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WO2025078574A1 - Nouveaux esters de composés 1,2,3,4,4a,5,6,7,8,9,10,10a-dodécahydrobenzo[g]quinolin-6-ol et leurs utilisations - Google Patents

Nouveaux esters de composés 1,2,3,4,4a,5,6,7,8,9,10,10a-dodécahydrobenzo[g]quinolin-6-ol et leurs utilisations Download PDF

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Publication number
WO2025078574A1
WO2025078574A1 PCT/EP2024/078649 EP2024078649W WO2025078574A1 WO 2025078574 A1 WO2025078574 A1 WO 2025078574A1 EP 2024078649 W EP2024078649 W EP 2024078649W WO 2025078574 A1 WO2025078574 A1 WO 2025078574A1
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WIPO (PCT)
Prior art keywords
pharmaceutically acceptable
compound
acceptable salt
formula
disease
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PCT/EP2024/078649
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English (en)
Inventor
Clas Sonesson
Sverker Von Unge
Henrik GRADÉN
David BLIMAN
Johan Kajanus
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Integrative Research Laboratories Sweden AB
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Integrative Research Laboratories Sweden AB
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Publication of WO2025078574A1 publication Critical patent/WO2025078574A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/08—Aza-anthracenes
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
    • C07C59/255—Tartaric acid

