CA2693390C - Derivatives of n-(arylamino) sulfonamides including polymorphs as inhibitors of mek as well as compositions, methods of use and methods for preparing the same - Google Patents
Derivatives of n-(arylamino) sulfonamides including polymorphs as inhibitors of mek as well as compositions, methods of use and methods for preparing the same Download PDFInfo
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- CA2693390C CA2693390C CA2693390A CA2693390A CA2693390C CA 2693390 C CA2693390 C CA 2693390C CA 2693390 A CA2693390 A CA 2693390A CA 2693390 A CA2693390 A CA 2693390A CA 2693390 C CA2693390 C CA 2693390C
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- Prior art keywords
- phenyl
- additional embodiments
- compound
- formula
- alkyl
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- 229940124530 sulfonamide Drugs 0.000 title claims description 27
- 239000000203 mixture Substances 0.000 title abstract description 266
- 238000000034 method Methods 0.000 title abstract description 129
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- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 65
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 57
- 238000000113 differential scanning calorimetry Methods 0.000 claims abstract description 40
- 239000002904 solvent Substances 0.000 claims description 26
- WMSPXQIQBQAWLL-UHFFFAOYSA-N cyclopropanesulfonamide Chemical compound NS(=O)(=O)C1CC1 WMSPXQIQBQAWLL-UHFFFAOYSA-N 0.000 claims description 17
- 238000002844 melting Methods 0.000 claims description 15
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Classifications
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- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
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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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- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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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| CA2924418A CA2924418A1 (en) | 2007-07-30 | 2008-07-28 | Derivatives of n-(arylamino) sulfonamides including polymorphs as inhibitors of mek as well as compositions, methods of use and methods for preparing the same |
Applications Claiming Priority (9)
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| US11/830,733 | 2007-07-30 | ||
| US11/830,733 US8101799B2 (en) | 2005-07-21 | 2007-07-30 | Derivatives of N-(arylamino) sulfonamides as inhibitors of MEK |
| US3446408P | 2008-03-06 | 2008-03-06 | |
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Related Child Applications (2)
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| CA2924418A Division CA2924418A1 (en) | 2007-07-30 | 2008-07-28 | Derivatives of n-(arylamino) sulfonamides including polymorphs as inhibitors of mek as well as compositions, methods of use and methods for preparing the same |
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| KR101822319B1 (ko) * | 2008-09-09 | 2018-01-25 | 에프. 호프만-라 로슈 아게 | 아실 설폰아미드의 다형체 |
| TWI506037B (zh) | 2008-09-26 | 2015-11-01 | Oncomed Pharm Inc | 捲曲結合劑類及彼等之用途 |
| UY32486A (es) * | 2009-03-11 | 2010-10-29 | Ardea Biosciences Inc | Tratamiento del cáncer de páncreas |
| SG174272A1 (en) * | 2009-03-11 | 2011-10-28 | Ardea Biosciences Inc | Pharmaceutical combinations comprising rdea119/bay 869766 for the treatment of specific cancers |
| CN102666512B (zh) | 2009-10-13 | 2014-11-26 | 奥斯特姆医疗公司 | 对疾病治疗有用的mek抑制剂 |
| EP2491015A1 (en) * | 2009-10-21 | 2012-08-29 | Bayer Pharma Aktiengesellschaft | Substituted benzosulphonamides |
| TWI535445B (zh) | 2010-01-12 | 2016-06-01 | 安可美德藥物股份有限公司 | Ｗｎｔ拮抗劑及治療和篩選方法 |
| CN102020651B (zh) | 2010-11-02 | 2012-07-18 | 北京赛林泰医药技术有限公司 | 6-芳基氨基吡啶酮甲酰胺mek抑制剂 |
| CN102649773A (zh) * | 2011-02-23 | 2012-08-29 | 苏州波锐生物医药科技有限公司 | 氨基芳香烃类化合物及其在制备抗恶性肿瘤药物中的用途 |
| BR112013027448A2 (pt) * | 2011-04-28 | 2020-09-01 | Sloan-Kettering Institute For Cancer Research | terapia de combinação com hsp90 |
| UA113850C2 (xx) * | 2011-05-27 | 2017-03-27 | Хіральний синтез n-{3,4-дифтор-2-$(2-фтор-4-йодфеніл)аміно]-6-метоксифеніл}-1-$2,3-дигідроксипропіл]циклопропансульфонамідів | |
| US20150132301A1 (en) * | 2011-12-09 | 2015-05-14 | Oncomed Pharmaceuticals, Inc. | Combination Therapy for Treatment of Cancer |
| WO2013109142A1 (en) | 2012-01-16 | 2013-07-25 | Stichting Het Nederlands Kanker Instituut | Combined pdk and mapk/erk pathway inhibition in neoplasia |
| KR20150013332A (ko) * | 2012-05-31 | 2015-02-04 | 바이엘 파마 악티엔게젤샤프트 | 간세포 암종(hcc) 환자 치료제의 효과적 반응을 결정하기 위한 바이오마커 |
