AR127126A1 - Compuestos de pirazolo[3,4-b]piridina para el tratamiento de enfermedades autoinmunitarias - Google Patents
Compuestos de pirazolo[3,4-b]piridina para el tratamiento de enfermedades autoinmunitariasInfo
- Publication number
- AR127126A1 AR127126A1 ARP220102558A ARP220102558A AR127126A1 AR 127126 A1 AR127126 A1 AR 127126A1 AR P220102558 A ARP220102558 A AR P220102558A AR P220102558 A ARP220102558 A AR P220102558A AR 127126 A1 AR127126 A1 AR 127126A1
- Authority
- AR
- Argentina
- Prior art keywords
- compound
- formula
- alkyl
- base
- amino
- Prior art date
Links
- 238000011282 treatment Methods 0.000 title abstract 2
- 208000023275 Autoimmune disease Diseases 0.000 title 1
- 150000005230 pyrazolo[3,4-b]pyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 5
- -1 3,4,4a,5,7,7a-hexahydro-2H-pyrrolo[3,4-b][1,4]oxazinyl Chemical group 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 abstract 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 abstract 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical group [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 abstract 2
- 125000004193 piperazinyl group Chemical group 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 101000669402 Homo sapiens Toll-like receptor 7 Proteins 0.000 abstract 1
- 101000800483 Homo sapiens Toll-like receptor 8 Proteins 0.000 abstract 1
- 208000005777 Lupus Nephritis Diseases 0.000 abstract 1
- 102000008235 Toll-Like Receptor 9 Human genes 0.000 abstract 1
- 108010060818 Toll-Like Receptor 9 Proteins 0.000 abstract 1
- 102100039390 Toll-like receptor 7 Human genes 0.000 abstract 1
- 102100033110 Toll-like receptor 8 Human genes 0.000 abstract 1
- 239000005557 antagonist Substances 0.000 abstract 1
- 125000002393 azetidinyl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000006664 bond formation reaction Methods 0.000 abstract 1
- 229910000024 caesium carbonate Inorganic materials 0.000 abstract 1
- MXFYYFVVIIWKFE-UHFFFAOYSA-N dicyclohexyl-[2-[2,6-di(propan-2-yloxy)phenyl]phenyl]phosphane Chemical group CC(C)OC1=CC=CC(OC(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 MXFYYFVVIIWKFE-UHFFFAOYSA-N 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 238000005755 formation reaction Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000003386 piperidinyl group Chemical group 0.000 abstract 1
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 abstract 1
Classifications
-
- 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
-
- 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
- A61K31/495—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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61K31/495—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
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- 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
- A61K31/495—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
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
-
- 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]
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Reivindicación 1: Un compuesto de fórmula (1), en donde R¹ es un resto de fórmula (a); en donde R⁴ es H o alquil C₁₋₆; R⁵ es alquil C₁₋₆; R² es H o alquil C₁₋₆; R³ es piperazinilo, (alcoxi C₁₋₆alquil C₁₋₆)piperazinilo, 3,4,4a,5,7,7a-hexahidro-2H-pirrolo[3,4-b][1,4]oxazinilo, 4,7-diazaespiro[2.5]octanilo, 5-oxa-2,8-diazaespiro[3.5]nonanilo, amino-1,4-oxazepanilo, amino(alcoxi C₁₋₆)piperidinilo, amino(alcoxi C₁₋₆)pirrolidinilo, amino(alquil C₁₋₆)azetidinilo o aminohalopiperidinilo; A es N o CR⁶; en donde R⁶ es H, alquil C₁₋₆ o alcoxi C₁₋₆; M es N o CR⁷; en donde R⁷ es H o alquil C₁₋₆; W es N o CH; Q es N o CH; siempre que no más de dos de A, M, W y Q sean N en simultáneo; o una sal farmacéuticamente aceptable de este. Reivindicación 21: Un proceso para la preparación de un compuesto de acuerdo con cualquiera de las reivindicaciones 1 a 20 que comprende la siguiente etapa: a) la formación de