IL318929A - Indoline derivatives as serotonergic agents useful for the treatment of disorders related thereto - Google Patents

Indoline derivatives as serotonergic agents useful for the treatment of disorders related thereto

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Publication number
IL318929A
IL318929A IL318929A IL31892925A IL318929A IL 318929 A IL318929 A IL 318929A IL 318929 A IL318929 A IL 318929A IL 31892925 A IL31892925 A IL 31892925A IL 318929 A IL318929 A IL 318929A
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Israel
Prior art keywords
6alkyl
independently selected
compound
pct
halo
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IL318929A
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Hebrew (he)
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Abdelmalik Slassi
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Mindset Pharma Inc
Abdelmalik Slassi
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Application filed by Mindset Pharma Inc, Abdelmalik Slassi filed Critical Mindset Pharma Inc
Publication of IL318929A publication Critical patent/IL318929A/en

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    • 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
    • C07D403/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • 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
    • A61K31/425—Thiazoles
    • A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D401/14—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 three or more hetero rings
    • 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
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    • 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
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring

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  • Chemical Kinetics & Catalysis (AREA)
  • Neurosurgery (AREA)
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Claims (20)

PCT/CA2023/0511 1 CLAIMS 1. A compound of Formula I-A: I-A or a pharmaceutically acceptable salt, solvate, and/or prodrug thereof, wherein: Rand R1' are independently selected from H, halo, OH, NH, C1-6alkyl, C1-6alkoxyl, NH(C1-6alkyl), and N(C1-6alkyl); R and R2' are independently selected from H, halo, NH, C1-6alkyl, C1-6alkoxyl, NH(C1-6alkyl), and N(C1-6alkyl); Q is selected from Q1, Q2, Q3, Q4, Q5, and Q6: (Q1), (Q2), (Q3), (Q4), (Q5), and (Q6); is a single bond or a double bond provided that when in Q1 is a double bond then R and R are not present, when in Q2 is a double bond then R and R are not present, and when in Q5 is a double bond then R and R are not present; one or both of R and R is independently selected from H, halo, C1-6alkyl, and C1-6alkoxy, or PCT/CA2023/0511 1 R and R are linked together to form O-(CH)1-2O, or one of R and R is selected from X-L-A and the other of R and R is selected from H, halo, C1-alkyl, and C1-6alkoxy, X is selected from a direct bond, O, C(O), NRa, NRaC(O), C(O)NRa, OC(O), C(O)O, OC(O)O, NRaC(O)O, OC(O)NRa, and NRaC(O)NRa; L is selected from a direct bond, C1-6alkylene, C2-6alkenylene, C1-6alkyleneO, C2-6alkenyleneO, C1-alkyleneC(O), C2-6alkenyleneC(O), C1-6alkyleneNRbC(O), C2-6alkenyleneNRbC(O), C1-alkyleneC(O)NRb, C2-6alkenyleneC(O)NRb, C1-6alkyleneOC(O), C2-6alkenyleneOC(O), C1-alkyleneC(O)O, C2-6alkenyleneC(O)O, C1-6alkyleneOC(O)NRb, C2-6alkenyleneOC(O)NRb, C1-alkyleneNRbC(O)O, C2-6alkenyleneNRbC(O)O, C1-6alkyleneOC(O)O, C2-6alkenyleneOC(O)O, C1-alkyleneNRbC(O)NRb, and C2-6alkenyleneNRbC(O)NRb; Ra is selected from H and C1-6alkyl; Rb is selected from H, C1-6alkyl, and A; A is selected from H, C1-30alkyl, C2-30alkenyl, phenyl, C-cycloalkyl, 3- to 6-membered heterocycloalkyl comprising 1 to 4 heteromoieties independently selected from O, S, S(O), SO, N, and