JP2009510161A - 認知症及び神経変性疾患の治療に用いるためのグリコーゲンシンターゼキナーゼ３阻害剤としての新規なイミダゾ「４，５−ｂ］ピリジン誘導体 - Google Patents

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Publication number

JP2009510161A

JP2009510161A JP2008534484A JP2008534484A JP2009510161A JP 2009510161 A JP2009510161 A JP 2009510161A JP 2008534484 A JP2008534484 A JP 2008534484A JP 2008534484 A JP2008534484 A JP 2008534484A JP 2009510161 A JP2009510161 A JP 2009510161A

Authority

JP

Japan

Prior art keywords

alkyl

imidazo

haloalkyl

phenyl

pyridin

Prior art date

2005-10-03

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.)

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• 238000011282 treatment Methods 0.000 title claims description 38
• 206010012289 Dementia Diseases 0.000 title claims description 20
• 230000004770 neurodegeneration Effects 0.000 title claims description 7
• 208000015122 neurodegenerative disease Diseases 0.000 title claims description 7
• 239000003572 glycogen synthase kinase 3 inhibitor Substances 0.000 title 1
• 150000003222 pyridines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 314
• 150000003839 salts Chemical class 0.000 claims abstract description 72
• 238000000034 method Methods 0.000 claims abstract description 55
• 239000012453 solvate Substances 0.000 claims abstract description 48
• 239000012458 free base Substances 0.000 claims abstract description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 3
• 125000000217 alkyl group Chemical group 0.000 claims description 361
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 135
• 229910052739 hydrogen Inorganic materials 0.000 claims description 128
• 239000001257 hydrogen Substances 0.000 claims description 108
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 106
• 125000005843 halogen group Chemical group 0.000 claims description 96
• -1 OR a Chemical group 0.000 claims description 88
• 150000002431 hydrogen Chemical class 0.000 claims description 88
• 125000000623 heterocyclic group Chemical group 0.000 claims description 81
• 125000003545 alkoxy group Chemical group 0.000 claims description 64
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 62
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 57
• 125000001072 heteroaryl group Chemical group 0.000 claims description 54
• 125000005842 heteroatom Chemical group 0.000 claims description 49
• 125000004429 atom Chemical group 0.000 claims description 47
• 125000003118 aryl group Chemical group 0.000 claims description 40
• 229910052799 carbon Inorganic materials 0.000 claims description 35
• QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 32
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
• 229910052760 oxygen Inorganic materials 0.000 claims description 32
• 238000006243 chemical reaction Methods 0.000 claims description 28
• 229910052717 sulfur Inorganic materials 0.000 claims description 28
• 229940095102 methyl benzoate Drugs 0.000 claims description 27
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 23
• KXLRANARIIPDBC-UHFFFAOYSA-N 4-(4-methoxyphenyl)pyridine-2,3-diamine Chemical compound C1=CC(OC)=CC=C1C1=CC=NC(N)=C1N KXLRANARIIPDBC-UHFFFAOYSA-N 0.000 claims description 21
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 21
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
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• 208000024827 Alzheimer disease Diseases 0.000 claims description 17
• 150000002367 halogens Chemical class 0.000 claims description 17
• 230000002265 prevention Effects 0.000 claims description 17
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 16
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 16
• 238000001816 cooling Methods 0.000 claims description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 239000005711 Benzoic acid Substances 0.000 claims description 14
• 150000001412 amines Chemical class 0.000 claims description 14
• 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 claims description 13
