AU2013230128B2 - Pyrazolo[1,5-a]pyrimidine-based compounds, compositions comprising them, and methods of their use - Google Patents
Pyrazolo[1,5-a]pyrimidine-based compounds, compositions comprising them, and methods of their use Download PDFInfo
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- AU2013230128B2 AU2013230128B2 AU2013230128A AU2013230128A AU2013230128B2 AU 2013230128 B2 AU2013230128 B2 AU 2013230128B2 AU 2013230128 A AU2013230128 A AU 2013230128A AU 2013230128 A AU2013230128 A AU 2013230128A AU 2013230128 B2 AU2013230128 B2 AU 2013230128B2
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- pyrimidin
- pyrazolo
- ric
- hydrocarbyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 135
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 title description 57
- 238000000034 method Methods 0.000 title description 30
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 54
- 125000005843 halogen group Chemical group 0.000 claims description 37
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 32
- 238000006467 substitution reaction Methods 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 137
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 97
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 73
- 238000006243 chemical reaction Methods 0.000 description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 59
- 235000019439 ethyl acetate Nutrition 0.000 description 57
- 239000000047 product Substances 0.000 description 56
- 238000005481 NMR spectroscopy Methods 0.000 description 49
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 47
- -1 4,4-dimethylpentyl Chemical group 0.000 description 46
- 239000000243 solution Substances 0.000 description 41
- 230000015572 biosynthetic process Effects 0.000 description 40
- 238000003786 synthesis reaction Methods 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 31
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 28
- 230000002829 reductive effect Effects 0.000 description 27
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 26
- 239000000843 powder Substances 0.000 description 26
- 239000007787 solid Substances 0.000 description 25
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 24
- 238000003756 stirring Methods 0.000 description 24
- 239000012267 brine Substances 0.000 description 23
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 23
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 19
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000011282 treatment Methods 0.000 description 12
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- NVOLYUXUHWBCRJ-UHFFFAOYSA-N (2-methoxypyridin-3-yl)boronic acid Chemical compound COC1=NC=CC=C1B(O)O NVOLYUXUHWBCRJ-UHFFFAOYSA-N 0.000 description 10
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 235000011181 potassium carbonates Nutrition 0.000 description 9
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- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 8
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
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- 239000006180 TBST buffer Substances 0.000 description 7
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- 125000003118 aryl group Chemical group 0.000 description 7
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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- RMNIZOOYFMNEJJ-UHFFFAOYSA-K tripotassium;phosphate;hydrate Chemical compound O.[K+].[K+].[K+].[O-]P([O-])([O-])=O RMNIZOOYFMNEJJ-UHFFFAOYSA-K 0.000 description 6
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
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Classifications
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- 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