NR, and 5- to 6-membered heteroaryl comprising 1 to 4 heteromoieties independently selected from O, S, S(O), SO, N, and NR, wherein the phenyl, C-cycloalkyl, 3- to 6-membered heterocycloalkyl, and 5- to 6-membered heteroaryl are optionally substituted with one or more substituents independently selected from halo, C1-4alkyl, and OC1-4alkyl; R and R are independently selected from H, halo, OH, C1-6alkyl, and C1-6alkoxy; R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, and R are independently selected from H, halo, and C-alkyl; R, R, R, R, and Rare independently selected from H, C1-6alkyl, C(O)C-alkyl, and C(O)-A'; R and R are independently selected from H and C1-6alkyl; or one of R and R is C(O)-A' and the other is selected from H and C1-6alkyl; wherein A' is selected from Y, O-Y, and O-C-alkylene-O-C(O)-Y; and Y is selected from C7-30alkyl and C7-30alkenyl; or PCT/CA2023/0511
1. 1 R and R, together with the N atom to which they are bound, form a 3- to 6-membered heterocyclic ring which optionally comprises one or two additional heteromoieties independently selected from O, S, S(O), SO, N, and NR and which is optionally substituted with one or more substituents independently selected from halo, OH, C1-4alkyl, and OC1-4alkyl; R and R are independently selected from H and C1-6alkyl; and all available hydrogen atoms are optionally and independently replaced with a fluorine atom or a chlorine atom and/or all available atoms are optionally replaced with alternate isotope thereof, provided when Q is Q6 then the compound of Formula I comprises D, when Q is Q3 or Q4, R, R1', R, R2', R, R, R, R, R, R, R to R, R, R, R, and R to R are not all H, when R is H or OCH, and R or R is CH; and when Q is Q4 and R, R1', R, R2', R, R, R, R, and R to R are all H, then R and R are not both D, when R is CD.
2. The compound of claim 1, wherein R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, and R are independently selected from H and D.
3. The compound of claim 1, wherein Q is selected from one of the following groups: PCT/CA2023/0511 1 , PCT/CA2023/0511 1 wherein R, R, R, R, R, R, and R are independently selected from H, D, C1-6alkyl, C1-fluoroalkyl, C1-6deuteroalkyl, and C(O)- A’.
4. The compound of claim 1 or claim 2, wherein R, R, R, R, R, R, and R are independently selected from H, C1-4alkyl, C1-4fluoroalkyl, and C1-4deuteroalkyl.
5. The compound of claim 1 or claim 3, wherein R, R, R, R, R, R, and R are independently selected from C(O)- A’, wherein all available hydrogen atoms are optionally and independently replaced with a fluorine atom or a chlorine atom and/or a deuterium atom.
6. The compound of claim 1 or claim 3, wherein one of R and R is C(O)-A' and the other is selected from H and C1-6alkyl, wherein all available hydrogen atoms are optionally and independently replaced with a fluorine atom or a chlorine atom and/or a deuterium atom.
7. The compound of any one of claims 1 to 6, wherein R and R1’ are independently selected from H, D, and CH.
8. The compound of any one of claims 1 to 7, wherein R and R2’ are independently H, D, or F.
9. The compound of any one of claims 1 to 8, wherein R and R are independently selected from H, D, Cl, F, OH, C1-4alkyl, C1-4alkoxy, C1-4fluoroalkoxy, C1-4deuteroalkoxy, C1-4fluoroalkyl, and C1-4deuteroalkyl.
10. The compound of any one of claims 1 to 9, wherein one or both of R and R is independently selected from H, D, F, Cl, C1-6alkyl, C1-6fluoroalkyl, C1-6deuteroalkyl, C1-6alkoxy, C1-fluoroalkoxy, and C1-6deuteroalkoxy.
11. The compound of any one of claims 1 to 9, wherein R and R are linked together to form O-CHO.
12. The compound of any one of claims 1 to 9, wherein one of R and R is selected from X-L-A and the other of R and R is selected from H, halo, C1-6alkyl, and C1-6alkoxy.