• IJXJGIWROCZHKS-UHFFFAOYSA-N 4-[7-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]benzoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)C(O)=O)N2 IJXJGIWROCZHKS-UHFFFAOYSA-N 0.000 claims description 13
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 13
• 235000010233 benzoic acid Nutrition 0.000 claims description 12
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 12
• 125000004076 pyridyl group Chemical group 0.000 claims description 12
• BALCZNSTFKAYEZ-UHFFFAOYSA-N 3-[7-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]benzoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=NC2=C1N=C(C=1C=C(C=CC=1)C(O)=O)N2 BALCZNSTFKAYEZ-UHFFFAOYSA-N 0.000 claims description 11
• 150000002148 esters Chemical class 0.000 claims description 11
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 11
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 11
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 10
• 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 description 10
• 208000028698 Cognitive impairment Diseases 0.000 claims description 10
• 201000011240 Frontotemporal dementia Diseases 0.000 claims description 10
• FXHZWSCNTVBMJZ-UHFFFAOYSA-N [4-(7-chloro-1h-imidazo[4,5-b]pyridin-2-yl)phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2NC3=NC=CC(Cl)=C3N=2)C=C1 FXHZWSCNTVBMJZ-UHFFFAOYSA-N 0.000 claims description 10
• 239000003054 catalyst Substances 0.000 claims description 10
• 230000008569 process Effects 0.000 claims description 10
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
• 238000006880 cross-coupling reaction Methods 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 9
• 125000001188 haloalkyl group Chemical group 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
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• 241000124008 Mammalia Species 0.000 claims description 8
• 150000004985 diamines Chemical class 0.000 claims description 8
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• 208000035475 disorder Diseases 0.000 claims description 8
• 238000010438 heat treatment Methods 0.000 claims description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 201000000980 schizophrenia Diseases 0.000 claims description 8
• XNQXCKZRTQGHQV-UHFFFAOYSA-N 7-chloro-2-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C1CN(C)CCN1CC1=CC=C(C=2NC3=NC=CC(Cl)=C3N=2)C=C1 XNQXCKZRTQGHQV-UHFFFAOYSA-N 0.000 claims description 7
• 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 description 7
• 230000006999 cognitive decline Effects 0.000 claims description 7
• 210000002682 neurofibrillary tangle Anatomy 0.000 claims description 7
• 241000894007 species Species 0.000 claims description 7
• HLVDXDQDRNTZDL-UHFFFAOYSA-N [5-[7-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]pyridin-3-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1=CC(OC)=CC=C1C1=CC=NC2=C1N=C(C=1C=C(C=NC=1)C(=O)N1CCN(C)CC1)N2 HLVDXDQDRNTZDL-UHFFFAOYSA-N 0.000 claims description 6
• 206010012601 diabetes mellitus Diseases 0.000 claims description 6
• 206010027175 memory impairment Diseases 0.000 claims description 6
• FACBSERRRVDKFO-UHFFFAOYSA-N 4-(3-methoxyphenyl)pyridine-2,3-diamine Chemical compound COC1=CC=CC(C=2C(=C(N)N=CC=2)N)=C1 FACBSERRRVDKFO-UHFFFAOYSA-N 0.000 claims description 5
• 206010019196 Head injury Diseases 0.000 claims description 5
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 5
• 210000000988 bone and bone Anatomy 0.000 claims description 5
• 230000001684 chronic effect Effects 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 230000009467 reduction Effects 0.000 claims description 5
• PQLCSWPDNRIYPJ-UHFFFAOYSA-N 4-(3-methoxyphenyl)-3-nitro-2-phenylmethoxypyridine Chemical compound COC1=CC=CC(C=2C(=C(OCC=3C=CC=CC=3)N=CC=2)[N+]([O-])=O)=C1 PQLCSWPDNRIYPJ-UHFFFAOYSA-N 0.000 claims description 4
• XGBAZKBVSNNKJF-UHFFFAOYSA-N 4-(7-iodo-1h-imidazo[4,5-b]pyridin-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC2=C(I)C=CN=C2N1 XGBAZKBVSNNKJF-UHFFFAOYSA-N 0.000 claims description 4
