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WO2023033679A4 - (azacycloalkyl)methoxy-substituted benzamides as modulators of trace amine-associated receptor 1 (taar1) - Google Patents

(azacycloalkyl)methoxy-substituted benzamides as modulators of trace amine-associated receptor 1 (taar1) Download PDF

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WO2023033679A4
WO2023033679A4 PCT/RU2022/050270 RU2022050270W WO2023033679A4 WO 2023033679 A4 WO2023033679 A4 WO 2023033679A4 RU 2022050270 W RU2022050270 W RU 2022050270W WO 2023033679 A4 WO2023033679 A4 WO 2023033679A4
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disorder
ylmethoxy
piperidin
disease
methanone
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WO2023033679A1 (en
Inventor
Raul Radikovich GAINETDINOV
Andrey Sergeevich GERASIMOV
Aleksey Yurievich LUKIN
Nikolay Ilyich ZHURILO
Mikhail Yurievich KRASAVIN
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"accellena Research And Development" "accellena" LLC LLC
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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    • A61K31/5375—1,4-Oxazines, e.g. morpholine
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    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms

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Abstract

(Azacycloalkyl)methoxy-substituted benzamides of general formula 1 and their pharmaceutically acceptable salts which are modulators of trace amine-associated receptor 1 (TAAR1) are disclosed. The method for producing the compounds of formula 1, pharmaceutical composition on their basis and use of said compounds and pharmaceutical composition for treating a disease, disorder or condition mediated by trace amine receptors TAAR1 such as mental disorders, cognitive disorders, metabolic disorders, neurological and neurodegenerative diseases are provided.

