# US 10,501,457 B2 · Compounds for bone growth

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- Number: US 10,501,457 B2
- Document ID: US10501457B2
- Status: Granted
- Kind: B2
- Application number: 15/365,283
- Filed: 2016-11-30
- Published: 2017-10-19
- Granted: 2019-12-10
- Earliest claimed: 2013-03-14
- Assignees: OsteoQC Inc.
- Applicants: OsteoQC Inc.
- Inventors: Debra Ellies; Jean-Philippe Rey; F. Scott Kimball
- Web page: https://patentgrep.com/patent/US10501457B2

## CPC

- C07D 471/04: Ortho-condensed systems
- A61P 1/02: Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
- A61P 13/12: of the kidneys
- A61P 19/00: Drugs for skeletal disorders
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 19/08: for bone diseases, e.g. rachitism, Paget's disease
- A61P 19/10: for osteoporosis
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07C 53/06: Salts thereof
- C07C 59/265: Citric acid
- C07D 209/86: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

In one aspect, the invention provides compounds of Formula I, and salts, hydrates and isomers thereof. In another aspect, the invention provides a method of promoting bone formation in a subject in need thereof by administering to the subject a therapeutically effective amount of a compound of Formula I, Formula II, or Formula III. The present invention also provides orthopedic and periodontal devices, as well as methods for the treatment of renal disease and cancer, using a compound of Formula I, Formula II, or Formula III.

## Claims

### Claim 1

A compound having the formula:
or a salt, or hydrate thereof; wherein
R2 is selected from the group consisting of H, C1-6 alkoxy, —OH, and C1-6 alkyl-OH;
R3a and R3b are independently selected from the group consisting of H, halo, C1-6 alkoxy, and —OH;
R3d is selected from the group consisting of H, C1-6 alkyl and C1-6 haloalkyl; and
the moiety
is selected from the group consisting of:

### Claim 2 (depends on 1)

The compound of claim 1, wherein
R2 is selected from the group consisting of —OH and methoxy; and
R3a and R3b are H.

### Claim 3 (depends on 2)

The compound of claim 2, wherein
R2 is —OH.

### Claim 4 (depends on 2)

The compound of claim 2, wherein
R2 is methoxy.

### Claim 5 (depends on 2)

The compound of claim 2, wherein
R3d is methyl or trifluoromethyl.

### Claim 6 (depends on 2)

The compound of claim 2, wherein
R3d is trifluoromethyl.

### Claim 7 (depends on 2)

The compound of claim 2, wherein
R3d is methyl.

### Claim 8 (depends on 5)

The compound of claim 5, wherein
is selected from the group consisting of:

### Claim 9 (depends on 5)

The compound of claim 5, wherein
is selected from the group consisting of:

### Claim 10 (depends on 1)

The compound of claim 1, wherein said compound is selected from the group consisting of
2-((2-(7-methoxy-1-methyl-9H-pyrido[3,4-b]indol-9-yl)ethyl)(methyl)amino)ethanol;
2-((2-(7-methoxy-1-(trifluoromethyl)-9H-pyrido[3,4-b]indol-9-yl)ethyl)amino)ethanol;
2,2′-((2-(7-methoxy-1-(trifluoromethyl)-9H-pyrido[3,4-b]indol-9-yl)ethyl)azanediyl)diethanol; and
2,2′-((2-(7-hydroxy-1-(trifluoromethyl)-9H-pyrido[3,4-b]indol-9-yl)ethyl)azanediyl)diethanol.

### Claim 11 (depends on 1)

A formate salt of the compound of claim 1.

### Claim 12 (depends on 1)

A citrate salt of the compound of claim 1.

### Claim 13 (depends on 1)

A hydrochloride salt of the compound of claim 1.

### Claim 14 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable excipient.