• DRJFKMUKYAQPQR-UHFFFAOYSA-N 4-[2-[4-(4-methylpiperazine-1-carbonyl)phenyl]-1h-imidazo[4,5-b]pyridin-7-yl]benzonitrile;hydrochloride Chemical compound Cl.C1CN(C)CCN1C(=O)C1=CC=C(C=2NC3=NC=CC(=C3N=2)C=2C=CC(=CC=2)C#N)C=C1 DRJFKMUKYAQPQR-UHFFFAOYSA-N 0.000 claims description 4
• YXJDTECHHFCYKK-UHFFFAOYSA-N 4-[3-(morpholin-4-ylmethyl)phenyl]pyridine-2,3-diamine Chemical compound NC1=NC=CC(C=2C=C(CN3CCOCC3)C=CC=2)=C1N YXJDTECHHFCYKK-UHFFFAOYSA-N 0.000 claims description 4
• MWRHGSOULIQURG-UHFFFAOYSA-N 4-[3-[2-[4-(4-methylpiperazine-1-carbonyl)phenyl]-3-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-7-yl]phenoxy]butanenitrile Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2N(C3=NC=CC(=C3N=2)C=2C=C(OCCCC#N)C=CC=2)COCC[Si](C)(C)C)C=C1 MWRHGSOULIQURG-UHFFFAOYSA-N 0.000 claims description 4
• VBVGVQSWIKMKJZ-UHFFFAOYSA-N 4-[7-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]-n-(2-morpholin-4-ylethyl)benzamide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)C(=O)NCCN1CCOCC1)N2 VBVGVQSWIKMKJZ-UHFFFAOYSA-N 0.000 claims description 4
• HZZDDVDYASKIHO-UHFFFAOYSA-N 4-[7-[3-(3-hydroxypropyl)phenyl]-3-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-2-yl]benzoic acid Chemical compound C1=CN=C2N(COCC[Si](C)(C)C)C(C=3C=CC(=CC=3)C(O)=O)=NC2=C1C1=CC=CC(CCCO)=C1 HZZDDVDYASKIHO-UHFFFAOYSA-N 0.000 claims description 4
• LMWYVGFPAOYHGP-UHFFFAOYSA-N 4-[7-[3-(morpholin-4-ylmethyl)phenyl]-1h-imidazo[4,5-b]pyridin-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC2=NC=CC(C=3C=C(CN4CCOCC4)C=CC=3)=C2N1 LMWYVGFPAOYHGP-UHFFFAOYSA-N 0.000 claims description 4
• QGUVPBFAOYXJKS-UHFFFAOYSA-N 4-[[4-[7-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]phenyl]methyl]morpholine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1=CC=NC2=C1N=C(C=1C=CC(CN3CCOCC3)=CC=1)N2 QGUVPBFAOYXJKS-UHFFFAOYSA-N 0.000 claims description 4
• GKRRBTNYWQUJMS-UHFFFAOYSA-N 5-[7-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]pyridine-3-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=NC2=C1N=C(C=1C=C(C=NC=1)C(O)=O)N2 GKRRBTNYWQUJMS-UHFFFAOYSA-N 0.000 claims description 4
• DGUACQWNOOVTBK-UHFFFAOYSA-N 7-(3-methoxyphenyl)-2-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]-1h-imidazo[4,5-b]pyridine;hydrochloride Chemical compound Cl.COC1=CC=CC(C=2C=3N=C(NC=3N=CC=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCN(C)CC2)=C1 DGUACQWNOOVTBK-UHFFFAOYSA-N 0.000 claims description 4
• LUFOXOGQGFQGKD-UHFFFAOYSA-N 7-(4-methoxyphenyl)-2-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]-1h-imidazo[4,5-b]pyridine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)S(=O)(=O)N1CCN(C)CC1)N2 LUFOXOGQGFQGKD-UHFFFAOYSA-N 0.000 claims description 4
• ABRSGLVDQLXKBF-UHFFFAOYSA-N 7-(4-methoxyphenyl)-2-[4-(piperidin-1-ylmethyl)phenyl]-1h-imidazo[4,5-b]pyridine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1=CC=NC2=C1N=C(C=1C=CC(CN3CCCCC3)=CC=1)N2 ABRSGLVDQLXKBF-UHFFFAOYSA-N 0.000 claims description 4
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
• 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 4
• 201000010374 Down Syndrome Diseases 0.000 claims description 4
• 208000023105 Huntington disease Diseases 0.000 claims description 4
• 208000019022 Mood disease Diseases 0.000 claims description 4
• 208000014060 Niemann-Pick disease Diseases 0.000 claims description 4
• 208000018737 Parkinson disease Diseases 0.000 claims description 4
• 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 4
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 4
• HBFNRIYXMFRSEJ-UHFFFAOYSA-N [4-(7-chloro-1h-imidazo[4,5-b]pyridin-2-yl)phenyl]-piperidin-1-ylmethanone Chemical compound N=1C=2C(Cl)=CC=NC=2NC=1C(C=C1)=CC=C1C(=O)N1CCCCC1 HBFNRIYXMFRSEJ-UHFFFAOYSA-N 0.000 claims description 4
• CGZHTOZBOPFKEQ-UHFFFAOYSA-N [4-[7-(2,4-dimethoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]phenyl]-morpholin-4-ylmethanone;hydrochloride Chemical compound Cl.COC1=CC(OC)=CC=C1C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)C(=O)N1CCOCC1)N2 CGZHTOZBOPFKEQ-UHFFFAOYSA-N 0.000 claims description 4
