RU2015133989A - Ингибирующие jak соединения на основе пиразолопиримидина и способы - Google Patents
Ингибирующие jak соединения на основе пиразолопиримидина и способы Download PDFInfo
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- RU2015133989A RU2015133989A RU2015133989A RU2015133989A RU2015133989A RU 2015133989 A RU2015133989 A RU 2015133989A RU 2015133989 A RU2015133989 A RU 2015133989A RU 2015133989 A RU2015133989 A RU 2015133989A RU 2015133989 A RU2015133989 A RU 2015133989A
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- RU
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- Prior art keywords
- disease
- pyrazolo
- pyrimidin
- carboxamide
- pyridin
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims 6
- 238000000034 method Methods 0.000 title claims 3
- 230000002401 inhibitory effect Effects 0.000 title claims 2
- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 title 1
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 206010012442 Dermatitis contact Diseases 0.000 claims 2
- 208000032027 Essential Thrombocythemia Diseases 0.000 claims 2
- 102000015617 Janus Kinases Human genes 0.000 claims 2
- 108010024121 Janus Kinases Proteins 0.000 claims 2
- 208000008601 Polycythemia Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 208000010247 contact dermatitis Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 206010028537 myelofibrosis Diseases 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 206010053613 Type IV hypersensitivity reaction Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- NWPPXBSDHOYQBX-UHFFFAOYSA-N n-[3-(2-fluorophenyl)pyridin-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC1=CC=CC=C1C1=CN=CC=C1NC(=O)C1=C2N=CC=CN2N=C1 NWPPXBSDHOYQBX-UHFFFAOYSA-N 0.000 claims 1
- GJJWKAPPVNNWLJ-UHFFFAOYSA-N n-[3-(3-chlorophenyl)pyridin-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound ClC1=CC=CC(C=2C(=CC=NC=2)NC(=O)C2=C3N=CC=CN3N=C2)=C1 GJJWKAPPVNNWLJ-UHFFFAOYSA-N 0.000 claims 1
- OEIOCPLLBAECAL-UHFFFAOYSA-N n-[3-(3-fluorophenyl)pyridin-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC1=CC=CC(C=2C(=CC=NC=2)NC(=O)C2=C3N=CC=CN3N=C2)=C1 OEIOCPLLBAECAL-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000005951 type IV hypersensitivity Effects 0.000 claims 1
- 208000027930 type IV hypersensitivity disease Diseases 0.000 claims 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
- A61K31/435—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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- 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
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
- C07D403/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (17)
1. Соединение формулы I
I
или его фармацевтически приемлемые соли, где
R1 представляет собой водород;
R2 представляет собой пиридинил, где R2 необязательно замещен 1-3 R4;
R3 представляет собой фенил, где R3 необязательно замещен 1-5 R5;
R4 независимо представляет собой C1-C6алкил;
R5 независимо представляет собой C1-C6алкил, галоген или -(C0-C3алкил)CF3.
2. Соединение по п.1, выбранное из:
N-(3-(2-фторфенил)пиридин-4-ил)пиразоло[1,5-a]пиримидин-3-карбоксамида,
N-(3-(3-фторфенил)пиридин-4-ил)пиразоло[1,5-a]пиримидин-3-карбоксамида и
N-(3-(3-хлорфенил)пиридин-4-ил)пиразоло[1,5-a]пиримидин-3-карбоксамида.
3. Фармацевтическая композиция, ингибирующая активность Janus-киназы, содержащая соединение по п.1 и фармацевтически приемлемый носитель, адъювант или наполнитель.
4. Способ профилактики, лечения или снижения тяжести заболевания или состояния, отвечающего на ингибирование активности Janus-киназы у пациента, включающий введение указанному пациенту терапевтически эффективного количества соединения по п.1.
5. Способ по п.4, где указанное заболевание или состояние представляет собой злокачественную опухоль, истинную полицитемию, идиопатический тромбоцитоз, миелофиброз, хронический миелогенный лейкоз (CML), ревматоидный артрит, синдром воспаленного кишечника, болезнь Крона, псориаз, контактный дерматит или реакцию гиперчувствительности замедленного типа.
6. Применение соединения по п.1 для лечения злокачественной опухоли, истинной полицитемии, идиопатического тромбоцитоза, миелофиброза, хронического миелогенного лейкоза (CML), ревматоидного артрита, синдрома воспаленного кишечника, болезни Крона, псориаза, контактного дерматита или реакции гиперчувствительности замедленного типа.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US22291809P | 2009-07-02 | 2009-07-02 | |
US61/222,918 | 2009-07-02 |
Related Parent Applications (1)
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RU2012103487/04A Division RU2567238C2 (ru) | 2009-07-02 | 2010-07-02 | Ингибирующие jak соединения на основе пиразолопиримидина и способы |
Publications (3)
Publication Number | Publication Date |
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RU2015133989A3 RU2015133989A3 (ru) | 2018-12-24 |
RU2015133989A true RU2015133989A (ru) | 2018-12-24 |
RU2675857C2 RU2675857C2 (ru) | 2018-12-25 |
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RU2012103487/04A RU2567238C2 (ru) | 2009-07-02 | 2010-07-02 | Ингибирующие jak соединения на основе пиразолопиримидина и способы |
RU2015133989A RU2675857C2 (ru) | 2009-07-02 | 2010-07-02 | Ингибирующие jak соединения на основе пиразолопиримидина и способы |
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RU2012103487/04A RU2567238C2 (ru) | 2009-07-02 | 2010-07-02 | Ингибирующие jak соединения на основе пиразолопиримидина и способы |
Country Status (35)
Country | Link |
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US (6) | US8999998B2 (ru) |
EP (3) | EP3333169B1 (ru) |
JP (4) | JP5769261B2 (ru) |
KR (3) | KR20180108858A (ru) |
CN (2) | CN102482284B (ru) |
AU (1) | AU2010266188B2 (ru) |
BR (1) | BRPI1010197A2 (ru) |
CA (1) | CA2767097A1 (ru) |
CL (1) | CL2012000001A1 (ru) |
CO (1) | CO6491081A2 (ru) |
CR (2) | CR20170115A (ru) |
DK (1) | DK2448941T3 (ru) |
EC (1) | ECSP12011645A (ru) |
ES (1) | ES2657839T3 (ru) |
HR (1) | HRP20180157T1 (ru) |
HU (1) | HUE035537T2 (ru) |
IL (3) | IL217224B (ru) |
IN (1) | IN2012DN00755A (ru) |
LT (1) | LT2448941T (ru) |
MA (1) | MA33502B1 (ru) |
MX (1) | MX2012000169A (ru) |
MY (1) | MY160156A (ru) |
NO (1) | NO2448941T3 (ru) |
NZ (4) | NZ738778A (ru) |
PE (2) | PE20151249A1 (ru) |
PH (1) | PH12015500666A1 (ru) |
PL (1) | PL2448941T3 (ru) |
PT (1) | PT2448941T (ru) |
RS (1) | RS56671B1 (ru) |
RU (2) | RU2567238C2 (ru) |
SG (2) | SG177454A1 (ru) |
SI (1) | SI2448941T1 (ru) |
UA (1) | UA110324C2 (ru) |
WO (1) | WO2011003065A2 (ru) |
ZA (2) | ZA201200490B (ru) |
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