WO2022049377A1 - Novel compounds - Google Patents

Novel compounds Download PDF

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Publication number
WO2022049377A1
WO2022049377A1 PCT/GB2021/052262 GB2021052262W WO2022049377A1 WO 2022049377 A1 WO2022049377 A1 WO 2022049377A1 GB 2021052262 W GB2021052262 W GB 2021052262W WO 2022049377 A1 WO2022049377 A1 WO 2022049377A1
Authority
WO
WIPO (PCT)
Prior art keywords
indazol
acrylamide
disease
alkyl
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/GB2021/052262
Other languages
English (en)
French (fr)
Inventor
Neil Miller
Richard Rutter
Tammy LADDUWAHETTY
John Maclean
Eric Talbot
Jan KULAGOWSKI
Richard Morphy
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nrg Therapeutics Ltd
Original Assignee
Nrg Therapeutics Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nrg Therapeutics Ltd filed Critical Nrg Therapeutics Ltd
Priority to AU2021336750A priority Critical patent/AU2021336750A1/en
Priority to CN202180053586.6A priority patent/CN116096712B/zh
Priority to IL300904A priority patent/IL300904A/en
Priority to JP2023537724A priority patent/JP7784431B2/ja
Priority to CA3190786A priority patent/CA3190786A1/en
Priority to US18/023,488 priority patent/US12497359B2/en
Priority to EP21769790.3A priority patent/EP4208448B1/en
Publication of WO2022049377A1 publication Critical patent/WO2022049377A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • 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
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/74—Benzo[b]pyrans, hydrogenated in the carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Definitions

