CA2879400A1 - Deuterated ibrutinib - Google Patents
Deuterated ibrutinib Download PDFInfo
- Publication number
- CA2879400A1 CA2879400A1 CA2879400A CA2879400A CA2879400A1 CA 2879400 A1 CA2879400 A1 CA 2879400A1 CA 2879400 A CA2879400 A CA 2879400A CA 2879400 A CA2879400 A CA 2879400A CA 2879400 A1 CA2879400 A1 CA 2879400A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- deuterium
- hydrogen
- equiv
- mmol
- 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.)
- Abandoned
Links
- 150000004925 Ibrutinib derivatives Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 164
- 150000003839 salts Chemical class 0.000 claims abstract description 18
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 239000001257 hydrogen Substances 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 57
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 34
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07B59/002—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261677307P | 2012-07-30 | 2012-07-30 | |
| US61/677,307 | 2012-07-30 | ||
| PCT/US2013/052721 WO2014022390A1 (en) | 2012-07-30 | 2013-07-30 | Deuterated ibrutinib |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2879400A1 true CA2879400A1 (en) | 2014-02-06 |
Family
ID=48917743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2879400A Abandoned CA2879400A1 (en) | 2012-07-30 | 2013-07-30 | Deuterated ibrutinib |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US9422295B2 (en:Method) |
| EP (1) | EP2882751B1 (en:Method) |
| JP (1) | JP6261580B2 (en:Method) |
| KR (1) | KR20150038486A (en:Method) |
| CN (1) | CN104507946A (en:Method) |
| AU (1) | AU2013296627C9 (en:Method) |
| BR (1) | BR112015001839A2 (en:Method) |
| CA (1) | CA2879400A1 (en:Method) |
| EA (1) | EA201590296A1 (en:Method) |
| ES (1) | ES2682043T3 (en:Method) |
| IN (1) | IN2015DN00598A (en:Method) |
| MX (1) | MX2015001246A (en:Method) |
| WO (1) | WO2014022390A1 (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103965201A (zh) * | 2014-04-30 | 2014-08-06 | 淮海工学院 | 一种合成依鲁替尼中间体4-氨基-3-(4-苯氧基苯基)-1H-吡唑并[3,4-d]嘧啶的方法 |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104507946A (zh) * | 2012-07-30 | 2015-04-08 | 康塞特医药品有限公司 | 氘代依鲁替尼 |
| CN105017256A (zh) | 2014-04-29 | 2015-11-04 | 浙江导明医药科技有限公司 | 多氟化合物作为布鲁顿酪氨酸激酶抑制剂 |
| CN104945404B (zh) * | 2014-06-25 | 2018-09-14 | 广东东阳光药业有限公司 | 一种n-丙烯羰基哌啶衍生物的制备方法 |
| MA41350A (fr) * | 2015-01-14 | 2017-11-21 | Janssen Pharmaceutica Nv | Synthèse d'un inhibiteur de la tyrosine kinase de bruton |
| CN111018862B (zh) * | 2015-02-12 | 2021-12-24 | 正大天晴药业集团股份有限公司 | 伊布替尼的制备方法 |
| WO2016132383A1 (en) * | 2015-02-18 | 2016-08-25 | Mylan Laboratories Limited | Process for the preparation of ibrutinib |
| CN106146508A (zh) * | 2015-03-19 | 2016-11-23 | 浙江导明医药科技有限公司 | 优化的联合用药及其治疗癌症和自身免疫疾病的用途 |
| US9717745B2 (en) | 2015-03-19 | 2017-08-01 | Zhejiang DTRM Biopharma Co. Ltd. | Pharmaceutical compositions and their use for treatment of cancer and autoimmune diseases |
| WO2016151438A1 (en) * | 2015-03-20 | 2016-09-29 | Sun Pharmaceutical Industries Limited | A process for the preparation of ibrutinib |
| LT3452039T (lt) * | 2016-05-04 | 2024-10-25 | Sun Pharmaceutical Industries, Inc. | Plaukų slinkimo sutrikimo gydymas deuterintais jak inhibitoriais |
| WO2018187187A1 (en) * | 2017-04-04 | 2018-10-11 | Combiphos Catalysts, Inc. | Deuterated (s)-2-(4-(piperidin-3-yl)phenyl)-2h-indazole-7-carboxamide |
| TW201922256A (zh) | 2017-10-27 | 2019-06-16 | 中國大陸商浙江導明醫藥科技有限公司 | 治療淋巴樣惡性疾病之方法 |
| CN109988175A (zh) * | 2019-04-28 | 2019-07-09 | 梯尔希（南京）药物研发有限公司 | 一种依鲁替尼-d5的制备方法 |
| CN112876484B (zh) * | 2020-08-31 | 2022-06-28 | 绍兴舜邦医药科技有限公司 | 一种氘代依鲁替尼的制备方法 |
| CN114105990A (zh) * | 2020-08-31 | 2022-03-01 | 北京四环制药有限公司 | 一种伊布替尼的合成方法 |
| CN112125913B (zh) * | 2020-10-29 | 2024-07-19 | 瑞阳制药股份有限公司 | 高纯度伊布替尼的合成方法 |
| CN115611810B (zh) * | 2021-07-16 | 2025-03-04 | 深圳市塔吉瑞生物医药有限公司 | 取代的吡唑类化合物及包含该化合物的组合物及其用途 |
| CN118056832A (zh) * | 2022-11-21 | 2024-05-21 | 天津征程医药科技有限公司 | 具有btk抑制作用的吡唑并嘧啶衍生物 |
| CN118063429B (zh) * | 2022-11-23 | 2025-02-25 | 天津瑞程健达医药科技有限公司 | 作为btk抑制剂的吡啶酰胺类化合物 |