13. The compound of claim 1, wherein the compound of Formula I-A is defined as follows: PCT/CA2023/0511 1 I-A or a pharmaceutically acceptable salt, solvate, and/or prodrug thereof, wherein: R, R1’, R, R2’, R, and R are independently selected from H, D, and F; Q is selected from Q1, Q2, Q3, Q4, Q5, and Q6: (Q1), (Q2), (Q3), (Q4), (Q5), and (Q6); is a single bond or a double bond provided that when in Q1 is a double bond then R and R are not present, when in Q2 is a double bond then R and R are not present, and when in Q5 is a double bond then R and R are not present; one or both of R and R is selected from H, C1-4alkoxy, C1-4fluoralkoxy, and C1-4deuteroalkoxy, or R and R are linked together to form O-(CH)1-2O; R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, and R are independently selected from H and D; PCT/CA2023/0511 1 R, R, R, R, and Rare independently selected from H, C1-4alkyl, C1-4fluoroalkyl, and C1-deuteroalkyl; and R and R are independently selected from H and C1-6alkyl, provided when Q is Q6 then the compound of Formula I comprises D, when Q is Q3 or Q4, R, R1’, R, R2’, R, R, R, R, R, R, R to R, R, R, R, and R to R are not all H, when R is H or OCH, and R or R is CH.
14. The compound of claim 1, wherein the compound of Formula I-A is defined as follows: I-A or a pharmaceutically acceptable salt, solvate, and/or prodrug thereof, wherein: R and R1’ are independently selected from H, halo, OH, NH, C1-6alkyl, C1-6alkoxyl, NH(C1-6alkyl), and N(C1-6alkyl); R and R2’ are independently selected from H, halo, NH, C1-6alkyl, C1-6alkoxyl, NH(C1-6alkyl), and N(C1-6alkyl); Q is selected from Q1, Q2, Q3, Q4, Q5, and Q6: (Q1), (Q2), (Q3), (Q4), (Q5), and (Q6); PCT/CA2023/0511 1 is a single bond or a double bond provided that when in Q1 is a double bond then R and R are not present, when in Q2 is a double bond then R and R are not present, and when in Q5 is a double bond then R and R are not present; one or both of R and R is independently selected from H, halo, C1-6alkyl, and C1-6alkoxy, or R and R are linked together to form O-(CH)1-2O, or one of R and R is selected from X-L-A and the other of R and R is selected from H, halo, C1-alkyl, and C1-6alkoxy, X is selected from a direct bond, O, C(O), NRa, NRaC(O), C(O)NRa, OC(O), C(O)O, OC(O)O, NRaC(O)O, OC(O)NRa, and NRaC(O)NRa; L is selected from a direct bond, C1-6alkylene, C2-6alkenylene, C1-6alkyleneO, C2-6alkenyleneO, C1-alkyleneC(O), C2-6alkenyleneC(O), C1-6alkyleneNRbC(O), C2-6alkenyleneNRbC(O), C1-alkyleneC(O)NRb, C2-6alkenyleneC(O)NRb, C1-6alkyleneOC(O), C2-6alkenyleneOC(O), C1-alkyleneC(O)O, C2-6alkenyleneC(O)O, C1-6alkyleneOC(O)NRb, C2-6alkenyleneOC(O)NRb, C1-alkyleneNRbC(O)O, C2-6alkenyleneNRbC(O)O, C1-6alkyleneOC(O)O, C2-6alkenyleneOC(O)O, C1-alkyleneNRbC(O)NRb, and C2-6alkenyleneNRbC(O)NRb; Ra is selected from H and C1-6alkyl; Rb is selected from H, C1-6alkyl, and A; A is selected from H, C1-30alkyl, C2-30alkenyl, phenyl, C-cycloalkyl, 3- to 6-membered heterocycloalkyl comprising 1 to 4 heteromoieties independently selected from O, S, S(O), SO, N, and NR, and 5- to 6-membered heteroaryl comprising 1 to 4 heteromoieties independently selected from O, S, S(O), SO, N, and NR, wherein the phenyl, C-cycloalkyl, 3- to 6-membered heterocycloalkyl, and 5- to 6-membered heteroaryl are optionally substituted with one or more substituents independently selected