# US 10,501,437 B2 · Crystalline forms of N-[2-(3-Hydroxy-3-methylbutyl)-6-(2-hydroxypropan-2-yl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide

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- Number: US 10,501,437 B2
- Document ID: US10501437B2
- Status: Granted
- Kind: B2
- Application number: 16/097,506
- Filed: 2017-04-25
- Published: 2019-05-23
- Granted: 2019-12-10
- Earliest claimed: 2016-04-29
- Assignees: Bayer Pharma Aktiengesellschaft
- Applicants: Bayer Pharma Aktiengesellschaft
- Inventors: Tobias Thaler; Johannes Platzek; Nicolas Guimond
- Web page: https://patentgrep.com/patent/US10501437B2

## CPC

- C07D 401/12: linked by a chain containing hetero atoms as chain links
- A61K 9/2095: {Tabletting processes}
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 13/00: Drugs for disorders of the urinary system
- A61P 15/00: Drugs for genital or sexual disorders (for disorders of sex hormones A61P5/24); Contraceptives
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/06: Antipsoriatics
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 19/06: Antigout agents, e.g. antihyperuricemic or uricosuric agents
- A61P 19/08: for bone diseases, e.g. rachitism, Paget's disease
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 27/00: Drugs for disorders of the senses
- A61P 27/02: Ophthalmic agents
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 35/00: Antineoplastic agents
- A61P 37/00: Drugs for immunological or allergic disorders
- A61P 37/02: Immunomodulators
- A61P 37/04: Immunostimulants
- A61P 37/06: Immunosuppressants, e.g. drugs for graft rejection
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The present invention relates to crystalline forms of N-[2-(3-Hydroxy-3-methylbutyl)-6-(2-hydroxypropan-2-yl)-2H-indazol-5-yl]-6-(trifluoromethyl)pyridine-2-carboxamide, to processes for their preparation, to pharmaceutical compositions comprising them and to their use in the control of disorders.

## Claims

### Claim 1

A hydrate of the compound of formula (I)
wherein the hydrate has a X-ray powder diffraction diagram at 25° C. and with Cu-K alpha 1 as radiation source displaying at least the following reflections, quoted as 2Theta value ±0.2°: 9.4, 10.8, and 15.0.

### Claim 2 (depends on 1)

The hydrate of the compound of formula (I) of claim 1, wherein the hydrate has a X-ray powder diffraction diagram at 25° C. and with Cu-K alpha 1 as radiation source displaying at least the following reflections, quoted as 2Theta value ±0.2°: 9.4, 10.8, 15.0, 16.0, and 17.0.

### Claim 3 (depends on 1)

The hydrate of the compound of formula (I) of claim 1, wherein the hydrate has a X-ray powder diffraction diagram at 25° C. and with Cu-K alpha 1 as radiation source displaying at least the following reflections, quoted as 2Theta value ±0.2°: 9.4, 10.8, 15.0, 16.0, 17.0, 20.1, and 22.9.

### Claim 4 (depends on 1)

The hydrate of the compound of formula (I) of claim 1, wherein the hydrate has a X-ray powder diffraction diagram at 25° C. and with Cu-K alpha 1 as radiation source displaying at least the following reflections, quoted as 2Theta value ±0.2°: 9.4, 10.8, 15.0, 16.0, 17.0, 20.1, 22.9, 24.3, 26.6, and 29.8.

### Claim 5 (depends on 1)

A pharmaceutical composition comprising only a hydrate of the compound of formula (I) according to claim 1 mainly and no significant fractions of another form of the compound of formula (I).

### Claim 6 (depends on 1)

A pharmaceutical composition comprising a hydrate of the compound of formula (I) according to claim 1 and pharmaceutically acceptable excipients.

### Claim 7 (depends on 6)

The pharmaceutical composition of claim 6, comprising only the hydrate of the compound of formula (I) mainly and no significant fractions of another form of the compound of formula (I).

### Claim 8 (depends on 6)

The pharmaceutical composition of claim 6, comprising the hydrate of the compound of formula (I) in more than 85 percent by weight related to the total amount of all forms of the compound of the formula (I) present in the composition.

### Claim 9 (depends on 8)

The pharmaceutical composition of claim 8, comprising the hydrate of the compound of formula (I) in more than 90 percent by weight related to the total amount of all forms of the compound of formula (I) present in the composition.

### Claim 10 (depends on 1)

A method for treatment of rheumatoid arthritis in a human in need thereof, comprising administering to the human an effective amount of a hydrate of the compound of formula (I) according to claim 1.

### Claim 11 (depends on 5)

A method for treatment of rheumatoid arthritis in a human in need thereof, comprising administering to the human an effective amount of a pharmaceutical composition according to claim 5.

### Claim 12 (depends on 6)

A method for treatment of rheumatoid arthritis in a human in need thereof, comprising administering to the human an effective amount of a pharmaceutical composition according to claim 6.