# US 2019/0169147 A1 · Vortioxetine pamoic acid salt and crystal form thereof

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- Number: US 2019/0169147 A1
- Document ID: US20190169147A1
- Status: Published application
- Kind: A1
- Application number: 16/086,615
- Filed: 2017-03-28
- Published: 2019-06-06
- Earliest claimed: 2016-03-29
- Assignees: SHANGHAI SYNERGY PHARMACEUTICAL SCIENCES CO., LTD Wang, Yijin
- Applicants: SHANGHAI SYNERGY PHARMACEUTICAL SCIENCES CO., LTD Wang, Yijin
- Inventors: Yunfei LI; Xiaoer XIA; Xin XU; Zhen ZHANG; Lei LIU; Xiaojuan ZHANG; Liming ZHANG; Dongsheng LI; Yijin WANG; Jian GE
- Web page: https://patentgrep.com/patent/US20190169147A1

## CPC

- C07D 295/096: with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- A61K 31/495: having six-membered rings with two {or more} nitrogen atoms as the only ring heteroatoms, e.g. piperazine {or tetrazines}(A61K31/48 takes precedence {; with three nitrogen atoms A61K31/53})
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 25/22: Anxiolytics
- A61P 25/24: Antidepressants
- A61P 25/28: 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
- A61P 25/30: for treating abuse or dependence
- A61P 25/32: Alcohol-abuse
- A61P 25/34: Tobacco-abuse
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C07C 51/41: Preparation of salts of carboxylic acids ({C07C51/093 - C07C51/34 take precedence} preparation of soap C11D)
- C07C 65/11: with carboxyl groups on a condensed ring system containing two rings
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The present application provides a vortioxetine pamoic acid salt, which includes a crystal form, a solvate or an amorphous substance of the vortioxetine pamoic acid salt. The present application provides a preparation method and use of the vortioxetine pamoic acid salt and the crystal form thereof. The vortioxetine pamoic acid salt prepared in the present application prolongs the residence time of the vortioxetine in vivo, achieving a slow release of the vortioxetine in vivo, and is suitable for preparing a long-acting dosage form.

## Claims

### Claim 1

A compound, which is a vortioxetine pamoic acid salt, with a structural formula of (C18H22N2S)r.C23H16O6.nH2O, wherein r is 1 or 2, n=0˜10.

### Claim 2 (depends on 1)

The compound according to claim 1, characterized in that n is 0, 1, 2, 3, 4, 5 or 6.

### Claim 3 (depends on 1)

The compound according to claim 1, characterized in that the vortioxetine pamoic acid salt is a crystalline substance, a solvate, or an amorphous substance.

### Claim 4 (depends on 3)

The compound according to claim 3, characterized in that crystal form of the vortioxetine pamoic acid salt is crystal form A, and in an X ray powder diffraction pattern of the crystal form A, there are peaks at positions where 2θ is 12.96±0.2, 13.56±0.2, 16.67±0.2, 17.26±0.2 and 18.28±0.2 degrees.

### Claim 5 (depends on 4)

The compound according to claim 4, characterized in that in an X ray powder diffraction pattern of the crystal form A, there are peaks at one or more of positions where 2θ is 14.77±0.2, 18.28±0.2, 18.77±0.2, 19.98±0.2, 22.08±0.2, and 23.03±0.2 degrees.

### Claim 6 (depends on 4)

The compound according to claim 4, characterized in that in an X ray powder diffraction pattern of the crystal form A, there are peaks at one or more of positions where 2θ is 11.71±0.2, 12.41±0.2, 14.77±0.2, 18.28±0.2, 18.77±0.2, 19.98±0.2, 21.02±0.2, 22.08±0.2, 23.03±0.2, 24.03±0.2, 24.99±0.2, 25.94±0.2, 27.33±0.2, 27.99±0.2, 29.80±0.2, 30.59±0.2, 31.09±0.2, 32.70±0.2, 35.46±0.2, 39.21±0.2, 42.81±0.2, and 46.98±0.2 degrees, or X ray powder diffraction pattern of the crystal form A is shown in FIG. 3.