Claims

AMENDED CLAIMS received by the International Bureau on 31 March 2023 (31.03.2023)
1. A compound of formula 1 or a pharmaceutically acceptable salt thereof, wherein the compound of formula 1 is:
Figure imgf000002_0001
where n is 0, 1 or 2; m is 0 if n is 2, or m is 1 if n is 0 or 1;
R1 and R2 are independently selected from the group consisting of: hydrogen atom;
Ci-Cio alkyl optionally substituted with C3-C10 cycloalkyl;
C3-C10 cycloalkyl; or R1 and R2 together with the nitrogen atom to which they are attached form a 5- or 6- membered saturated heterocyclyl containing 1 nitrogen atom and optionally substituted with C1-C10 alkyl; or R1 and R2 together with the nitrogen atom to which they are attached form a 6-membered saturated heterocyclyl containing 1 nitrogen atom and 1 heteroatom selected from oxygen, sulfur and nitrogen.
2. The compound of claim 1, wherein R1 is hydrogen and R2 is C1-C10 alkyl.
3. The compound of claim 1, wherein R1 is hydrogen and R2 is C3-C10 cycloalkyl.
4. The compound of claim 1, wherein R1 and R2 together with the nitrogen atom to which they are attached form pyrrolidinyl or piperidinyl optionally substituted with C1-C10 alkyl.
5. The compound of claim 1, wherein R1 and R2 together with the nitrogen atom to which they are attached form morpholinyl.
6. The compound of claim 1, wherein the compound of formula 1 is selected from the group including:
(piperidin-l-yl)[4-(piperidin-3-ylmethoxy)phenyl]methanone,
7V-isopropyl-4-(piperidin-3-ylmethoxy)benzamide,
4-(piperidin-3-ylmethoxy)-7V-cyclopropylbenzamide, morpholino[4-(piperidin-3-ylmethoxy)phenyl]methanone,
[4-(piperidin-3-ylmethoxy)phenyl](pyrrolidin-l-yl)methanone,
25
AMENDED SHEET (ARTICLE 19) (4-methylpiperidin-l-yl)[3-(piperidin-3-ylmethoxy)phenyl]methanone, [3-(piperidin-3-ylmethoxy)phenyl](pyrrolidin-l-yl)methanone, (piperidin-l-yl)[3-(piperidin-3-ylmethoxy)phenyl]methanone, N-i sopropyl -4-(pyrrolidi n-2-ylm ethoxy)benzamide, 4-(pyrrolidin-2-ylmethoxy)-A-cyclopropylbenzamide, morpholino[4-(pyrrolidin-2-ylmethoxy)phenyl]methanone, (pyrrolidin-l-yl)[4-(pyrrolidin-2-ylmethoxy)phenyl]methanone, morpholino[4-(piperidin-4-ylmethoxy)phenyl]methanone, (4-methylpiperidin-l-yl)[4-(piperidin-4-ylmethoxy)phenyl]methanone, (piperidin-l-yl)[4-(piperidin-4-ylmethoxy)phenyl]methanone, A-isopropyl-4-(piperidin-4-ylmethoxy)benzamide, 4-(piperidin-4-ylmethoxy)-A-cyclopropylbenzamide, [4-(piperidin-4-ylmethoxy)phenyl](pyrrolidin-l-yl)methanone.
7. The compound of claim 1 for use in the treatment of a disease, disorder or condition treated by activation of trace amine receptors TAAR1, wherein the disease, disorder or condition is selected from the group consisting of a mental disorder, a cognitive disorder, a metabolic disorder, a neurological disease, a neurodegenerative disease and a cardiovascular disorder.
8. The compound of claim 7, wherein the disease, disorder or condition is selected from the group consisting of depression, anxiety, bipolar disorder, attention deficit hyperactivity disorder (ADHD), stress-induced disorder, psychosis, schizophrenia, obsessive-compulsive disorder, Parkinson’s disease, Alzheimer’s disease, epilepsy, migraine, high blood pressure, alcohol or drug abuse, nicotine addiction, eating disorder, diabetes, diabetes complications, obesity, dyslipidemia, disorders associated with energy consumption and expenditure, disorders associated with impaired body temperature homeostasis, sleep and circadian rhythm disorder.
9. A pharmaceutical composition comprising a therapeutically effective amount of the compound of formula 1 or a pharmaceutically acceptable salt thereof and at least one pharmaceutically acceptable excipient, wherein the compound of formula 1 is:
Figure imgf000003_0001
where n is 0, 1 or 2; m is 0 if n is 2, or m is 1 if n is 0 or 1;
R1 and R2 are independently selected from the group consisting of:
26
AMENDED SHEET (ARTICLE 19) hydrogen atom;
C1-C10 alkyl optionally substituted with C3-C10 cycloalkyl;
C3-C10 cycloalkyl; or R1 and R2 together with the nitrogen atom to which they are attached form a 5- or 6- membered saturated heterocyclyl containing 1 nitrogen atom and optionally substituted with C1-C10 alkyl; or R1 and R2 together with the nitrogen atom to which they are attached form a 6 -membered saturated heterocyclyl containing 1 nitrogen atom and 1 heteroatom selected from oxygen, sulfur and nitrogen.
10. The pharmaceutical composition of claim 9, wherein the excipient is selected from the group including a pharmaceutically acceptable carrier, diluent, filler and solvent.
11. The pharmaceutical composition of claim 9 or claim 10 for use in the treatment of a disease, disorder or condition treated by activation of trace amine receptors TAAR1, wherein the disease, disorder or condition is selected from the group consisting of a mental disorder, a cognitive disorder, a metabolic disorder, a neurological disease and a neurodegenerative disease and a cardiovascular disorder.
12. The pharmaceutical composition of claim 11, wherein the disease, disorder or condition is selected from the group consisting of depression, anxiety, bipolar disorder, attention deficit hyperactivity disorder (ADHD), stress-induced disorder, psychosis, schizophrenia, obsessive- compulsive disorder, Parkinson’s disease, Alzheimer’s disease, epilepsy, migraine, high blood pressure, alcohol or drug abuse, nicotine addiction, eating disorder, diabetes, diabetes complications, obesity, dyslipidemia, disorders associated with energy consumption and expenditure, disorders associated with impaired body temperature homeostasis, sleep and circadian rhythm disorder.
13. The pharmaceutical composition of any one of claims 9-12, wherein the pharmaceutical composition is present as a dosage form selected from the group including tablet, powder, granule, pill, suspension, pellet, capsule, sachet and injectable solution.
27
AMENDED SHEET (ARTICLE 19)
PCT/RU2022/050270 2021-09-01 2022-09-01 (azacycloalkyl)methoxy-substituted benzamides as modulators of trace amine-associated receptor 1 (taar1) Ceased WO2023033679A1 (en)

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EA202192216 EA043105B1 (en) 2021-09-01 (AZACYCLOALKYL)METHOXY-SUBSTITUTED BENZAMIDES AS MODULATORS OF Trace Amine-Associated Receptor 1 (TAAR1)
EA202192216 2021-09-01

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WO2023033679A4 true WO2023033679A4 (en) 2023-05-19

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7294637B2 (en) * 2000-09-11 2007-11-13 Sepracor, Inc. Method of treating addiction or dependence using a ligand for a monamine receptor or transporter
EP2076497B1 (en) 2006-10-19 2012-02-22 F. Hoffmann-La Roche AG Aminomethyl-4-imidazoles
EP2086959B1 (en) 2006-11-02 2011-11-16 F. Hoffmann-La Roche AG Substituted 2-imidazoles as modulators of the trace amine associated receptors
WO2013104591A1 (en) 2012-01-12 2013-07-18 F. Hoffmann-La Roche Ag Heterocyclic derivatives as trace amine associated receptors (taars)
WO2016015333A1 (en) 2014-08-01 2016-02-04 F.Hoffmann-La Roche Ag 2-oxa-5-azabicyclo [2.2.1] heptan-3-yl derivatives

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