AU2006297948B2 - Novel imidazo [4,5 -b] pyridine derivatives as inhibitors of glycogen synthase kinase 3 for use in the treatment of dementia and neurodegenerative disorders - Google Patents

Info

Publication number

AU2006297948B2

AU2006297948B2 AU2006297948A AU2006297948A AU2006297948B2 AU 2006297948 B2 AU2006297948 B2 AU 2006297948B2 AU 2006297948 A AU2006297948 A AU 2006297948A AU 2006297948 A AU2006297948 A AU 2006297948A AU 2006297948 B2 AU2006297948 B2 AU 2006297948B2

Authority

AU

Australia

Prior art keywords

alkyl

imidazo

haloalkyl

phenyl

optionally substituted

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.)

Ceased

Links

• Espacenet
• Global Dossier
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• 206010012289 Dementia Diseases 0.000 title claims description 15
• GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical class C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 title claims description 11
• 208000015122 neurodegenerative disease Diseases 0.000 title claims description 7
• 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 title description 38
• 239000003112 inhibitor Substances 0.000 title description 6
• 102000001267 GSK3 Human genes 0.000 title 1
• 125000000217 alkyl group Chemical group 0.000 claims description 376
• 150000001875 compounds Chemical class 0.000 claims description 312
• 125000001188 haloalkyl group Chemical group 0.000 claims description 245
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 147
• 229910052739 hydrogen Inorganic materials 0.000 claims description 127
• 239000001257 hydrogen Substances 0.000 claims description 116
• 125000005843 halogen group Chemical group 0.000 claims description 103
• 150000002431 hydrogen Chemical group 0.000 claims description 95
• 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 79
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 79
• 150000003839 salts Chemical class 0.000 claims description 74
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 67
• 125000003545 alkoxy group Chemical group 0.000 claims description 66
• -1 OR' Chemical group 0.000 claims description 55
• 125000001072 heteroaryl group Chemical group 0.000 claims description 53
• 125000005842 heteroatom Chemical group 0.000 claims description 51
• 239000012453 solvate Substances 0.000 claims description 49
• 125000004429 atom Chemical group 0.000 claims description 48
• 125000000623 heterocyclic group Chemical group 0.000 claims description 43
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 39
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 37
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 37
• 125000003118 aryl group Chemical group 0.000 claims description 36
• 238000006243 chemical reaction Methods 0.000 claims description 34
• 125000001963 4 membered heterocyclic group Chemical group 0.000 claims description 30
• 238000000034 method Methods 0.000 claims description 29
• 239000012458 free base Substances 0.000 claims description 26
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 25
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 25
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 22
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 21
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
• 150000002367 halogens Chemical group 0.000 claims description 18
• 230000002265 prevention Effects 0.000 claims description 18
• 229910052736 halogen Inorganic materials 0.000 claims description 17
• 125000004076 pyridyl group Chemical group 0.000 claims description 17
• 208000024827 Alzheimer disease Diseases 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
• AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 16
• 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 15
• 241000894007 species Species 0.000 claims description 15
• 150000001412 amines Chemical class 0.000 claims description 14
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 13
• 208000010877 cognitive disease Diseases 0.000 claims description 13
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 12
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 12
• 230000008569 process Effects 0.000 claims description 12
• 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 11
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
• 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 11
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 11
• 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 10
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 10
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 10
• 201000011240 Frontotemporal dementia Diseases 0.000 claims description 10
• 239000003054 catalyst Substances 0.000 claims description 10