### Claim 7 (depends on 3)

The compound according to claim 3, characterized in that crystal form of the vortioxetine pamoic acid salt is crystal form B, and in an X ray powder diffraction pattern of the crystal form B, there are peaks at positions where 2θ is 15.23±0.2, 19.37±0.2, and 22.24±0.2 degrees.

### Claim 8 (depends on 7)

The compound according to claim 7, characterized in that in an X ray powder diffraction pattern of the crystal form B, there are peaks at one or more of positions where 2θ is 12.50±0.2, 14.93±0.2, 23.25±0.2, 24.49±0.2, 28.28±0.2, and 30.58±0.2 degrees.

### Claim 9 (depends on 7)

The compound according to claim 7, characterized in that in an X ray powder diffraction pattern of the crystal form B, there are peaks at one or more of positions where 2θ is 11.89±0.2, 12.50±0.2, 14.93±0.2, 18.63±0.2, 20.15±0.2, 23.25±0.2, 24.49±0.2, 24.82±0.2, 28.28±0.2, 30.58±0.2, 36.97±0.2, 37.58±0.2, 38.73±0.2, 40.67±0.2, and 41.81±0.2 degrees, or X ray powder diffraction pattern of the crystal form B is shown in FIG. 5.

### Claim 10 (depends on 3)

The compound according to claim 3, characterized in that crystal form of the vortioxetine pamoic acid salt is crystal form D, and in an X ray powder diffraction pattern of the crystal form D, there are peaks at positions where 2θ is 12.34±0.2, 16.16±0.2 and 18.05±0.2 degrees.

### Claim 11 (depends on 10)

The compound according to claim 10, characterized in that in an X ray powder diffraction pattern of the crystal form D, there are peaks at one or more of positions where 2θ is 11.51±0.2, 16.48±0.2, 17.69±0.2, 19.36±0.2, 21.50±0.2, 22.50±0.2, 24.01±0.2, and 27.65±0.2 degrees.

### Claim 12 (depends on 10)

The compound according to claim 10, characterized in that in an X ray powder diffraction pattern of the crystal form D, there are peaks at one or more of positions where 2θ is 11.51±0.2, 13.66±0.2, 14.5680.2, 16.48±0.2, 17.69±0.2, 18.83±0.2, 19.36±0.2, 20.09±0.2, 21.20±0.2, 21.50±0.2, 22.50±0.2, 24.01±0.2, 24.96±0.2, 26.40±0.2, 26.94±0.2, 27.62±0.2, 28.4860.2, 29.59±0.2, 30.58±0.2, 31.08±0.2, 31.28±0.2, 35.81±0.2, 41.45±0.2, 41.51±0.2, 43.38±0.2, and 48.23±0.2 degrees, or X ray powder diffraction pattern of the crystal form D is shown in FIG. 7.

### Claim 13

(canceled)

### Claim 14

(canceled)

### Claim 15 (depends on 1)

A pharmaceutical composition, comprising a crystal form, a solvate, or an amorphous form of the compound of claim 1 as active Ingredients, and pharmaceutically acceptable carriers.

### Claim 16 (depends on 15)

The pharmaceutical composition according to claim 15, characterized in that the carrier is a viscous aqueous or non-aqueous carrier.

### Claim 17 (depends on 15)

The pharmaceutical composition according to claim 15, characterized in that the carrier comprises a suspending agent, a tension agent and a wetting agent.

### Claim 18 (depends on 15)

The pharmaceutical composition according to claim 15, characterized in that the active ingredient exerts a medical effect in a human body for at least 48 hours;
preferably, the active ingredient exerts a medical effect in a human body for at least 7 days;
preferably, the active ingredient exerts a medical effect in a human body for at least two weeks;
preferably, the active ingredient exerts a medical effect in a human body for at least a month.

### Claim 19

(canceled)

### Claim 20

(canceled)

### Claim 21

(canceled)

### Claim 22 (depends on 15)

A method for treating depression or pain, comprising administering the pharmaceutical composition according to claim 15 to a patient.

### Claim 23 (depends on 22)

The method according to claim 22, wherein the composition is administered by injection.

### Claim 24 (depends on 22)

The method according to claim 22, wherein the composition is administered by muscle or subcutaneous injection.

### Claim 25 (depends on 22)

The method according to claim 22, characterized in that the drug can be released to the body according to a daily dose of 5-50 mg after administration.