# US 8,785,438 B2 · Imidazopyridin-2-one derivatives

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- Number: US 8,785,438 B2
- Document ID: US8785438B2
- Status: Granted
- Kind: B2
- Application number: 13/800,907
- Filed: 2013-03-13
- Published: 2013-12-19
- Granted: 2014-07-22
- Earliest claimed: 2008-08-05
- Assignees: Daiichi Sankyo Company, Limited
- Applicants: Daiichi Sankyo Company, Limited
- Inventors: Masami Ohtsuka; Noriyasu Haginoya; Masanori Ichikawa; Hironori Matsunaga; Hironao Saito; Yoshihiro Shibata; Tomoyuki Tsunemi
- Web page: https://patentgrep.com/patent/US8785438B2

## CPC

- C07D 487/04: Ortho-condensed systems
- A61K 31/437: the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A61K 31/4709: Non-condensed quinolines and containing further heterocyclic rings
- A61K 31/4725: containing further heterocyclic rings
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 471/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A compound represented by formula (I) having mTOR inhibitory activity or a pharmacologically acceptable salt thereof.

## Claims

### Claim 1

A method for inhibiting a tumor treatable by inhibiting the mammalian target of rapamycin (mTOR), comprising administering a therapeutically effective amount of a compound of formula (I) or a pharmacologically acceptable salt thereof to a subject in need thereof, the compound of formula (I) having the structure:
wherein
A is an 8- to 10-membered partially saturated or aromatic fused bicyclic nitrogen-containing heterocyclic group having 1 to 3 nitrogen atoms,
A may have the same or different n R1s as substituents,
R1 is a substituent selected from the group consisting of a hydroxy group, a halogen atom, a cyano group, an oxo group, a C1-4 alkyl group (wherein the C1-4 alkyl group may be substituted with one or two same or different C1-4 alkoxy groups or —NR7aR7bs), a C1-4 alkoxy group, a halogeno-C1-4 alkyl group, —NR7aR7b, —C(O)R8 and —C(O)NR9aR9b,
n is any integer of 0 to 3,
R7a, R7b, R9a and R9b are the same or different and are each a hydrogen atom or a C1-4 alkyl group (wherein the C1-4 alkyl group may be substituted with 1 or 2 hydroxy groups),
R8 is a hydrogen atom, a hydroxy group, a C1-4 alkyl group or a C1-4 alkoxy group,
B is a 3- to 7-membered saturated or partially saturated monocyclic hydrocarbon group and may contain 1 or 2 oxygen atoms, sulfur atoms, nitrogen atoms, sulfinyl groups and/or sulfonyl groups as ring constituents,
B may have the same or different m R2s as substituents,
R2 is a substituent present on a carbon atom or nitrogen atom forming B,
R2 is a substituent selected from the group consisting of a hydroxy group, a halogen atom, a cyano group, an oxo group, a C1-4 alkyl group (wherein the C1-4 alkyl group may be substituted with 1 or 2 C1-4 alkoxy groups), a C1-4 alkoxy group, a halogeno-C1-4 alkyl group, a C1-4 alkylsulfonyl group, a C1-4 alkylcarbonyl group and —NR10aR10b when R2 is a substituent present on a carbon atom forming B, and R2 is a substituent selected from the group consisting of a hydroxy group, a C1-4 alkyl group (wherein the C1-4 alkyl group may be substituted with 1 or 2 C1-4 alkoxy groups), a C1-4 alkoxy group, a halogeno-C1-4 alkyl group, a C1-4 alkylsulfonyl group, a C1-4 alkylcarbonyl group and —NR10aR10b when R2 is a substituent present on a nitrogen atom forming B,
R10a and R10b are the same or different and are each a hydrogen atom or a C1-4 alkyl group,
m is any integer of 0 to 3,
Q is a bond or a C1-4 alkylene group,
R3 and R4 are the same or different and are each a hydrogen atom, a halogen atom, a C1-4 alkyl group, a halogeno-C1-4 alkyl group or a cyano group, and
R5 and R6 are the same or different and are each a hydrogen atom, a halogen atom or a C1-4 alkyl group, or R5 and R6 together may form an oxo group or together with the carbon atom to which R5 and R6 are bonded may form a C3-8 cycloalkyl group.

### Claim 2 (depends on 1)

The method of claim 1, wherein the subject is a human.

