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NZ739951B2 - Colony stimulating factor-1 receptor (csf-1r) inhibitors - Google Patents

Colony stimulating factor-1 receptor (csf-1r) inhibitors Download PDF

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Publication number
NZ739951B2
NZ739951B2 NZ739951A NZ73995116A NZ739951B2 NZ 739951 B2 NZ739951 B2 NZ 739951B2 NZ 739951 A NZ739951 A NZ 739951A NZ 73995116 A NZ73995116 A NZ 73995116A NZ 739951 B2 NZ739951 B2 NZ 739951B2
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New Zealand
Prior art keywords
methyl
imidazo
methoxy
dihydrobenzo
dioxinyl
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NZ739951A
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NZ739951A (en
Inventor
Claude Barberis
Mark Czekaj
Paul Erdman
Barret Giese
John L Kane Jr
Michael Kothe
Tieu Binh Le
Jinyu Liu
Liang Ma
Markus Metz
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Genzyme Corporation
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Application filed by Genzyme Corporation filed Critical Genzyme Corporation
Priority claimed from PCT/US2016/042917 external-priority patent/WO2017015267A1/en
Publication of NZ739951A publication Critical patent/NZ739951A/en
Publication of NZ739951B2 publication Critical patent/NZ739951B2/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/00—Medicinal preparations containing organic active ingredients
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
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    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Abstract

Compounds of formula VII, which are useful as colony stimulating factor-1 receptor inhibitors ("CSF 1R inhibitors") in the treatment of Multiple Sclerosis, ALS, Huntington’s disease, lupus, lupus nephritis, and rheumatoid arthritis.

Claims (17)

1. A compound comprising the structure of Formula (VII): 5 (VII) or the pharmaceutically acceptable salt thereof, wherein: the dashed lines represent optional double bonds, n is 1; 10 p is 1; X2 is N; X3, X4, and X5, are each ndently selected from CR7, wherein each R7 is independently selected from the group consisting of H, (C1-C10)alkyl, (C3-C10)cycloalkyl, (C2-C9)heterocycloalkyl, (C6-C14)aryl, 15 (C2-C9)heteroaryl, (C2-C10)alkylnyl, (C1-C10)alkylamine, ((C1-C10)alkyl)2amine, 0)alkynylamine, C(O)-, (C1-C10)alkyl-C(O)O-, heteroalkyl-C(O)-, COOH-(C1-C10)alkyl-, COOH-(C3-C10)cycloalkyl-, (C1-C10)alkoxy-, R8-(C1-C10)alkyl-, R8-(C3-C10)cycloalkyl, R8-(C2-C9)heterocycloalkyl, R8-(C6-C14)aryl, 20 R8-(C2-C9)heteroaryl, -C10)alkylnyl, R8-(C1-C10)alkylamine, R8-((C1-C10)alkyl)2amine, R8-(C2-C10)alkynylamine, R8-C(O)-, R8-(C1-C10)alkyl-C(O)O-, -C10)alkoxy-, (C3-C10)cycloalkyl-O-, (C2-C9)heterocycloalkyl-O-, (C6-C14)aryl-O-, (C2-C9)heteroaryl-O-, R8-(C3-C10)cycloalkyl-O-, -C9)heterocycloalkyl-O-, 20559659_1 (GHMatters) P43761NZ00 -C14)aryl-O-, -C9)heteroaryl-O-, HO-, halo, cyano, H2N-, (CH3)HN-, (CH3)2N-, R8R9N-, O)C-, R8(R9C(O))N-, R8R9NC(O)O-, R8R9NC(O)R8N-, (C1-C10)alkyl-OC(O)R8N-, (C3-C10)cycloalkyl-OC(O)R8N-, (C2-C9)heterocycloalkyl-OC(O)R8N-, 5 (C6-C14)aryl-OC(O)R8N-, (C2-C9)heteroaryl-OC(O)R8N-, F3C-, F2HC-, CH3F2C-, FH2C-, CH3FHC-, (CH3)2FC-; NC-, (C1-C10)alkyl(O)P-, (C1-C10)alkyl-S-, (C1-C10)alkyl-S-(C1-C10)alkyl-, (C3-C10)cycloalkyl-S-, 4)aryl-S-, (C2-C9)heteroalkyl-S-, (C2-C9)heterocycloalkyl-S-, (C2-C9)heteroaryl-S-, (C1-C10)alkyl-S(O)-, (C3-C10)cycloalkyl-S(O)-, 10 (C6-C14)aryl-S(O)-, (C2-C9)heterocycloalkyl-S(O)-, (C2-C9)heteroaryl- S(O)-, (C3-C10)alkyl-S(O)2-, (C3-C10)cycloalkyl-S(O)2-, (C6-C14)aryl- S(O)2-, (C2-C9)heterocycloalkyl-S(O)2-, (C2-C9)heteroaryl-S(O)2-, R8R9NS(O)2-, (C1-C10)alkyl-S(O)2R8N-, (C3-C10)cycloalkyl-S(O)2R8N-, (C6-C14)aryl-S(O)2R8N-, (C2-C9)heterocycloalkyl-SO2R8N-, and 15 (C2-C9)heteroaryl-S(O)2R8N-; wherein R8 and R9 are each independently selected from the group ting of H, (C1-C10)alkyl, (C3-C10)cycloalkyl, (C2-C9)heterocycloalkyl, (C6-C14)aryl, (C2-C9)heteroaryl, (C1-C10)alkylamine, ((C1-C10)alkyl)2amine, (C1-C3)alkynylamine, 20 (C1-C10)alkyl-C(O)O-, COOH-(C1-C10)alkyl, COOH-(C3-C10)cycloalkyl, (C1-C10)alkoxy-, (C1-C10)alkoxy-(C1-C10)alkyl-, (C3-C10)cycloalkyl-O-, )heterocycloalkyl-O-, (C6-C14)aryl-O-, (C2-C9)heteroaryl-O-, HO-, halo, N-, and H2N-; 25 or R8 and R9 are taken together to form a 3 to 10 member cycloalkyl, heterocycloalkyl, aryl