 7-chloro-2-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2NC3=NC=CC(Cl)=C3N=2)C=C1 KZJDYFKBRIBSEN-UHFFFAOYSA-N 0.000 claims 1
- NXLVBOFEKKCHNY-UHFFFAOYSA-N 7-chloro-2-[4-(piperidin-1-ylmethyl)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound N=1C=2C(Cl)=CC=NC=2NC=1C(C=C1)=CC=C1CN1CCCCC1 NXLVBOFEKKCHNY-UHFFFAOYSA-N 0.000 claims 1
- OWURUNJNKVMBQR-UHFFFAOYSA-N 7-chloro-2-[4-(trifluoromethyl)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC2=C(Cl)C=CN=C2N1 OWURUNJNKVMBQR-UHFFFAOYSA-N 0.000 claims 1
- 208000000044 Amnesia Diseases 0.000 claims 1
- 208000031091 Amnestic disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- ZDWBVFOAMYMACW-UHFFFAOYSA-N CC=CC=C(C=CC=C)C(=O)O Chemical compound CC=CC=C(C=CC=C)C(=O)O ZDWBVFOAMYMACW-UHFFFAOYSA-N 0.000 claims 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 1
- 201000010374 Down Syndrome Diseases 0.000 claims 1
- 206010019196 Head injury Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 208000009829 Lewy Body Disease Diseases 0.000 claims 1
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
- 208000014060 Niemann-Pick disease Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims 1
- 208000036757 Postencephalitic parkinsonism Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- PYDQOBHBRGWVIL-UHFFFAOYSA-N [4-(7-chloro-1h-imidazo[4,5-b]pyridin-2-yl)phenyl]-morpholin-4-ylmethanone Chemical compound N=1C=2C(Cl)=CC=NC=2NC=1C(C=C1)=CC=C1C(=O)N1CCOCC1 PYDQOBHBRGWVIL-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 230000007000 age related cognitive decline Effects 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 230000006986 amnesia Effects 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 206010068168 androgenetic alopecia Diseases 0.000 claims 1
- 201000002996 androgenic alopecia Diseases 0.000 claims 1
- 210000004227 basal ganglia Anatomy 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 208000013677 cerebrovascular dementia Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 239000003433 contraceptive agent Substances 0.000 claims 1
- 230000002254 contraceptive effect Effects 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 230000007850 degeneration Effects 0.000 claims 1
- 208000017004 dementia pugilistica Diseases 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 208000024963 hair loss Diseases 0.000 claims 1
- 230000003676 hair loss Effects 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 230000003902 lesion Effects 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 208000027061 mild cognitive impairment Diseases 0.000 claims 1
- WVEDZVBTVYVMGA-UHFFFAOYSA-N n-(3-methoxypropyl)-2-(3-methylsulfonylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide;hydrochloride Chemical compound Cl.N=1C=2C(C(=O)NCCCOC)=CC=NC=2NC=1C1=CC=CC(S(C)(=O)=O)=C1 WVEDZVBTVYVMGA-UHFFFAOYSA-N 0.000 claims 1
- PLNPFTMTTVFNTR-UHFFFAOYSA-N n-(3-methoxypropyl)-2-(4-methylsulfonylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide;hydrochloride Chemical compound Cl.N=1C=2C(C(=O)NCCCOC)=CC=NC=2NC=1C1=CC=C(S(C)(=O)=O)C=C1 PLNPFTMTTVFNTR-UHFFFAOYSA-N 0.000 claims 1
