ES2676224T3 - Compuestos a base de pirazolo[1,5-a]pirimidina, composiciones que los comprenden y métodos para usarlos - Google Patents
Compuestos a base de pirazolo[1,5-a]pirimidina, composiciones que los comprenden y métodos para usarlos Download PDFInfo
- Publication number
- ES2676224T3 ES2676224T3 ES13710250.5T ES13710250T ES2676224T3 ES 2676224 T3 ES2676224 T3 ES 2676224T3 ES 13710250 T ES13710250 T ES 13710250T ES 2676224 T3 ES2676224 T3 ES 2676224T3
- Authority
- ES
- Spain
- Prior art keywords
- pyrazolo
- mmol
- piperazin
- pyrimidin
- carboxylate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 118
- 239000000203 mixture Substances 0.000 title description 56
- 238000000034 method Methods 0.000 title description 27
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 title description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 45
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 38
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 238000006467 substitution reaction Methods 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- -1 2-Methoxy-pyridin-3-yl Chemical group 0.000 claims description 219
- 125000005843 halogen group Chemical group 0.000 claims description 31
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 12
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 abstract 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 138
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 76
- 239000000047 product Substances 0.000 description 74
- 238000006243 chemical reaction Methods 0.000 description 71
- 235000019439 ethyl acetate Nutrition 0.000 description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 51
- 239000000243 solution Substances 0.000 description 42
- 230000015572 biosynthetic process Effects 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- OGGPATCZSITEFC-UHFFFAOYSA-N 2-methylpropanoic acid;piperazine Chemical compound CC(C)C(O)=O.C1CNCCN1 OGGPATCZSITEFC-UHFFFAOYSA-N 0.000 description 38
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 38
- 235000019341 magnesium sulphate Nutrition 0.000 description 38
- 238000003786 synthesis reaction Methods 0.000 description 38
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 34
- 238000003756 stirring Methods 0.000 description 34
- 238000005160 1H NMR spectroscopy Methods 0.000 description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 32
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 29
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 29
- 230000002829 reductive effect Effects 0.000 description 29
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 28
- 239000007787 solid Substances 0.000 description 27
- 239000000843 powder Substances 0.000 description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 25
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 23
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 22
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
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- 239000003921 oil Substances 0.000 description 21
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 20
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- 239000012044 organic layer Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 201000010099 disease Diseases 0.000 description 18
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 17
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 17
- MFINLMYILJJJND-UHFFFAOYSA-N 3-bromo-5-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound N=1C2=C(Br)C=NN2C=CC=1N1CCNCC1 MFINLMYILJJJND-UHFFFAOYSA-N 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 16
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 238000011282 treatment Methods 0.000 description 14
- 241000699670 Mus sp. Species 0.000 description 13
- 229910052794 bromium Inorganic materials 0.000 description 13
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 12
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
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- RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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- 201000000980 schizophrenia Diseases 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
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- 239000003112 inhibitor Substances 0.000 description 9
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- MIBPJQNRFGOOTH-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidin-5-amine Chemical compound N1=C(N)C=CN2N=CC=C21 MIBPJQNRFGOOTH-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
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- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 230000007935 neutral effect Effects 0.000 description 8
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Classifications
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- 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
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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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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
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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
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- 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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- 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
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- 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
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Psychiatry (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)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261608765P | 2012-03-09 | 2012-03-09 | |