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- 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
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- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- 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]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
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- Medicinal Chemistry (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
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|---|---|---|---|
| US201261608765P | 2012-03-09 | 2012-03-09 | |
| US61/608,765 | 2012-03-09 | ||
| PCT/US2013/029056 WO2013134228A1 (en) | 2012-03-09 | 2013-03-05 | PYRAZOLO[1,5-a]PYRIMIDINE-BASED COMPOUNDS, COMPOSITIONS COMPRISING THEM, AND METHODS OF THEIR USE |
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| TR (1) | TR201808280T4 (OSRAM) |
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| EP2822559B1 (en) | 2012-03-09 | 2018-05-02 | Lexicon Pharmaceuticals, Inc. | Imidazo[1,2-b]pyridazine-based compounds, compositions comprising them, and uses thereof |
| US8901305B2 (en) | 2012-07-31 | 2014-12-02 | Bristol-Myers Squibb Company | Aryl lactam kinase inhibitors |
| US9708337B2 (en) | 2013-02-22 | 2017-07-18 | Bristol-Myers Squibb Company | Aryl amide-based kinase inhibitors |
| TW201542550A (zh) * | 2013-09-06 | 2015-11-16 | Lexicon Pharmaceuticals Inc | 吡唑并［１，５－ａ］嘧啶基化合物、包含彼之組合物以及使用彼之方法 |
| EP3054955B1 (en) | 2013-10-11 | 2018-05-30 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| WO2015112806A2 (en) | 2014-01-24 | 2015-07-30 | Tp Therapeutics, Inc. | Diaryl macrocycles as modulators of protein kinases |
| EA201691397A1 (ru) * | 2014-01-31 | 2016-11-30 | Бристол-Майерс Сквибб Компани | Хинолиновые ингибиторы киназы |
| TW201620911A (zh) * | 2014-03-17 | 2016-06-16 | 雷西肯製藥股份有限公司 | 銜接子關聯激酶１之抑制劑、包含其之組成物、及其使用方法 |
| US20170239249A1 (en) * | 2014-09-30 | 2017-08-24 | Bristol-Myers Squibb Company | Quinazoline-based kinase inhibitors |
| PL3233863T3 (pl) * | 2014-12-15 | 2024-11-12 | Cmg Pharmaceutical Co., Ltd. | Związki heteroarylowe ze skondensowanymi pierścieniami i ich zastosowanie jako inhibitorów trk |
| US10174044B2 (en) | 2015-04-10 | 2019-01-08 | Bristol-Myers Squibb Company | Fused pyridines as kinase inhibitors |
| ES2864839T3 (es) | 2015-07-02 | 2021-10-14 | Turning Point Therapeutics Inc | Macrociclos de diarilo quirales como moduladores de proteína quinasas |
| ES2979111T3 (es) | 2015-07-06 | 2024-09-24 | Turning Point Therapeutics Inc | Polimorfo de macrociclo de diarilo |
| MX383823B (es) | 2015-07-21 | 2025-03-14 | Turning Point Therapeutics Inc | Macrociclos de diarilo quirales y usos de los mismo. |
| HK1256751A1 (zh) | 2015-11-02 | 2019-10-04 | Janssen Pharmaceutica Nv | [1，2，4]三唑并[1，5-a]嘧啶-7-基化合物 |
| CN109715165A (zh) | 2016-07-28 | 2019-05-03 | Tp生物医药公司 | 巨环激酶抑制剂 |
| ES2912264T3 (es) | 2016-11-02 | 2022-05-25 | Janssen Pharmaceutica Nv | Compuestos de [1,2,4]triazolo[1,5-a]pirimidina como inhibidores de PDE2 |
| EA039102B1 (ru) | 2016-11-02 | 2021-12-03 | Янссен Фармацевтика Нв | Соединения [1,2,4]триазоло[1,5-a]пиримидина в качестве ингибиторов pde2 |
| TWI764950B (zh) * | 2016-11-02 | 2022-05-21 | 比利時商健生藥品公司 | Ｐｄｅ２抑制劑 |
| TWI808958B (zh) | 2017-01-25 | 2023-07-21 | 美商特普醫葯公司 | 涉及二芳基巨環化合物之組合療法 |
| US11046698B2 (en) | 2017-07-28 | 2021-06-29 | Nimbus Lakshmi, Inc. | TYK2 inhibitors and uses thereof |
| MY201925A (en) | 2017-07-28 | 2024-03-23 | Turning Point Therapeutics Inc | Macrocyclic compounds and uses thereof |
| AU2018383571B2 (en) * | 2017-12-15 | 2023-09-21 | Pyramid Biosciences, Inc. | 5-(2-(2,5-difluorophenyl)pyrrolidin-1 -yl)-3-(1H-pyrazol-1-yl)pyrazolo(1,5-a)pyrimidine derivatives and related compounds as Trk kinase inhibitors for treating cancer |
