AR105820A1 - Análogos de nucleósidos sustituidos en el anillo aromático bicíclico 6-6 para su uso como inhibidores de prmt5 - Google Patents
Análogos de nucleósidos sustituidos en el anillo aromático bicíclico 6-6 para su uso como inhibidores de prmt5Info
- Publication number
- AR105820A1 AR105820A1 ARP160102600A ARP160102600A AR105820A1 AR 105820 A1 AR105820 A1 AR 105820A1 AR P160102600 A ARP160102600 A AR P160102600A AR P160102600 A ARP160102600 A AR P160102600A AR 105820 A1 AR105820 A1 AR 105820A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- group
- cycloalkyl
- halo
- aromatic ring
- Prior art date
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- VZQXUWKZDSEQRR-UHFFFAOYSA-N Nucleosid Natural products C12=NC(SC)=NC(NCC=C(C)C)=C2N=CN1C1OC(CO)C(O)C1O VZQXUWKZDSEQRR-UHFFFAOYSA-N 0.000 title 1
- 102100034607 Protein arginine N-methyltransferase 5 Human genes 0.000 title 1
- 101710084427 Protein arginine N-methyltransferase 5 Proteins 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 29
- 229910052739 hydrogen Inorganic materials 0.000 abstract 12
- 239000001257 hydrogen Substances 0.000 abstract 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 7
- 125000005843 halogen group Chemical group 0.000 abstract 7
- 125000001424 substituent group Chemical group 0.000 abstract 7
- 125000003118 aryl group Chemical group 0.000 abstract 6
- 229910052757 nitrogen Inorganic materials 0.000 abstract 6
- 150000002431 hydrogen Chemical group 0.000 abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 4
- 125000002619 bicyclic group Chemical group 0.000 abstract 4
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 4
- 229910052717 sulfur Inorganic materials 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000001963 4 membered heterocyclic group Chemical group 0.000 abstract 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 125000002950 monocyclic group Chemical group 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000012453 solvate Substances 0.000 abstract 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
Classifications
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- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/14—Pyrrolo-pyrimidine radicals
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A61K31/7076—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid
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- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
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- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
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Abstract
Reivindicación 1: Un compuesto de fórmula (1), donde R¹ representa hidrógeno o -C(=O)-(alquilo C₁₋₄); R² representa hidrógeno o -C(=O)-(alquilo C₁₋₄); Y representa -O-, -CH₂- o -CF₂-; Z representa -CH₂-, -X-CR⁵ᵃR⁵ᵇ-, -CR⁵ᶜ=CR⁵ᵈ-, -CR⁵ᵉR⁵ᵍ-CR⁵ᶠR⁵ʰ- o -CºC-; y cuando Y representa -CH₂- o -CF₂-, entonces Z también puede representar -O- o -CR⁵ᵃR⁵ᵇ-X-; R⁵ᵃ, R⁵ᵇ, R⁵ᶜ, R⁵ᵈ, R⁵ᵉ, R⁵ᶠ, R⁵ᵍ y R⁵ʰ representan cada uno independientemente hidrógeno o alquilo C₁₋₄; X representa -O-, -S- o -NR¹¹-; R¹¹ representa hidrógeno, alquilo