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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- C07D487/00—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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- A—HUMAN NECESSITIES
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- 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
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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)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Child & Adolescent Psychology (AREA)
- Immunology (AREA)
- Rheumatology (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 (https=) |
| EP (1) | EP1678180B1 (https=) |
| JP (1) | JP2007508290A (https=) |
| AT (1) | ATE369370T1 (https=) |
| BR (1) | BRPI0415185A (https=) |
| CA (1) | CA2541832C (https=) |
| DE (1) | DE602004008098T8 (https=) |
| ES (1) | ES2288270T3 (https=) |
| MX (1) | MXPA06004043A (https=) |
| WO (1) | WO2005035532A1 (https=) |
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| AU2004289638B2 (en) | 2003-11-04 | 2009-10-01 | Merck Sharp & Dohme Corp. | Substituted naphthyridinone derivatives |
| EP2258358A3 (en) | 2005-08-26 | 2011-09-07 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| EP1928437A2 (en) | 2005-08-26 | 2008-06-11 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| EP1940389A2 (en) | 2005-10-21 | 2008-07-09 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| US20070112017A1 (en) | 2005-10-31 | 2007-05-17 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| AU2007249399A1 (en) | 2006-05-09 | 2007-11-22 | 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 |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | 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 |
| EP2526102B1 (en) | 2010-01-22 | 2017-03-08 | Fundación Centro Nacional de Investigaciones Oncológicas Carlos III | 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 |
| CA2807546C (en) | 2010-08-10 | 2022-08-23 | Rempex Pharmaceuticals, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| 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 |
| 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 |
| 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 |
| US9241947B2 (en) | 2013-01-04 | 2016-01-26 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| KR20150103269A (ko) | 2013-01-04 | 2015-09-09 | 렘펙스 파머수티클스 인코퍼레이티드 | 보론산 유도체 및 그의 치료적 용도 |
| US9101638B2 (en) | 2013-01-04 | 2015-08-11 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| MX2015008627A (es) | 2013-01-04 | 2015-09-23 | Rempex Pharmaceuticals Inc | Derivados de acido boronico y usos terapeuticos de los mismos. |
| SI3105218T1 (sl) | 2014-02-13 | 2019-11-29 | Incyte Corp | Ciklopropilamini kot inhibitorji LSD1 |
| EP3105219B9 (en) | 2014-02-13 | 2018-10-03 | Incyte Corporation | Cyclopropylamines as lsd1 inhibitors |
| MX373103B (es) | 2014-02-13 | 2020-04-17 | Incyte Holdings Corp | Ciclopropilaminas como inhibidores de desmetilasa específica de lisina 1 (lsd1). |
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| US20170165230A1 (en) | 2014-04-09 | 2017-06-15 | Christopher Rudd | Use of gsk-3 inhibitors or activators which modulate pd-1 or t-bet expression to modulate t cell immunity |
| EP3139930B1 (en) | 2014-05-05 | 2024-08-14 | Melinta Therapeutics, Inc. | Salts and polymorphs of cyclic boronic acid ester derivatives and therapeutic uses thereof |
| ES2750805T3 (es) | 2014-05-05 | 2020-03-27 | Rempex Pharmaceuticals Inc | Síntesis de sales de boronato y usos de las mismas |
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| BR112016029825B1 (pt) * | 2014-06-17 | 2020-10-27 | Cisen Pharmaceutical Co., Ltd. | composto |
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| TWI687419B (zh) | 2014-07-10 | 2020-03-11 | 美商英塞特公司 | 作為ｌｓｄ１抑制劑之咪唑并吡啶及咪唑并吡嗪 |
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| US10662205B2 (en) | 2014-11-18 | 2020-05-26 | Qpex Biopharma, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| US20180051041A1 (en) | 2015-03-17 | 2018-02-22 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| EP3277689B1 (en) | 2015-04-03 | 2019-09-04 | Incyte Corporation | Heterocyclic compounds as lsd1 inhibitors |
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| JP6999574B2 (ja) | 2016-04-22 | 2022-01-18 | インサイト・コーポレイション | Ｌｓｄ１阻害剤の製剤 |
| MX389349B (es) | 2016-06-30 | 2025-03-20 | Qpex Biopharma Inc | Derivados de ácido borónico y usos terapéuticos de los mismos. |
| 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 |
| KR102598895B1 (ko) | 2016-07-12 | 2023-11-07 | 레볼루션 메디슨즈, 인크. | 다른자리 입체성 shp2 억제제로서의 2,5-이치환 3-메틸 피라진 및 2,5,6-3치환 3-메틸 피라진 |
| MX2019008695A (es) | 2017-01-23 | 2019-09-11 | Revolution Medicines Inc | Compuestos biciclicos como inhibidores alostericos de shp2. |
| MX2019008696A (es) | 2017-01-23 | 2019-09-13 | Revolution Medicines Inc | Compuestos de piridina como inhibidores de shp2 alostericos. |
| US11286270B2 (en) | 2017-10-11 | 2022-03-29 | Qpex Biopharma, Inc. | Boronic acid derivatives and synthesis thereof |
| MX2020003579A (es) | 2017-10-12 | 2020-07-22 | Revolution Medicines Inc | Compuestos de piridina, pirazina, y triazina como inhibidores de shp2 alostericos. |
| BR112020009757A2 (pt) | 2017-12-15 | 2020-11-03 | Revolution Medicines, Inc. | compostos policíclicos como inibidores alostéricos de shp2 |
| WO2019156989A1 (en) * | 2018-02-06 | 2019-08-15 | Ideaya Biosciences, Inc. | COMPOUNDS AND METHODS FOR THE MODULATION OF AhR |
| EP3781576B1 (en) | 2018-04-20 | 2024-06-12 | Qpex Biopharma, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| WO2020047198A1 (en) | 2018-08-31 | 2020-03-05 | Incyte Corporation | Salts of an lsd1 inhibitor and processes for preparing the same |
| AU2021266715A1 (en) | 2020-05-05 | 2022-11-17 | Qpex Biopharma, Inc. | Boronic acid derivatives and synthesis, polymorphic forms, and therapeutic uses thereof |
| 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 |
| PY2501648A (es) | 2024-01-12 | 2025-10-31 | Syngenta Crop Protection Ag | Nuevos compuestos de carboxamida |
| WO2025149637A1 (en) | 2024-01-12 | 2025-07-17 | Syngenta Crop Protection Ag | Novel carboxamide compounds |
| 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 |
| DE60232669D1 (de) * | 2001-04-30 | 2009-07-30 | Vertex Pharma | Inhibitoren von gsk-3 und kristallstrukturen von gsk-3beta-protein und -proteinkomplexen |
| 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 |
| BRPI0407926A (pt) | 2003-03-27 | 2006-02-21 | Pfizer Prod Inc | 4-amino[1,2,4]triazol[4,3-a]quinoxalinas substituìdas |
-
2004
- 2004-09-27 CA CA002541832A patent/CA2541832C/en not_active Expired - Fee Related
- 2004-09-27 JP JP2006530734A patent/JP2007508290A/ja active Pending
- 2004-09-27 MX MXPA06004043A patent/MXPA06004043A/es not_active Application Discontinuation
- 2004-09-27 ES ES04769486T patent/ES2288270T3/es not_active Expired - Lifetime
- 2004-09-27 AT AT04769486T patent/ATE369370T1/de not_active IP Right Cessation
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- 2004-09-27 BR BRPI0415185-2A patent/BRPI0415185A/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATE369370T1 (de) | 2007-08-15 |
| JP2007508290A (ja) | 2007-04-05 |
| MXPA06004043A (es) | 2006-06-28 |
| WO2005035532A1 (en) | 2005-04-21 |
| EP1678180A1 (en) | 2006-07-12 |
| DE602004008098D1 (de) | 2007-09-20 |
| DE602004008098T8 (de) | 2008-04-17 |
| ES2288270T3 (es) | 2008-01-01 |
| US7709473B2 (en) | 2010-05-04 |
| CA2541832A1 (en) | 2005-04-21 |
| US20070249612A1 (en) | 2007-10-25 |
| EP1678180B1 (en) | 2007-08-08 |
| BRPI0415185A (pt) | 2006-11-28 |
| DE602004008098T2 (de) | 2007-12-13 |
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