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NZ746628B2 - Heterocyclic compound - Google Patents

Heterocyclic compound

Info

Publication number
NZ746628B2
NZ746628B2 NZ746628A NZ74662817A NZ746628B2 NZ 746628 B2 NZ746628 B2 NZ 746628B2 NZ 746628 A NZ746628 A NZ 746628A NZ 74662817 A NZ74662817 A NZ 74662817A NZ 746628 B2 NZ746628 B2 NZ 746628B2
Authority
NZ
New Zealand
Prior art keywords
salt
substituents selected
compound
optionally substituted
ring
Prior art date
Application number
NZ746628A
Other versions
NZ746628A (en
Inventor
Jumpei Aida
Shuhei Ikeda
Masataka Murakami
Minoru Nakamura
Yuya Oguro
Tomohiro Okawa
Hideyuki Sugiyama
Hidekazu Tokuhara
Original Assignee
Takeda Pharmaceutical Company Limited
Filing date
Publication date
Application filed by Takeda Pharmaceutical Company Limited filed Critical Takeda Pharmaceutical Company Limited
Priority claimed from PCT/JP2017/014597 external-priority patent/WO2017171100A1/en
Publication of NZ746628A publication Critical patent/NZ746628A/en
Publication of NZ746628B2 publication Critical patent/NZ746628B2/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/08—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing alicyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing alicyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Abstract

The present invention provides a compound having an MAGL inhibitory action, and useful as an agent for the prophylaxis or treatment of neurodegenerative diseases (e.g., Alzheimer's disease, Parkinson's disease, Huntington's disease, amyotrophic lateral sclerosis, traumatic brain injury, glaucoma, multiple sclerosis etc.), anxiety disorder, pains (e.g., inflammatory pain, cancerous pain, neurogenic pain etc.), epilepsy, depression and the like. The present invention relates to a compound represented by the formula (I) : wherein each symbol is as defined in the specification, or a salt thereof.

Claims (13)

