# US 10,501,447 B2 · Imidazolecarboxamides and their use as FAAH inhibitors

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- Number: US 10,501,447 B2
- Document ID: US10501447B2
- Status: Granted
- Kind: B2
- Application number: 14/906,822
- Filed: 2014-07-24
- Published: 2016-06-23
- Granted: 2019-12-10
- Earliest claimed: 2013-07-24
- Assignees: Bial - Portela & Ca, S.A.
- Applicants: BIAL-PORTELA & Ca, S.A.
- Inventors: Carla Patrícia Da Costa Pereira Rosa; Rita Gusmão De Noronha; Laszlo Erno Kiss
- Web page: https://patentgrep.com/patent/US10501447B2

## CPC

- C07D 405/12: linked by a chain containing hetero atoms as chain links
- A61K 31/4178: not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
- A61K 31/454: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 1/08: for nausea, cinetosis or vertigo; Antiemetics
- A61P 1/14: Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- 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 3/04: Anorexiants; Antiobesity agents
- A61P 9/00: Drugs for disorders of the cardiovascular system
- 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 9/12: Antihypertensives
- A61P 11/06: Antiasthmatics
- A61P 17/02: for treating wounds, ulcers, burns, scars, keloids, or the like
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 19/10: for osteoporosis
- A61P 21/02: Muscle relaxants, e.g. for tetanus or cramps
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 25/08: Antiepileptics; Anticonvulsants
- A61P 25/14: for treating abnormal movements, e.g. chorea, dyskinesia
- A61P 25/16: Anti-Parkinson drugs
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61P 25/20: Hypnotics; Sedatives
- 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 25/32: Alcohol-abuse
- A61P 25/34: Tobacco-abuse
- A61P 25/36: Opioid-abuse
- A61P 27/06: Antiglaucoma agents or miotics
- 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 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- A61P 39/02: Antidotes
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 235/24: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- 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 having a structure selected from the following: or a pharmaceutically acceptable salt thereof. The compound may be used as an inhibitor of fatty acid amide hydrolase.

## Claims

### Claim 1

A compound having a structure selected from the group consisting of:
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the pharmaceutically acceptable salt is selected from the group consisting of a hydrochloride salt, acetate salt, trifluoroacetate salt, methanesulfonate salt, 2-hydroxypropane-1,2,2-tricarboxylate salt, (2R,3R)-2,3-dihydroxysuccinate salt, phosphate salt, sulphate salt, benzoate salt, 2-hydroxy-benzoate salt, S-(+)-mandelate salt, S-(−)-malate salt, S-(−) pyroglutamate salt, pyruvate salt, p-toluenesulfonate salt, 1-R-(−)-camphorsulfonate salt, fumarate salt, maleate salt and oxalate salt.

### Claim 3 (depends on 1)

The compound of claim 1 or the pharmaceutically acceptable salt thereof, wherein the compound has the structure

### Claim 4 (depends on 1)

The compound of claim 1 or the pharmaceutically acceptable salt thereof, wherein the compound has the structure

### Claim 5 (depends on 1)

The compound of claim 1 or the pharmaceutically acceptable salt thereof, wherein the compound has the structure

### Claim 6 (depends on 1)

A pharmaceutical composition comprising a compound according to claim 1, together with one or more pharmaceutically acceptable excipients.

### Claim 7 (depends on 6)

The pharmaceutical composition of claim 6, further comprising one or more additional active pharmaceutical ingredients.

### Claim 8 (depends on 6)

The pharmaceutical composition of claim 6, wherein the composition is formulated for oral administration.

### Claim 9 (depends on 6)

The pharmaceutical composition of claim 6, wherein the composition is in the form of a sterile injectable preparation.

### Claim 10 (depends on 7)

The pharmaceutical composition of claim 7, wherein the one or more additional active pharmaceutical ingredients are selected from the group consisting of anandamide, oleoyl ethanolamide, and palmitoyl ethanolamide.

### Claim 11 (depends on 1)

A method of treatment of an eye condition selected from the group consisting of ocular hypertension and glaucoma, the method comprising the administration, to a subject in need of such treatment, of a therapeutically effective amount of a compound according to claim 1.

### Claim 12 (depends on 11)

The method of claim 11, wherein the method comprises further administration of one or more additional active pharmaceutical ingredients, wherein the compound is administered simultaneously with or staggered with respect to, the one or more additional active pharmaceutical ingredients.

### Claim 13 (depends on 12)

The method of claim 12, wherein the one or more additional active pharmaceutical ingredients are selected from the group consisting of anandamide, oleoyl ethanolamide and palmitoyl ethanolamide.

### Claim 14 (depends on 11)

The method of claim 11, wherein the eye condition is ocular hypertension.

### Claim 15 (depends on 11)

The method of claim 11, wherein the eye condition is glaucoma.