or heteroaryl ring; wherein each (C1-C10)alkyl, (C6-C14)aryl, (C2-C9)heteroaryl, (C3-C10)cycloalkyl, or (C2-C9)heterocycloalkyl are further optionally substituted by one to four groups selected from 30 (C1-C10)alkyl, (C3-C10)cycloalkyl, )heterocycloalkyl, (C6-C14)aryl, (C2-C9)heteroaryl, (C1-C10)alkylamine, 20559659_1 (GHMatters) P43761NZ00 ((C1-C10)alkyl)2amine, (C1-C3)alkynylamine, (C1-C10)alkyl-C(O)O- , COOH-(C1-C10)alkyl, COOH-(C3-C10)cycloalkyl, (C1-C10)alkoxy-, (C1-C10)alkoxy-(C1-C10)alkyl-, (C3-C10)cycloalkyl-O-, (C2-C9)heterocycloalkyl-O-, (C6-C14)aryl- 5 O-, (C2-C9)heteroaryl-O-, HO-, halo, or H2N-; T1, T2, and T3 is each independently selected from are each independently ed from N or CR10, wherein each R10 is independently selected from the group ting of H, (C1-C10)alkyl, (C3-C10)cycloalkyl, (C2-C9)heterocycloalkyl, (C6-C14)aryl, 10 (C2-C9)heteroaryl, (C2-C10)alkylnyl, (C1-C10)alkylamine, ((C1-C10)alkyl)2amine, (C2-C10)alkynylamine, C(O)-, (C1-C10)alkyl-C(O)O-, COOH-(C1-C10)alkyl-, COOH-(C3-C10)cycloalkyl-, (C1-C10)alkoxy-, R10A-(C1-C10)alkyl-, R10A-(C3-C10)cycloalkyl, C2-C9)heterocycloalkyl, R10A-(C6-C14)aryl, R10A-(C2-C9)heteroaryl, 15 R10A-(C2-C10)alkylnyl, R10A-(C1-C10)alkylamine, R10A-((C1-C10)alkyl)2amine, R10A-(C2-C10)alkynylamine, R10A-(C1-C10)alkyl-C(O)O-, R10A-(C1-C10)alkoxy-, (C3-C10)cycloalkyl-O-, (C2-C9)heterocycloalkyl-O-, (C6-C14)aryl-O-, (C2-C9)heteroaryl-O-, C3-C10)cycloalkyl-O-, R10A-(C2-C9)heterocycloalkyl-O-, 20 R10A-(C6-C14)aryl-O-, R10A-(C2-C9)heteroaryl-O-, HO-, halo, cyano, H2N-, (CH3)HN-, (CH3)2N-, R10AR11N-, R10AR11N(O)C-, R10A(R11C(O))N-, R10AR11NC(O)O-, R10AC(O)-, R10AR11NC(O)R10AN-, (C1-C10)alkyl- OC(O)R10AN-, 0)cycloalkyl-OC(O)R10AN-, (C2-C9)heterocycloalkyl-OC(O)R10AN-, (C6-C14)aryl-OC(O)R10AN-, 25 (C2-C9)heteroaryl-OC(O)R10AN-, F3C-, F2HC-, CH3F2C-, FH2C-, CH3FHC-, (CH3)2FC-; NC-, (C1-C10)alkyl(O)P-, (C1-C10)alkyl-S-, (C1-C10)alkyl-S-(C1-C10)alkyl-, (C3-C10)cycloalkyl-S-, (C6-C14)aryl-S-, (C2-C9)heteroalkyl-S-, (C2-C9)heterocycloalkyl-S-, (C2-C9)heteroaryl-S-, 0)alkyl-S(O)-, (C3-C10)cycloalkyl-S(O)-, 4)aryl-S(O)-, 30 (C2-C9)heterocycloalkyl-S(O)-, (C2-C9)heteroaryl-S(O)-, (C3-C10)alkyl- S(O)2-, 0)cycloalkyl-S(O)2-, (C6-C14)aryl-S(O)2-, 20559659_1 (GHMatters) P43761NZ00 (C2-C9)heterocycloalkyl-S(O)2-, (C2-C9)heteroaryl-S(O)2-, R10AR11NS(O)2-, (C1-C10)alkyl-S(O)2R10AN-, (C3-C10)cycloalkyl-S(O)2R10AN-, (C6-C14)aryl-S(O)2R10AN-, (C2-C9)heterocycloalkyl-SO2R10AN-, and (C2-C9)heteroaryl-S(O)2R10AN-; 5 wherein R10A and R11 are each independently selected from the group consisting of H, (C1-C10)alkyl, (C3-C10)cycloalkyl, (C2-C9)heterocycloalkyl, 4)aryl, (C2-C9)heteroaryl, (C1-C10)alkylamine, ((C1-C10)alkyl)2amine, )alkynylamine, (C1-C10)alkyl-C(O)O-, COOH-(C1-C10)alkyl, 10 COOH-(C3-C10)cycloalkyl, 0)alkoxy-, (C1-C10)alkoxy-(C1-C10)alkyl-, (C3-C10)cycloalkyl-O-, (C2-C9)heterocycloalkyl-O-, (C6-C14)aryl-O-, (C2-C9)heteroaryl-O-, HO-, halo, (CH3)2N-, and H2N-; or R10A and R11 are taken together to form a 3 to 10 member cycloalkyl, 15 heterocycloalkyl, aryl or heteroaryl ring; wherein each (C1-C10)alkyl, (C6-C14)aryl, (C2-C9)heteroaryl, (C3-C10)cycloalkyl, or (C2-C9)heterocycloalkyl are further optionally substituted by one to four groups selected from (C1-C10)alkyl, (C3-C10)cycloalkyl, )heterocycloalkyl, 20 (C6-C14)aryl, (C2-C9)heteroaryl, (C1-C10)alkylamine, ((C1-C10)alkyl)2amine, (C1-C3)alkynylamine, (C1-C10)alkyl-C(O)O- , COOH-(C1-C10)alkyl, COOH-(C3-C10)cycloalkyl, (C1-C10)alkoxy-, (C1-C10)alkoxy-(C1-C10)alkyl-, (C3-C10)cycloalkyl-O-, (C2-C9)heterocycloalkyl-O-, (C6-C14)aryl- 25 O-, (C2-C9)heteroaryl-O-, HO-, halo, or H2NY1 is O, S, NR12, or CR12R13, wherein R12 is absent or R12 and R13 are each independently ed from the group consisting of H, 0)alkyl, (C3-C10)cycloalkyl, (C2-C9)heterocycloalkyl, (C6-C14)aryl, (C2-C9)heteroaryl, 30 (C1-C10)alkylamine, 10)alkyl)2amine, (C1-C3)alkynylamine, (C1-C10)alkyl-C(O)O-, COOH-(C1-C10)alkyl, 20559659_1 (GHMatters) P43761NZ00 COOH-(C3-C10)cycloalkyl, (C1-C10)alkoxy-, (C1-C10)alkoxy-(C1-C10)alkyl-, (C3-C10)cycloalkyl-O-, (C2-C9)heterocycloalkyl-O-, (C6-C14)aryl-O-, (C2-C9)heteroaryl-O-, HO-, halo, and H2N-; 5 R1 and R2 are each H; R5 is absent or selected from the group consisting of H, (C1-C10)alkyl, 