CO2023007624A2 - Derivados de n-(imidazo)[1,2-b]piridazin-3-il)-1-ciclohexil-2h-indazol-5-carboxamida y de n-(pirazolo[1,5-a]pirimidin-3-il)-1-ciclohexil-2h-indazol-5-carboxamida como inhibidores de irak4 para el tratamiento del asma - Google Patents
Derivados de n-(imidazo)[1,2-b]piridazin-3-il)-1-ciclohexil-2h-indazol-5-carboxamida y de n-(pirazolo[1,5-a]pirimidin-3-il)-1-ciclohexil-2h-indazol-5-carboxamida como inhibidores de irak4 para el tratamiento del asmaInfo
- Publication number
- CO2023007624A2 CO2023007624A2 CONC2023/0007624A CO2023007624A CO2023007624A2 CO 2023007624 A2 CO2023007624 A2 CO 2023007624A2 CO 2023007624 A CO2023007624 A CO 2023007624A CO 2023007624 A2 CO2023007624 A2 CO 2023007624A2
- Authority
- CO
- Colombia
- Prior art keywords
- carboxamide
- indazol
- formula
- cyclohexyl
- pyridazin
- Prior art date
Links
- 229940127590 IRAK4 inhibitor Drugs 0.000 title abstract 2
- 208000006673 asthma Diseases 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- 208000023275 Autoimmune disease Diseases 0.000 abstract 1
- 208000011594 Autoinflammatory disease Diseases 0.000 abstract 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 abstract 1
- 206010012438 Dermatitis atopic Diseases 0.000 abstract 1
- 201000009273 Endometriosis Diseases 0.000 abstract 1
- 201000005569 Gout Diseases 0.000 abstract 1
- 201000002481 Myositis Diseases 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- HLUMPUAUCWMXKL-UHFFFAOYSA-N O=C(C1=CC2=CN(C(CC3)CCC33NCCC3)N=C2C=C1)NC1=C2N=CC=CN2N=C1 Chemical compound O=C(C1=CC2=CN(C(CC3)CCC33NCCC3)N=C2C=C1)NC1=C2N=CC=CN2N=C1 HLUMPUAUCWMXKL-UHFFFAOYSA-N 0.000 abstract 1
- OWWONESKONXVFI-UHFFFAOYSA-N O=C(C1=CC2=CN(C(CC3)CCC33NCCC3)N=C2C=C1)NC1=CN=C2N1N=CC=C2 Chemical compound O=C(C1=CC2=CN(C(CC3)CCC33NCCC3)N=C2C=C1)NC1=CN=C2N1N=CC=C2 OWWONESKONXVFI-UHFFFAOYSA-N 0.000 abstract 1
- PIEFBWDHIVDFLX-UHFFFAOYSA-N O=C(C1=CC=C2N(C3CCCCC3)NCC2=C1)NC1=C2N=CC=CN2N=C1 Chemical compound O=C(C1=CC=C2N(C3CCCCC3)NCC2=C1)NC1=C2N=CC=CN2N=C1 PIEFBWDHIVDFLX-UHFFFAOYSA-N 0.000 abstract 1
- SLFYLMUBNWHOSJ-UHFFFAOYSA-N O=C(C1=CC=C2N(C3CCCCC3)NCC2=C1)NC1=CN=C2N1N=CC=C2 Chemical class O=C(C1=CC=C2N(C3CCCCC3)NCC2=C1)NC1=CN=C2N1N=CC=C2 SLFYLMUBNWHOSJ-UHFFFAOYSA-N 0.000 abstract 1
- 201000004681 Psoriasis Diseases 0.000 abstract 1
- 208000021386 Sjogren Syndrome Diseases 0.000 abstract 1
- 201000009594 Systemic Scleroderma Diseases 0.000 abstract 1
- 206010042953 Systemic sclerosis Diseases 0.000 abstract 1
- 201000008937 atopic dermatitis Diseases 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 208000027866 inflammatory disease Diseases 0.000 abstract 1
- 206010039073 rheumatoid arthritis Diseases 0.000 abstract 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- 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
-
- 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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
- A61P37/08—Antiallergic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
La presente solicitud se refiere a un compuesto de Fórmula (A), en donde R1 se selecciona entre la Fórmula (II) y Fórmula (III) y R2 se selecciona entre la Fórmula (IV), Fórmula (V) y Fórmula (VI) como inhibidores de IRAK4 para su uso en métodos de tratamiento de, por ejemplo, asma y enfermedad pulmonar obstructiva crónica (EPOC), cáncer, enfermedades inflamatorias y enfermedades autoinflamatorias/autoinmunitarias tales como, por ejemplo, el lupus eritematoso sistémico, artritis reumatoide, miositis, síndrome de Sjögren, esclerosis sistémica, gota, endometriosis, dermatitis atópica y psoriasis. Los compuestos preferidos de