• MPVDXIMFBOLMNW-UHFFFAOYSA-N chembl1615565 Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1N=NC1=CC=CC=C1 MPVDXIMFBOLMNW-UHFFFAOYSA-N 0.000 claims description 10
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 238000006880 cross-coupling reaction Methods 0.000 claims description 9
• 238000010438 heat treatment Methods 0.000 claims description 9
• 206010027175 memory impairment Diseases 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• 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 8
• 208000020925 Bipolar disease Diseases 0.000 claims description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
• 230000015572 biosynthetic process Effects 0.000 claims description 8
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
• 201000010099 disease Diseases 0.000 claims description 8
• 208000035475 disorder Diseases 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 201000004384 Alopecia Diseases 0.000 claims description 7
• 150000004985 diamines Chemical class 0.000 claims description 7
• 150000002148 esters Chemical class 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 201000000980 schizophrenia Diseases 0.000 claims description 7
• 241000124008 Mammalia Species 0.000 claims description 6
• 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 6
• 206010012601 diabetes mellitus Diseases 0.000 claims description 6
• 230000004770 neurodegeneration Effects 0.000 claims description 6
• 206010019196 Head injury Diseases 0.000 claims description 5
• 208000027089 Parkinsonian disease Diseases 0.000 claims description 5
• 206010034010 Parkinsonism 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
• KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims description 5
• 230000001684 chronic effect Effects 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 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 5
• FVAZSNNBIWFQHL-UHFFFAOYSA-N methyl 4-[7-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC2=C(C=3C=CC(OC)=CC=3)C=CN=C2N1 FVAZSNNBIWFQHL-UHFFFAOYSA-N 0.000 claims description 5
• SSTZONWYPGYLEG-UHFFFAOYSA-N methyl 4-[7-iodo-3-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC2=C(I)C=CN=C2N1COCC[Si](C)(C)C SSTZONWYPGYLEG-UHFFFAOYSA-N 0.000 claims description 5
• 229910052757 nitrogen Inorganic materials 0.000 claims description 5
• 230000009467 reduction Effects 0.000 claims description 5
• 229910052702 rhenium Inorganic materials 0.000 claims description 5
• 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
• JLLKIKHUTZDFCG-UHFFFAOYSA-N 4-[2-(4-carboxyphenyl)-1h-imidazo[4,5-b]pyridin-7-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC2=C(C=3C=CC(=CC=3)C(O)=O)C=CN=C2N1 JLLKIKHUTZDFCG-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
• 208000011990 Corticobasal Degeneration Diseases 0.000 claims description 4
• 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 4
• 201000010374 Down Syndrome 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
• NHECRIZPDJYOLQ-UHFFFAOYSA-N [4-[7-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]phenyl]-piperidin-1-ylmethanone Chemical compound C1=CC(OC)=CC=C1C1=CC=NC2=C1N=C(C=1C=CC(=CC=1)C(=O)N1CCCCC1)N2 NHECRIZPDJYOLQ-UHFFFAOYSA-N 0.000 claims description 4
• 239000004480 active ingredient Substances 0.000 claims description 4
• 150000001408 amides Chemical class 0.000 claims description 4
• 230000006999 cognitive decline Effects 0.000 claims description 4
• 238000009833 condensation Methods 0.000 claims description 4
• 230000005494 condensation Effects 0.000 claims description 4
• 239000003433 contraceptive agent Substances 0.000 claims description 4
• 208000017004 dementia pugilistica Diseases 0.000 claims description 4
• 230000003676 hair loss Effects 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• BUURIHMBJYACFK-UHFFFAOYSA-N methyl 3-(1h-imidazo[4,5-b]pyridin-2-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2NC3=NC=CC=C3N=2)=C1 BUURIHMBJYACFK-UHFFFAOYSA-N 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
• HZEOQABBGYBGSX-UHFFFAOYSA-N methyl 4-[7-(3-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC2=C(C=3C=C(OC)C=CC=3)C=CN=C2N1 HZEOQABBGYBGSX-UHFFFAOYSA-N 0.000 claims description 4
• RWXXZUMEMMCJJJ-UHFFFAOYSA-N methyl 4-[7-(3-phenylmethoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC2=C(C=3C=C(OCC=4C=CC=CC=4)C=CC=3)C=CN=C2N1 RWXXZUMEMMCJJJ-UHFFFAOYSA-N 0.000 claims description 4
• WRMXPSDRFWYNRQ-UHFFFAOYSA-N methyl 4-[7-(3-phenylmethoxyphenyl)-3-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC2=C(C=3C=C(OCC=4C=CC=CC=4)C=CC=3)C=CN=C2N1COCC[Si](C)(C)C WRMXPSDRFWYNRQ-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
• WYFUKOPEMTUKDY-UHFFFAOYSA-N methyl 6-[7-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OC)=CC=C1C1=NC2=C(C=3C=CC(OC)=CC=3)C=CN=C2N1 WYFUKOPEMTUKDY-UHFFFAOYSA-N 0.000 claims description 4