  • Cyclosporin A originally identified as an immunosuppressant by virtue of its inhibitory activity at calcineurin, was also found to inhibit Ppif as well as other members of the peptidyl prolyl cis-trans isomerase (Ppi) enzyme family.
  • Ppi peptidyl prolyl cis-trans isomerase
  • R 2c is C 1-4 haloalkyl, such as CF 3 .
  • R 2c is aryl, such as phenyl.
  • R 2c is 4-7 membered heterocycloalkyl, such as azetidinyl or oxetanyl.
  • R 2c is methyl.
  • the aryl is substituted by 1, 2 or 3 substituents, such as 1 or 2, e.g.1 substituent, each independently selected from methyl, chloro and fluoro. In one embodiment, the aryl is not substituted.
  • R 2 is H, methyl, CH 2 OH, CH 2 OMe, CH 2 OPh, OCH 2 Ph, CH 2 O(1-(2-fluoroethyl)azetidin-3-yl, CH 2 (3- fluoroazetidin-1-yl), CH 2 CH 2 (3-fluoroazetidin-1-yl) or CH 2 OCH 2 C ⁇ CH, then m is 0.
  • R 2 is not C 1-4 alkenylO(4-7 membered heterocycloalkyl).
  • R 2 is not CH 2 CH 2 (3-fluoroazetidin-1-yl).
  • R 9 is in the 7-position.
  • R 9 is in the 6- position.
  • R 9 is in the 5-position.
  • X is a bond
  • substituent position numbering will change in accordance with the total number of atoms in the bicyclic ring system, for example: .
  • Suitable examples of R 9 substituents when X is a bond are 4-fluoro and 5-fluoro.
  • q is 1 or 2.
  • D, E and F are C(R 10 ).
  • D is N
  • E and F are C(R 10 ).
  • E is N
  • D and F are C(R 10 ).
  • the disease or disorder is selected from degenerative or neurodegenerative diseases, disorders of the central nervous system, ischemia or re-perfusion injury, metabolic diseases, inflammatory or autoimmune diseases, diseases of aging and renal diseases.
  • the disease or disorder is a degenerative or neurodegenerative disease, such as Parkinson’s disease, dementia with Lewy bodies, Alzheimer’s disease, amyotrophic lateral sclerosis, multiple sclerosis, frontal temporal dementia, chemotherapy induced neuropathy, Huntington’s disease, spinocerebellar ataxias, progressive supranuclear palsy, hereditary spastic paraplegia, Duchenne muscular dystrophy, congenital muscular dystrophy, traumatic brain injury and Friedreich’s ataxia.
  • a pharmaceutical composition comprising a compound of formula (I), or a pharmaceutically acceptable salt and/or solvate (e.g. salt) thereof, for use in the treatment or prophylaxis of a disease or disorder as described herein.
  • a pharmaceutical composition comprising a compound of formula (I), or a pharmaceutically acceptable salt and/or solvate (e.g. salt) thereof, for use in the treatment of a disease or disorder as described herein.
  • a pharmaceutical composition comprising a compound of formula (I), or a pharmaceutically acceptable salt and/or solvate (e.g. salt) thereof, for use in the prophylaxis of a disease or disorder as described herein.
  • the pharmaceutical formulations according to the invention include those suitable for oral, parenteral (including subcutaneous, intradermal, intramuscular, intravenous [bolus or infusion], and intraarticular), intranasal (also known as nasal administration), inhalation (including fine particle dusts or mists which may be generated by means of various types of metered dose pressurized aerosols, nebulizers or insufflators) insufflation, rectal, intraperitoneal, topical (including dermal, buccal, sublingual, and intraocular) and intrathecal administration, although the most suitable route may depend upon, for example, the condition and disorder of the recipient.
  • the formulations of this invention may include other agents conventional in the art having regard to the type of formulation in question, for example those suitable for oral administration may include flavouring agents.
  • the compounds of formula (I) are expected to display one or more of the following advantageous properties: - inhibitory activity of mPTP as demonstrated in the assay of Biological Example 1; and - improved solubility and/or improved intrinsic clearance (CL int ) resulting in e.g. improved oral bioavailability and/or improved systemic exposure as demonstrated in the assays of Biological Examples 2 and 3.
  • the invention is further exemplified by the following non-limiting examples. EXAMPLES The invention is illustrated by the compounds described below.
  • Example 38 (E)-3-(1H-indazol-6-yl)-N-(7-methyl-2,3-dihydro-1H-inden-1-yl)acrylamide
  • Step 1 Into a 8-mL sealed tube, was placed methyl 3-[1-(oxan-2-yl)indazol-6-yl]prop-2-enoate (150.0 mg, 0.52 mmol, 1.00 eq), 7-methyl-2,3-dihydro-1H-inden-1-amine (154.3 mg, 1.05 mmol, 2.00 eq) and THF (3.00 mL). This was followed by the addition of LiHMDS (2.1 mL, 2.09 mmol, 4.00 eq) at room temperature.
  • LiHMDS LiHMDS
  • Test compounds were prepared in 384 well polypropylene assay plates as described above for the liver mitochondria assay.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
PCT/GB2021/052262 2020-09-01 2021-09-01 Novel compounds Ceased WO2022049377A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
AU2021336750A AU2021336750A1 (en) 2020-09-01 2021-09-01 Novel compounds
CN202180053586.6A CN116096712B (zh) 2020-09-01 2021-09-01 新型化合物
IL300904A IL300904A (en) 2020-09-01 2021-09-01 Novel compounds
JP2023537724A JP7784431B2 (ja) 2020-09-01 2021-09-01 新規化合物
CA3190786A CA3190786A1 (en) 2020-09-01 2021-09-01 Novel compounds
US18/023,488 US12497359B2 (en) 2020-09-01 2021-09-01 Acrylamide derivatives
EP21769790.3A EP4208448B1 (en) 2020-09-01 2021-09-01 Acrylamide derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB2013731.1 2020-09-01
GBGB2013731.1A GB202013731D0 (en) 2020-09-01 2020-09-01 Novel cmpounds

Publications (1)

Publication Number Publication Date
WO2022049377A1 true WO2022049377A1 (en) 2022-03-10

Family

ID=72749727

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2021/052262 Ceased WO2022049377A1 (en) 2020-09-01 2021-09-01 Novel compounds

Country Status (9)

