CA2541832C - Substituted 2h-[1,2,4]triazolo[4,3-a]pyrazines as gsk-3 inhibitors - Google Patents
Substituted 2h-[1,2,4]triazolo[4,3-a]pyrazines as gsk-3 inhibitors Download PDFInfo
- Publication number
- CA2541832C CA2541832C CA002541832A CA2541832A CA2541832C CA 2541832 C CA2541832 C CA 2541832C CA 002541832 A CA002541832 A CA 002541832A CA 2541832 A CA2541832 A CA 2541832A CA 2541832 C CA2541832 C CA 2541832C
- Authority
- CA
- Canada
- Prior art keywords
- optionally substituted
- triazolo
- tert
- butyl
- alkyl
- 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.)
- Expired - Fee Related
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- 239000003112 inhibitor Substances 0.000 title claims description 21
- SETPVHMQKAXDMY-UHFFFAOYSA-N 2,3-dihydro-[1,2,4]triazolo[4,3-a]pyrazine Chemical class C1=NC=CN2CNN=C21 SETPVHMQKAXDMY-UHFFFAOYSA-N 0.000 title 1
- 101150090422 gsk-3 gene Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 134
- 239000000651 prodrug Substances 0.000 claims abstract description 53
- 229940002612 prodrug Drugs 0.000 claims abstract description 53
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
- -1 methylenedioxy Chemical group 0.000 claims description 83
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 75
- 125000003118 aryl group Chemical group 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 72
- 229910052736 halogen Inorganic materials 0.000 claims description 71
- 150000002367 halogens Chemical class 0.000 claims description 67
- 125000001072 heteroaryl group Chemical group 0.000 claims description 51
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 43
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 230000002401 inhibitory effect Effects 0.000 claims description 11
- 239000001301 oxygen Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Chemical group 0.000 claims description 10
- 239000011593 sulfur Chemical group 0.000 claims description 10
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
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- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical group O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 claims description 6
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- 206010036049 Polycystic ovaries Diseases 0.000 claims description 3
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims description 3
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- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- BNKVGZXDUVAYFS-UHFFFAOYSA-N ethyl 4-[(6-tert-butyl-3-oxo-2h-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC1=NC(C(C)(C)C)=CN2C(=O)NN=C12 BNKVGZXDUVAYFS-UHFFFAOYSA-N 0.000 claims description 3
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- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical group C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 claims description 3
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 claims description 2
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 claims description 2
- BDHXUVFUQBVLKW-UHFFFAOYSA-N 6-tert-butyl-8-(2-ethylsulfanylethylamino)-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound CCSCCNC1=NC(C(C)(C)C)=CN2C(=O)NN=C12 BDHXUVFUQBVLKW-UHFFFAOYSA-N 0.000 claims description 2
- HYQVWXMXOTZEPD-UHFFFAOYSA-N 6-tert-butyl-8-[2-(4-methoxyphenoxy)ethylamino]-2h-[1,2,4]triazolo[4,3-a]pyrazin-3-one Chemical compound C1=CC(OC)=CC=C1OCCNC1=NC(C(C)(C)C)=CN2C(=O)NN=C12 HYQVWXMXOTZEPD-UHFFFAOYSA-N 0.000 claims description 2
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 claims description 2
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 claims description 2
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- 229960000647 gepirone Drugs 0.000 claims description 2
- QOIGKGMMAGJZNZ-UHFFFAOYSA-N gepirone Chemical compound O=C1CC(C)(C)CC(=O)N1CCCCN1CCN(C=2N=CC=CN=2)CC1 QOIGKGMMAGJZNZ-UHFFFAOYSA-N 0.000 claims description 2
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- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 claims description 2