- CDATUQBVMNNCIL-UHFFFAOYSA-N n-(3-methoxypropyl)-2-(4-pyrrolidin-1-ylsulfonylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide;hydrochloride Chemical compound Cl.N=1C=2C(C(=O)NCCCOC)=CC=NC=2NC=1C(C=C1)=CC=C1S(=O)(=O)N1CCCC1 CDATUQBVMNNCIL-UHFFFAOYSA-N 0.000 claims 1
- HAPMJYMBXZUTHK-UHFFFAOYSA-N n-(3-methoxypropyl)-2-[2-(trifluoromethyl)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide;hydrochloride Chemical compound Cl.N=1C=2C(C(=O)NCCCOC)=CC=NC=2NC=1C1=CC=CC=C1C(F)(F)F HAPMJYMBXZUTHK-UHFFFAOYSA-N 0.000 claims 1
- IXHBQUUHEQPHCH-UHFFFAOYSA-N n-(3-methoxypropyl)-2-[3-(2,2,3,3-tetrafluoropropoxymethyl)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide;hydrochloride Chemical compound Cl.N=1C=2C(C(=O)NCCCOC)=CC=NC=2NC=1C1=CC=CC(COCC(F)(F)C(F)F)=C1 IXHBQUUHEQPHCH-UHFFFAOYSA-N 0.000 claims 1
- AZHHGMYBCIZTCL-UHFFFAOYSA-N n-(3-methoxypropyl)-2-[3-(morpholin-4-ylmethyl)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide;hydrochloride Chemical compound Cl.N=1C=2C(C(=O)NCCCOC)=CC=NC=2NC=1C(C=1)=CC=CC=1CN1CCOCC1 AZHHGMYBCIZTCL-UHFFFAOYSA-N 0.000 claims 1
- SHWGWJLYZANITI-UHFFFAOYSA-N n-(3-methoxypropyl)-2-[3-(trifluoromethyl)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide;hydrochloride Chemical compound Cl.N=1C=2C(C(=O)NCCCOC)=CC=NC=2NC=1C1=CC=CC(C(F)(F)F)=C1 SHWGWJLYZANITI-UHFFFAOYSA-N 0.000 claims 1
- MTEBTOLIJZKHHK-UHFFFAOYSA-N n-(3-methoxypropyl)-2-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide;hydrochloride Chemical compound Cl.N=1C=2C(C(=O)NCCCOC)=CC=NC=2NC=1C(C=1)=CC=CC=1CN1CCN(C)CC1 MTEBTOLIJZKHHK-UHFFFAOYSA-N 0.000 claims 1
- ICXFCSGRHNHLRH-UHFFFAOYSA-N n-(3-methoxypropyl)-2-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide;hydrochloride Chemical compound Cl.N=1C=2C(C(=O)NCCCOC)=CC=NC=2NC=1C(C=C1)=CC=C1S(=O)(=O)N1CCN(C)CC1 ICXFCSGRHNHLRH-UHFFFAOYSA-N 0.000 claims 1
- VHNWDGYJDMNRLY-UHFFFAOYSA-N n-(3-methoxypropyl)-2-[4-(4-methylpiperazine-1-carbonyl)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide;hydrochloride Chemical compound Cl.N=1C=2C(C(=O)NCCCOC)=CC=NC=2NC=1C(C=C1)=CC=C1C(=O)N1CCN(C)CC1 VHNWDGYJDMNRLY-UHFFFAOYSA-N 0.000 claims 1
- XEPQTQCOILMWIY-UHFFFAOYSA-N n-(3-methoxypropyl)-2-[4-(morpholin-4-ylmethyl)-3-(trifluoromethyl)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide;hydrochloride Chemical compound Cl.N=1C=2C(C(=O)NCCCOC)=CC=NC=2NC=1C(C=C1C(F)(F)F)=CC=C1CN1CCOCC1 XEPQTQCOILMWIY-UHFFFAOYSA-N 0.000 claims 1
- MMAIRIMTLHILKV-UHFFFAOYSA-N n-(3-methoxypropyl)-2-[4-(morpholin-4-ylmethyl)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide;hydrochloride Chemical compound Cl.N=1C=2C(C(=O)NCCCOC)=CC=NC=2NC=1C(C=C1)=CC=C1CN1CCOCC1 MMAIRIMTLHILKV-UHFFFAOYSA-N 0.000 claims 1
- RZGWNQSXCWYHHW-UHFFFAOYSA-N n-(3-methoxypropyl)-2-[4-(morpholine-4-carbonyl)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide;hydrochloride Chemical compound Cl.N=1C=2C(C(=O)NCCCOC)=CC=NC=2NC=1C(C=C1)=CC=C1C(=O)N1CCOCC1 RZGWNQSXCWYHHW-UHFFFAOYSA-N 0.000 claims 1
- ZZTJLLAGBYOSJR-UHFFFAOYSA-N n-(3-methoxypropyl)-2-[4-(piperidin-1-ylmethyl)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide;hydrochloride Chemical compound Cl.N=1C=2C(C(=O)NCCCOC)=CC=NC=2NC=1C(C=C1)=CC=C1CN1CCCCC1 ZZTJLLAGBYOSJR-UHFFFAOYSA-N 0.000 claims 1