1. A compound ented by the formula (I): A H D N n O (I) 5 wherein Ring A is a 3- to 14-membered non-aromatic heterocycle optionally further substituted by 1 to 3 substituents selected (a) a C1-6 alkyl group optionally substituted by 1 to 3 10 substituents selected from (i) a C6-14 aryloxy group optionally substituted by 1 to 3 substituents selected from (I) a halogen atom, (II) an optionally halogenated C1-6 alkyl group, 15 (III) a C3-10 cycloalkyl group, (IV) a 3- to bered non-aromatic heterocyclic group optionally substituted by 1 to 3 n atoms, (V) a cyano group, 20 (ii) a C6-14 aryl group optionally substituted by 1 to 3 substituents selected from (I) a halogen atom, and (II) an optionally halogenated C1-6 alkyl group, (iii) a halogen atom, and 25 (iv) a C7-16 aralkyloxy group optionally substituted by 1 to 3 substituents ed from (I) a halogen atom, and (II) a C1-6 alkyl group, (b) a C7-16 aralkyloxy group optionally substituted by 1 to 3 substituents selected from (i) a halogen atom, (ii) an optionally halogenated C1-6 alkyl group, and 5 (iii) an optionally halogenated C1-6 alkoxy group, (c) a C2-6 alkenyl group optionally substituted by 1 to 3 substituents selected from (i) a C6-14 aryl group optionally substituted by 1 to 3 substituents selected from 10 (I) a halogen atom, and (II) an optionally halogenated C1-6 alkyl group, and (ii) a n atom, (d) a C6-14 y group optionally tuted by 1 to 3 halogen atoms, and 15 (e) a 3- to 14-membered non-aromatic heterocyclic group optionally substituted by 1 to 3 substituents ed from (i) a halogen atom, and (ii) an optionally halogenated C1-6 alkyl group, Ring D is a C4-5 cycloalkane, 20 n is 1 or 2, X is -O-, -CH2- or -O-CH2-, Ra and Rb are both hydrogen atoms, or a salt thereof.
2. The compound or salt of claim 1, wherein Ring D is a cyclobutane ring; n is 1; X is -O-; and 30 Ra and Rb are both hydrogen atoms.
3. The compound or salt of claim 1, wherein Ring A is (1) an azetidine ring optionally r substituted by 1 to 3 substituents selected from (a) a benzyloxy group optionally substituted by 1 to 3 substituents selected from (i) a halogen atom, and 5 (ii) an optionally halogenated C1-6 alkyl group, (2) a piperidine ring optionally further substituted by 1 to 3 substituents selected from (a) a C1-6 alkyl group optionally substituted by 1 to 3 substituents selected from 10 (i) a phenoxy group optionally substituted by 1 to 3 substituents selected from (I) a halogen atom, (II) an optionally halogenated C1-6 alkyl group, and (III) an azetidinyl group optionally substituted by 1 15 to 3 halogen atoms, (ii) a phenyl group optionally substituted by 1 to 3 halogen atoms, and (iii) a halogen atom, and (b) a dihydrobenzofuryl group optionally substituted by 1 20 to 3 substituents ed from (i) a halogen atom, and (ii) an optionally halogenated C1-6 alkyl group, or (3) a 7-azaspiro[3.5]nonane ring optionally further substituted by 1 to 3 substituents selected from 25 (a) a y group optionally substituted by 1 to 3 halogen atoms; Ring D is a utane ring; n is 1; X is -O-; and 30 Ra and Rb are both hydrogen atoms.
4. The compound or salt of claim 1, wherein Ring A is (1) an ine ring further substituted by 1 to 3 substituents selected from (a) a benzyloxy group substituted by 1 to 3 substituents selected from (i) a halogen atom, and 5 (ii) an optionally halogenated C1-6 alkyl group; Ring D is a cyclobutane ring; n is 1; X is -O-; and Ra and Rb are both hydrogen atoms.
5. The compound or salt of claim 1, wherein the nd is (2s,4s)((3-((2-Fluoro (trifluoromethyl)benzyl)oxy)azetidinyl)carbonyl)oxa azaspiro[3.4]octanone, or a salt thereof.
6. The compound or salt of claim 1, wherein the compound is (2s,4s)((3-((2-Methyl uoromethyl)benzyl)oxy)azetidinyl)carbonyl)oxa azaspiro[3.4]octanone, or a salt thereof.
7. The compound or salt of claim 1, wherein the compound is )((3-((3-Chloromethylbenzyl)oxy)azetidin yl)carbonyl)oxaazaspiro[3.4]octanone, or a salt thereof.
8. A medicament comprising the compound or salt of claim 1.
9. The medicament of claim 8, which is a monoacylglycerol lipase inhibitor.
10. The medicament of claim 8, which is an agent for the prophylaxis or treatment of Alzheimer’s disease, Parkinson’s disease, Huntington’s disease, amyotrophic lateral sclerosis, multiple sis, y disorder, pain, epilepsy or depression.
11. Use of the compound or salt of claim 1 for the production of an agent for the prophylaxis or treatment of Alzheimer’s 5 disease, Parkinson’s disease, Huntington’s disease, amyotrophic lateral sclerosis, multiple sclerosis, anxiety disorder, pain, sy or depression.
12. The compound or salt of claim 1 for use in the prophylaxis 10 or treatment of Alzheimer’s e, Parkinson’s disease, Huntington’s disease, amyotrophic lateral sis, multiple sclerosis, anxiety disorder, pain, sy or depression.
13. The compound or salt of claim 1, substantially as herein 15 described with reference to any one of the examples thereof.
NZ746628A 2017-03-30 Heterocyclic compound NZ746628B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2016071181 2016-03-31
PCT/JP2017/014597 WO2017171100A1 (en) 2016-03-31 2017-03-30 Heterocyclic compound

Publications (2)

Publication Number Publication Date
NZ746628A NZ746628A (en) 2025-05-02
NZ746628B2 true NZ746628B2 (en) 2025-08-05

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