| US201261608765P | 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2676224T3 true ES2676224T3 (es) | 2018-07-17 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13710250.5T Active ES2676224T3 (es) | 2012-03-09 | 2013-03-05 | Compuestos a base de pirazolo[1,5-a]pirimidina, composiciones que los comprenden y métodos para usarlos |
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| IL (1) | IL234486A (enExample) |
| IN (1) | IN2014DN07384A (enExample) |
| MX (2) | MX345830B (enExample) |
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Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2834243T3 (en) | 2012-03-09 | 2018-07-23 | Lexicon Pharmaceuticals Inc | Pyrazole [1,5-a] pyrimidine-based compounds, compositions comprising them and methods for their use |
| CN104470523B (zh) | 2012-03-09 | 2017-07-11 | 莱西肯医药有限公司 | 基于咪唑并[1,2‑b]哒嗪的化合物、包含它们的组合物及其使用方法 |
| US8901305B2 (en) | 2012-07-31 | 2014-12-02 | Bristol-Myers Squibb Company | Aryl lactam kinase inhibitors |
| EP2958924B1 (en) | 2013-02-22 | 2016-12-28 | Bristol-Myers Squibb Company | 5h-chromeno[3,4-c]pyridines as inhibitors of adaptor associated kinase 1 (aak1) |
| 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 |
| CN105979950A (zh) | 2013-10-11 | 2016-09-28 | 百时美施贵宝公司 | 吡咯并三嗪激酶抑制剂 |
| HRP20191283T1 (hr) | 2014-01-24 | 2019-10-18 | Turning Point Therapeutics, Inc. | Diaril makrocikli kao modulatori protein kinaze |
| MX2016009352A (es) * | 2014-01-31 | 2016-10-13 | Bristol Myers Squibb Co | Inhibidores de quinasa a base de quinolina. |
| 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 |
| WO2016053794A1 (en) * | 2014-09-30 | 2016-04-07 | Bristol-Myers Squibb Company | Quinazoline-based kinase inhibitors |
| AU2015365587B2 (en) * | 2014-12-15 | 2020-07-23 | Cmg Pharmaceutical Co., Ltd. | Fused ring heteroaryl compounds and their use as TRK inhibitors |
| ES2740224T3 (es) | 2015-04-10 | 2020-02-05 | Bristol Myers Squibb Co | 6H-isocromeno[3,4-c]piridinas y benzo[c][1,7]naftiridin-6-(5H)-onas como inhibidores de la cinasa asociada a adaptador 1 (AAK1) |
| EP3317285B1 (en) | 2015-07-02 | 2021-01-27 | Turning Point Therapeutics, Inc. | Chiral diaryl macrocycles as modulators of protein kinases |
| EP3319969B1 (en) | 2015-07-06 | 2024-04-03 | Turning Point Therapeutics, Inc. | Diaryl macrocycle polymorph |
| SMT202400496T1 (it) | 2015-07-21 | 2025-01-14 | Turning Point Therapeutics Inc | Macrociclo diarilico chirale e suo uso nel trattamento del cancro |
| WO2017076900A1 (en) | 2015-11-02 | 2017-05-11 | Janssen Pharmaceutica Nv | [1,2,4]TRIAZOLO[1,5-a]PYRIMIDIN-7-YL COMPOUND |
| TW201815799A (zh) | 2016-07-28 | 2018-05-01 | 美商Ｔｐ生物醫藥公司 | 巨環激酶抑制劑 |
| MY193511A (en) * | 2016-11-02 | 2022-10-17 | Janssen Pharmaceutica Nv | [1,2,4]triazolo[1,5-a]pyrimidine derivatives as pde2 inhibitors |
| CA3038916A1 (en) | 2016-11-02 | 2018-05-11 | Janssen Pharmaceutica Nv | [1,2,4]triazolo[1,5-a]pyrimidine compounds as pde2 inhibitors |
| CA3038913A1 (en) | 2016-11-02 | 2018-05-11 | Janssen Pharmaceutica Nv | [1,2,4]triazolo[1,5-a]pyrimidine compounds as pde2 inhibitors |
| 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 |
| SMT202400343T1 (it) | 2017-07-28 | 2024-11-15 | Turning Point Therapeutics Inc | Composti macrociclici e loro usi |
| EP4438117A3 (en) | 2017-07-28 | 2024-12-18 | Takeda Pharmaceutical Company Limited | Tyk2 inhibitors and uses thereof |
| ES2992993T3 (en) * | 2017-12-15 | 2024-12-20 | Biohaven Therapeutics Ltd | 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 |
| PT3728271T (pt) | 2017-12-19 | 2022-10-06 | Turning Point Therapeutics Inc | Compostos macrocíclicos para tratar doenças |
| CN111362949B (zh) | 2017-12-22 | 2021-12-21 | 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 |
| US20220041588A1 (en) * | 2018-09-27 | 2022-02-10 | Fochon Pharmaceuticals, Ltd. | Substituted imidazo[1,2-a]pyridine and [1,2,4]triazolo[1,5-a]pyridine compounds as ret kinase inhibitors |
| EP3866789A4 (en) * | 2018-10-15 | 2022-07-06 | Nimbus Lakshmi, Inc. | TYK2 INHIBITORS AND USES THEREOF |
| CA3175970A1 (en) | 2020-04-21 | 2021-10-28 | Suma GOPINATHAN | Aak1 inhibitors for use in treating viral infections |
| 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 |
| US11478733B2 (en) | 2020-11-24 | 2022-10-25 | Caterpillar Inc. | Filter interlock with tabs mating with a pedestal or a housing |
| US20250122207A1 (en) * | 2023-09-08 | 2025-04-17 | Satellos Bioscience Inc. | Ap2 associated kinase 1 inhibitors and uses thereof |
Family Cites Families (16)
| 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 |
| US6194410B1 (en) | 1998-03-11 | 2001-02-27 | Hoffman-La Roche Inc. | Pyrazolopyrimidine and pyrazolines and process for preparation thereof |
| 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 |
| DE602007013441D1 (de) | 2006-09-29 | 2011-05-05 | Novartis Ag | Pyrazolopyrimidine als pi3k-lipidkinasehemmer |
| 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 |
| EA019507B1 (ru) * | 2008-05-13 | 2014-04-30 | Айрм Ллк | Конденсированные азотсодержащие гетероциклы и содержащие их композиции в качестве ингибиторов киназы |
| TWI577680B (zh) * | 2008-10-22 | 2017-04-11 | 亞雷生物製藥股份有限公司 | 作為ＴＲＫ激酶抑制劑之經取代吡唑并〔１，５－ａ〕嘧啶化合物 |
| 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 |
| US8946237B2 (en) * | 2010-01-14 | 2015-02-03 | Merck Sharp & Dohme Corp. | Pyrazolo[1,5-A]pyrimidines as mark inhibitors |
| WO2013013188A1 (en) * | 2011-07-21 | 2013-01-24 | Tolero Pharmaceuticals, Inc. | Heterocyclic protein kinase inhibitors |
| DK2834243T3 (en) | 2012-03-09 | 2018-07-23 | Lexicon Pharmaceuticals Inc | Pyrazole [1,5-a] pyrimidine-based compounds, compositions comprising them and methods for their use |
| EP3235499A3 (en) | 2012-03-09 | 2018-01-17 | Lexicon Pharmaceuticals, Inc. | Inhibition of adaptor associated kinase 1 for the treatment of pain |
| CN104470523B (zh) | 2012-03-09 | 2017-07-11 | 莱西肯医药有限公司 | 基于咪唑并[1,2‑b]哒嗪的化合物、包含它们的组合物及其使用方法 |
| 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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2013
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