- XJAQDHHEMXUDCK-UHFFFAOYSA-N n-(3-methoxypropyl)-2-[4-(trifluoromethyl)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide;hydrochloride Chemical compound Cl.N=1C=2C(C(=O)NCCCOC)=CC=NC=2NC=1C1=CC=C(C(F)(F)F)C=C1 XJAQDHHEMXUDCK-UHFFFAOYSA-N 0.000 claims 1
- UGXDCKYIVWQWJA-UHFFFAOYSA-N n-[(3-methoxyphenyl)methyl]-2-[4-(morpholin-4-ylmethyl)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound COC1=CC=CC(CNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2C=CC(CN3CCOCC3)=CC=2)=C1 UGXDCKYIVWQWJA-UHFFFAOYSA-N 0.000 claims 1
- LZTLWFUNTXVSBT-UHFFFAOYSA-N n-cyclopentyl-2-[4-(morpholin-4-ylmethyl)phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3C=CC(CN4CCOCC4)=CC=3)=NC=2C=1C(=O)NC1CCCC1 LZTLWFUNTXVSBT-UHFFFAOYSA-N 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 210000002682 neurofibrillary tangle Anatomy 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000000170 postencephalitic Parkinson disease Diseases 0.000 claims 1
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0502173 | 2005-10-03 | ||
| PCT/SE2006/001115 WO2007040439A1 (en) | 2005-10-03 | 2006-10-02 | New compounds ii |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009510162A JP2009510162A (ja) | 2009-03-12 |
| JP2009510162A5 true JP2009510162A5 (OSRAM) | 2009-11-26 |
Family
ID=37906402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008534485A Pending JP2009510162A (ja) | 2005-10-03 | 2006-10-02 | 認知症および神経変性疾患を治療するためのグリコーゲンシンターゼキナーゼ阻害剤としての新規な２−フェニル−イミダゾ［４，５−ｂ］ピリジン誘導体 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20080255106A1 (OSRAM) |
| EP (1) | EP1934217A4 (OSRAM) |
| JP (1) | JP2009510162A (OSRAM) |
| KR (1) | KR20080057334A (OSRAM) |
| CN (1) | CN101321754A (OSRAM) |
| AR (1) | AR057525A1 (OSRAM) |
| AU (1) | AU2006297889A1 (OSRAM) |
| BR (1) | BRPI0616663A2 (OSRAM) |
| CA (1) | CA2624869A1 (OSRAM) |
| IL (1) | IL189945A0 (OSRAM) |
| NO (1) | NO20082054L (OSRAM) |
| SA (1) | SA06270365B1 (OSRAM) |
| TW (1) | TW200800984A (OSRAM) |
| UY (1) | UY29823A1 (OSRAM) |
| WO (1) | WO2007040439A1 (OSRAM) |
| ZA (1) | ZA200802637B (OSRAM) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR055669A1 (es) * | 2005-10-03 | 2007-08-29 | Astrazeneca Ab | Derivados de 3h - imidazo[4, 5 -b]piridina como inhibidores selectivos de gsk3, metodos e internediarios para su preparacion, composiciones farmaceuticas que los contienen y su uso para la elaboracion de un medicamento para el tratamiento de enfermedades neurodegenerativas y mentales. |
| CA2637392A1 (en) * | 2006-01-23 | 2007-07-26 | Crystalgenomics, Inc. | Imidazopyridine derivatives inhibiting protein kinase activity, method for the preparation thereof and pharmaceutical composition containing same |
| WO2008121063A1 (en) * | 2007-03-30 | 2008-10-09 | Astrazeneca Ab | New imidazo[ 4,5-b]pyridine-7-carboxamides 704 |
| CN102127070A (zh) * | 2010-01-15 | 2011-07-20 | 山东轩竹医药科技有限公司 | 吡啶并环衍生物 |
| WO2012033149A1 (ja) * | 2010-09-10 | 2012-03-15 | 塩野義製薬株式会社 | Ａｍｐｋ活性化作用を有するヘテロ環縮合イミダゾール誘導体 |
| EP3741375A1 (en) | 2014-07-17 | 2020-11-25 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for treating neuromuscular junction-related diseases |