### Claim 3 (depends on 1)

The method of claim 1, wherein the cancer is selected from the group consisting of leukemia, lymphoma, multiple myeloma, brain tumor, head and neck cancer, esophageal cancer, gastric cancer, appendiceal cancer, colon cancer, anal cancer, gallbladder cancer, bile duct cancer, pancreatic cancer, gastrointestinal stromal tumor, lung cancer, liver cancer, mesothelioma, thyroid cancer, renal cancer, prostate cancer, neuroendocrine tumor, melanoma, breast cancer, endometrial cancer, cervical cancer, ovarian cancer, osteosarcoma, soft tissue sarcoma, Kaposi's sarcoma, myosarcoma, renal cancer, bladder cancer, and testicular cancer.

### Claim 4 (depends on 1)

The method of claim 1, wherein A is a fused bicyclic nitrogen-containing heterocyclic group having 1 to 3 nitrogen atoms in which:
(a) the ring directly bonded to the imidazopyridine ring is a partially saturated or aromatic 6-membered ring containing 0 to 2 nitrogen atoms and
(b) the ring not directly bonded to the imidazopyridine ring is a partially saturated or aromatic 5-membered ring containing 1 or 2 nitrogen atoms.

### Claim 5 (depends on 1)

The method of claim 1, wherein A is an indolyl group, an isoindolyl group, an indazolyl group, a pyrrolopyridyl group, a pyrazolopyridyl group, an imidazopyridyl group, a pyrrolopyridazinyl group, a pyrazolopyridazinyl group, an imidazopyridazinyl group, a pyrrolopyrimidinyl group, a pyrazolopyrimidinyl group, an imidazopyrimidinyl group, a pyrrolopyrazinyl group, a pyrazolopyrazinyl group or an imidazopyrazinyl group.

### Claim 6 (depends on 1)

The method of claim 1, wherein R1 is a substituent identically or differently selected from the group consisting of a fluorine atom, a chlorine atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a methoxy group, an ethoxy group, a trifluoromethyl group, a methoxymethyl group, an ethoxymethyl group, an amino group, a methylamino group, a dimethylamino group, a methylethylamino group, a propylamino group, a (2-hydroxyethyl)(methyl)amino group, a formyl group, an acetyl group, an ethylcarbonyl group, an ethoxycarbonyl group, a carboxyl group, a carbamoyl group and a methylcarbamoyl group and n is any integer of 0 to 2.

### Claim 7 (depends on 1)

The method of claim 1, wherein R3 is a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group or a methyl group and R4 is a hydrogen atom.

### Claim 8 (depends on 1)

The method of claim 1, wherein Q is a bond or a methylene group.

### Claim 9 (depends on 1)

The method of claim 1, wherein R5 and R6 are the same or different and are each a hydrogen atom, a halogen atom or a C1-4 alkyl group.

### Claim 10 (depends on 1)

The method of claim 1, wherein B is a C3-7 cycloalkyl group, a tetrahydrofuryl group, a dihydropyranyl group, a tetrahydropyranyl group, a dioxanyl group, a piperidyl group, a piperazinyl group or a 1,1-dioxidotetrahydrothiopyranyl group.

### Claim 11 (depends on 1)

The method of claim 1, wherein R2 is a hydroxy group, a halogen atom, a cyano group, an oxo group, a C1-4 alkyl group, a C1-4 alkoxy-C1-4 alkyl group, a C1-4 alkoxy group, a C1-4 alkylsulfonyl group or a C1-4 alkylcarbonyl group when R2 is a substituent present on a carbon atom forming B, R2 is a C1-4 alkyl group, a C1-4 alkylsulfonyl group or a C1-4 alkylcarbonyl group when R2 is a substituent present on a nitrogen atom forming B, and m is any integer of 0 to 2.

