PE20190909A1 - Derivados de 5-[2-(piridin-2-ilamino)-1,3-tiazol-5-il]-2,3-dihidro-1h-isoindol-1-ona y su uso como inhibidores dobles de fosfatidilinositol ¨3-cinasa delta y gamma - Google Patents
Derivados de 5-[2-(piridin-2-ilamino)-1,3-tiazol-5-il]-2,3-dihidro-1h-isoindol-1-ona y su uso como inhibidores dobles de fosfatidilinositol ¨3-cinasa delta y gammaInfo
- Publication number
- PE20190909A1 PE20190909A1 PE2019000702A PE2019000702A PE20190909A1 PE 20190909 A1 PE20190909 A1 PE 20190909A1 PE 2019000702 A PE2019000702 A PE 2019000702A PE 2019000702 A PE2019000702 A PE 2019000702A PE 20190909 A1 PE20190909 A1 PE 20190909A1
- Authority
- PE
- Peru
- Prior art keywords
- alkyl
- isoindol
- phosphatidylinositol
- thiazol
- pyridin
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title 1
- 150000003905 phosphatidylinositols Chemical class 0.000 title 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 108091007960 PI3Ks Proteins 0.000 abstract 2
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 abstract 2
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- LLUGOCWVLNJQNI-AWEZNQCLSA-N 5-[4-methyl-2-[[6-(2-oxopyrrolidin-1-yl)pyridin-2-yl]amino]-1,3-thiazol-5-yl]-7-methylsulfonyl-2-[(2S)-1,1,1-trifluoropropan-2-yl]-3H-isoindol-1-one Chemical compound CC=1N=C(SC=1C=1C=C2CN(C(C2=C(C=1)S(=O)(=O)C)=O)[C@H](C(F)(F)F)C)NC1=NC(=CC=C1)N1C(CCC1)=O LLUGOCWVLNJQNI-AWEZNQCLSA-N 0.000 abstract 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 abstract 1
- VGBZVXNIRCSRBK-AWEZNQCLSA-N N-[6-[[5-[2-[(1S)-1-cyclopropylethyl]-7-methylsulfonyl-1-oxo-3H-isoindol-5-yl]-4-methyl-1,3-thiazol-2-yl]amino]pyridin-2-yl]acetamide Chemical compound C[C@@H](C1CC1)N1CC2=CC(=CC(=C2C1=O)S(C)(=O)=O)C1=C(C)N=C(NC2=CC=CC(NC(C)=O)=N2)S1 VGBZVXNIRCSRBK-AWEZNQCLSA-N 0.000 abstract 1
- 208000006673 asthma Diseases 0.000 abstract 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 206010025482 malaise Diseases 0.000 abstract 1
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 208000023504 respiratory system disease Diseases 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- 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
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Pulmonology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Se refiere a un compuesto de formula (I), donde X puede ser C(O) o SO2; Y puede ser SO2NHR5 o SO2R6; R1 puede ser alquilo C1-4, sustituido opcionalmente con ciclopropilo, entre otros; R2 puede ser H o CH3; R3 puede ser H o alquilo C1-3; R4 puede ser alquilo C1-3; R3 Y R4 junto con el atomo de N y X forman un anillo cicloheteroalquilo de 5, 6 o 7 miembros; R5 puede ser alquilo C1-3 u (oxetan-3-ilo); R6 puede ser alquilo C1-3. Son compuestos preferidos N-{6-[(5-{2-[(1S)-1-ciclopropiletil]-7-(metilsulfonil)-1-oxo-2,3-dihidro-1H-isoindol-5-il}-4-metil-1,3-tiazol-2-il)amino]piridin-2-il}acetamida; 5-(4-metil-2-{[6-(2-oxopirrolidin-1-il)piridin-2-il]amino}-1,3-tiazol-5-il)-7-(metilsulfonil)-2-[(2S)-1,1,1-trifluoropropan-2-il]-2,3-dihidro-1H-isoindol-1-ona, entre otros. Dicho compuesto quimico incluida las sales farmaceuticamente aceptables de estos modulan la actividad de fosfatidilinositol 3-cinasa delta y fosfatidilinositol 3-cinasa gamma y es util en el tratamiento y/o prevencion de afecciones clinicas que incluyen enfermedades respiratorias, tales como el asma y la enfermedad pulmonar obstructiva cronica (EPOC).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662398006P | 2016-09-22 | 2016-09-22 | |