C₁₋₄ o alquilo C₁₋₄ sustituido con un sustituyente seleccionado a partir del grupo constituido por -OH, -O-(alquilo C₁₋₄), R¹², -NH₂, -NH-(alquilo C₁₋₄) y -N(alquilo C₁₋₄)₂; R¹² representa un anillo heterocíclico de 4, 5, 6 ó 7 miembros y contiene un átomo de nitrógeno y opcionalmente un átomo de oxigeno; donde dicho anillo heterocíclico de 4, 5, 6 ó 7 miembros está unido al resto de la molécula mediante un átomo de nitrógeno anular; Ar representa un sistema anular aromático bicíclico de 10 miembros constituido por dos anillos de 6 miembros condensados, donde opcionalmente 1 ó 2 átomos de carbono anulares son reemplazados por un átomo de nitrógeno; siempre que cuando el átomo de nitrógeno reemplace uno de los dos átomos de carbono condensados, un grupo carbonilo esté presente en dicho sistema anular aromático bicíclico; Ar está sustituido opcionalmente con uno, dos, tres o cuatro sustituyentes cada uno seleccionado independientemente a partir del grupo constituido por halo, -OH, -NH₂, -NH-(alquilo C₁₋₄), -N(alquilo C₁₋₄)₂, -NHR¹⁰ᵈ, -NR¹⁰ᶜR¹⁰ᵈ, ciano, -CF₃, -C(=O)-NH₂, -C(=O)-NH-(alquilo C₁₋₄), -C(=O)-(alquilo C₁₋₄), alquiloxi C₁₋₄ -C(=O)-O-(alquilo C₁₋₄), cicloalquilo C₃₋₆, -O-(cicloalquilo C₃₋₆), -NH-(cicloalquilo C₃₋₆), -N(cicloalquilo C₃₋₆)₂, alquenilo C₂₋₆, alquilo C₁₋₄ sustituido con un alquiloxi C₁₋₄ y alquilo C₁₋₄ sustituido opcionalmente con un -NR¹⁰ᵃR¹⁰ᵇ; R¹⁰ᵃ y R¹⁰ᵇ representan cada uno independientemente hidrógeno o alquilo C₁₋₄; R¹⁰ᶜ y R¹⁰ᵈ representan cada uno independientemente cicloalquilo C₃₋₆; R¹³; R¹⁴; cicloalquilo C₃₋₆ sustituido con uno, dos o tres sustituyentes cada uno seleccionado independientemente a partir del grupo constituido por halo, -OH y -O-(alquilo C₁₋₄); alquilo C₁₋₄ sustituido con uno, dos o tres sustituyentes cada uno seleccionado independientemente a partir del grupo constituido por halo, -OH y -O-(alquilo C₁₋₄); o alquilo C₁₋₄ sustituido con un sustituyente seleccionado a partir del grupo constituido por cicloalquilo C₃₋₆, R¹³ y R¹⁴; R¹³ representa un anillo aromático monocíclico de 4 a 7 miembros que contiene uno, dos o tres heteroátomos cada uno seleccionado independientemente entre O, S, S(=O)ₚ y N; o un anillo aromático condensado bicíclico de 6 a 11 miembros que contiene uno, dos o tres heteroátomos cada uno seleccionado independientemente entre O, S, S(=O)ₚ y N; dicho anillo aromático monocíclico de 4 a 7 miembros o anillo aromático condensado bicíclico de 6 a 11 miembros está sustituido opcionalmente con uno o dos sustituyentes seleccionados a partir del grupo constituido por alquilo C₁₋₄; p representa 1 ó 2; R¹⁴ representa fenilo sustituido opcionalmente con uno, dos o tres sustituyentes cada uno seleccionado independientemente a partir del grupo constituido por halo; Het representa un sistema anular heterocíclico aromático bicíclico seleccionado a partir del grupo constituido por (a-1), (a-2), (a-3), (a-4) y (a-5) del grupo de fórmulas (2); R³ᵃ, R³ᵇ, R³ᶜ, R³ᵈ y R³ᵉ representan cada uno independientemente hidrógeno, halo, -NR⁷ᵃR⁷ᵇ, alquilo C₁₋₄, alquenilo C₂₋₄, cicloalquilo C₃₋₆, -OH o -O-(alquilo C₁₋₄); R⁷ᵃ representa hidrógeno; R⁷ᵇ representa hidrógeno, cicloalquilo C₃₋₆ o alquilo C₁₋₄; R⁴ᵃ, R⁴ᵇ, R⁴ᶜ, R⁴ᵈ, R⁴ᵉ, R⁴ᶠ y R⁴ᵍ representan cada uno hidrógeno, halo, -NR⁸ᵃR⁸ᵇ o alquilo C₁₋₄; R⁸ᵃ y R⁸ᵇ representan cada uno independientemente hidrógeno o alquilo C₁₋₄; Q¹ representa N o CR⁶ᵃ; Q² representa N o CR⁶ᵇ; Q³ representa N o CR⁶ᶜ; Q⁴ representa N o CR⁶ᵈ; siempre que como máximo uno de Q³ y Q⁴ represente N; Q⁸ representa N o CR⁶ᵍ; Q⁹ representa N o CR⁶ʰ; Q¹⁰ representa N o CR⁶ⁱ; Q¹¹ representa N o CR⁶ʲ; Q⁵ representa CR³ᵈ; Q⁶ representa N; y Q⁷ representa CR⁴ᶠ; o Q⁵ representa CR³ᵈ; Q⁶ representa CR⁴ᵉ; y Q⁷ representa N; o Q⁵ representa N; Q⁶ representa CR⁴ᵉ; y Q⁷ representa CR⁴ᶠ; o Q⁵ representa N; Q⁶ representa CR⁴ᵉ; y Q⁷ representa N; o Q⁵ representa N; Q⁶ representa N; y Q⁷ representa CR⁴ᶠ; o Q⁵ representa N; Q⁶ representa N; y Q⁷ representa N; R⁶ᵃ, R⁶ᵇ, R⁶ᶜ, R⁶ᵈ, R⁶ᵉ, R⁶ᶠ, R⁶ᵍ, R⁶ʰ, R⁶ⁱ y R⁶ʲ representan cada uno independientemente hidrógeno, halógeno, alquilo C₁₋₄, -NR⁹ᵃR⁹ᵇ o alquilo C₁₋₄ sustituido con uno, dos o tres átomos halo; R⁹ᵃ y R⁹ᵇ representan cada uno independientemente hidrógeno o alquilo C₁₋₄; o uno de sus solvatos o una de sus sales de adición farmacéuticamente aceptables; siempre que se excluyan los compuestos y sus solvatos y sales de adición farmacéuticamente aceptables de fórmula (3), (4) y (5).
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562209941P | 2015-08-26 | 2015-08-26 | |
| EP15184011 | 2015-09-07 | ||
| US201662306233P | 2016-03-10 | 2016-03-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR105820A1 true AR105820A1 (es) | 2017-11-15 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP160102600A AR105820A1 (es) | 2015-08-26 | 2016-08-25 | Análogos de nucleósidos sustituidos en el anillo aromático bicíclico 6-6 para su uso como inhibidores de prmt5 |
Country Status (35)
| Country | Link |
|---|---|
| US (4) | US10653711B2 (es) |
| EP (3) | EP4219496A1 (es) |
| JP (3) | JP6917978B2 (es) |
| KR (1) | KR102716092B1 (es) |
| CN (2) | CN107922413B (es) |
| AR (1) | AR105820A1 (es) |
| AU (4) | AU2016311295B2 (es) |
| BR (2) | BR112018003595B1 (es) |
| CA (1) | CA2992688A1 (es) |
| CL (1) | CL2018000510A1 (es) |
| CO (1) | CO2018002063A2 (es) |
| CY (1) | CY1125359T1 (es) |
| DK (1) | DK3341368T3 (es) |
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2021
- 2021-01-20 AU AU2021200345A patent/AU2021200345B2/en active Active
- 2021-04-21 IL IL282537A patent/IL282537A/en unknown
- 2021-07-20 JP JP2021120042A patent/JP7720732B2/ja active Active
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2022
- 2022-01-04 CY CY20221100008T patent/CY1125359T1/el unknown
- 2022-03-09 US US17/690,587 patent/US11883367B2/en active Active
- 2022-08-11 AU AU2022215260A patent/AU2022215260B2/en active Active
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2023
- 2023-03-21 US US18/187,463 patent/US20230330127A1/en not_active Abandoned
- 2023-10-27 JP JP2023184701A patent/JP2024012405A/ja not_active Withdrawn
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2024
- 2024-03-28 AU AU2024202052A patent/AU2024202052A1/en active Pending
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