### Claim 12 (depends on 1)

The method of claim 1, wherein the compound is selected from the group consisting of:
1-[(2S)-1,4-dioxan-2-ylmethyl]-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1,3-dihydro-imidazo[4,5-b]pyridin-2-one,
1-[(2S)-1,4-dioxan-2-ylmethyl]-6-(4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1,3-dihydro-imidazo[4,5-b]pyridin-2-one,
6-(3,4-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-[(2S)-1,4-dioxan-2-ylmethyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one,
6-(3-chloro-4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-[(2S)-1,4-dioxan-2-ylmethyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one,
1-[(2S)-1,4-dioxan-2-ylmethyl]-6-(3-fluoro-4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one,
2,6-anhydro-1,3,5-trideoxy-4-O-methyl-1-[6-(4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-L-threo-hexitol,
2,6-anhydro-1,3,4-trideoxy-5-O-methyl-1-[6-(4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-L-threo-hexitol,
2,6-anhydro-1,3,4-trideoxy-1-[6-(3,4-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-5-O-methyl-L-threo-hexitol,
2,6-anhydro-1-[6-(3-chloro-4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-1,3,4-trideoxy-5-O-methyl-L-threo-hexitol,
2,6-anhydro-1,3,5-trideoxy-1-[6-(3,4-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-4-O-methyl-L-threo-hexitol, and
2,6-anhydro-1-[6-(3-chloro-4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-1,3,5-trideoxy-4-O-methyl-L-threo-hexitol.

### Claim 13 (depends on 1)

The method of claim 1, wherein the compound is 1-[(2S)-1,4-dioxan-2-ylmethyl]-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1,3-dihydro-imidazo[4,5-b]pyridin-2-one.

### Claim 14 (depends on 1)

The method of claim 1, wherein the compound is 1-[(2S)-1,4-dioxan-2-ylmethyl]-6-(4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1,3-dihydro-imidazo[4,5-b]pyridin-2-one.

### Claim 15 (depends on 1)

The method of claim 1, wherein the compound is 6-(3,4-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-[(2S)-1,4-dioxan-2-ylmethyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one.

### Claim 16 (depends on 1)

The method of claim 1, wherein the compound is 6-(3-chloro-4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-[(2S)-1,4-dioxan-2-ylmethyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one.

### Claim 17 (depends on 1)

The method of claim 1, wherein the compound is 1-[(2S)-1,4-dioxan-2-ylmethyl]-6-(3-fluoro-4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one.

### Claim 18 (depends on 1)

The method of claim 1, wherein the compound is 2,6-anhydro-1,3,5-trideoxy-4-O-methyl-1-[6-(4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-L-threo-hexitol.

### Claim 19 (depends on 1)

The method of claim 1, wherein the compound is 2,6-anhydro-1,3,4-trideoxy-5-O-methyl-1-[6-(4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-L-threo-hexitol.

### Claim 20 (depends on 1)

The method of claim 1, wherein the compound is 2,6-anhydro-1,3,4-trideoxy-1-[6-(3,4-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-5-O-methyl-L-threo-hexitol.

### Claim 21 (depends on 1)

The method of claim 1, wherein the compound is 2,6-anhydro-1-[6-(3-chloro-4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-1,3,4-trideoxy-5-O-methyl-L-threo-hexitol.

### Claim 22 (depends on 1)

The method of claim 1, wherein the compound is 2,6-anhydro-1,3,5-trideoxy-1-[6-(3,4-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-4-O-methyl-L-threo-hexitol.

### Claim 23 (depends on 1)

The method of claim 1, wherein the compound is 2,6-anhydro-1-[6-(3-chloro-4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-1,3,5-trideoxy-4-O-methyl-L-threo-hexitol.