0)cycloalkyl, )heterocycloalkyl, (C6-C14)aryl, (C2-C9)heteroaryl, (C1-C10)alkylamine, ((C1-C10)alkyl)2amine, (C1-C3)alkynylamine, (C1-C10)alkoxy-, (C1-C10)alkoxy-(C1-C10)alkyl-, 10 (C3-C10)cycloalkyl-O-, (C2-C9)heterocycloalkyl-O-, (C6-C14)aryl-O-, )heteroaryl-O-, HO-, halo, and H2N-; and R6 is selected from the group consisting of 0)alkyl, (C3-C10)cycloalkyl, (C2-C9)heterocycloalkyl, (C6-C14)aryl, (C2-C9)heteroaryl, (C2-C10)alkylnyl, (C1-C10)alkylamine, ((C1-C10)alkyl)2amine, 0)alkynylamine, C(O)-, 15 (C1-C10)alkyl-C(O)O-, COOH-(C1-C10)alkyl-, COOH-(C3-C10)cycloalkyl-, (C1-C10)alkoxy-, R14-(C1-C10)alkyl-, R14-(C3-C10)cycloalkyl, R14-(C2-C9)heterocycloalkyl, R14-(C6-C14)aryl, R14-(C2-C9)heteroaryl, R14-(C2-C10)alkylnyl, R14-(C1-C10)alkylamine, R14-((C1-C10)alkyl)2amine, R14-(C2-C10)alkynylamine, R14-C(O)-, R14-(C1-C10)alkyl-C(O)O-, 20 R14-(C1-C10)alkoxy-, 0)cycloalkyl-O-, (C2-C9)heterocycloalkyl-O-, (C6-C14)aryl-O-, (C2-C9)heteroaryl-O-, R14-(C3-C10)cycloalkyl-O-, R14-(C2-C9)heterocycloalkyl-O-, R14-(C6-C14)aryl-O-, R14-(C2-C9)heteroaryl-O-, HO-, halo, cyano, H2N-, (CH3)HN-, (CH3)2N-, R14R15N-, R14R15N(O)C-, R14(R15C(O))N-, NC(O)O-, R14C(O)-, 25 R14R15NC(O)R14N-, (C1-C10)alkyl-OC(O)R14N-, (C3-C10)cycloalkyl- OC(O)R14N-, (C2-C9)heterocycloalkyl-OC(O)R14N-, (C6-C14)aryl- OC(O)R14N-, (C2-C9)heteroaryl-OC(O)R14N-, F3C-, F2HC-, CH3F2C-, FH2C-, CH3FHC-, (CH3)2FC-; NC-, (C1-C10)alkyl(O)P-, (C1-C10)alkyl-S-, (C1-C10)alkyl-S-(C1-C10)alkyl-, (C3-C10)cycloalkyl-S-, (C6-C14)aryl-S-, 30 (C2-C9)heteroalkyl-S-, )heterocycloalkyl-S-, (C2-C9)heteroaryl-S-, (C1-C10)alkyl-S(O)-, (C3-C10)cycloalkyl-S(O)-, 4)aryl-S(O)-, 20559659_1 (GHMatters) P43761NZ00 (C2-C9)heterocycloalkyl-S(O)-, (C2-C9)heteroaryl-S(O)-, (C3-C10)alkyl- S(O)2-, (C3-C10)cycloalkyl-S(O)2-, (C6-C14)aryl-S(O)2-, (C2-C9)heterocycloalkyl-S(O)2-, (C2-C9)heteroaryl-S(O)2-, R14R15NS(O)2-, (C1-C10)alkyl-S(O)2R14N-, (C3-C10)cycloalkyl-S(O)2R14N-, (C6-C14)aryl- 5 14N-, (C2-C9)heterocycloalkyl-SO2R14N-, and (C2-C9)heteroaryl- S(O)2R14N-; wherein R14 and R15 are each independently selected from the group consisting of H, (C1-C10)alkyl, (C3-C10)cycloalkyl, (C2-C9)heterocycloalkyl, 4)aryl, (C2-C9)heteroaryl, 10 (C1-C10)alkylamine, ((C1-C10)alkyl)2amine, (C1-C3)alkynylamine, (C1-C10)alkyl-C(O)O-, COOH-(C1-C10)alkyl, COOH-(C3-C10)cycloalkyl, (C1-C10)alkoxy-, (C1-C10)alkoxy-(C1-C10)alkyl-, 0)cycloalkyl-O-, (C2-C9)heterocycloalkyl-O-, (C6-C14)aryl-O-, 15 (C2-C9)heteroaryl-O-, HO-, F2HC-O-,halo, (CH3)2N-, H2N-, F3CC (O)-, F3C-, and F2HC-; or R14 and R15 are taken together to form a 3 to 10 member cycloalkyl, heterocycloalkyl, aryl or heteroaryl ring; wherein each (C1-C10)alkyl, (C6-C14)aryl, (C2-C9)heteroaryl, 20 (C3-C10)cycloalkyl, or (C2-C9)heterocycloalkyl are r optionally substituted by one to four groups selected from (C1-C10)alkyl, (C3-C10)cycloalkyl, (C2-C9)heterocycloalkyl, (C6-C14)aryl, (C2-C9)heteroaryl, (C1-C10)alkylamine, ((C1-C10)alkyl)2amine, (C1-C3)alkynylamine, (C1-C10)alkyl-C(O)O- 25 , COOH-(C1-C10)alkyl, COOH-(C3-C10)cycloalkyl, 0)alkoxy-, (C1-C10)alkoxy-(C1-C10)alkyl-, (C3-C10)cycloalkyl-O-, (C2-C9)heterocycloalkyl-O-, (C6-C14)aryl- O-, (C2-C9)heteroaryl-O-, HO-, halo, or H2N-; and Z1 is each ndently selected from H, halo, (C1-C10)alkyl, 30 (C2-C9)heteroalkyl, (C1-C10)alkylamine, 59_1 (GHMatters) P43761NZ00 ((C1-C10)alkyl)2amine, (C2-C10)alkynylamine, (C1- C10)alkoxy-, or H2N-; Y2 is O, S, NR17, or CR17R18, wherein R17 is absent or R17 and R18 are each independently 5 selected from H, (C1-C10)alkyl, (C3-C10)cycloalkyl, (C2-C9)heterocycloalkyl, (C6-C14)aryl, (C2-C9)heteroaryl, (C1-C10)alkylamine, ((C1-C10)alkyl)2amine, )alkynylamine, 0)alkyl-C(O)O-, COOH-(C1-C10)alkyl, COOH-(C3-C10)cycloalkyl, 10 (C1-C10)alkoxy-, (C1-C10)alkoxy-(C1-C10)alkyl-, (C3-C10)cycloalkyl-O-, (C2-C9)heterocycloalkyl-O-, 4)aryl-O-, (C2-C9)heteroaryl-O-, HO-, halo, or H2N-.
2. =A compound according to claim 1, wherein Y1 is selected from O, S, and CR12R13, and Y2 is selected from O, S, NR17, or CR17R18, wherein R12 and R17 are 15 each independently absent or H; and R13 and R18 are each independently H or (C1- C10)alkyl.
3. A compound according to claim 1, wherein Y1 and/or Y2 are each ndently
4. A compound according to claim 1 or 2, wherein T1 is CR10, T2 is CR10, and T3 is 20 CR10.
5. A compound according to claim 1 or 2, wherein R10 is selected from the group ting of H, 0)alkyl, (C3-C10)cycloalkyl, (C1-C10)alkoxy, and halo.