• 230000007170 pathology Effects 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
• 229910052701 rubidium Inorganic materials 0.000 claims description 4
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
• 230000009466 transformation Effects 0.000 claims description 4
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
• FRZIFMKSYWAOSE-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyridine;hydrochloride Chemical compound Cl.C1=CC=C2NC=NC2=N1 FRZIFMKSYWAOSE-UHFFFAOYSA-N 0.000 claims description 3
• GLSSLQQFUSWGCO-UHFFFAOYSA-N 2-(butoxymethyl)-7-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound C1=CN=C2NC(COCCCC)=NC2=C1C1=CC=C(OC)C=C1 GLSSLQQFUSWGCO-UHFFFAOYSA-N 0.000 claims description 3
• AVUCVRZLKJBJNI-UHFFFAOYSA-N 2-[4-[2-[4-(morpholin-4-ylmethyl)phenyl]-1h-imidazo[4,5-b]pyridin-7-yl]phenyl]acetonitrile;hydrochloride Chemical compound Cl.C1=CC(CC#N)=CC=C1C1=CC=NC2=C1N=C(C=1C=CC(CN3CCOCC3)=CC=1)N2 AVUCVRZLKJBJNI-UHFFFAOYSA-N 0.000 claims description 3
• ZALZZNHYZCGVKO-UHFFFAOYSA-N 4-(7-chloro-1h-imidazo[4,5-b]pyridin-2-yl)-n-(2-morpholin-4-ylethyl)benzamide Chemical compound N=1C=2C(Cl)=CC=NC=2NC=1C(C=C1)=CC=C1C(=O)NCCN1CCOCC1 ZALZZNHYZCGVKO-UHFFFAOYSA-N 0.000 claims description 3
• PVOZVSDWDTVFIO-UHFFFAOYSA-N 4-[7-[3-(2-cyanoethylcarbamoyl)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(C(=O)NCCC#N)=C1 PVOZVSDWDTVFIO-UHFFFAOYSA-N 0.000 claims description 3
• DHDKTDJNVQASCH-UHFFFAOYSA-N 7-(4-methoxyphenyl)-2-phenyl-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(OC)=CC=C1C1=CC=NC2=C1N=C(C=1C=CC=CC=1)N2 DHDKTDJNVQASCH-UHFFFAOYSA-N 0.000 claims description 3
• AEXZTLNXKLHAAS-UHFFFAOYSA-N 7-(4-methoxyphenyl)-2-pyridazin-4-yl-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(OC)=CC=C1C1=CC=NC2=C1N=C(C=1C=NN=CC=1)N2 AEXZTLNXKLHAAS-UHFFFAOYSA-N 0.000 claims description 3
• 208000028698 Cognitive impairment Diseases 0.000 claims description 3
• 206010067889 Dementia with Lewy bodies Diseases 0.000 claims description 3
• 201000002832 Lewy body dementia Diseases 0.000 claims description 3
• 208000037658 Parkinson-dementia complex of Guam Diseases 0.000 claims description 3
• 208000006011 Stroke Diseases 0.000 claims description 3
• 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 3
• 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 3
• 230000007000 age related cognitive decline Effects 0.000 claims description 3
• 206010068168 androgenetic alopecia Diseases 0.000 claims description 3
• 201000002996 androgenic alopecia Diseases 0.000 claims description 3
• SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 claims description 3
• 230000001149 cognitive effect Effects 0.000 claims description 3
• 230000002254 contraceptive effect Effects 0.000 claims description 3
• 230000007423 decrease Effects 0.000 claims description 3
• 229940079593 drug Drugs 0.000 claims description 3
• 208000024963 hair loss Diseases 0.000 claims description 3
• HSUXPKGWFKGHSX-UHFFFAOYSA-N methyl 3-(7-chloro-1h-imidazo[4,5-b]pyridin-2-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2NC3=NC=CC(Cl)=C3N=2)=C1 HSUXPKGWFKGHSX-UHFFFAOYSA-N 0.000 claims description 3
• NCKKFDNUOSKORE-UHFFFAOYSA-N methyl 4-[7-(4-cyanophenyl)-1h-imidazo[4,5-b]pyridin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC2=C(C=3C=CC(=CC=3)C#N)C=CN=C2N1 NCKKFDNUOSKORE-UHFFFAOYSA-N 0.000 claims description 3
• VFVMCKVYXTYDDH-UHFFFAOYSA-N methyl 4-[7-[3-(2-cyanoethylcarbamoyl)phenyl]-3-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-2-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC2=C(C=3C=C(C=CC=3)C(=O)NCCC#N)C=CN=C2N1COCC[Si](C)(C)C VFVMCKVYXTYDDH-UHFFFAOYSA-N 0.000 claims description 3
• 208000027061 mild cognitive impairment Diseases 0.000 claims description 3
• JLUVYUKBEDVRHA-UHFFFAOYSA-N n-(3-methoxypropyl)-4-(7-pyridin-4-yl-1h-imidazo[4,5-b]pyridin-2-yl)benzamide;hydrochloride Chemical compound Cl.C1=CC(C(=O)NCCCOC)=CC=C1C1=NC2=C(C=3C=CN=CC=3)C=CN=C2N1 JLUVYUKBEDVRHA-UHFFFAOYSA-N 0.000 claims description 3
• 238000002560 therapeutic procedure Methods 0.000 claims description 3
• RPMVELKOENZIBB-UHFFFAOYSA-N 1,2-dimethylpyrrolidin-3-amine Chemical compound CC1C(N)CCN1C RPMVELKOENZIBB-UHFFFAOYSA-N 0.000 claims description 2
• MIORAZJRJQHQHZ-UHFFFAOYSA-N 2-(furan-2-ylmethyl)-7-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(OC)=CC=C1C1=CC=NC2=C1N=C(CC=1OC=CC=1)N2 MIORAZJRJQHQHZ-UHFFFAOYSA-N 0.000 claims description 2
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• HMLRBRPZIQSPBV-UHFFFAOYSA-N 3-[7-(4-carbamoylphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]benzoic acid Chemical compound C1=CC(C(=O)N)=CC=C1C1=CC=NC2=C1N=C(C=1C=C(C=CC=1)C(O)=O)N2 HMLRBRPZIQSPBV-UHFFFAOYSA-N 0.000 claims description 2
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