Country Link
US (1) US12497359B2 (https=)
EP (1) EP4208448B1 (https=)
JP (1) JP7784431B2 (https=)
CN (1) CN116096712B (https=)
AU (1) AU2021336750A1 (https=)
CA (1) CA3190786A1 (https=)
GB (1) GB202013731D0 (https=)
IL (1) IL300904A (https=)
WO (1) WO2022049377A1 (https=)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024153946A1 (en) 2023-01-19 2024-07-25 Nrg Therapeutics Ltd Inhibitors of mptp
WO2025052129A1 (en) 2023-09-05 2025-03-13 Nrg Therapeutics Ltd Pyridine derivatives which act as inhibitors of mptp.
WO2026018015A2 (en) 2024-07-18 2026-01-22 Nrg Therapeutics Ltd Novel methods and uses

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB202013728D0 (en) * 2020-09-01 2020-10-14 Nrg Therapeutics Ltd Novel compounds
CN118255724A (zh) * 2024-03-27 2024-06-28 河北天成药业股份有限公司 盐酸利多卡因杂质的合成方法及其反应检测方法
CN120025281A (zh) * 2025-04-22 2025-05-23 九洲药业(杭州)有限公司 一种n,n-二异丁基-1h-吲唑-4-胺的中间体及制备方法

Citations (3)

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WO2004037751A2 (en) * 2002-08-29 2004-05-06 Temple University - Of The Commonwealth System Of Higher Education Aryl and heteroaryl propene amides, derivatives thereof and therapeutic uses thereof
WO2010049768A1 (en) 2008-10-27 2010-05-06 Congenia Srl Acrylamido derivatives useful as inhibitors of the mitochondrial permeability transition
CA2884607A1 (en) 2015-03-11 2016-09-11 Stealth Peptides International, Inc. Therapeutic compositions including acrylamido compounds or phenyl-substiituted maleimide compounds and uses thereof to treat and prevent mitochondrial diseases and conditions

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WO2010049768A1 (en) 2008-10-27 2010-05-06 Congenia Srl Acrylamido derivatives useful as inhibitors of the mitochondrial permeability transition
CA2884607A1 (en) 2015-03-11 2016-09-11 Stealth Peptides International, Inc. Therapeutic compositions including acrylamido compounds or phenyl-substiituted maleimide compounds and uses thereof to treat and prevent mitochondrial diseases and conditions

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CHEN MAO XIANG ET AL: "Probing Mitochondrial Permeability Transition Pore Activity in Nucleated Cells and Platelets by High-Throughput Screening Assays Suggests Involvement of Protein Phosphatase 2B in Mitochondrial Dynamics", ASSAY AND DRUG DEVELOPMENT TECHNOLOGIES, vol. 16, no. 8, 1 December 2018 (2018-12-01), US, pages 445 - 455, XP055848095, ISSN: 1540-658X, Retrieved from the Internet <URL:https://www.liebertpub.com/doi/pdf/10.1089/adt.2018.872> DOI: 10.1089/adt.2018.872 *
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024153946A1 (en) 2023-01-19 2024-07-25 Nrg Therapeutics Ltd Inhibitors of mptp
WO2024153945A1 (en) 2023-01-19 2024-07-25 Nrg Therapeutics Ltd Inhibitors of mptp
WO2025052129A1 (en) 2023-09-05 2025-03-13 Nrg Therapeutics Ltd Pyridine derivatives which act as inhibitors of mptp.
WO2026018015A2 (en) 2024-07-18 2026-01-22 Nrg Therapeutics Ltd Novel methods and uses
WO2026018015A3 (en) * 2024-07-18 2026-02-26 Nrg Therapeutics Ltd Novel methods and uses of ligands of nlrx1

Also Published As

Publication number Publication date
EP4208448A1 (en) 2023-07-12
IL300904A (en) 2023-04-01
US12497359B2 (en) 2025-12-16
EP4208448B1 (en) 2025-04-23
CA3190786A1 (en) 2022-03-10
GB202013731D0 (en) 2020-10-14
CN116096712B (zh) 2026-03-17
JP7784431B2 (ja) 2025-12-11
JP2023539695A (ja) 2023-09-15
CN116096712A (zh) 2023-05-09
US20230312466A1 (en) 2023-10-05
AU2021336750A1 (en) 2023-03-02

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