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- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 claims description 2
- 230000004044 response Effects 0.000 claims description 2
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 claims description 2
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- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 claims description 2
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- WNUQCGWXPNGORO-NRFANRHFSA-N sonepiprazole Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1CCN(CC[C@H]2C3=CC=CC=C3CCO2)CC1 WNUQCGWXPNGORO-NRFANRHFSA-N 0.000 claims description 2
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- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
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- POLAUOGHQIDJOL-UHFFFAOYSA-N 3-[(6-tert-butyl-3-oxo-2h-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)amino]propanenitrile Chemical compound N#CCCNC1=NC(C(C)(C)C)=CN2C(=O)NN=C21 POLAUOGHQIDJOL-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A—HUMAN NECESSITIES
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- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Child & Adolescent Psychology (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51022403P | 2003-10-10 | 2003-10-10 | |
| US60/510,224 | 2003-10-10 | ||
| PCT/IB2004/003137 WO2005035532A1 (en) | 2003-10-10 | 2004-09-27 | Substituted 2h-[1,2,4]triazolo[4,3-a]pyrazines as gsk-3 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2541832A1 CA2541832A1 (en) | 2005-04-21 |
| CA2541832C true CA2541832C (en) | 2009-11-24 |
Family
ID=34435073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002541832A Expired - Fee Related CA2541832C (en) | 2003-10-10 | 2004-09-27 | Substituted 2h-[1,2,4]triazolo[4,3-a]pyrazines as gsk-3 inhibitors |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7709473B2 (enExample) |
| EP (1) | EP1678180B1 (enExample) |
| JP (1) | JP2007508290A (enExample) |
| AT (1) | ATE369370T1 (enExample) |
| BR (1) | BRPI0415185A (enExample) |
| CA (1) | CA2541832C (enExample) |
| DE (1) | DE602004008098T8 (enExample) |
| ES (1) | ES2288270T3 (enExample) |
| MX (1) | MXPA06004043A (enExample) |
| WO (1) | WO2005035532A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2005047285A1 (en) | 2003-11-04 | 2005-05-26 | Merck & Co., Inc. | Substituted naphthyridinone derivatives |
| EP2275096A3 (en) | 2005-08-26 | 2011-07-13 | Braincells, Inc. | Neurogenesis via modulation of the muscarinic receptors |
| EP2258357A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| WO2007047978A2 (en) | 2005-10-21 | 2007-04-26 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| EP2314289A1 (en) | 2005-10-31 | 2011-04-27 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| EP2021000A2 (en) | 2006-05-09 | 2009-02-11 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| DE102007012645A1 (de) * | 2007-03-16 | 2008-09-18 | Bayer Healthcare Ag | Substituierte Imidazo- und Triazolopyrimidine |
| DE102007032349A1 (de) * | 2007-07-11 | 2009-01-15 | Bayer Healthcare Ag | Imidazo-, Pyrazolopyrazine und Imidazotriazine und ihre Verwendung |
| WO2009017453A1 (en) * | 2007-07-30 | 2009-02-05 | Astrazeneca Ab | New therapeutic combination of an antipsychotic and a gsk3 inhibitor 958 |
| PE20091074A1 (es) * | 2007-12-13 | 2009-07-26 | Bayer Healthcare Ag | Triazolotriazinas y triazolopirazinas y su uso |
| DE102008023801A1 (de) | 2008-05-15 | 2009-11-19 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Imidazo- und Triazolopyrimidine, Imidazo- und Pyrazolopyrazine und Imidazotriazine |
| US20100216805A1 (en) | 2009-02-25 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| JP5559604B2 (ja) * | 2009-05-27 | 2014-07-23 | 富山化学工業株式会社 | ３，６−ジクロロ−２−ピラジンカルボニトリルの製造法 |
| CA2787714C (en) | 2010-01-22 | 2019-04-09 | Joaquin Pastor Fernandez | Inhibitors of pi3 kinase |