6. A compound ing to claim 1 or 2, wherein T1 is CR10, wherein R10 is H, T2 is CR10, wherein R10 is (C1-C10)alkyl, and T3 is CR10, wherein R10 is H. 25
7. A compound according to claim 1 or 2, wherein Z1 is H, halo, (C1-C10)alkyl, (C2-C9)heteroalkyl, (C1-C10)alkylamine, ((C1-C10)alkyl)2amine, (C2-C10)alkynylamine, (C1-C10)alkoxy-, or H2N-; Y1 is O; Y2 is O; 30 R5 is H; and R6 is (C2-C9)heteroaryl. 20559659_1 (GHMatters) P43761NZ00
8. A compound according to claim 1 or 2, wherein Z1 is each independently selected from H, halo, and (C1-C10)alkyl.
9. A compound according to claim 1 or 2, wherein R7 is each independently selected from H, (C2-C9)heterocycloalkyl, (C2-C9)heteroaryl, (C2-C10)alkynylamine, (C1- 5 C10)alkoxy-, (C1-C10 )alkyl-(C2-C9)heterocycloalkyl, (C2-C9)heterocycloalkyl-(C1- C10)alkoxy-, (C1-C10)alkoxy-(C2-C9)heterocycloalkyl-, )heteroalkyl-C(O)-, or F2HC-, wherein each 0)alkyl, (C2-C9)heteroaryl, or (C2- C9)heterocycloalkyl are further optionally substituted by one to four groups selected from (C1-C10)alkyl.
10.10. A compound ing to claim 1 or 2, wherein R5 is absent or selected from the group consisting of H, (C1-C10)alkyl, HO-, halo, and H2N-.
11. A compound according to claim 1 or 2, wherein R6 is selected from the group consisting of (C1-C10)alkyl, (C3-C10)cycloalkyl, (C2-C9)heteroaryl, R14-(C6- yl, R14-(C2-C9)heteroaryl, and R14-(C1-C10)alkylamine; n R14 is each 15 independently selected from the group consisting of H, (C1-C10)alkyl, (C3- C10)cycloalkyl, (C2-C9)heterocycloalkyl, (C6-C14)aryl, (C2-C9)heteroaryl, (C1- C10)alkylamine, (C1-C10)alkoxy-, HO-, F2HC-O-, F3C-C(O)-, F3C-, and F2HC-; and wherein each (C1-C10)alkyl, (C6-C14)aryl, (C2-C9)heteroaryl, (C3- C10)cycloalkyl, or (C2-C9)heterocycloalkyl is further optionally substituted by one 20 to four groups selected from (C1-C10)alkyl, (C3-C10)cycloalkyl, (C2- C9)heterocycloalkyl, 4)aryl, (C2-C9)heteroaryl, HO-, halo, or H2N-.
12. A compound that is selected from the group ting of: (2-(4-methoxyphenyl)-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)-1H-benzo[d]imidazolyl)methylbutynamine 4-(3-((2-(4-methoxyphenyl)-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)-3H-imidazo[4,5-b]pyridinyl)methylbutynamine (S)(3-((2-(4-methoxyphenyl)-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)-3H-imidazo[4,5-b]pyridinyl)methylbutynamine (R)(3-((2-(4-methoxyphenyl)-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)-3H-imidazo[4,5-b]pyridinyl)methylbutynamine 3-((2-(4-methoxyphenyl)-2,3-dihydrobenzo[b][1,4]dioxinyl)methyl)- 6-(4-methylpiperazinyl)-3H-imidazo[4,5-b]pyridine (4-methoxyphenyl)-2,3-dihydrobenzo[b][1,4]dioxinyl)methyl)- 20559659_1 (GHMatters) P43761NZ00 6-(1-methyl-1H-pyrazolyl)-3H-imidazo[4,5-b]pyridine 4-(3-((2-(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)-3H-imidazo[4,5-b]pyridinyl)methylbutynamine (S)(3-((2-(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin hyl)-3H-imidazo[4,5-b]pyridinyl)methylbutynamine (R)(3-((2-(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)-3H-imidazo[4,5-b]pyridinyl)methylbutynamine 3-((2-(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)(4-methylpiperazinyl)-3H-imidazo[4,5-b]pyridine 3-((2-(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin hyl)-3H-imidazo[4,5-b]pyridinecarbonitrile 6-(azetidinyl)((2-(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 6-cyclopropyl((2-(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 4-(3-((2-(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)-3H-imidazo[4,5-b]pyridinyl)morpholine 6-methoxy((2-(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 4-(3-((2-(4-methoxyphenyl)methyl-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)-3H-imidazo[4,5-b]pyridinyl)methylbutynamine 6-methoxy((2-(6-methoxypyridinyl)methyl-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 4-(3-((2-(2,4-dichlorophenyl)-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)-3H-imidazo[4,5-b]pyridinyl)methylbutynamine trifluoro-N-((6-((6-(1-methyl-1H-pyrazolyl)-3H-imidazo[4,5- b]pyridinyl)methyl)-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)acetamide 6-(3-methoxyazetidinyl)((2-(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 2-methyl(3-((2-(1-methyl-1H-pyrazolyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)butynamine 4-(3-(1-(2-(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin yl)ethyl)-3H-imidazo[4,5-b]pyridinyl)methylbutynamine 3-((2-(4-(difluoromethoxy)phenyl)-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)-3H-imidazo[4,5-b]pyridine 6-(1,3-dimethyl-1H-pyrazolyl)((2-(2-fluoromethoxyphenyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 6-bromo((2-(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin- 59_1 (GHMatters) P43761NZ00 6-yl)methyl)pyrazolo[1,5-a]pyrimidine 3-((2-(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)pyrazolo[1,5-a]pyridine (2-(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)imidazo[1,2-b]pyridazinyl)methylbutynamine N-ethyl((2-(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin- ethyl)picolinamide 4-((2-(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)picolinamide 4-((2-(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)-N-methylpicolinamide 2-(1-methyl-1H-pyrazolyl)((2-(4-(trifluoromethyl)phenyl)-2,3- obenzo[b][1,4]dioxinyl)methyl)pyridine 2,2,2-trifluoroacetate 5-((2-(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)pyrimidine-2,4-diamine 4-(3-((8-fluoro(4-(trifluoromethyl)phenyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methylbutynamine 3-((8-fluoro(4-(trifluoromethyl)phenyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(4-methylpiperazinyl)- 3H-imidazo[4,5-b]pyridine 3-((8-fluoro(4-(trifluoromethyl)phenyl)-2,3- obenzo[b][1,4]dioxinyl)methyl)(piperidinylethynyl)-3H- imidazo[4,5-b]pyridine hydrochloride 3-((8-fluoro(4-(trifluoromethyl)phenyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(1-methyl-1H-pyrazolyl)- 3H-imidazo[4,5-b]pyridine 2,2,2-trifluoroacetate 3-((8-fluoro(6-methoxypyridinyl)methyl-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)iodo-3H-imidazo[4,5- b]pyridine 6-cyclopropyl((8-fluoro(6-methoxypyridinyl)methyl-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 2,2,2-trifluoroacetate 4-(3-((8-fluoro(6-methoxypyridinyl)methyl-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methylbutynamine 3-((8-fluoro(6-methoxypyridinyl)methyl-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(1-methyl-1H-pyrazolyl)- 