la presente invención son, por ejemplo: derivados de ● N-(imidazo[1,2-b]piridazin-3-il)-1-ciclohexil-2H-indazol-5-carboxamida, ● N-(pirazolo[1,5-a]pirimidin-3-il)-1-ciclohexil-2H-indazol-5-carboxamida, ● N-(imidazo[1,2-b]piridazin-3-il)-1-azaespiro[4.5]decan-8-il-2H-indazol-5-carboxamida y ● N-(pirazolo[1,5-a]pirimidin-3-il)-1-azaespiro[4.5]decan-8-il-2H-indazol-5-carboxamida. Un compuesto de ejemplo de la presente invención es, por ejemplo, N-(imidazo[1,2-b]piridazin-3-il)-6-metoxi-2-((5r,8r)-1-metil-2-oxo-1-azaespiro[4.5]decan-8-il)-2H-indazol-5-carboxamida (Ejemplo 1): Fórmula (VII).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202063199160P | 2020-12-10 | 2020-12-10 | |
| PCT/EP2021/084916 WO2022122876A1 (en) | 2020-12-10 | 2021-12-09 | N-(imidazo[1,2-b]pyridazin-3-yl)-1-cyclohexyl-2h-indazole-5-carboxamide and n-(pyrazolo[1,5-a]pyrimidin-3-yl)-1-cyclohexyl-2h-indazole-5-carboxamide derivatives as irak4 inhibitors for the treatment of asthma |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CO2023007624A2 true CO2023007624A2 (es) | 2023-06-30 |
Family
ID=79230946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CONC2023/0007624A CO2023007624A2 (es) | 2020-12-10 | 2023-06-09 | Derivados de n-(imidazo)[1,2-b]piridazin-3-il)-1-ciclohexil-2h-indazol-5-carboxamida y de n-(pirazolo[1,5-a]pirimidin-3-il)-1-ciclohexil-2h-indazol-5-carboxamida como inhibidores de irak4 para el tratamiento del asma |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US11866405B2 (es) |
| EP (1) | EP4259632B1 (es) |
| JP (1) | JP2023552838A (es) |
| KR (1) | KR20230118153A (es) |
| CN (1) | CN116583285A (es) |
| AR (1) | AR124303A1 (es) |
| AU (1) | AU2021395816B2 (es) |
| CA (1) | CA3203569A1 (es) |
| CL (1) | CL2023001662A1 (es) |
| CO (1) | CO2023007624A2 (es) |
| CR (1) | CR20230264A (es) |
| DO (1) | DOP2023000119A (es) |
| EC (1) | ECSP23050553A (es) |
| IL (1) | IL303356A (es) |
| LT (1) | LT4259632T (es) |
| MX (1) | MX2023006816A (es) |
| PE (1) | PE20240684A1 (es) |
| TW (1) | TW202237612A (es) |
| UY (1) | UY39561A (es) |
| WO (1) | WO2022122876A1 (es) |
| ZA (1) | ZA202306848B (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7555519B2 (ja) | 2022-02-14 | 2024-09-24 | アストラゼネカ・アクチエボラーグ | Ｉｒａｋ４阻害剤 |
| WO2023227703A1 (en) * | 2022-05-26 | 2023-11-30 | Astrazeneca Ab | Solid forms of heterocyclylamides as irak4 inhibitors |
| WO2024209044A1 (en) | 2023-04-07 | 2024-10-10 | Astrazeneca Ab | Irak4 protacs |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX340490B (es) | 2010-07-13 | 2016-07-11 | F Hoffmann-La Roche Ag * | Derivados de pirazolo [1, 5a] pirimidina y de tieno [3, 2b] pirimidina como moduladores de la cinasa asociada al receptor de la interleucina 4 (irak4). |
| HUE029617T2 (en) | 2010-12-20 | 2017-03-28 | Merck Serono Sa | Indazolyl triazole derivatives as IRAK inhibitors |
| AU2014228344C1 (en) | 2013-03-15 | 2019-02-07 | Biomarin Pharmaceutical Inc. | HDAC inhibitors |
| AU2015205348A1 (en) | 2014-01-10 | 2016-07-28 | Aurigene Discovery Technologies Limited | Indazole compounds as IRAK4 inhibitors |
| CU24406B1 (es) | 2014-04-04 | 2019-05-03 | Pfizer | 1-{[(2s,3s,4s)-3-etil-4-fluoro-5-oxopirrolidin-2-il]metoxi}-7 -metoxiisoquinolin-6-carboxamida |
| JO3705B1 (ar) | 2014-11-26 | 2021-01-31 | Bayer Pharma AG | إندازولات مستبدلة جديدة، عمليات لتحضيرها، مستحضرات دوائية تحتوي عليها واستخدامها في إنتاج أدوية |
| UY36660A (es) | 2015-04-30 | 2016-11-30 | Bayer Pharma AG | Combinaciones de inhibidores de irak4 |
| AU2016293446A1 (en) | 2015-07-15 | 2018-02-15 | Aurigene Discovery Technologies Limited | Substituted aza compounds as IRAK-4 inhibitors |