| CN118307541A (zh) * | 2023-01-09 | 2024-07-09 | 天津济坤医药科技有限公司 | 氘代吡唑并嘧啶衍生物及其制备方法和药物组合物、结合物及应用 |
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| ATE372966T1 (de) | 1994-03-25 | 2007-09-15 | Isotechnika Inc | Verbesserung der effektivität von arzneimitteln duren deuterierung |
| US6221335B1 (en) | 1994-03-25 | 2001-04-24 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| US6440710B1 (en) | 1998-12-10 | 2002-08-27 | The Scripps Research Institute | Antibody-catalyzed deuteration, tritiation, dedeuteration or detritiation of carbonyl compounds |
| PT1104760E (pt) | 1999-12-03 | 2003-06-30 | Pfizer Prod Inc | Compostos de sulfamoil-heteroarilpirazole como agentes analgesicos e anti-inflamatorios |
| DE10155018A1 (de) | 2001-11-07 | 2003-07-10 | Berolina Drug Dev Ab Svedala | Deuterierte Pyrazolopyrimidinone sowie diese Verbindungen enthaltende Arzneimittel |
| TW200413273A (en) | 2002-11-15 | 2004-08-01 | Wako Pure Chem Ind Ltd | Heavy hydrogenation method of heterocyclic rings |
| JP2006219373A (ja) | 2003-06-13 | 2006-08-24 | Daiichi Asubio Pharma Co Ltd | Ｐｄｅ７阻害作用を有するピリジニルピラゾロピリミジノン誘導体 |
| BRPI0617987A2 (pt) | 2005-10-06 | 2011-08-16 | Auspex Pharmaceuticals Inc | composição, composição farmacêutica, forma de dosagem efervescente, composição farmacêutica oral de comprimidos unitários múltiplos, forma de dosagem farmacêutica de liberação prolongada, forma de dosagem farmacêutica revestida entérica, forma de dosagem farmacêutica estável para administração oral a sujeitos mamìferos, método para tratamento de doenças relacionadas a ácido gástrico pela inibição de secreção de ácido gástrico, método para tratamento de uma infecção bacteriana provocada ou mediada por helicobacter pylori, processo para preparar um composto da fórmula 3, processo para preparar um composto da fórmula 5, uso de um composto da fórmula 1 para a preparação de um medicamento para tratamento de doenças relacionadas a ácido gástrico, pela inibição de secreção de ácido gástrico, uso de um composto da fórmula 1 para a preparação de um medicamento para tratamento de uma infecção bacteriana provocada ou mediada por helicobacter pylori uso de um composto da fórmula 1 para a preparação de um medicamento para tratamento de doenças relecionadas a ácido gástrico pela inibição de secreção de ácido gástrico |
| US7750168B2 (en) | 2006-02-10 | 2010-07-06 | Sigma-Aldrich Co. | Stabilized deuteroborane-tetrahydrofuran complex |
| JO2630B1 (en) | 2006-04-13 | 2012-06-17 | نوفارتيس ايه جي | Organic compounds |
| JP2010502702A (ja) | 2006-09-05 | 2010-01-28 | シェーリング コーポレイション | 脂質管理およびアテローム性動脈硬化症および脂肪肝の治療治療において使用される医薬組成物 |
| CA2847852A1 (en) * | 2006-09-22 | 2008-04-03 | Pharmacyclics, Inc. | Inhibitors of bruton's tyrosine kinase |
| WO2013118150A1 (en) | 2012-02-08 | 2013-08-15 | Council Of Scientific & Industrial Research | "electronically conducting carbon and carbon-based material by pyrolysis of dead leaves and other similar natural waste" |
| CN104507946A (zh) | 2012-07-30 | 2015-04-08 | 康塞特医药品有限公司 | 氘代依鲁替尼 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103965201A (zh) * | 2014-04-30 | 2014-08-06 | 淮海工学院 | 一种合成依鲁替尼中间体4-氨基-3-(4-苯氧基苯基)-1H-吡唑并[3,4-d]嘧啶的方法 |
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| WO2014022390A1 (en) | 2014-02-06 |
| IN2015DN00598A (en:Method) | 2015-06-26 |
| KR20150038486A (ko) | 2015-04-08 |
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| US9422295B2 (en) | 2016-08-23 |
| AU2013296627B2 (en) | 2016-07-14 |
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| JP2015528020A (ja) | 2015-09-24 |
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| EP2882751B1 (en) | 2018-06-27 |
| EA201590296A1 (ru) | 2015-07-30 |
| AU2013296627C1 (en) | 2016-12-15 |
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| US20170015670A1 (en) | 2017-01-19 |
| EP2882751A1 (en) | 2015-06-17 |
| JP6261580B2 (ja) | 2018-01-17 |
| MX2015001246A (es) | 2015-04-10 |
| US9777009B2 (en) | 2017-10-03 |
| AU2013296627C9 (en) | 2018-03-22 |
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