3H-imidazo[4,5-b]pyridine 3-((5-cyclopropylfluoro(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(1-methyl-1H-pyrazolyl)- 20559659_1 (GHMatters) P43761NZ00 dazo[4,5-b]pyridine 4-(3-((8-fluoro(6-methoxypyridinyl)-5,7-dimethyl-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methylbutynamine 2,2,2-trifluoroacetate 4-(3-((8-fluoro(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methylbutynamine 3-((8-fluoro(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin- 6-yl)methyl)(piperidinylethynyl)-3H-imidazo[4,5-b]pyridine 4-(3-((8-fluoro(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)morpholine 3-((8-fluoro(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin- 6-yl)methyl)(2-methyl-1H-imidazolyl)-3H-imidazo[4,5-b]pyridine 3-((8-fluoro(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin- ethyl)methoxyimidazo[1,2-a]pyridine 6-bromo((8-fluoro(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)pyrazolo[1,5-a]pyrimidine 3-((8-fluoro(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin- 6-yl)methyl)methoxypyrazolo[1,5-a]pyrimidine 3-((8-fluoro(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin- 6-yl)methyl)pyrazolo[1,5-a]pyrimidine 7-chloro((8-fluoro(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)imidazo[1,2-b]pyridazine 3-((8-fluoro(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin- ethyl)(3-methoxyazetidinyl)pyrazolo[1,5-a]pyridine 4-((8-fluoro(4-(trifluoromethyl)phenyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(1-methyl-1H-pyrazol yl)pyridine 3-((8-fluoro(4-(trifluoromethyl)phenyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(1-methyl-1H-pyrazol yl)pyridine 3-((8-fluoro(4-(trifluoromethyl)phenyl)-2,3- obenzo[b][1,4]dioxinyl)methyl)(1-methyl-1H-pyrazol yl)pyridine 4-(3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methylbutynamine (S)(3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methylbutynamine 20559659_1 (GHMatters) P43761NZ00 (R)(3-((8-methoxy(6-methoxypyridinyl)-2,3- obenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methylbutynamine 3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(1-methyl-1H-pyrazolyl)- 3H-imidazo[4,5-b]pyridine 4-(3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)morpholine 6-cyclopropyl((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 4-(3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methylbutynol 6-(3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)oxaazaspiro[3.3]heptane 3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(3-methoxypropynyl)- 3H-imidazo[4,5-b]pyridine 4-(3-((8-methoxy(6-methoxypyridinyl)-2,3- obenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)isoxazole 6-methoxy((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine (S)methoxy((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine methoxy((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(3-methoxyazetidinyl)- 3H-imidazo[4,5-b]pyridine 6-(azetidinyl)((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 2-((3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)oxy)-N,N-dimethylethanamine 3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(oxetanyloxy)-3H- imidazo[4,5-b]pyridine 3-((8-methoxy(6-methoxypyridinyl)-2,3- 20559659_1 (GHMatters) P43761NZ00 dihydrobenzo[b][1,4]dioxinyl)methyl)-N,N-dimethyl-3H-imidazo[4,5- b]pyridinamine 1-(3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin methylazetidinol 3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(1H-1,2,4-triazolyl)-3H- imidazo[4,5-b]pyridine 3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(1H-pyrazolyl)-3H- imidazo[4,5-b]pyridine 6-(1H-imidazolyl)((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(2-methyl-1H-imidazol yl)-3H-imidazo[4,5-b]pyridine 6-(2,4-dimethyl-1H-imidazolyl)((8-methoxy(6-methoxypyridin- 3-yl)-2,3-dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5- b]pyridine 3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)((1-methylazetidin yl)oxy)-3H-imidazo[4,5-b]pyridine 3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)methyl-3H-imidazo[4,5- b]pyridine 3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-N-methyl-3H-imidazo[4,5- b]pyridinamine 6-(1,3-dimethyl-1H-pyrazolyl)((8-methoxy(6-methoxypyridin- 3-yl)-2,3-dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5- b]pyridine 6-(6-fluoropyridinyl)((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine (8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin tidinol 3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(4-methylpiperazinyl)- 3H-imidazo[4,5-b]pyridine 1-(3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methylazetidinamine 59_1 (GHMatters) P43761NZ00 6-(3-fluoroazetidinyl)((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 6-fluoro((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine azetidinyl(3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methanone (S)-azetidinyl(3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methanone (R)-azetidinyl(3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methanone (3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methanol 3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(methoxymethyl)-3H- imidazo[4,5-b]pyridine luoromethyl)((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine (S)(difluoromethyl)((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine (R)(difluoromethyl)((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 6-methoxy((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)methyl-3H-imidazo[4,5- b]pyridine 6-(azetidinyl)((8-methoxy(6-methoxypyridinyl)-2,3- obenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 2,2,2-trifluoroacetate 5,6-dimethoxy((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-1H-benzo[d]imidazole 6-(1H-imidazolyl)((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine formate 3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(4-methyl-1H-imidazol yl)-3H-imidazo[4,5-b]pyridine 20559659_1 (GHMatters) P43761NZ00 3-((8-methoxy(6-methoxypyridinyl)methyl-2,3- obenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-(((2R,3S)methoxy(6-methoxypyridinyl)methyl-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-(((2R,3R)methoxy(6-methoxypyridinyl)methyl-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-(((2S,3R)methoxy(6-methoxypyridinyl)methyl-2,3- obenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-(((2S,3S)methoxy(6-methoxypyridinyl)methyl-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 