### Claim 24

A method for inhibiting the mammalian target of rapamycin (mTOR) is a subject, comprising administering a therapeutically effective amount of a compound of formula (I) or a pharmacologically acceptable salt thereof to a subject in need thereof, the compound of formula (I) having the structure:
wherein
A is an 8- to 10-membered partially saturated or aromatic fused bicyclic nitrogen-containing heterocyclic group having 1 to 3 nitrogen atoms,
A may have the same or different n R1s as substituents,
R1 is a substituent selected from the group consisting of a hydroxy group, a halogen atom, a cyano group, an oxo group, a C1-4 alkyl group (wherein the C1-4 alkyl group may be substituted with one or two same or different C1-4 alkoxy groups or —NR7aR7bs), a C1-4 alkoxy group, a halogeno-C1-4 alkyl group, —NR7aR7b, —C(O)R8 and —C(O)NR9aR9b,
n is any integer of 0 to 3,
R7a, R7b, R9a and R9b are the same or different and are each a hydrogen atom or a C1-4 alkyl group (wherein the C1-4 alkyl group may be substituted with 1 or 2 hydroxy groups),
R8 is a hydrogen atom, a hydroxy group, a C1-4 alkyl group or a C1-4 alkoxy group,
B is a 3- to 7-membered saturated or partially saturated monocyclic hydrocarbon group and may contain 1 or 2 oxygen atoms, sulfur atoms, nitrogen atoms, sulfinyl groups and/or sulfonyl groups as ring constituents,
B may have the same or different m R2s as substituents,
R2 is a substituent present on a carbon atom or nitrogen atom forming B,
R2 is a substituent selected from the group consisting of a hydroxy group, a halogen atom, a cyano group, an oxo group, a C1-4 alkyl group (wherein the C1-4 alkyl group may be substituted with 1 or 2 C1-4 alkoxy groups), a C1-4 alkoxy group, a halogeno-C1-4 alkyl group, a C1-4 alkylsulfonyl group, a C1-4 alkylcarbonyl group and —NR10aR10b when R2 is a substituent present on a carbon atom forming B, and R2 is a substituent selected from the group consisting of a hydroxy group, a C1-4 alkyl group (wherein the C1-4 alkyl group may be substituted with 1 or 2 C1-4 alkoxy groups), a C1-4 alkoxy group, a halogeno-C1-4 alkyl group, a C1-4 alkylsulfonyl group, a C1-4 alkylcarbonyl group and —NR10aR10b when R2 is a substituent present on a nitrogen atom forming B,
R10a and R10b are the same or different and are each a hydrogen atom or a C1-4 alkyl group,
m is any integer of 0 to 3,
Q is a bond or a C1-4 alkylene group,
R3 and R4 are the same or different and are each a hydrogen atom, a halogen atom, a C1-4 alkyl group, a halogeno-C1-4 alkyl group or a cyano group, and
R5 and R6 are the same or different and are each a hydrogen atom, a halogen atom or a C1-4 alkyl group, or R5 and R6 together may form an oxo group or together with the carbon atom to which R5 and R6 are bonded may form a C3-8 cycloalkyl group.

### Claim 25 (depends on 24)

The method of claim 24, wherein the subject is a human.

### Claim 26 (depends on 24)

The method of claim 24, wherein A is a fused bicyclic nitrogen-containing heterocyclic group having 1 to 3 nitrogen atoms in which:
(a) the ring directly bonded to the imidazopyridine ring is a partially saturated or aromatic 6-membered ring containing 0 to 2 nitrogen atoms and
(b) the ring not directly bonded to the imidazopyridine ring is a partially saturated or aromatic 5-membered ring containing 1 or 2 nitrogen atoms.

### Claim 27 (depends on 24)

The method of claim 24, wherein A is an indolyl group, an isoindolyl group, an indazolyl group, a pyrrolopyridyl group, a pyrazolopyridyl group, an imidazopyridyl group, a pyrrolopyridazinyl group, a pyrazolopyridazinyl group, an imidazopyridazinyl group, a pyrrolopyrimidinyl group, a pyrazolopyrimidinyl group, an imidazopyrimidinyl group, a pyrrolopyrazinyl group, a pyrazolopyrazinyl group or an imidazopyrazinyl group.

### Claim 28 (depends on 24)

The method of claim 24, wherein R1 is a substituent identically or differently selected from the group consisting of a fluorine atom, a chlorine atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a methoxy group, an ethoxy group, a trifluoromethyl group, a methoxymethyl group, an ethoxymethyl group, an amino group, a methylamino group, a dimethylamino group, a methylethylamino group, a propylamino group, a (2-hydroxyethyl)(methyl)amino group, a formyl group, an acetyl group, an ethylcarbonyl group, an ethoxycarbonyl group, a carboxyl group, a carbamoyl group and a methylcarbamoyl group and n is any integer of 0 to 2.

### Claim 29 (depends on 24)

The method of claim 24, wherein R3 is a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group or a methyl group and R4 is a hydrogen atom.

### Claim 30 (depends on 24)

The method of claim 24, wherein Q is a bond or a methylene group.

### Claim 31 (depends on 24)

The method of claim 24, wherein R5 and R6 are the same or different and are each a hydrogen atom, a halogen atom or a C1-4 alkyl group.

### Claim 32 (depends on 24)

The method of claim 24, wherein B is a C3-7 cycloalkyl group, a tetrahydrofuryl group, a dihydropyranyl group, a tetrahydropyranyl group, a dioxanyl group, a piperidyl group, a piperazinyl group or a 1,1-dioxidotetrahydrothiopyranyl group.