| JP7194188B2 (ja) | 2017-12-19 | 2022-12-21 | ターニング・ポイント・セラピューティクス・インコーポレイテッド | 疾患を治療するための大環状化合物 |
| WO2019120194A1 (zh) * | 2017-12-22 | 2019-06-27 | 深圳市塔吉瑞生物医药有限公司 | 一种取代的吡唑并[1,5-a]嘧啶化合物及其药物组合物及用途 |
| CN109575025B (zh) | 2018-01-23 | 2020-09-11 | 深圳市塔吉瑞生物医药有限公司 | 取代的吡唑并[1,5-a]嘧啶类的大环化合物 |
| WO2020063751A1 (en) * | 2018-09-27 | 2020-04-02 | Fochon Pharmaceuticals, Ltd. | Substituted imidazo [1, 2-a] pyridine and [1, 2, 4] triazolo [1, 5-a] pyridine compounds as ret kinase inhibitors |
| US11414431B2 (en) * | 2018-10-15 | 2022-08-16 | Nimbus Lakshmi, Inc. | Substituted pyrazolo[1,5-a]pyrimidines as TYK2 inhibitors |
| EP4138844A1 (en) | 2020-04-21 | 2023-03-01 | Lexicon Pharmaceuticals, Inc. | 4-(3-(pyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperazine for use in the the treatment of cov-229e or cov-oc43 coronaviruses infections |
| EP4138829A1 (en) | 2020-04-21 | 2023-03-01 | Lexicon Pharmaceuticals, Inc. | Aak1 inhibitors for use in treating viral infections |
| US11478733B2 (en) | 2020-11-24 | 2022-10-25 | Caterpillar Inc. | Filter interlock with tabs mating with a pedestal or a housing |
| TW202525819A (zh) * | 2023-09-08 | 2025-07-01 | 加拿大商薩泰洛斯生物科學公司 | Ａｐ２相關激酶１抑制劑及其用途 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6194410B1 (en) * | 1998-03-11 | 2001-02-27 | Hoffman-La Roche Inc. | Pyrazolopyrimidine and pyrazolines and process for preparation thereof |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5464764A (en) | 1989-08-22 | 1995-11-07 | University Of Utah Research Foundation | Positive-negative selection methods and vectors |
| AU2515992A (en) | 1991-08-20 | 1993-03-16 | Genpharm International, Inc. | Gene targeting in animal cells using isogenic dna constructs |
| JP4847275B2 (ja) * | 2005-10-21 | 2011-12-28 | 田辺三菱製薬株式会社 | ピラゾロ［１，５−ａ］ピリミジン化合物 |
| KR20090073121A (ko) | 2006-09-29 | 2009-07-02 | 노파르티스 아게 | Ｐｉ3ｋ 지질 키나제 억제제로서의 피라졸로피리미딘 |
| US20120058997A1 (en) * | 2006-11-06 | 2012-03-08 | Supergen, Inc. | Imidazo[1,2-b]pyridazine and pyrazolo[1,5-a]pyrimidine derivatives and their use as protein kinase inhibitors |
| BRPI0912668A2 (pt) * | 2008-05-13 | 2016-01-26 | Irm Llc | composto e composições como inibidores de quinase |
| KR101853026B1 (ko) * | 2008-10-22 | 2018-04-27 | 어레이 바이오파마 인크. | ＴＲＫ 키나아제 억제제로서 치환된 피라졸로［１,５ａ］ 피리미딘 화합물 |
| AR077468A1 (es) * | 2009-07-09 | 2011-08-31 | Array Biopharma Inc | Compuestos de pirazolo (1,5 -a) pirimidina sustituidos como inhibidores de trk- quinasa |
| TW201113286A (en) | 2009-09-03 | 2011-04-16 | Array Biopharma Inc | Substituted pyrazolo[1,5-a]pyrimidine compounds as mTOR inhibitors |
| EP2523552B1 (en) | 2010-01-14 | 2015-05-13 | Merck Sharp & Dohme Corp. | Pyrazolo[1,5-a]pyrimidines as mark inhibitors |
| EP3409278B8 (en) * | 2011-07-21 | 2020-11-04 | Sumitomo Dainippon Pharma Oncology, Inc. | Heterocyclic protein kinase inhibitors |
| MX381849B (es) | 2012-03-09 | 2025-03-13 | Lexicon Pharmaceuticals Inc | Compuestos a base de pirazol[1,5-a]pirimidina, composiciones que los comprenden, y métodos para su uso. |
| HK1199814A1 (en) * | 2012-03-09 | 2015-07-24 | Lexicon Pharmaceuticals, Inc. | Inhibition of adaptor associated kinase 1 for the treatment of pain |
| EP2822559B1 (en) | 2012-03-09 | 2018-05-02 | Lexicon Pharmaceuticals, Inc. | Imidazo[1,2-b]pyridazine-based compounds, compositions comprising them, and uses thereof |
| TW201620911A (zh) * | 2014-03-17 | 2016-06-16 | 雷西肯製藥股份有限公司 | 銜接子關聯激酶１之抑制劑、包含其之組成物、及其使用方法 |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6194410B1 (en) * | 1998-03-11 | 2001-02-27 | Hoffman-La Roche Inc. | Pyrazolopyrimidine and pyrazolines and process for preparation thereof |
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