| PCT/EP2017/073916 WO2018055040A1 (en) | 2016-09-22 | 2017-09-21 | 5-[2-(pyridin-2-ylamino)-1,3-thiazol-5-yl]-2,3-dihydro-1 h-isoindol-1 -one derivatives and their use as dual inhibitors of phosphatidylinositol 3-kinase delta & gamma |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20190909A1 true PE20190909A1 (es) | 2019-06-26 |
Family
ID=59966739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2019000702A PE20190909A1 (es) | 2016-09-22 | 2017-09-21 | Derivados de 5-[2-(piridin-2-ilamino)-1,3-tiazol-5-il]-2,3-dihidro-1h-isoindol-1-ona y su uso como inhibidores dobles de fosfatidilinositol ¨3-cinasa delta y gamma |
Country Status (36)
| Country | Link |
|---|---|
| US (2) | US10961236B2 (es) |
| EP (1) | EP3515910B1 (es) |
| JP (1) | JP6765516B2 (es) |
| KR (1) | KR102226098B1 (es) |
| CN (1) | CN109715623A (es) |
| AR (1) | AR109706A1 (es) |
| AU (1) | AU2017331940B2 (es) |
| BR (1) | BR112019004719A2 (es) |
| CA (1) | CA3036304A1 (es) |
| CL (1) | CL2019000707A1 (es) |
| CO (1) | CO2019003440A2 (es) |
| CR (1) | CR20190200A (es) |
| CY (1) | CY1123346T1 (es) |
| DK (1) | DK3515910T3 (es) |
| DO (1) | DOP2019000073A (es) |
| EA (1) | EA036176B1 (es) |
| EC (1) | ECSP19027780A (es) |
| ES (1) | ES2818583T3 (es) |
| HR (1) | HRP20201175T1 (es) |
| HU (1) | HUE051634T2 (es) |
| IL (1) | IL265298B (es) |
| JO (1) | JOP20190052A1 (es) |
| LT (1) | LT3515910T (es) |
| MA (1) | MA46268B1 (es) |
| MX (2) | MX381898B (es) |
| PE (1) | PE20190909A1 (es) |
| PH (1) | PH12019500615A1 (es) |
| PL (1) | PL3515910T3 (es) |
| PT (1) | PT3515910T (es) |
| RS (1) | RS60764B1 (es) |
| SI (1) | SI3515910T1 (es) |
| SM (1) | SMT202000481T1 (es) |
| SV (1) | SV2019005857A (es) |
| TW (1) | TW201813967A (es) |
| UA (1) | UA123558C2 (es) |
| WO (1) | WO2018055040A1 (es) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020102198A1 (en) | 2018-11-13 | 2020-05-22 | Incyte Corporation | Heterocyclic derivatives as pi3k inhibitors |
| WO2020102216A1 (en) | 2018-11-13 | 2020-05-22 | Incyte Corporation | Substituted heterocyclic derivatives as pi3k inhibitors |
| WO2020102150A1 (en) | 2018-11-13 | 2020-05-22 | Incyte Corporation | Heterocyclic derivatives as pi3k inhibitors |
| ES3053348T3 (en) * | 2019-04-10 | 2026-01-21 | Nanjing Zenshine Pharmaceuticals Co Ltd | Phosphatidylinositol 3-kinase inhibitors |
| EP3980010A4 (en) | 2019-06-04 | 2023-06-07 | Arcus Biosciences, Inc. | 2,3,5-TRISUBSTITUTED PYRAZOLO[1,5-A]PYRIMIDINE COMPOUNDS |
| WO2022017371A1 (zh) * | 2020-07-21 | 2022-01-27 | 中国医药研究开发中心有限公司 | 具有磷脂酰肌醇3-激酶δ和γ的双重抑制剂活性的杂环化合物及其医药用途 |
| WO2022023456A1 (en) | 2020-07-29 | 2022-02-03 | Astrazeneca Ab | Pharmaceutical compositions comprising nano embedded microparticles and methods of use |
| CN116813608B (zh) * | 2023-06-08 | 2024-03-22 | 英矽智能科技(上海)有限公司 | 噻唑类化合物及其应用 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0303538A2 (hu) * | 2000-12-21 | 2005-02-28 | Bristol-Myers Squibb Co. | Tirozin kinázok Tec családjának tiazolil-vegyület inhibitorai és ezeket tartalmazó gyógyszerkészítmények |
| GB0305152D0 (en) * | 2003-03-06 | 2003-04-09 | Novartis Ag | Organic compounds |
| GB0320197D0 (en) * | 2003-08-28 | 2003-10-01 | Novartis Ag | Organic compounds |
| JP2008543754A (ja) * | 2005-06-09 | 2008-12-04 | メルク エンド カムパニー インコーポレーテッド | チェックポイントキナーゼの阻害剤 |
| AU2008282728B2 (en) * | 2007-08-02 | 2012-04-19 | Amgen Inc. | Pl3 kinase modulators and methods of use |
| UY33337A (es) * | 2010-10-18 | 2011-10-31 | Respivert Ltd | DERIVADOS SUSTITUIDOS DE 1H-PIRAZOL[ 3,4-d]PIRIMIDINA COMO INHIBIDORES DE LAS FOSFOINOSITIDA 3-QUINASAS |
| AU2012284088B2 (en) | 2011-07-19 | 2015-10-08 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| CN103946226A (zh) | 2011-07-19 | 2014-07-23 | 无限药品股份有限公司 | 杂环化合物及其应用 |
