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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Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
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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 |
| CA2924436A CA2924436A1 (en) | 2007-07-30 | 2008-07-28 | Pharmaceutical combinations of n-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-6-methoxyphenyl)-1-(2,3-dihydroxypropyl)cyclopropane-1-sulfonamide as inhibitors of mek and methods of use |
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
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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 | |
| US3446608P | 2008-03-06 | 2008-03-06 | |
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| US4488608P | 2008-04-14 | 2008-04-14 | |
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| PCT/US2008/071392 WO2009018233A1 (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 |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
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| CA2924436A Division CA2924436A1 (en) | 2007-07-30 | 2008-07-28 | Pharmaceutical combinations of n-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-6-methoxyphenyl)-1-(2,3-dihydroxypropyl)cyclopropane-1-sulfonamide as inhibitors of mek and methods of use |
| 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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| US7723477B2 (en) | 2005-10-31 | 2010-05-25 | Oncomed Pharmaceuticals, Inc. | Compositions and methods for inhibiting Wnt-dependent solid tumor cell growth |
| EP2291350A4 (en) * | 2008-04-14 | 2012-09-19 | Ardea Biosciences Inc | COMPOSITIONS AND METHODS FOR THEIR MANUFACTURE AND USE |
| BR122021020474B1 (pt) * | 2008-09-09 | 2022-06-07 | F. Hoffmann-La Roche Ag | Polimorfos de acil sulfonamidas, seu uso, seu processo de preparação e composição farmacêutica que os compreende |
| BRPI0919473A2 (pt) | 2008-09-26 | 2017-08-29 | Oncomed Pharm Inc | Agentes de ligação frizzled e usos dos mesmos |
| PE20120105A1 (es) | 2009-03-11 | 2012-02-22 | Ardea Biosciences Inc | Combinaciones farmaceuticas que comprenden refametinib |
| UY32486A (es) * | 2009-03-11 | 2010-10-29 | Ardea Biosciences Inc | Tratamiento del cáncer de páncreas |
| 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 |
| WO2011047788A1 (en) * | 2009-10-21 | 2011-04-28 | Bayer Schering 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 |
| NZ618062A (en) * | 2011-04-28 | 2016-04-29 | Sloan Kettering Inst Cancer | Hsp90 combination therapy |
| WO2012163799A1 (en) * | 2011-05-27 | 2012-12-06 | Bayer Intellectual Property Gmbh | Chiral synthesis of n-{3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]-6-methoxyphenyl}-1-[2,3-dihydroxy-propyl]cyclopropanesulfonamides |
| WO2013086260A2 (en) * | 2011-12-09 | 2013-06-13 | 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 |
| US20150267258A1 (en) * | 2012-05-31 | 2015-09-24 | Bayer Pharma Aktiengesellschaft | Biomarkers for determining effective response of treatments of hepatocellular carcinoma (hcc) patients |
| TWI662963B (zh) | 2012-06-04 | 2019-06-21 | 美商製藥有限責任公司 | 布魯頓氏酪胺酸激酶抑制劑之結晶形式 |
| SI2909182T1 (sl) * | 2012-10-19 | 2020-03-31 | Array Biopharma Inc. | Priprava inhibitorja MEK in formulacije, ki obsegajo inhibitor MEK |
| CA2890238A1 (en) | 2012-11-02 | 2014-05-08 | Merck Patent Gmbh | Method of reducing adverse effects in a cancer patient undergoing treatment with a mek inhibitor |
| CN105073195A (zh) | 2013-02-04 | 2015-11-18 | 昂科梅德制药有限公司 | 使用Wnt途径抑制剂进行治疗的方法及对该治疗的监测 |
| 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 |
| US9629851B2 (en) | 2013-09-20 | 2017-04-25 | Stitching Het Nederlands Kanker Institut—Antoni Van Leeuwenhoek Ziekenhuis | 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 |
| KR102541110B1 (ko) | 2014-08-25 | 2023-06-08 | 에이뮨 테라퓨틱스, 인코퍼레이티드 | 난 단백질 제형 및 이의 제조 방법 |
| IL315294A (en) | 2015-03-03 | 2024-10-01 | Pharmacyclics Llc | Pharmaceutical formulations of bruton's tyrosine kinase inhibitor |
| WO2018232235A1 (en) | 2017-06-16 | 2018-12-20 | 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 |
| AU2020242287A1 (en) | 2019-03-21 | 2021-09-02 | INSERM (Institut National de la Santé et de la Recherche Médicale) | 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 |
| KR20220098759A (ko) | 2019-11-08 | 2022-07-12 | 인쎄름 (엥스띠뛰 나씨오날 드 라 쌍떼 에 드 라 흐쉐르슈 메디깔) | 키나제 억제제에 대해 내성을 획득한 암의 치료 방법 |
| 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 |
| EP0656887B1 (en) * | 1992-08-25 | 1998-10-28 | G.D. Searle & Co. | Hydroxyethylamino sulfonamides useful as retroviral protease inhibitors |
| US7115632B1 (en) * | 1999-05-12 | 2006-10-03 | G. D. Searle & Co. | Sulfonyl aryl or heteroaryl hydroxamic acid compounds |
| IL144215A0 (en) * | 1999-01-13 | 2002-05-23 | Warner Lambert Co | 1-heterocycle substituted diarylamines |
| GB0003224D0 (en) * | 2000-02-11 | 2000-04-05 | Glaxo Group Ltd | Chemical compounds |
| US7235567B2 (en) * | 2000-06-15 | 2007-06-26 | Schering Corporation | Crystalline polymorph of a bisulfate salt of a thrombin receptor antagonist |
| JP2005508322A (ja) * | 2001-09-24 | 2005-03-31 | ジェシー エル エス オウ | 併用療法に用いられるスラミンの化学増感用量を決定するための方法及び成分 |
| MXPA05000555A (es) * | 2002-07-17 | 2005-04-28 | Titan Pharmaceuticals Inc | Combinacion de farmacos quimioterapeuticos para incrementar la actividad antitumoral. |
| WO2004012744A1 (de) * | 2002-07-30 | 2004-02-12 | Zentaris Gmbh | Anwendung von alkylphosphocholinen in kombination mit antitumormedikamenten |
| WO2006110811A1 (en) * | 2005-04-12 | 2006-10-19 | Elan Pharma International Limited | Nanoparticulate quinazoline derivative formulations |
| PE20061317A1 (es) * | 2005-04-22 | 2006-12-29 | Kissei Pharmaceutical | Cristal polimorfico de hidrocloruro del acido 4'-{2-[(1s,2r)-2-hidroxi-2-(4-hidroxifenil)-1-metiletilamino]etoxi}-3-isopropil-3'-5'-dimetilbifenilcarboxilico |
| EP1912636B1 (en) * | 2005-07-21 | 2014-06-25 | 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 |
| TW200800150A (en) * | 2005-12-21 | 2008-01-01 | Organon Nv | Compounds with medicinal effects due to interaction with the glucocorticoid receptor |
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