6-methoxy((8-methoxy(6-methoxypyridinyl)methyl-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 6-methoxy(((2R,3S)methoxy(6-methoxypyridinyl)methyl- 2,3-dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 4-(3-((8-methoxy(6-methoxypyridinyl)methyl-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methylbutynamine 7-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-7H-imidazo[4,5-c]pyridazine 6-bromo((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)pyrazolo[1,5-a]pyrimidine 3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)pyrazolo[1,5-a]pyrimidine 3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(3-methoxyazetidin yl)pyrazolo[1,5-a]pyrimidine 4-(3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)pyrazolo[1,5-a]pyrimidin yl)morpholine 6-methoxy((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)pyrazolo[1,5-a]pyrimidine 3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)((1-methylazetidin )pyrazolo[1,5-a]pyrimidine 7-chloro((8-methoxy(6-methoxypyridinyl)-2,3- obenzo[b][1,4]dioxinyl)methyl)imidazo[1,2-b]pyridazine 4-(3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)imidazo[1,2-b]pyridazinyl)- 2-methylbutynamine 4-(3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)imidazo[1,2-b]pyridazin 20559659_1 (GHMatters) P43761NZ00 yl)morpholine 3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(3-methoxyazetidin yl)imidazo[1,2-b]pyridazine 3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)imidazo[1,2-a]pyridine 3-((8-methoxy(6-methoxypyridinyl)-2,3- obenzo[b][1,4]dioxinyl)methyl)imidazo[1,2-b]pyridazine 7-methoxy((8-methoxy(6-methoxypyridinyl)-2,3- obenzo[b][1,4]dioxinyl)methyl)imidazo[1,2-a]pyridine 3-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-1H-pyrrolo[2,3-b]pyridine 3-((2-(6-cyclopropylpyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 1-((2-(6-cyclopropylpyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-1H-benzo[d]imidazole 3-((2-(6-cyclopropylpyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)methyl-3H-imidazo[4,5- b]pyridine 1-((2-(6-cyclopropylpyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-1H-imidazo[4,5-c]pyridine 3-((2-(6-cyclopropylpyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)imidazo[1,2-a]pyrazine 9-((2-(6-cyclopropylpyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-9H-purine 3-((2-(6-cyclopropylpyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)((1-methylazetidin yl)oxy)-3H-imidazo[4,5-b]pyridine (3-((2-(6-cyclopropylpyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin hanol 4-(3-((8-methoxy(6-methylpyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methylbutynamine 3-((8-methoxy(6-methylpyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(2-methyl-1H-imidazol yl)-3H-imidazo[4,5-b]pyridine hloride 6-methoxy((8-methoxy(6-methylpyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-((8-methoxy(6-methylpyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 20559659_1 (GHMatters) P43761NZ00 3-((8-methoxy(6-methylpyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(3-methoxyazetidinyl)- 3H-imidazo[4,5-b]pyridine 1-(3-((8-methoxy(6-methylpyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)azetidinol 3-((8-methoxy(6-methylpyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(3-methoxyazetidin yl)imidazo[1,2-b]pyridazine 3-((8-methoxy(6-propylpyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin- 6-yl)methyl)-3H-imidazo[4,5-b]pyridine 3-((2-(6-ethylpyridinyl)methoxy-2,3-dihydrobenzo[b][1,4]dioxin- ethyl)-3H-imidazo[4,5-b]pyridine 4-(3-((2-(6-ethylpyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)morpholine 3-((2-(6-ethylpyridinyl)methoxy-2,3-dihydrobenzo[b][1,4]dioxin- 6-yl)methyl)((1-methylazetidinyl)oxy)-3H-imidazo[4,5-b]pyridine (6-ethylpyridinyl)methoxy-2,3-dihydrobenzo[b][1,4]dioxin- 6-yl)methyl)methoxy-3H-imidazo[4,5-b]pyridine (6-ethylpyridinyl)methoxy-2,3-dihydrobenzo[b][1,4]dioxin- 6-yl)methyl)methoxypyrazolo[1,5-a]pyrimidine 3-((2-(6-ethylpyridinyl)methoxy-2,3-dihydrobenzo[b][1,4]dioxin- 6-yl)methyl)(3-methoxyazetidinyl)pyrazolo[1,5-a]pyrimidine 3-((8-methoxy(6-methylpyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(trifluoromethyl)-3H- imidazo[4,5-b]pyridine 3-((2-(4,6-dimethylpyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)methoxy-3H-imidazo[4,5- b]pyridine 3-((2-(4,6-dimethylpyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(3-methoxyazetidinyl)- 3H-imidazo[4,5-b]pyridine (8-methoxy(4-methoxyphenyl)-2,3-dihydrobenzo[b][1,4]dioxin- 6-yl)methyl)-3H-imidazo[4,5-b]pyridinyl)methylbutynamine 3-((8-methoxy(4-methoxyphenyl)-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)(1-methyl-1H-imidazolyl)-3H-imidazo[4,5-b]pyridine 6-bromo((2-(4-(difluoromethoxy)phenyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine hydrochloride 3-((2-(4-(difluoromethoxy)phenyl)methoxy-2,3- 20559659_1 (GHMatters) P43761NZ00 dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine hydrochloride 4-(3-((2-(4-(difluoromethoxy)phenyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methylbutynamine 1-(3-((2-(4-(difluoromethoxy)phenyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)-N,N-dimethylazetidinamine 3-((2-(4-(difluoromethoxy)phenyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-N-methyl-3H-imidazo[4,5- b]pyridinamine 7-chloro((2-(4-(difluoromethoxy)phenyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)imidazo[1,2-b]pyridazine (2-(4-(difluoromethoxy)phenyl)methoxy-2,3- obenzo[b][1,4]dioxinyl)methyl)imidazo[1,2-b]pyridazinyl)- 3-methylazetidinol 3-((2-(4-(difluoromethoxy)phenyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)imidazo[1,2-b]pyridazine 7-chloro((2-(4-(difluoromethoxy)phenyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)(methoxy)methyl)imidazo[1,2- b]pyridazine (2-(4-(difluoromethoxy)phenyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)imidazo[1,2-b]pyridazinyl)- 2-methylbutynamine 4-(3-((8-methoxy(pyridinyl)-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)-3H-imidazo[4,5-b]pyridinyl)methylbutynamine 6-(1H-imidazolyl)((8-methoxy(pyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 4-(3-((8-methoxy(2-methylthiazolyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methylbutynamine 4-(6-((6-(3-(1H-imidazolyl)propynyl)-3H-imidazo[4,5- b]pyridinyl)methyl)methoxy-2,3-dihydrobenzo[b][1,4]dioxin yl)methylthiazole 4-(3-((8-methoxy(2-methylthiazolyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)morpholine 