# US 10,369,139 B2 · Crystalline compound as semicarbazide-sensitive amine oxidase (SSAO) enzyme inhibitor

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- Number: US 10,369,139 B2
- Document ID: US10369139B2
- Status: Granted
- Kind: B2
- Application number: 15/567,549
- Filed: 2016-04-22
- Published: 2018-03-29
- Granted: 2019-08-06
- Earliest claimed: 2015-04-24
- Assignees: Benevolentai Cambridge Limited
- Applicants: Benevolentai Cambridge Limited
- Inventors: Edward Savory
- Web page: https://patentgrep.com/patent/US10369139B2

## CPC

- A61K 31/437: the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- 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 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 9/04: Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 9/14: Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 11/06: Antiasthmatics
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/06: Antipsoriatics
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/08: Antiepileptics; Anticonvulsants
- A61P 25/16: Anti-Parkinson drugs
- 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 27/02: Ophthalmic agents
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 31/04: Antibacterial agents
- A61P 35/00: Antineoplastic agents
- A61P 37/00: Drugs for immunological or allergic disorders
- A61P 37/02: Immunomodulators
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07C 309/04: containing only one sulfo group
- C07D 307/20: Oxygen atoms
- C07D 407/14: containing three or more hetero rings
- C07D 471/04: Ortho-condensed systems
- C30B 29/10: Inorganic compounds or compositions
- A61K 2300/00: Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C30B: SINGLE-CRYSTAL GROWTH (by using ultra-high pressure, e.g. for the formation of diamonds, B01J3/06); UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL (zone-refining of metals or alloys C22B); PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE (casting of metals, casting of other substances by the same processes or devices B22D; working of plastics B29; modifying the physical structure of metals or alloys C21D, C22F); SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE (for producing semiconductor devices or parts thereof H10); APPARATUS THEREFOR

## Abstract

A specific crystalline mesylate salt form of (3S)-Tetrahydrofuran-3-yl (4S)-4-isopropyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate, and the use of the same in medicine. (Formula (I)).

## Claims

### Claim 1

Crystalline (3S)-Tetrahydrofuran-3-yl (4S)-4-isopropyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate mesylate salt having the space group P2(1)2(1)2(1), and unit cell dimensions substantially as follows:
a
8.75780(10)Å
α
90°
b
9.70830(10)Å,
β
90°,
c
20.6736(2)Å,
γ
90°.

### Claim 2

Crystalline (3S)-Tetrahydrofuran-3-yl (4S)-4-isopropyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate mesylate salt having an XRPD pattern containing the following 2θ value measured using CuKα radiation: 21.948.

### Claim 3 (depends on 2)

The salt according to claim 2 having an XRPD pattern containing the following 2θ values measured using CuKα radiation: 17.744 and 21.948.

### Claim 4 (depends on 2)

The salt according to claim 2 having an XRPD pattern containing the following 2θ values measured using CuKα radiation: 17.744, 20.886, 21.948.

### Claim 5 (depends on 2)

The salt according to claim 2 having an XRPD pattern containing the following 2θ values measured using CuKα radiation: 17.744, 20.886, 21.948, and 9.851.

### Claim 6 (depends on 2)

The salt according to claim 2 having an XRPD pattern containing the following 2θ values measured using CuKα radiation: 17.744, 20.886, 21.948, 9.851 and 16.280.

### Claim 7 (depends on 2)

The salt according to claim 2 having an XRPD pattern containing the following 2θ values measured using CuKα radiation: 9.851, 16.280, 17.097, 17.744, 19.694, 20.443, 20.886, 21.948, 22.112, 23.194, 23.653, 24.144, 27.084, 27.283 and 29.912.

### Claim 8 (depends on 2)

The salt according to claim 2 having an XRPD pattern as set out in Table 4 and/or FIG. 2.

### Claim 9 (depends on 1)

A salt according to claim 1 having a purity of greater than 95%.

### Claim 10 (depends on 1)

A salt according to claim 1 having a purity of greater than 99%.

### Claim 11 (depends on 1)

A salt according to claim 1 having a purity of greater than 99.5%.

### Claim 12 (depends on 1)

A salt according to claim 1 having an enantiomeric purity of greater than 95%.

### Claim 13 (depends on 1)

A salt according to claim 1 having an enantiomeric purity of greater than 99%.

### Claim 14 (depends on 1)

A salt according to claim 1 having an enantiomeric purity of greater than 99.5%.

### Claim 15 (depends on 1)

A pharmaceutical composition comprising a salt according to claim 1, and one or more suitable excipients.

### Claim 16

A process of making crystalline (3S)-Tetrahydrofuran-3-yl (4S)-4-isopropyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate mesylate salt by forming the mesylate salt from the free base of (3S)-Tetrahydrofuran-3-yl (4S)-4-isopropyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate.

### Claim 17 (depends on 16)

A process according to claim 16 wherein the mesylate salt is formed by addition of methanesulphonic acid to the free base.

### Claim 18 (depends on 16)

Crystalline (3S)-Tetrahydrofuran-3-yl (4S)-4-isopropyl-1,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate mesylate obtained by the process according to claim 16.