| HK1199725A1 (en) | 2011-08-29 | 2015-07-17 | 无限药品股份有限公司 | Heterocyclic compounds and uses thereof |
| WO2013052699A2 (en) * | 2011-10-04 | 2013-04-11 | Gilead Calistoga Llc | Novel quinoxaline inhibitors of pi3k |
| UA119315C2 (uk) | 2012-07-03 | 2019-06-10 | Гіліад Фармассет Елелсі | Інгібітори вірусу гепатиту с |
| AR094797A1 (es) | 2013-02-15 | 2015-08-26 | Almirall Sa | Derivados de pirrolotriazina como inhibidores de pi3k |
| CN105431437B (zh) | 2013-07-02 | 2020-03-10 | 理森制药股份公司 | PI3K蛋白激酶抑制剂，特别是δ抑制剂和/或γ抑制剂 |
| UY35675A (es) | 2013-07-24 | 2015-02-27 | Novartis Ag | Derivados sustituidos de quinazolin-4-ona |
| CN106661029B (zh) | 2014-06-27 | 2019-04-05 | 理森制药股份公司 | 作为PI3δ和γ蛋白激酶的选择性双重抑制剂的取代色烯衍生物 |
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2017
- 2017-06-16 JO JOP/2019/0052A patent/JOP20190052A1/ar unknown
- 2017-09-21 KR KR1020197010973A patent/KR102226098B1/ko not_active Expired - Fee Related
- 2017-09-21 HU HUE17772381A patent/HUE051634T2/hu unknown
- 2017-09-21 CA CA3036304A patent/CA3036304A1/en not_active Abandoned
- 2017-09-21 SM SM20200481T patent/SMT202000481T1/it unknown
- 2017-09-21 BR BR112019004719A patent/BR112019004719A2/pt not_active IP Right Cessation
- 2017-09-21 WO PCT/EP2017/073916 patent/WO2018055040A1/en not_active Ceased
- 2017-09-21 EP EP17772381.4A patent/EP3515910B1/en active Active
- 2017-09-21 HR HRP20201175TT patent/HRP20201175T1/hr unknown
- 2017-09-21 UA UAA201903648A patent/UA123558C2/uk unknown
- 2017-09-21 PE PE2019000702A patent/PE20190909A1/es unknown
- 2017-09-21 JP JP2019515477A patent/JP6765516B2/ja not_active Expired - Fee Related
- 2017-09-21 DK DK17772381.4T patent/DK3515910T3/da active
- 2017-09-21 MX MX2019003194A patent/MX381898B/es unknown
- 2017-09-21 CN CN201780057289.2A patent/CN109715623A/zh active Pending
- 2017-09-21 LT LTEP17772381.4T patent/LT3515910T/lt unknown
- 2017-09-21 RS RS20201077A patent/RS60764B1/sr unknown
- 2017-09-21 ES ES17772381T patent/ES2818583T3/es active Active
- 2017-09-21 CR CR20190200A patent/CR20190200A/es unknown
- 2017-09-21 US US16/332,620 patent/US10961236B2/en not_active Expired - Fee Related
- 2017-09-21 EA EA201990664A patent/EA036176B1/ru not_active IP Right Cessation
- 2017-09-21 MA MA46268A patent/MA46268B1/fr unknown
- 2017-09-21 PL PL17772381.4T patent/PL3515910T3/pl unknown
- 2017-09-21 AU AU2017331940A patent/AU2017331940B2/en not_active Ceased
- 2017-09-21 SI SI201730357T patent/SI3515910T1/sl unknown
- 2017-09-21 TW TW106132359A patent/TW201813967A/zh unknown
- 2017-09-21 PT PT177723814T patent/PT3515910T/pt unknown
- 2017-09-22 AR ARP170102631A patent/AR109706A1/es unknown
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2019
- 2019-03-11 IL IL265298A patent/IL265298B/en active IP Right Grant
- 2019-03-19 CL CL2019000707A patent/CL2019000707A1/es unknown
- 2019-03-20 DO DO2019000073A patent/DOP2019000073A/es unknown
- 2019-03-20 MX MX2021004748A patent/MX2021004748A/es unknown
- 2019-03-21 PH PH12019500615A patent/PH12019500615A1/en unknown
- 2019-03-22 SV SV2019005857A patent/SV2019005857A/es unknown
- 2019-04-08 CO CONC2019/0003440A patent/CO2019003440A2/es unknown
- 2019-04-17 EC ECSENADI201927780A patent/ECSP19027780A/es unknown
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2020
- 2020-09-09 CY CY20201100856T patent/CY1123346T1/el unknown
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2021
- 2021-02-11 US US17/173,826 patent/US20210246130A1/en not_active Abandoned
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