| JP2018524372A (ja) | 2015-07-15 | 2018-08-30 | アウリジーン ディスカバリー テクノロジーズ リミテッド | Ｉｒａｋ−４阻害剤としてのインダゾール及びアザインダゾール化合物 |
| US10435396B2 (en) | 2016-03-03 | 2019-10-08 | Bayer Pharma Aktiegesellschaft | 2-substituted indazoles, methods for producing same, pharmaceutical preparations that contain same, and use of same to produce drugs |
| US10059708B2 (en) | 2016-04-26 | 2018-08-28 | Northwestern University | Therapeutic targeting of the interleukin 1 receptor-associated kinase 4 (IRAK4) in leukemias characterized by rearrangements in the mixed lineage leukemia gene (MLL-r) |
| SG11201810769QA (en) | 2016-06-01 | 2018-12-28 | Bayer Pharma AG | Use of 2-substituted indazoles for the treatment and prophylaxis of autoimmune diseases |
| CN110785418A (zh) | 2017-06-21 | 2020-02-11 | 豪夫迈·罗氏有限公司 | 作为irak4调节剂的异二氢吲哚酮衍生物 |
| EP3642199B1 (en) | 2017-06-21 | 2022-04-27 | F. Hoffmann-La Roche AG | Benzofurans as irak4 modulators |
| US20230087118A1 (en) | 2019-06-27 | 2023-03-23 | Biogen Ma Inc. | IMIDAZO[1,2-a]PYRIDINYL DERIVATIVES AND THEIR USE IN THE TREATMENT OF DISEASE |
| US20230002361A1 (en) | 2019-06-27 | 2023-01-05 | Biogen Ma Inc. | 2h-indazole derivatives and their use in the treatment of disease |
-
2021
- 2021-12-01 US US17/457,249 patent/US11866405B2/en active Active
- 2021-12-09 CA CA3203569A patent/CA3203569A1/en active Pending
- 2021-12-09 LT LTEPPCT/EP2021/084916T patent/LT4259632T/lt unknown
- 2021-12-09 PE PE2023001857A patent/PE20240684A1/es unknown
- 2021-12-09 MX MX2023006816A patent/MX2023006816A/es unknown
- 2021-12-09 CN CN202180082181.5A patent/CN116583285A/zh active Pending
- 2021-12-09 AU AU2021395816A patent/AU2021395816B2/en active Active
- 2021-12-09 TW TW110145977A patent/TW202237612A/zh unknown
- 2021-12-09 CR CR20230264A patent/CR20230264A/es unknown
- 2021-12-09 WO PCT/EP2021/084916 patent/WO2022122876A1/en active Application Filing
- 2021-12-09 EP EP21836097.2A patent/EP4259632B1/en active Active
- 2021-12-09 JP JP2023535016A patent/JP2023552838A/ja active Pending
- 2021-12-09 KR KR1020237023107A patent/KR20230118153A/ko unknown
- 2021-12-09 IL IL303356A patent/IL303356A/en unknown
- 2021-12-10 UY UY0001039561A patent/UY39561A/es unknown
- 2021-12-10 AR ARP210103432A patent/AR124303A1/es unknown
-
2023
- 2023-06-08 CL CL2023001662A patent/CL2023001662A1/es unknown
- 2023-06-09 DO DO2023000119A patent/DOP2023000119A/es unknown
- 2023-06-09 CO CONC2023/0007624A patent/CO2023007624A2/es unknown
- 2023-07-05 ZA ZA2023/06848A patent/ZA202306848B/en unknown
- 2023-07-05 EC ECSENADI202350553A patent/ECSP23050553A/es unknown
- 2023-11-02 US US18/500,155 patent/US20240182479A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| UY39561A (es) | 2022-06-30 |
| KR20230118153A (ko) | 2023-08-10 |
| WO2022122876A1 (en) | 2022-06-16 |
| US20220185817A1 (en) | 2022-06-16 |
| ECSP23050553A (es) | 2023-08-31 |
| DOP2023000119A (es) | 2023-07-09 |
| US11866405B2 (en) | 2024-01-09 |
| EP4259632A1 (en) | 2023-10-18 |
| AU2021395816A1 (en) | 2023-07-13 |
| ZA202306848B (en) | 2024-04-24 |
| CN116583285A (zh) | 2023-08-11 |
| MX2023006816A (es) | 2023-06-21 |
| US20240182479A1 (en) | 2024-06-06 |
| CA3203569A1 (en) | 2022-06-16 |
| PE20240684A1 (es) | 2024-04-10 |
| EP4259632B1 (en) | 2024-07-24 |
| IL303356A (en) | 2023-08-01 |
| CR20230264A (es) | 2023-07-26 |
| JP2023552838A (ja) | 2023-12-19 |
| AU2021395816B2 (en) | 2024-04-04 |
| LT4259632T (lt) | 2024-10-10 |
| TW202237612A (zh) | 2022-10-01 |
| CL2023001662A1 (es) | 2024-01-12 |
| AR124303A1 (es) | 2023-03-15 |
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