| WO2016207366A1 (en) | 2015-06-26 | 2016-12-29 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of viral infections |
| GB201519573D0 (en) | 2015-11-05 | 2015-12-23 | King S College London | Combination |
| CN107151235B (zh) * | 2016-03-04 | 2019-12-13 | 上海市计划生育科学研究所 | 噻二唑烷二酮基gsk3抑制剂在调节精子运动能力中的用途 |
| US10774086B2 (en) * | 2016-11-28 | 2020-09-15 | Bristol-Myers Squibb Company | GSK-3 inhibitors |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1264381A (zh) * | 1997-08-05 | 2000-08-23 | 辉瑞产品公司 | 4－氨基吡咯并(3,2－d)嘧啶作为神经肽Y受体拮抗药 |
| US6187777B1 (en) * | 1998-02-06 | 2001-02-13 | Amgen Inc. | Compounds and methods which modulate feeding behavior and related diseases |
| SG159380A1 (en) * | 2002-02-06 | 2010-03-30 | Vertex Pharma | Heteroaryl compounds useful as inhibitors of gsk-3 |
| IL163625A0 (en) * | 2002-03-27 | 2005-12-18 | Altana Pharma Ag | Alkoxy-pyridine derivatives and pharmaceutical compositions containing the same |
| SE0202462D0 (sv) * | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | Novel use |
| JP2006515013A (ja) * | 2003-01-23 | 2006-05-18 | クリスタルジェノミクス、インコーポレイテッド | グリコーゲン合成酵素キナーゼ３β活性抑制剤、組成物及びその製造方法 |
| MXPA06003349A (es) * | 2003-10-01 | 2006-06-08 | Altana Pharma Ag | Derivados de imidazopiridina como inhibidores de no-sintasa inducible. |
| RS20060200A (sr) * | 2003-10-01 | 2008-08-07 | Altana Pharma Ag., | Derivati imidazopiridina kao inhibitori inducibilne no-sintaze |
| AR055669A1 (es) * | 2005-10-03 | 2007-08-29 | Astrazeneca Ab | Derivados de 3h - imidazo[4, 5 -b]piridina como inhibidores selectivos de gsk3, metodos e internediarios para su preparacion, composiciones farmaceuticas que los contienen y su uso para la elaboracion de un medicamento para el tratamiento de enfermedades neurodegenerativas y mentales. |
| CA2637392A1 (en) * | 2006-01-23 | 2007-07-26 | Crystalgenomics, Inc. | Imidazopyridine derivatives inhibiting protein kinase activity, method for the preparation thereof and pharmaceutical composition containing same |
-
2006
- 2006-09-29 AR ARP060104309A patent/AR057525A1/es not_active Application Discontinuation
- 2006-09-29 UY UY29823A patent/UY29823A1/es not_active Application Discontinuation
- 2006-10-02 JP JP2008534485A patent/JP2009510162A/ja active Pending
- 2006-10-02 CA CA002624869A patent/CA2624869A1/en not_active Abandoned
- 2006-10-02 EP EP06799715A patent/EP1934217A4/en not_active Withdrawn
- 2006-10-02 BR BRPI0616663-6A patent/BRPI0616663A2/pt not_active IP Right Cessation
- 2006-10-02 WO PCT/SE2006/001115 patent/WO2007040439A1/en not_active Ceased
- 2006-10-02 US US12/088,897 patent/US20080255106A1/en not_active Abandoned
- 2006-10-02 KR KR1020087010754A patent/KR20080057334A/ko not_active Withdrawn
- 2006-10-02 CN CNA2006800453255A patent/CN101321754A/zh active Pending
- 2006-10-02 AU AU2006297889A patent/AU2006297889A1/en not_active Abandoned
- 2006-10-03 SA SA06270365A patent/SA06270365B1/ar unknown
- 2006-10-03 TW TW095136782A patent/TW200800984A/zh unknown
-
2008
- 2008-03-04 IL IL189945A patent/IL189945A0/en unknown
- 2008-03-25 ZA ZA200802637A patent/ZA200802637B/xx unknown
- 2008-04-30 NO NO20082054A patent/NO20082054L/no not_active Application Discontinuation
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