| WO2013184572A1 (en) | 2012-06-04 | 2013-12-12 | Pharmacyclics, Inc. | Crystalline forms of a bruton's tyrosine kinase inhibitor |
| PL3702351T3 (pl) * | 2012-10-19 | 2024-04-02 | Array Biopharma, Inc. | Formulacja zawierająca inhibitor mek |
| EP2916859B1 (en) | 2012-11-02 | 2017-06-28 | The U.S.A. as represented by the Secretary, Department of Health and Human Services | Method of reducing adverse effects in a cancer patient undergoing treatment with a mek inhibitor |
| JP2016510411A (ja) | 2013-02-04 | 2016-04-07 | オンコメッド ファーマシューティカルズ インコーポレイテッド | Ｗｎｔ経路インヒビターによる処置の方法およびモニタリング |
| EP2848246A1 (en) | 2013-09-13 | 2015-03-18 | Bayer Pharma Aktiengesellschaft | Pharmaceutical compositions containing refametinib |
| WO2015041534A1 (en) | 2013-09-20 | 2015-03-26 | Stichting Het Nederlands Kanker Instituut | P90rsk in combination with raf/erk/mek |
| EP3046557A1 (en) | 2013-09-20 | 2016-07-27 | Stichting Het Nederlands Kanker Instituut | Rock in combination with mapk-pathway |
| US20170027940A1 (en) | 2014-04-10 | 2017-02-02 | Stichting Het Nederlands Kanker Instituut | Method for treating cancer |
| WO2015178770A1 (en) | 2014-05-19 | 2015-11-26 | Stichting Het Nederlands Kanker Instituut | Compositions for cancer treatment |
| WO2015196072A2 (en) | 2014-06-19 | 2015-12-23 | Whitehead Institute For Biomedical Research | Uses of kinase inhibitors for inducing and maintaining pluripotency |
| CN106535931A (zh) * | 2014-08-25 | 2017-03-22 | 艾慕恩治疗公司 | 卵蛋白制剂及其制备方法 |
| IL315294A (en) | 2015-03-03 | 2024-10-01 | Pharmacyclics Llc | Pharmaceutical formulations of bruton's tyrosine kinase inhibitor |
| AU2018283289B2 (en) | 2017-06-16 | 2021-03-25 | Beta Pharma, Inc. | Pharmaceutical formulations of N-(2-(2-(dimethylamino)ethoxy)-4-methoxy-5-((4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl)amino)phenyl)acrylamide and salts thereof |
| EP3942045A1 (en) | 2019-03-21 | 2022-01-26 | Onxeo | A dbait molecule in combination with kinase inhibitor for the treatment of cancer |
| WO2021067772A1 (en) * | 2019-10-04 | 2021-04-08 | Sumitomo Dainippon Pharma Oncology, Inc. | Axl inhibitor formulations |
| EP4054579A1 (en) | 2019-11-08 | 2022-09-14 | Institut National de la Santé et de la Recherche Médicale (INSERM) | Methods for the treatment of cancers that have acquired resistance to kinase inhibitors |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| US12371667B2 (en) | 2021-05-13 | 2025-07-29 | Washington University | Enhanced methods for inducing and maintaining naive human pluripotent stem cells |
| WO2025073765A1 (en) | 2023-10-03 | 2025-04-10 | Institut National de la Santé et de la Recherche Médicale | Methods of prognosis and treatment of patients suffering from melanoma |
| CN118834328B (zh) * | 2024-07-02 | 2025-09-16 | 江苏海洋大学 | 金属蛋白酶9抗原决定基印迹纳米颗粒的制备方法及应用 |
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| US5162117A (en) * | 1991-11-22 | 1992-11-10 | Schering Corporation | Controlled release flutamide composition |
| JP2575590B2 (ja) * | 1992-07-31 | 1997-01-29 | 塩野義製薬株式会社 | トリアゾリルチオメチルチオセファロスポリン塩酸塩およびその水和物結晶ならびにそれらの製法 |
| JP3657002B2 (ja) * | 1992-08-25 | 2005-06-08 | ジー．ディー．サール アンド カンパニー | レトロウイルスプロテアーゼ阻害剤として有用なα−およびβ−アミノ酸ヒドロキシエチルアミノスルホンアミド |
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| GEP20032999B (en) * | 1999-01-13 | 2003-06-25 | Warner Lambert Co | 1-Heterocycle Substituted Diarylamines |
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| US7235567B2 (en) * | 2000-06-15 | 2007-06-26 | Schering Corporation | Crystalline polymorph of a bisulfate salt of a thrombin receptor antagonist |
| CA2461227C (en) * | 2001-09-24 | 2012-05-15 | Jessie L.-S Au | Methods and compositions to determine the chemosensitizing dose of suramin used in combination therapy |
| US20060089410A1 (en) * | 2002-07-17 | 2006-04-27 | Titan Pharmaceuticals, Inc. | Combination of chemotherapeutic drugs for increasing antitumor activity |
| JP2005535688A (ja) * | 2002-07-30 | 2005-11-24 | ツェンタリス ゲゼルシャフト ミット ベシュレンクテル ハフツング | 抗腫瘍医薬との組合せにおけるアルキルホスホコリンの使用 |
| BRPI0607537A2 (pt) * | 2005-04-12 | 2009-09-15 | Elan Pharma Int Ltd | formulações de derivado de quinazolina nanoparticulado |
| CA2605381A1 (en) * | 2005-04-22 | 2006-11-02 | Kissei Pharmaceutical Co., Ltd. | Crystal polymorphism of 4'-{2-[(1s,2r)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethylamino]ethoxy}-3-isopropyl-3',5'-dimethylbiphenylcarboxylic acid hydrochloride |
| WO2007014011A2 (en) * | 2005-07-21 | 2007-02-01 | Ardea Biosciences, Inc. | N-(arylamino)-sulfonamide inhibitors of mek |
| JP2007099763A (ja) * | 2005-09-08 | 2007-04-19 | Toyama Chem Co Ltd | ピペラシリンナトリウム・１水和物の新規な結晶及びその製造方法 |
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