• CVDNBZXGWVGYPR-UHFFFAOYSA-N [4-[7-(3-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]phenyl]-(4-methylpiperazin-1-yl)methanone;hydrochloride Chemical compound Cl.COC1=CC=CC(C=2C=3N=C(NC=3N=CC=2)C=2C=CC(=CC=2)C(=O)N2CCN(C)CC2)=C1 CVDNBZXGWVGYPR-UHFFFAOYSA-N 0.000 claims description 4
• UABNBNVPWOZNRB-UHFFFAOYSA-N [4-[7-(4-chlorophenyl)-1h-imidazo[4,5-b]pyridin-2-yl]phenyl]-(4-methylpiperazin-1-yl)methanone;hydrochloride Chemical compound Cl.C1CN(C)CCN1C(=O)C1=CC=C(C=2NC3=NC=CC(=C3N=2)C=2C=CC(Cl)=CC=2)C=C1 UABNBNVPWOZNRB-UHFFFAOYSA-N 0.000 claims description 4
• GVWLOXZIVJHMAM-UHFFFAOYSA-N [4-[7-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]phenyl]-(4-methylpiperazin-1-yl)methanone;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)C(=O)N1CCN(C)CC1)N2 GVWLOXZIVJHMAM-UHFFFAOYSA-N 0.000 claims description 4
• FKKKXIVHZIEUTC-UHFFFAOYSA-N [4-[7-[3-(3-methoxypropoxy)phenyl]-1h-imidazo[4,5-b]pyridin-2-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound COCCCOC1=CC=CC(C=2C=3N=C(NC=3N=CC=2)C=2C=CC(=CC=2)C(=O)N2CCN(C)CC2)=C1 FKKKXIVHZIEUTC-UHFFFAOYSA-N 0.000 claims description 4
• 239000004480 active ingredient Substances 0.000 claims description 4
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• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
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• 230000003676 hair loss Effects 0.000 claims description 4
• 208000024963 hair loss Diseases 0.000 claims description 4
• FVFKDCKCUZPDHW-UHFFFAOYSA-N methyl 3-[7-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2NC3=NC=CC(=C3N=2)C=2C=CC(OC)=CC=2)=C1 FVFKDCKCUZPDHW-UHFFFAOYSA-N 0.000 claims description 4
• XIPIZLYYOZWNEX-UHFFFAOYSA-N methyl 4-(7-iodo-1h-imidazo[4,5-b]pyridin-2-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC2=C(I)C=CN=C2N1 XIPIZLYYOZWNEX-UHFFFAOYSA-N 0.000 claims description 4
• XCLZKTYDTPVQIK-UHFFFAOYSA-N methyl 4-[7-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CC(C=2NC3=NC=CC(=C3N=2)C=2C=CC(OC)=CC=2)=C1 XCLZKTYDTPVQIK-UHFFFAOYSA-N 0.000 claims description 4
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• WGAMUFDJOHTHRC-UHFFFAOYSA-N (2-methylpiperazin-1-yl)-[4-[7-(3-phenylmethoxyphenyl)-3-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-2-yl]phenyl]methanone Chemical compound CC1CNCCN1C(=O)C1=CC=C(C=2N(C3=NC=CC(=C3N=2)C=2C=C(OCC=3C=CC=CC=3)C=CC=2)COCC[Si](C)(C)C)C=C1 WGAMUFDJOHTHRC-UHFFFAOYSA-N 0.000 claims description 3
• CBCIAUMJVNQJRQ-UHFFFAOYSA-N (3,3-difluoropyrrolidin-1-yl)-[4-[7-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]phenyl]methanone Chemical compound C1=CC(OC)=CC=C1C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)C(=O)N1CC(F)(F)CC1)N2 CBCIAUMJVNQJRQ-UHFFFAOYSA-N 0.000 claims description 3
• LYSLFYAVVPQHDU-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-(7-pyridin-3-yl-1h-imidazo[4,5-b]pyridin-2-yl)phenyl]methanone;hydrochloride Chemical compound Cl.C1CN(C)CCN1C(=O)C1=CC=C(C=2NC3=NC=CC(=C3N=2)C=2C=NC=CC=2)C=C1 LYSLFYAVVPQHDU-UHFFFAOYSA-N 0.000 claims description 3
• CTGLAMQPUCKHHS-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-(7-pyridin-4-yl-1h-imidazo[4,5-b]pyridin-2-yl)phenyl]methanone;hydrochloride Chemical compound Cl.C1CN(C)CCN1C(=O)C1=CC=C(C=2NC3=NC=CC(=C3N=2)C=2C=CN=CC=2)C=C1 CTGLAMQPUCKHHS-UHFFFAOYSA-N 0.000 claims description 3
• CFTZTWRIOMKBFT-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-[7-(4-propan-2-yloxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]phenyl]methanone;hydrochloride Chemical compound Cl.C1=CC(OC(C)C)=CC=C1C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)C(=O)N1CCN(C)CC1)N2 CFTZTWRIOMKBFT-UHFFFAOYSA-N 0.000 claims description 3
• MXGZVMBBTXDMGO-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-[7-[4-(trifluoromethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-2-yl]phenyl]methanone;hydrochloride Chemical compound Cl.C1CN(C)CCN1C(=O)C1=CC=C(C=2NC3=NC=CC(=C3N=2)C=2C=CC(OC(F)(F)F)=CC=2)C=C1 MXGZVMBBTXDMGO-UHFFFAOYSA-N 0.000 claims description 3
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