| US20130131057A1 (en) | 2010-05-13 | 2013-05-23 | Centro Nacional De Investigaciones Oncologicas (Cnio | New bicyclic compounds as pi3-k and mtor inhibitors |
| RU2599791C2 (ru) | 2010-08-10 | 2016-10-20 | Ремпекс Фармасьютикэлз, Инч. | Циклические бороновые кислотно-эфирные производные и их использование в терапии |
| WO2013033461A1 (en) | 2011-08-31 | 2013-03-07 | Rempex Pharmaceuticals, Inc. | Heterocyclic boronic acid ester derivatives and therapeutic uses thereof |
| US9156858B2 (en) | 2012-05-23 | 2015-10-13 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| US10561675B2 (en) | 2012-06-06 | 2020-02-18 | Rempex Pharmaceuticals, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| CN103121969A (zh) * | 2012-12-04 | 2013-05-29 | 中国科学院昆明植物研究所 | 苯并咪唑及其衍生物，其药物组合物及其应用 |
| CN103121970B (zh) * | 2012-12-04 | 2015-04-29 | 中国科学院昆明植物研究所 | 苯并咪唑及其衍生物，其药物组合物及其在制备抗抑郁药物中的应用 |
| US9101638B2 (en) | 2013-01-04 | 2015-08-11 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| AU2014204045B2 (en) | 2013-01-04 | 2018-10-18 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| US9241947B2 (en) | 2013-01-04 | 2016-01-26 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| KR20150103270A (ko) | 2013-01-04 | 2015-09-09 | 렘펙스 파머수티클스 인코퍼레이티드 | 보론산 유도체 및 그의 치료적 용도 |
| WO2015123424A1 (en) | 2014-02-13 | 2015-08-20 | Incyte Corporation | Cyclopropylamines as lsd1 inhibitors |
| US9527835B2 (en) | 2014-02-13 | 2016-12-27 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| EP3392244A1 (en) | 2014-02-13 | 2018-10-24 | Incyte Corporation | Cyclopropylamines as lsd1 inhibitors |
| LT3105218T (lt) | 2014-02-13 | 2019-12-10 | Incyte Corp | Ciklopropilaminai kaip lsd1 inhibitoriai |
| WO2015155738A2 (en) | 2014-04-09 | 2015-10-15 | Christopher Rudd | Use of gsk-3 inhibitors or activators which modulate pd-1 or t-bet expression to modulate t cell immunity |
| US10385074B2 (en) | 2014-05-05 | 2019-08-20 | Rempex Pharmaceuticals, Inc. | Synthesis of boronate salts and uses thereof |
| WO2015171398A1 (en) | 2014-05-05 | 2015-11-12 | Rempex Pharmaceuticals, Inc. | Salts and polymorphs of cyclic boronic acid ester derivatives and therapeutic uses thereof |
| AU2015264418A1 (en) | 2014-05-19 | 2016-11-10 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| CN106470992B (zh) * | 2014-06-17 | 2018-11-06 | 正大天晴药业集团股份有限公司 | 作为pi3k抑制剂的吡啶并[1,2-a]嘧啶酮类似物 |
| WO2015192761A1 (zh) * | 2014-06-17 | 2015-12-23 | 辰欣药业股份有限公司 | 作为mTOR/PI3K抑制剂的吡啶并[1,2-a]嘧啶酮类似物 |
| AU2015284307A1 (en) | 2014-07-01 | 2017-02-02 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| WO2016007722A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| WO2016007731A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Imidazopyridines and imidazopyrazines as lsd1 inhibitors |
| WO2016007736A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Imidazopyrazines as lsd1 inhibitors |
| US9758523B2 (en) | 2014-07-10 | 2017-09-12 | Incyte Corporation | Triazolopyridines and triazolopyrazines as LSD1 inhibitors |
| WO2016081297A1 (en) | 2014-11-18 | 2016-05-26 | Rempex Pharmaceuticals, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| WO2016149393A1 (en) | 2015-03-17 | 2016-09-22 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| EA201792205A1 (ru) | 2015-04-03 | 2018-02-28 | Инсайт Корпорейшн | Гетероциклические соединения как ингибиторы lsd1 |
| DK3334709T3 (da) | 2015-08-12 | 2025-02-03 | Incyte Holdings Corp | Salte af en lsd1-hæmmer |
| CA3021678A1 (en) | 2016-04-22 | 2017-10-26 | Incyte Corporation | Formulations of an lsd1 inhibitor |
| AU2017290060B2 (en) | 2016-06-30 | 2021-07-22 | Qpex Biopharma, Inc | Boronic acid derivatives and therapeutic uses thereof |
| CN107602446B (zh) * | 2016-07-12 | 2020-04-07 | 中国科学院上海药物研究所 | 1,4-双取代-1,2,3,6-四氢吡啶类化合物、其制备方法、药物组合物及其应用 |
| IL311645B2 (en) | 2016-07-12 | 2025-11-01 | Revolution Medicines Inc | 2,5- disubstituted 3-methyl pyrazines and 2,5,6-trisubstituted 3-methyl pyrazines asallosteric shp2 inhibitors |
| CA3051054A1 (en) | 2017-01-23 | 2018-07-26 | Revolution Medicines, Inc. | Pyridine compounds as allosteric shp2 inhibitors |