### Claim 33 (depends on 24)

The method of claim 24, wherein R2 is a hydroxy group, a halogen atom, a cyano group, an oxo group, a C1-4 alkyl group, a C1-4 alkoxy-C1-4 alkyl group, a C1-4 alkoxy group, a C1-4 alkylsulfonyl group or a C1-4 alkylcarbonyl group when R2 is a substituent present on a carbon atom forming B, R2 is a C1-4 alkyl group, a C1-4 alkylsulfonyl group or a C1-4 alkylcarbonyl group when R2 is a substituent present on a nitrogen atom forming B, and m is any integer of 0 to 2.

### Claim 34 (depends on 24)

The method of claim 24, wherein the compound is selected from the group consisting of:
1-[(2S)-1,4-dioxan-2-ylmethyl]-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1,3-dihydro-imidazo[4,5-b]pyridin-2-one,
1-[(2S)-1,4-dioxan-2-ylmethyl]-6-(4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1,3-dihydro-imidazo[4,5-b]pyridin-2-one,
6-(3,4-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-[(2S)-1,4-dioxan-2-ylmethyl]-1,3-dihydro-2H-imidazo[b]pyridin-2-one,
6-(3-chloro-4-methyl-1H-pyrrolo[2,3-b]pyridin-5-1-[(2S)-1,4-dioxan-2-ylmethyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one,
1-[(2S)-1,4-dioxan-2-ylmethyl]-6-(3-fluoro-4-met 1H-pyrrolo[2,3-b]pyridin-5-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one,
2,6-anhydro-1,3,5-trideoxy-4-O-methyl-1-[6-(4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-L-threo-hexitol,
2,6-anhydro-1,3,4-trideoxy-5-O-methyl-1-[6-(4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-L-threo-hexitol,
2,6-anhydro-1,3,4-trideoxy-1-[6-(3,4-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-5-O-methyl-L-threo-hexitol,
2,6-anhydro-1-[6-(3-chloro-4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-1,3,4-trideoxy-5-O-methyl-L-threo-hexitol,
2,6-anhydro-1,3,5-trideoxy-1-[6-(3,4-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-4-O-methyl-L-threo-hexitol, and
2,6-anhydro-1-[6-(3-chloro-4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-1,3,5-trideoxy-4-O-methyl-L-threo-hexitol.

### Claim 35 (depends on 24)

The method of claim 24, wherein the compound is 1-[(2S)-1,4-dioxan-2-ylmethyl]-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1,3-dihydro-imidazo[4,5-b]pyridin-2-one.

### Claim 36 (depends on 24)

The method of claim 24, wherein the compound is 1-[(2S)-1,4-dioxan-2-ylmethyl]-6-(4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1,3-dihydro-imidazo[4,5-b]pyridin-2-one.

### Claim 37 (depends on 24)

The method of claim 24, wherein the compound is 6-(3,4-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-[(2S)-1,4-dioxan-2-ylmethyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one.

### Claim 38 (depends on 24)

The method of claim 24, wherein the compound is 6-(3-chloro-4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1-[(2S)-1,4-dioxan-2-ylmethyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one.

### Claim 39 (depends on 24)

The method of claim 24, wherein the compound is 1-[(2S)-1,4-dioxan-2-ylmethyl]-6-(3-fluoro-4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one.

### Claim 40 (depends on 24)

The method of claim 24, wherein the compound is 2,6-anhydro-1,3,5-trideoxy-4-O-methyl-1-[6-(4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-L-threo-hexitol.

### Claim 41 (depends on 24)

The method of claim 24, wherein the compound is 2,6-anhydro-1,3,4-trideoxy-5-O-methyl-1-[6-(4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-L-threo-hexitol.

### Claim 42 (depends on 24)

The method of claim 24, wherein the compound is 2,6-anhydro-1,3,4-trideoxy-1-[6-(3,4-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-5-O-methyl-L-threo-hexitol.

### Claim 43 (depends on 24)

The method of claim 24, wherein the compound is 2,6-anhydro-1-[6-(3-chloro-4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-1,3,4-trideoxy-5-O-methyl-L-threo-hexitol.

### Claim 44 (depends on 24)

The method of claim 24, wherein the compound is 2,6-anhydro-1,3,5-trideoxy-1-[6-(3,4-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-4-O-methyl-L-threo-hexitol.

### Claim 45 (depends on 24)

The method of claim 24, wherein the compound is 2,6-anhydro-1-[6-(3-chloro-4-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]-1,3,5-trideoxy-4-O-methyl-L-threo-hexitol.