enlace C-N de Buchwald-Hartwig entre el compuesto de fórmula (4), y R³-H, en presencia de un catalizador y una base; b) la reacción de formación de enlace C-N de Buchwald-Hartwig entre el compuesto de fórmula (6), y el compuesto de fórmula (2), en presencia de un catalizador y una base; c) la reacción de sustitución directa entre el compuesto de fórmula (6) y el compuesto de fórmula (2) en presencia de una base; en donde X es halógeno; en las etapas a) y b), el catalizador es RuPhos Pd G2 o Pd₂(dba)₃ / XantPhos; la base es Cs₂CO₃ o t-BuONa; en la etapa c), la base es DIPEA o CsF; en donde R¹ a R⁵, A, M, W y Q se definen como en cualquiera de las reivindicaciones 1 a 19. Reivindicación 24: El uso de un compuesto de acuerdo con cualquiera de las reivindicaciones 1 a 20 para el tratamiento o la profilaxis de lupus eritematoso sistémico o nefritis lúpica. Reivindicación 26: El uso de un compuesto de acuerdo con cualquiera de las reivindicaciones 1 a 20 para la preparación de un medicamento para antagonista de TLR7 y TLR8 y TLR9.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2021120406 | 2021-09-24 | ||
| CN2022089033 | 2022-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR127126A1 true AR127126A1 (es) | 2023-12-20 |
Family
ID=83688579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP220102558A AR127126A1 (es) | 2021-09-24 | 2022-09-22 | Compuestos de pirazolo[3,4-b]piridina para el tratamiento de enfermedades autoinmunitarias |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP4405051A1 (es) |
| JP (1) | JP2024534567A (es) |
| KR (1) | KR20240065092A (es) |
| CN (1) | CN118076604A (es) |
| AR (1) | AR127126A1 (es) |
| AU (1) | AU2022351495A1 (es) |
| CA (1) | CA3228485A1 (es) |
| CO (1) | CO2024003401A2 (es) |
| CR (1) | CR20240134A (es) |
| IL (1) | IL310443A (es) |
| MX (1) | MX2024003444A (es) |
| PE (1) | PE20240815A1 (es) |
| TW (1) | TW202328129A (es) |
| WO (1) | WO2023046806A1 (es) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016540013A (ja) * | 2013-12-13 | 2016-12-22 | 武田薬品工業株式会社 | Ｔｌｒ阻害剤としてのピロロ［３，２−ｃ］ピリジン誘導体 |
| US10954233B2 (en) | 2016-09-09 | 2021-03-23 | Novartis Ag | Compounds and compositions as inhibitors of endosomal toll-like receptors |
| EP3793998A1 (en) | 2018-05-18 | 2021-03-24 | Novartis AG | Crystalline forms of a tlr7/tlr8 inhibitor |
| EP4182032A1 (en) * | 2020-07-14 | 2023-05-24 | F. Hoffmann-La Roche AG | Hydroisoquinoline or hydronaphthyridine compounds for the treatment of autoimmune disease |
-
2022
- 2022-09-22 EP EP22786353.7A patent/EP4405051A1/en active Pending
- 2022-09-22 PE PE2024000482A patent/PE20240815A1/es unknown
- 2022-09-22 MX MX2024003444A patent/MX2024003444A/es unknown
- 2022-09-22 CN CN202280063841.XA patent/CN118076604A/zh active Pending
- 2022-09-22 CA CA3228485A patent/CA3228485A1/en active Pending
- 2022-09-22 KR KR1020247009335A patent/KR20240065092A/ko unknown
- 2022-09-22 AR ARP220102558A patent/AR127126A1/es unknown
- 2022-09-22 CR CR20240134A patent/CR20240134A/es unknown
- 2022-09-22 AU AU2022351495A patent/AU2022351495A1/en active Pending
- 2022-09-22 JP JP2024518351A patent/JP2024534567A/ja active Pending
- 2022-09-22 IL IL310443A patent/IL310443A/en unknown
- 2022-09-22 WO PCT/EP2022/076306 patent/WO2023046806A1/en active Application Filing
- 2022-09-23 TW TW111136043A patent/TW202328129A/zh unknown
-
2024
- 2024-03-19 CO CONC2024/0003401A patent/CO2024003401A2/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN118076604A (zh) | 2024-05-24 |
| CA3228485A1 (en) | 2023-03-30 |
| WO2023046806A1 (en) | 2023-03-30 |
| KR20240065092A (ko) | 2024-05-14 |
| AU2022351495A1 (en) | 2024-02-01 |
| EP4405051A1 (en) | 2024-07-31 |
| CR20240134A (es) | 2024-05-07 |
| MX2024003444A (es) | 2024-04-03 |
| CO2024003401A2 (es) | 2024-04-29 |
| PE20240815A1 (es) | 2024-04-18 |
| IL310443A (en) | 2024-03-01 |
| JP2024534567A (ja) | 2024-09-20 |
| TW202328129A (zh) | 2023-07-16 |
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