4-(6-((3H-imidazo[4,5-b]pyridinyl)methyl)methoxy-2,3- obenzo[b][1,4]dioxinyl)cyclopropylthiazole 4-(3-((2-(2-cyclopropylthiazolyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin 20559659_1 (GHMatters) P43761NZ00 yl)methylbutynamine 2-cyclopropyl(8-methoxy((6-methoxy-3H-imidazo[4,5-b]pyridin- ethyl)-2,3-dihydrobenzo[b][1,4]dioxinyl)thiazole 4-(3-((2-(2,5-dimethylthiazolyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methylbutynamine 4-(3-((8-methoxy(2-methyloxazolyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin methylbutynamine 4-(3-((2-(2,5-dimethyloxazolyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methylbutynamine 3-((8-methoxy(6-(2-methoxyethoxy)pyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 4-(3-((8-methoxy(6-(2-methoxyethoxy)pyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methylbutynamine 3-((8-methoxy(6-(2-methoxyethoxy)pyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(1-methyl-1H-imidazol yl)-3H-imidazo[4,5-b]pyridine 6-methoxy((8-methoxy(6-(2-methoxyethoxy)pyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-((2-(6-ethoxypyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-((2-(6-ethoxypyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)methoxy-3H-imidazo[4,5- (3-((2-(6-ethoxypyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methanol 3-((2-(6-ethoxypyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-1H-pyrrolo[2,3-b]pyridine 3-((2-(6-(difluoromethoxy)pyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)methoxy-3H-imidazo[4,5- b]pyridine 1-(3-((2-(6-(difluoromethoxy)pyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methylazetidinol 3-((2-(6-(difluoromethoxy)pyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-((8-methoxy-2,3-dihydrobenzo[b][1,4]dioxinyl)methyl)(1- 59_1 (GHMatters) P43761NZ00 idinyl)-1H-pyrazolyl)-3H-imidazo[4,5-b]pyridine 3-((8-methoxymethyl-2,3-dihydrobenzo[b][1,4]dioxinyl)methyl) (1-(piperidinyl)-1H-pyrazolyl)-3H-imidazo[4,5-b]pyridine methoxymethyl-2,3-dihydrobenzo[b][1,4]dioxinyl)methyl) (pyridinyl)-3H-imidazo[4,5-b]pyridine formate 3-((8-methoxymethyl-2,3-dihydrobenzo[b][1,4]dioxinyl)methyl) (1-methyl-1H-pyrazolyl)-3H-imidazo[4,5-b]pyridine formate 3-((2-cyclopropylmethoxy-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)(1-(piperidinyl)-1H-pyrazolyl)-3H-imidazo[4,5- b]pyridine 3-((2-cyclopropylmethoxy-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)(1-methyl-1H-imidazolyl)-3H-imidazo[4,5-b]pyridine (2-cyclopropylmethoxy-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)-3H-imidazo[4,5-b]pyridinyl)methylbutynamine 3-((2-isopropylmethoxy-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)(1-methyl-1H-pyrazolyl)-3H-imidazo[4,5-b]pyridine formate 4-(3-((2-isopropylmethoxy-2,3-dihydrobenzo[b][1,4]dioxin yl)methyl)-3H-imidazo[4,5-b]pyridinyl)-3,5-dimethylisoxazole 3-((2-cyclopropylmethoxymethyl-2,3-dihydrobenzo[b][1,4]dioxin- 6-yl)methyl)(1-methyl-1H-pyrazolyl)-3H-imidazo[4,5-b]pyridine (6-(difluoromethyl)pyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-((2-(2-cyclopropylpyrimidinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-((8-methoxy(6-methoxymethylpyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-((8-methoxy(6-methoxymethylpyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(3-methoxyazetidinyl)- 3H-imidazo[4,5-b]pyridine 6-methoxy((8-methoxy(6-methoxymethylpyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-((8-methoxy(6-methoxymethylpyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(3-methoxyazetidin yl)imidazo[1,2-b]pyridazine 3-((2-(2,6-dimethoxypyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-((2-(2,6-dimethoxypyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)methoxy-3H-imidazo[4,5- b]pyridine 3-((2-(2,6-dimethoxypyridinyl)methoxy-2,3- 20559659_1 (GHMatters) P43761NZ00 dihydrobenzo[b][1,4]dioxinyl)methyl)(3-methoxyazetidinyl)- 3H-imidazo[4,5-b]pyridine 3-((8-methoxy(6-(trifluoromethyl)pyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine ((8-methoxy(6-(trifluoromethyl)pyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine (R)((8-methoxy(6-(trifluoromethyl)pyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine oxy((8-methoxy(6-methoxymethylpyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-((8-methoxy(6-methoxymethylpyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 5-(6-((3H-imidazo[4,5-b]pyridinyl)methyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)-N,N-diethylpyridinamine 4-(5-(6-((3H-imidazo[4,5-b]pyridinyl)methyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)pyridinyl)morpholine 3-((8-methoxy(1-methyl-1H-pyrazolyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-((2-(1-cyclobutyl-1H-pyrazolyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-((2-(1-isopropyl-1H-pyrazolyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-((8-methoxy(6-(methoxymethyl)pyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-((8-methoxy(5-methoxypyrazinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine methoxy(2-methoxypyrimidinyl)-2,3- obenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-((2-(6-(1,1-difluoroethyl)pyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine (R)((2-(6-(1,1-difluoroethyl)pyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine (S)((2-(6-(1,1-difluoroethyl)pyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 5-(6-((3H-imidazo[4,5-b]pyridinyl)methyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)furo[2,3-b]pyridine 5-(6-((3H-imidazo[4,5-b]pyridinyl)methyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)-2,3-dihydrofuro[2,3-b]pyridine 3-((2-(1-(cyclopropylmethyl)-1H-pyrazolyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 20559659_1 (GHMatters) P43761NZ00 3-((2-(4,4-difluorocyclohexyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-((8-methoxy(1-(2-methoxyethyl)-1H-pyrazolyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-((2-butylmethoxy-2,3-dihydrobenzo[b][1,4]dioxinyl)methyl)-3H- imidazo[4,5-b]pyridine 6-methoxy((8-methoxy(1-methyl-1H-pyrazolyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-((2-(1,5-dimethyl-1H-pyrazolyl)methoxy-2,3- obenzo[b][1,4]dioxinyl)methyl)methoxy-3H-imidazo[4,5- 3-((2-(1,3-dimethyl-1H-pyrazolyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)methoxy-3H-imidazo[4,5- b]pyridine 3-((2-(1-(cyclopropylmethyl)-1H-pyrazolyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)methoxy-3H-imidazo[4,5- b]pyridine 