Definitions

  • L-dopa or apomorphine The state of the art treatment of Parkinson 's disease involves administering to the patient L-dopa or apomorphine. These compounds are known to exert their action by being agonists of the DI and/or D2 dopamine receptors. In the case of L-dopa, it is its active metabolite dopamine that is the species that interacts at the DI and/or D2 dopamine receptors.
  • therapies involving L-dopa or apomorphine are associated with drawbacks. For instance, L-dopa has low and variable bioavailability which depends on protein intake. Further, use of L-dopa may result in long term complications such as dyskinesias.
  • J. Med . Chem 2006, 49, 1494-1498 describes enone prodrugs of dopaminergic catecholamines in the research area of dopamine receptor agonists. It is disclosed that the (-)-enantiomer of the trans-isomer of the compound designated as 1-propyl- 2,3,4,4a,5,7,8,9,10,10a-decahydro-lH-benzo[g]quinolin-6-one (also named Compound 4) acts as an enone prodrug of a dopamine receptor agonist. It is suggested that said enone compound is converted in vivo to the corresponding catechol compound designated as /V-(n-propyl)-6,7-di-OH-benzo[g]quinoline (also named Compound 3).
  • WO 2010/097092 describes compounds for treating dyskinesia related disorders, such as Parkinson 's disease.
  • the compound (4aR,10aR)-l-propyl-l,2,3,4,4a,5,10,10a- octahydrobenzo[g]quinoline-6,7-diol also named Compound 10.
  • Compound 10 was found to be an active metabolite functioning as a potent agonist at both the DI and D2 receptors in vitro and possessing a superior profile as a dopamine agonist in vivo.
  • WO 2020/234273 discloses a process for the manufacture of the two compounds (6aR,10aR)-7-propyl-6,6a,7,8,9,10,10a,ll-octahydro-
  • PCT/EP2023/060703 relates to esters of 1, 2, 3, 4, 4a, 5, 6, 7, 8, 9, 10, 10a- dodecahydrobenzo[g]quinolin-6-ol compounds.
  • the compounds are for use in the treatment of one or more of the following: Parkinson 's disease, Huntington 's disease, Restless leg syndrome, Alzheimer's disease, schizophrenia, attention deficit hyperactivity disorder, drug addiction.
  • Parkinson's disease degeneration of the nigro-striatal dopamine pathways is associated with the core motor symptoms. This deficit is addressed by available dopamine receptor agonists. However, there is also a degeneration of other dopaminergic pathways of the brain. In particular, degeneration of the mesolimbic dopamine pathways is associated with important non-motor symptoms such as depression and apathy in Parkinson's disease.
  • R 1 is methyl, ethyl or n-propyl
  • the present disclosure also provides the use of a compound of Formula III as described herein, or a pharmaceutically acceptable salt thereof, or a pharmaceutical composition as described herein for the manufacture of a medicament for use in the treatment of one or more of the following: Parkinson 's disease, Huntington 's disease, Restless leg syndrome, Alzheimer's disease, schizophrenia, attention deficit hyperactivity disorder, drug addiction.
  • the present disclosure also provides a method for treatment of one or more of the following: Parkinson 's disease, Huntington 's disease, Restless leg syndrome, Alzheimer's disease, schizophrenia, attention deficit hyperactivity disorder, drug addiction, said method comprising administering to a mammal, such as a human or an animal, in need thereof, an effective amount such as a therapeutically effective amount of (i) a compound of Formula III as described herein, or a pharmaceutically acceptable salt thereof, or (ii) a pharmaceutical composition as described herein.
  • Fig. 1 shows a reaction scheme for the preparation of compounds of Formula II and Formula III, respectively.
  • R 2 is (CH2) m phenyl, said phenyl being substituted with 0, 1, 2 or 3 substituents independently selected from the group consisting of:
  • Cs-Cecycloalkyl denotes a cyclic alkyl group of three to six carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • R 1 of the compounds described herein may be methyl, ethyl or n-propyl.
  • R 1 may be ethyl or n-propyl.
  • R 1 is ethyl.
  • R 1 is n- propyl.
  • the Ci-C4alkyl group(s) may be unsubstituted or substituted with 1, 2, 3 or 4 F.
  • the skilled person will understand that the number of F (i.e. fluoro) substituents will depend on the number of carbon atoms of the Ci-C4alkyl group.
  • a Cialkyl group may comprise up to three F substituents while a Czalkyl group may comprise up to four F substituents.
  • the Ci-C4alkyl substituent(s), such as methyl may be located in the ortho, meta or para position on the phenyl ring.
  • the compound of the present disclosure is a compound of Formula Illa.
  • the compound of the present disclosure is a compound of Formula Illb.
  • the compound of Formula III is a mixture of the compound of Formula Illa and the compound of the Formula Illb, such as a 1: 1 mixture of the compound of Formula Illa and the compound of Formula Illb.
  • the compound of Formula III may be: (4a/?,6/?,10a/?)-l-propyl-l,2,3,4,4a,5,6,7,8,9,10,10a-dodecahydrobenzo[g]quinolin- 6-yl 2-methylbenzoate, and/or (4a/?,6/?,10a/?)-l-propyl-l,2,3,4,4a,5,6,7,8,9,10,10a-dodecahydrobenzo[g]quinolin- 6-yl benzoate.
  • a pharmaceutically acceptable salt such as a tartaric acid salt of any one of the foregoing compounds.
  • the present disclosure also provides a method for preparing a compound of Formula III as described herein, or a pharmaceutically acceptable salt thereof, said method comprising the steps of: a) reacting a compound of Formula II with a compound of Formula IV
  • compositions of the present disclosure may be provided in the form of a pharmaceutically acceptable salt.
  • pharmaceutically acceptable salt includes salt prepared from a pharmaceutically acceptable non-toxic acid, i.e. pharmaceutically acceptable acid addition salts.
  • the pharmaceutically acceptable salt may be formed by combining a compound as described herein with an organic acid or inorganic acid in a desired ratio using e.g. methods known in the art.
  • the pharmaceutically acceptable salt may be a combination of the compound of Formula III and an acid such as a combination of the compound of Formula III and an acid in a ratio of 1 : 1 or 2: 1.
  • Analyses were performed by using either an ACE 3 C8 (3.0 x 50 mm) column with a 10-97 % gradient of acetonitrile in 0.1 % aqueous TEA over 3 min and a flow of 1 mL/min, or an Xbridge C18 (3.0 x 50 mm) column with a 10-97 % gradient of acetonitrile in 10 mM ammonium bicarbonate over 3 min and a flow of 1 mL/min and UV detection.
  • a 10-100% gradient of acetonitrile in 0.03% acetic acid was used as eluent.
  • Low resolution mass spectra were recorded on a HP 5970A instrument operating at an ionization potential of 70 eV.
  • epimer 1 was determined to have /?- configuration at carbon 6 by X-ray crystallography and thus epimer 1 can also be named as (4a/?,6/?,10a/?)-l-propyl-l,2,3,4,4a,5,6,7,8,9,10,10a- dodecahydrobenzo[g]quinolin-6-ol.
  • Enzymatic stability in human plasma was determined as follows: 95 pl of plasma were incubated at room temperature in duplicate, except for time zero sample that was kept on ice. 5 pl of freshly made compound solution was added to a final concentration of 0.1 or 1 pM. The reaction was ended and proteins precipitated by adding 500 pl stopsolution (ACN + internal standard) and vortexing at pre-determined time points 0, 1, 3, 6, 12, 24 and 60 minutes. After centrifugation at 14000 rpm for 10 minutes at 4°C, 200 pl supernatant was placed in a glass vial and evaporated at 37°C under nitrogen. Samples were resuspended in 150 pl of 10% EtOH, filtered by centrifugation in 0.2 pm PTFE filter tubes and transferred to plates for analysis by LC-MS/MS.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Psychiatry (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne un composé de formule III, son procédé de fabrication ainsi que ses utilisations.
PCT/EP2024/078649 2023-10-12 2024-10-11 Nouveaux esters de composés 1,2,3,4,4a,5,6,7,8,9,10,10a-dodécahydrobenzo[g]quinolin-6-ol et leurs utilisations Pending WO2025078574A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE2351174 2023-10-12
SE2351174-4 2023-10-12