from halo, C1-4alkyl, and OC1-4alkyl; R and R are independently selected from H, halo, OH, C1-6alkyl, and C1-6alkoxy; R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, R, and R are independently selected from H, halo, and C-alkyl; R, R, R, R, and Rare independently selected from H, C1-6alkyl, C(O)C-alkyl, and C(O)-A’; R and R are independently selected from H and C1-6alkyl; or PCT/CA2023/0511 1 one of R and R is C(O)-A' and the other is selected from H and C1-6alkyl; wherein A' is selected from Y, O-Y, and O-C-alkylene-O-C(O)-Y; and Y is selected from C7-30alkyl and C7-30alkenyl; or R and R, together with the N atom to which they are bound, form a 3- to 6-membered heterocyclic ring which optionally comprises one or two additional heteromoieties independently selected from O, S, S(O), SO, N, and NR and which is optionally substituted with one or more substituents independently selected from halo, OH, C1-4alkyl, and OC1-4alkyl; R and R are independently selected from H and C1-6alkyl; and all available hydrogen atoms are optionally and independently replaced with a fluorine atom or a chlorine atom and/or all available atoms are optionally replaced with alternate isotope thereof, provided one of R, R, R, R, R, R, and R is C(O)-A'; or one of R and R is selected from H, halo, C1-6alkyl, and C1-6alkoxy provided A is not H, C1-6alkyl, or C1-6alkeynyl when X and L are both direct bonds.
15. The compound of claim 1 selected from: Compound ID Structure (R)-I- (S)-I- (R)-I- PCT/CA2023/0511 1 (R)-I- (R)-I- (S)-I- (R)-I- (R)-I- (R)-I- (R)-I- (R)-I- PCT/CA2023/0511 1 (S)-I- (R)-I- (R)-I- (R)-I- (R)-I- (R)-I- (R)-I- (R)-I- (R)-I- PCT/CA2023/0511 1 (R)-I- (R)-I- (R)-I- (R)-I- (R)-I- (R)-I- (R)-I- (R)-I- (R)-I- PCT/CA2023/0511 1 (R)-I- (R)-I- (R)-I- (R)-I- (R)-I- (R)-I- (R)-I- (R)-I- PCT/CA2023/0511 1 (R)-I- (R)-I- (R)-I- (R)-I- (R)-I- (R)-I- (R)-I- (R)-I- PCT/CA2023/0511 1 (R)-I- (R)-I- (R)-I- (S)-I- (R)-I- (S)-I- (R)-I- (R)-I- PCT/CA2023/0511 1 (R)-I- (R)-I- (S)-I- (R)-I- (R)-I- (R)-I- (R)-I- (R)-I- PCT/CA2023/0511 1 (S)-I- (R)-I- (R)-I- (S)-I- (S)-I- (R)-I- I- PCT/CA2023/0511 1 I- . (S)-I- I- I- I- I- PCT/CA2023/0511 1 (S)-I- (S)-I- (S)-I- I- , and I- or a pharmaceutically acceptable salt, solvate and/or prodrug thereof.
16. A composition comprising one or more compounds of any one of claims 1 to 15 and a carrier.
17. The compound of any one of claims 1 to 15, for use in treating a disease, disorder, or condition.
18. The compound of any one of claims 1 to 15, for use in treating a central nervous system (CNS) disease, disorder, or condition and/or a neurological disease, disorder, or condition. PCT/CA2023/0511 1
19. The compound of any one of claims 1 to 15, for use in treating a disease or disorder selected from the group consisting of: hyperkinetic disorders, autism spectrum disorder, eating disorders, anxiety disorders, depression disorders, personality disorders, mood disorders, psychotic disorders, addiction disorders, and combinations thereof.
20. A combination of the compound of any one of claims 1 to 15 and another known therapeutic agent, for use in treating a disease, disorder, or condition. Webb+Co. Patent Attorneys
IL318929A 2022-08-29 2023-08-29 Indoline derivatives as serotonergic agents useful for the treatment of disorders related thereto IL318929A (en)

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