3-((2-(1-cyclobutyl-1H-pyrazolyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)methoxy-3H-imidazo[4,5- b]pyridine 6-methoxy((8-methoxy(6-(methoxymethyl)pyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine butylmethoxy-2,3-dihydrobenzo[b][1,4]dioxinyl)methyl) methoxy-3H-imidazo[4,5-b]pyridine 6-(azetidinyl)((8-methoxy(1-methyl-1H-pyrazolyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 3-((8-methoxy(1-methyl-1H-pyrazolyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(3-methoxyazetidinyl)- 3H-imidazo[4,5-b]pyridine 6-cyclopropyl((8-methoxy(1-methyl-1H-pyrazolyl)-2,3- obenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 6-cyclopropyl((8-methoxy(6-(methoxymethyl)pyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 6-(difluoromethyl)((8-methoxy(6-(methoxymethyl)pyridinyl)- 2,3-dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine (3-((2-(1-cyclobutyl-1H-pyrazolyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)methanol 3-((8-methoxy(6-methylpyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)(trifluoromethyl)-3H- imidazo[4,5-b]pyridine 20559659_1 (GHMatters) P43761NZ00 (8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridin yl)azetidinone 7-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-5H-pyrrolo[2,3-b]pyrazine 4-((8-methoxy(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-1H-pyrrolo[2,3-b]pyridine 4-(3-((2-(6-methoxypyridinyl)chromanyl)methyl)-3H-imidazo[4,5- b]pyridinyl)methylbutynamine 4-(3-((8-methoxy(4-methoxyphenyl)chromanyl)methyl)-3H- imidazo[4,5-b]pyridinyl)methylbutynamine 6-fluoro((8-methoxy(6-methoxypyridinyl)chroman yl)methyl)-3H-imidazo[4,5-b]pyridine 4-(3-((8-methoxy(6-methoxypyridinyl)chromanyl)methyl)-3H- imidazo[4,5-b]pyridinyl)methylbutynamine (8-methoxy(6-methoxypyridinyl)chromanyl)methyl)-3H- imidazo[4,5-b]pyridinyl)morpholine 3-((8-methoxy(6-methoxypyridinyl)chromanyl)methyl)(2- methyl-1H-imidazolyl)-3H-imidazo[4,5-b]pyridine 3-((8-methoxy(6-methoxypyridinyl)chromanyl)methyl)-3H- imidazo[4,5-b]pyridine 4-(3-((8-methoxy(6-methoxypyridinyl)chroman yl)methyl)pyrazolo[1,5-a]pyrimidinyl)methylbutynamine 4-(3-((8-methoxy(6-methoxypyridinyl)chroman yl)methyl)pyrazolo[1,5-a]pyrimidinyl)morpholine 3-((8-methoxy(6-methoxypyridinyl)chromanyl)methyl)(2- -1H-imidazolyl)pyrazolo[1,5-a]pyrimidine 4-(3-((8-methoxy(6-methoxypyridinyl)chroman yl)methyl)pyrazolo[1,5-a]pyridinyl)methylbutynamine 4-(3-((8-methoxy(6-methoxypyridinyl)chroman yl)methyl)pyrazolo[1,5-a]pyridinyl)morpholine 3-((8-methoxy(6-methoxypyridinyl)chromanyl)methyl)(2- methyl-1H-imidazolyl)pyrazolo[1,5-a]pyridine 4-(3-((8-methoxy(6-methoxypyridinyl)chroman yl)methyl)imidazo[1,2-b]pyridazinyl)methylbutynamine 4-(3-((8-methoxy(6-methoxypyridinyl)chroman yl)methyl)imidazo[1,2-b]pyridazinyl)morpholine 4-(3-((8-fluoro(6-methoxypyridinyl)chromanyl)methyl)-3H- imidazo[4,5-b]pyridinyl)methylbutynamine 4-(3-((8-methoxy(6-methylpyridinyl)chromanyl)methyl)-3H- 20559659_1 (GHMatters) P43761NZ00 imidazo[4,5-b]pyridinyl)methylbutynamine 4-(3-((8-methoxy(6-methylpyridinyl)chromanyl)methyl)-3H- imidazo[4,5-b]pyridinyl)morpholine methoxy(6-methylpyridinyl)chromanyl)methyl)(2- methyl-1H-imidazolyl)-3H-imidazo[4,5-b]pyridine 6-cyclopropyl((8-methoxy(6-methylpyridinyl)chroman yl)methyl)-3H-imidazo[4,5-b]pyridine 4-(3-((2-(6-ethylpyridinyl)methoxychromanyl)methyl)-3H- imidazo[4,5-b]pyridinyl)methylbutynamine 4-(3-((2-(6-ethylpyridinyl)methoxychromanyl)methyl)-3H- imidazo[4,5-b]pyridinyl)morpholine 3-((2-(6-ethylpyridinyl)methoxychromanyl)methyl)(2- methyl-1H-imidazolyl)-3H-imidazo[4,5-b]pyridine (8-methoxy(2-methylthiazolyl)chromanyl)methyl)-3H- imidazo[4,5-b]pyridinyl)methylbutynamine 4-(3-((8-methoxy(2-methylthiazolyl)chromanyl)methyl)-3H- imidazo[4,5-b]pyridinyl)morpholine 2-methyl(3-((4-methyl(4-(trifluoromethyl)phenyl)-3,4-dihydro-2H- benzo[b][1,4]oxazinyl)methyl)-3H-imidazo[4,5-b]pyridinyl)but ynamine 4-methyl((6-(1-methyl-1H-pyrazolyl)-3H-imidazo[4,5-b]pyridin yl)methyl)(4-(trifluoromethyl)phenyl)-3,4-dihydro-2H- benzo[b][1,4]oxazine 6-bromo((2-(6-methoxypyridinyl)-2,3- dihydrobenzo[b][1,4]oxathiinyl)methyl)-3H-imidazo[4,5-b]pyridine 4-(3-((2-(6-methoxypyridinyl)-2,3-dihydrobenzo[b][1,4]oxathiin yl)methyl)-3H-imidazo[4,5-b]pyridinyl)methylbutynamine 3-(3-methoxy((6-methoxypyridinyl)methoxy)benzyl)(piperidin- 3-ylethynyl)-3H-imidazo[4,5-b]pyridine 3-(3-methoxy((6-methoxypyridinyl)methoxy)benzyl) (pyrrolidinylethynyl)-3H-imidazo[4,5-b]pyridine 4-(3-(3-methoxy((6-methylpyridinyl)methoxy)benzyl)-3H- imidazo[4,5-b]pyridinyl)methylbutynamine 4-(3-((5-ethoxy((6-methylpyridinyl)methoxy)pyridinyl)methyl)- dazo[4,5-b]pyridinyl)methylbutynamine 3-((5-ethoxy((6-methylpyridinyl)methoxy)pyridin yl)methyl)pyrazolo[1,5-a]pyrimidine ethoxy((6-(trifluoromethyl)pyridinyl)methoxy)pyridin yl)methyl)-N,N-dimethylimidazo[1,2-b]pyridazinecarboxamide 4-((6-((6-cyclopropylpyridinyl)methoxy)ethoxypyridin 20559659_1 (GHMatters) P43761NZ00 yl)methyl)-N-methylpicolinamide 6-((3H-imidazo[4,5-b]pyridinyl)methyl)methoxy((6- methoxypyridinyl)methyl)benzo[d]oxazole 3-((2-(6-(2-fluoropropanyl)pyridinyl)methoxy-2,3- dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5-b]pyridine 4-((6-((6-cyclopropylpyridinyl)methoxy)ethoxypyridinyl)oxy)- N-methylpicolinamide 4-((6-((6-cyclopropylpyridinyl)methoxy)fluoropyridinyl)oxy)- ylpicolinamide and/or stereoisomers, optical s, racemic and diastereomeric mixtures, and/or pharmaceutically acceptable salts thereof.
13. A compound chosen from 3-((8-methoxy(6-methoxypyridin yl)methyl-2,3-dihydrobenzo[b][1,4]dioxinyl)methyl)-3H-imidazo[4,5- 5 b]pyridine, and/or stereoisomers, optical isomers, racemic and diastereomeric mixtures, and/or pharmaceutically able salts thereof.
14. A compound of claim 13, which is 3-(((2S,3S)methoxy(6- methoxypyridinyl)methyl-2,3-dihydrobenzo[b][1,4]dioxinyl)methyl)-3H- imidazo[4,5-b]pyridine. 10
15. A pharmaceutical composition comprising a compound and/or a pharmaceutically acceptable salt as defined in any one of claims 1 to 14 and a pharmaceutically acceptable excipient.
16. Use of a compound as defined in any one of claims 1 to 14, wherein it is for the preparation of a medicament. 15
17. Use of a compound as defined in any one of claims 1 to 14, wherein it is for the preparation of a medicament for ng a disease or disorder ed from Multiple Sclerosis, ALS, Huntington’s e, lupus, lupus nephritis, and rheumatoid arthritis. 20559659_1 (GHMatters) P43761NZ00
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