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WO2025078574A1 true WO2025078574A1 (fr) 2025-04-17

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PCT/EP2024/078649 Pending WO2025078574A1 (fr) 2023-10-12 2024-10-11 Nouveaux esters de composés 1,2,3,4,4a,5,6,7,8,9,10,10a-dodécahydrobenzo[g]quinolin-6-ol et leurs utilisations

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Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001078713A1 (fr) 2000-04-18 2001-10-25 Axon Biochemicals B.V. Phenylethylamines et variantes cycliques condensees en tant que promedicament de catecholamines et utilisation de ces composes
WO2005099702A2 (fr) * 2004-04-13 2005-10-27 The Mclean Hospital Corporation Derives de r(?)-11-hydroxyaporphines et utilisations de ces derives
WO2009026935A1 (fr) * 2007-08-31 2009-03-05 H. Lundbeck A/S Dérivés de catécholamine et promédicaments associés
WO2010097092A1 (fr) 2009-02-27 2010-09-02 H. Lundbeck A/S Traitement de troubles liés à la dyskinésie
WO2019101917A1 (fr) 2017-11-24 2019-05-31 H. Lundbeck A/S Nouveaux promédicaments de catécholamine destinés à être utilisés dans le traitement de la maladie de parkinson
WO2020234273A1 (fr) 2019-05-20 2020-11-26 H. Lundbeck A/S Procédé de fabrication de (6ar, 10ar)-7-propyl -6,6a,7,8,9,10,10 a, 11-octahydro-[1,3] dioxolo [4',5':5,6] benzo[1,2-g]quinoléine et (4ar,10ar)-1-propyl-1,2,3,4,4 a,5,10,10a-octahydro-benzo[g] quinoléine-6,7-diol
WO2020234277A1 (fr) 2019-05-21 2020-11-26 H. Lundbeck A/S Promédicaments de carbamate de catécholamine destinés à être utilisés dans le traitement de la maladie de parkinson
WO2020234275A1 (fr) 2019-05-21 2020-11-26 H. Lundbeck A/S Nouveaux promédicaments de catécholamine destinés à être utilisés dans le traitement de maladies de parkinson
WO2020234276A1 (fr) 2019-05-21 2020-11-26 H. Lundbeck A/S Nouveaux promédicaments de catécholamine destinés à être utilisés dans le traitement de la maladie de parkinson
WO2020234270A1 (fr) 2019-05-20 2020-11-26 H. Lundbeck A/S Procédé de fabrication de (2s,3s,4s,5r,6s) -3,4,5-trihydroxy-6-(((4ar,10ar)-hydroxy-1-propyl-1,2,3,4,4 a,5,10,10a-octahydrobenzo[g]quinolin-6-yl)oxy)tétrahydro-2h-pyran-2-carboxylique et un intermédiaire de celui-ci
WO2020234271A1 (fr) 2019-05-20 2020-11-26 H. Lundbeck A/S Procédé de fabrication de (2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(((4 ar,10 r)-hydroxy-1-propyl-1,2,3,4,4 a,5,10,10 a-octahydrobenzo [g]quinolin-6-yl) oxy)tétrahydro-2h-pyran-2-carboxylique
WO2020234272A1 (fr) 2019-05-20 2020-11-26 H. Lundbeck A/S Nouvelles formes solides d'acide (2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(((4ar,10ar)-7-hydroxy-1-propyl-1,2,3,4,4 a,5,10,10a-octahydrobenzo[g]quinolin-6-yl) oxy)tétrahydro-2h-pyran-2-carboxylique
WO2020234274A1 (fr) 2019-05-21 2020-11-26 H. Lundbeck A/S Nouveaux promédicaments à base de catécholamine destinés à être utilisés dans le traitement de la maladie de parkinson