| CN110446709B (zh) | 2017-01-23 | 2023-09-12 | 锐新医药公司 | 作为变构shp2抑制剂的二环化合物 |
| BR112020007138B1 (pt) | 2017-10-11 | 2023-03-21 | Qpex Biopharma, Inc | Derivados de ácido borônico, métodos de síntese, composição farmacêutica e uso dos mesmos |
| BR112020007058A2 (pt) | 2017-10-12 | 2020-10-06 | Revolution Medicines, Inc. | compostos de piridina, pirazina, e triazina como inibidores de shp2 alostéricos |
| BR112020009757A2 (pt) | 2017-12-15 | 2020-11-03 | Revolution Medicines, Inc. | compostos policíclicos como inibidores alostéricos de shp2 |
| US11530220B2 (en) | 2018-02-06 | 2022-12-20 | Ideaya Biosciences, Inc. | Substituted imidazo[1,5-a]pyrazines and [1,2,4]triazolo[4,3-a]pyrazines for the modulation of AhR |
| CN112424209A (zh) | 2018-04-20 | 2021-02-26 | Qpex生物制药有限公司 | 硼酸衍生物及其治疗用途 |
| US10968200B2 (en) | 2018-08-31 | 2021-04-06 | Incyte Corporation | Salts of an LSD1 inhibitor and processes for preparing the same |
| US12636297B2 (en) | 2019-06-19 | 2026-05-26 | Qpex Biopharma, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| US12637481B2 (en) | 2020-03-18 | 2026-05-26 | Qpex Biopharma, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| IL297458A (en) | 2020-05-05 | 2022-12-01 | Qpex Biopharma Inc | Boronic acid derivatives and their synthesis, polymorphic forms and medicinal uses |
| AR131541A1 (es) | 2023-01-07 | 2025-04-09 | Syngenta Crop Protection Ag | Compuestos de carboxamida novedosos |
| WO2025032129A1 (en) | 2023-08-08 | 2025-02-13 | Syngenta Crop Protection Ag | Novel aminoindane and aminotetraline compounds |
| WO2025109114A1 (en) | 2023-11-24 | 2025-05-30 | Syngenta Crop Protection Ag | Novel carboxamide compounds |
| WO2025149637A1 (en) | 2024-01-12 | 2025-07-17 | Syngenta Crop Protection Ag | Novel carboxamide compounds |
| PY2501648A (es) | 2024-01-12 | 2025-10-31 | Syngenta Crop Protection Ag | Nuevos compuestos de carboxamida |
| WO2026008750A1 (en) | 2024-07-05 | 2026-01-08 | Syngenta Crop Protection Ag | Novel carboxamide compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1235910A (en) | 1968-12-10 | 1971-06-16 | Ici Ltd | Pharmaceutical compositions |
| FR2662163A1 (fr) | 1990-05-16 | 1991-11-22 | Lipha | Nouvelles 8-amino-1,2,4-triazolo(4,3-a) pyrazines, procedes de preparation et medicaments les contenant. |
| JP2002297477A (ja) * | 2001-03-28 | 2002-10-11 | Sony Computer Entertainment Inc | 配信システム及び配信方法 |
| EP2295550A3 (en) * | 2001-04-30 | 2011-12-14 | Vertex Pharmaceuticals Incorporated | Crystal structures of GSK-3beta protein and protein complexes and their use |
| EP1340759A1 (en) * | 2002-02-28 | 2003-09-03 | Sanofi-Synthelabo | 1-[alkyl], 1-[(heteroaryl)alkyl] and 1-[(aryl)alkyl]-7-(pyrimidin-4-yl)-imidazo[1,2-a]pyrimidin-5(1H)-one derivatives |
| EP1613629A1 (en) * | 2003-03-27 | 2006-01-11 | Pfizer Products Inc. | Substituted 4-amino 1,2,4 triazolo 4,3-a quinoxalines |
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2004
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- 2004-09-27 WO PCT/IB2004/003137 patent/WO2005035532A1/en not_active Ceased
- 2004-09-27 US US10/575,395 patent/US7709473B2/en not_active Expired - Fee Related
- 2004-09-27 AT AT04769486T patent/ATE369370T1/de not_active IP Right Cessation
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- 2004-09-27 EP EP04769486A patent/EP1678180B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2007508290A (ja) | 2007-04-05 |
| CA2541832A1 (en) | 2005-04-21 |
| US7709473B2 (en) | 2010-05-04 |
| EP1678180B1 (en) | 2007-08-08 |
| MXPA06004043A (es) | 2006-06-28 |
| ATE369370T1 (de) | 2007-08-15 |
| EP1678180A1 (en) | 2006-07-12 |
| US20070249612A1 (en) | 2007-10-25 |
| DE602004008098D1 (de) | 2007-09-20 |
| DE602004008098T2 (de) | 2007-12-13 |
| ES2288270T3 (es) | 2008-01-01 |
| WO2005035532A1 (en) | 2005-04-21 |
| DE602004008098T8 (de) | 2008-04-17 |
| BRPI0415185A (pt) | 2006-11-28 |
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