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001078713A1 (fr) 2000-04-18 2001-10-25 Axon Biochemicals B.V. Phenylethylamines et variantes cycliques condensees en tant que promedicament de catecholamines et utilisation de ces composes
WO2005099702A2 (fr) * 2004-04-13 2005-10-27 The Mclean Hospital Corporation Derives de r(?)-11-hydroxyaporphines et utilisations de ces derives
WO2009026935A1 (fr) * 2007-08-31 2009-03-05 H. Lundbeck A/S Dérivés de catécholamine et promédicaments associés
WO2010097092A1 (fr) 2009-02-27 2010-09-02 H. Lundbeck A/S Traitement de troubles liés à la dyskinésie
WO2019101917A1 (fr) 2017-11-24 2019-05-31 H. Lundbeck A/S Nouveaux promédicaments de catécholamine destinés à être utilisés dans le traitement de la maladie de parkinson
WO2020234270A1 (fr) 2019-05-20 2020-11-26 H. Lundbeck A/S Procédé de fabrication de (2s,3s,4s,5r,6s) -3,4,5-trihydroxy-6-(((4ar,10ar)-hydroxy-1-propyl-1,2,3,4,4 a,5,10,10a-octahydrobenzo[g]quinolin-6-yl)oxy)tétrahydro-2h-pyran-2-carboxylique et un intermédiaire de celui-ci
WO2020234273A1 (fr) 2019-05-20 2020-11-26 H. Lundbeck A/S Procédé de fabrication de (6ar, 10ar)-7-propyl -6,6a,7,8,9,10,10 a, 11-octahydro-[1,3] dioxolo [4',5':5,6] benzo[1,2-g]quinoléine et (4ar,10ar)-1-propyl-1,2,3,4,4 a,5,10,10a-octahydro-benzo[g] quinoléine-6,7-diol
WO2020234271A1 (fr) 2019-05-20 2020-11-26 H. Lundbeck A/S Procédé de fabrication de (2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(((4 ar,10 r)-hydroxy-1-propyl-1,2,3,4,4 a,5,10,10 a-octahydrobenzo [g]quinolin-6-yl) oxy)tétrahydro-2h-pyran-2-carboxylique
WO2020234272A1 (fr) 2019-05-20 2020-11-26 H. Lundbeck A/S Nouvelles formes solides d'acide (2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(((4ar,10ar)-7-hydroxy-1-propyl-1,2,3,4,4 a,5,10,10a-octahydrobenzo[g]quinolin-6-yl) oxy)tétrahydro-2h-pyran-2-carboxylique
WO2020234277A1 (fr) 2019-05-21 2020-11-26 H. Lundbeck A/S Promédicaments de carbamate de catécholamine destinés à être utilisés dans le traitement de la maladie de parkinson
WO2020234275A1 (fr) 2019-05-21 2020-11-26 H. Lundbeck A/S Nouveaux promédicaments de catécholamine destinés à être utilisés dans le traitement de maladies de parkinson
WO2020234276A1 (fr) 2019-05-21 2020-11-26 H. Lundbeck A/S Nouveaux promédicaments de catécholamine destinés à être utilisés dans le traitement de la maladie de parkinson
WO2020234274A1 (fr) 2019-05-21 2020-11-26 H. Lundbeck A/S Nouveaux promédicaments à base de catécholamine destinés à être utilisés dans le traitement de la maladie de parkinson

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* Cited by examiner, † Cited by third party
Title
"Extremely Potent Orally Active Benzo[g]quinoline Analogue of the Dopaminergic Prodrug: 1-Propyl-trans-2,3,4,4a,5,7,8,9,10,10a-decahydro-1H-benzo[g]quinoline-6-one", J. MED. CHEM., vol. 49, 2006, pages 6930
J. MED . CHEM, vol. 49, 2006, pages 1494 - 1498
LIU DANYANG ET AL: "Extremely Potent Orally Active Benzo[ g ]quinoline Analogue of the Dopaminergic Prodrug:? 6-( N , N -Di- n -propyl)amino-3,4,5,6,7,8-hexahydro-2 H -naphthalen-1-one", JOURNAL OF MEDICINAL CHEMISTRY, vol. 49, no. 4, 25 January 2006 (2006-01-25), US, pages 1494 - 1498, XP093043068, ISSN: 0022-2623, DOI: 10.1021/jm051111h *
LIU ET AL.: "A novel synthesis and pharmacological evaluation of a potential dopamine D1/D2 agonist: 1-Propyl 1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6,7-diol", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 16, 2008, pages 3438 - 3444, XP022558577, DOI: 10.1016/j.bmc.2007.06.036
LIU ET AL.: "Extremely Potent Orally Active Benzo[g]quinoline Analogue of the Dopaminergic Prodrug: 6-(N,N-Di-n-propyl)amino-3,4,5,6,7,8-hexahydro-2H-naphtalen-1-one", J. MED. CHEM., vol. 49, 2006, pages 1494 - 1498, XP093043068, DOI: 10.1021/jm051111h

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