AR090100A1 - Procesos para la preparacion de la (s)-1-(3-etoxi-4-metoxifenil)-2-metanosulfoniletilamina - Google Patents
Procesos para la preparacion de la (s)-1-(3-etoxi-4-metoxifenil)-2-metanosulfoniletilaminaInfo
- Publication number
- AR090100A1 AR090100A1 ARP130100512A ARP130100512A AR090100A1 AR 090100 A1 AR090100 A1 AR 090100A1 AR P130100512 A ARP130100512 A AR P130100512A AR P130100512 A ARP130100512 A AR P130100512A AR 090100 A1 AR090100 A1 AR 090100A1
- Authority
- AR
- Argentina
- Prior art keywords
- processes
- preparation
- alkyl
- aminosulfone
- ketosulfone
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 4
- 238000002360 preparation method Methods 0.000 title abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 abstract 3
- 108060008682 Tumor Necrosis Factor Proteins 0.000 abstract 2
- 102100040247 Tumor necrosis factor Human genes 0.000 abstract 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 abstract 2
- 150000002081 enamines Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- BXUJVINGXQGNFD-SNVBAGLBSA-N (1s)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethanamine Chemical compound CCOC1=CC([C@H](N)CS(C)(=O)=O)=CC=C1OC BXUJVINGXQGNFD-SNVBAGLBSA-N 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- JFDZBHWFFUWGJE-KWCOIAHCSA-N benzonitrile Chemical group N#[11C]C1=CC=CC=C1 JFDZBHWFFUWGJE-KWCOIAHCSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 238000010511 deprotection reaction Methods 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- IMOZEMNVLZVGJZ-UHFFFAOYSA-N n-[2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]acetamide Chemical compound C1=C(OC)C(OCC)=CC(C(CS(C)(=O)=O)N2C(C3=C(NC(C)=O)C=CC=C3C2=O)=O)=C1 IMOZEMNVLZVGJZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/02—Sulfinic acids; Derivatives thereof
- C07C313/06—Sulfinamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
-
- 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
-
- 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
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Procesos para la elaboración de compuestos intermedios de aminosulfona para la síntesis de la 2-[1-(3-etoxi-4-metoxifenil)-2-metilsulfoniletil]-4-acetilaminoisoindolin-1,3-diona, que es útil para la prevención o tratamiento de enfermedades o afecciones relacionadas con un nivel anormalmente alto de actividad del factor de necrosis tumoral a (TNF-a). Además, procesos para la producción comercial de la (S)-1-(3-etoxi-4-metoxifenil)-2-metanosulfoniletilamina. Reivindicación 1: Un proceso para la preparación de un compuesto de fórmula (1) o una sal, hidrato, solvato o polimorfo farmacéuticamente aceptable de éste, en donde: R es -CH(alquil C₁₋₆)Ar o un hidrógeno; R¹ es alquil C₁₋₆; cada uno de R², R³, R⁴, R⁵ y R⁶ es en cada aparición independientemente hidrógeno, halo, alquil C₁₋₆, alcoxi C₁₋₆, -CF₃, -CN o -NO₂; y Ar es aril, caracterizado porque comprende: (a) el acoplamiento de un benzonitrilo opcionalmente sustituido con una dialquilsulfona; (b) la hidrólisis del producto acoplado para producir una b-cetosulfona; (c) la reacción de la b-cetosulfona con un auxiliar quiral para formar una enamina quiral; (d) la reducción de la enamina quiral para producir una aminosulfona N-protegida; y (e) la desprotección opcionalmente de la aminosulfona N-protegida.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261601226P | 2012-02-21 | 2012-02-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR090100A1 true AR090100A1 (es) | 2014-10-22 |
Family
ID=47755073
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP130100512A AR090100A1 (es) | 2012-02-21 | 2013-02-19 | Procesos para la preparacion de la (s)-1-(3-etoxi-4-metoxifenil)-2-metanosulfoniletilamina |
| ARP200100066A AR117963A2 (es) | 2012-02-21 | 2020-01-10 | Procesos para la preparación de la (s)-1-(3-etoxi-4-metoxifenil)-2-metanosulfoniletilamina |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP200100066A AR117963A2 (es) | 2012-02-21 | 2020-01-10 | Procesos para la preparación de la (s)-1-(3-etoxi-4-metoxifenil)-2-metanosulfoniletilamina |
Country Status (36)
| Country | Link |
|---|---|
| US (3) | US9187417B2 (es) |
| EP (4) | EP3312156B1 (es) |
| JP (1) | JP2015509496A (es) |
| KR (1) | KR101993248B1 (es) |
| CN (3) | CN107033042A (es) |
| AR (2) | AR090100A1 (es) |
| AU (1) | AU2013203283B2 (es) |
| BR (3) | BR112014020444B1 (es) |
| CA (1) | CA2864517A1 (es) |
| CO (1) | CO7061071A2 (es) |
| CR (1) | CR20140395A (es) |
| CY (2) | CY1121833T1 (es) |
| DK (2) | DK3312156T3 (es) |
| ES (4) | ES2773686T3 (es) |
| HR (2) | HRP20191249T1 (es) |
| HU (2) | HUE048412T2 (es) |
| IL (3) | IL234135A (es) |
| IN (1) | IN2014DN06740A (es) |
| LT (2) | LT3378850T (es) |
| MX (2) | MX344190B (es) |
| MY (1) | MY168296A (es) |
| NI (1) | NI201400093A (es) |
| NZ (1) | NZ628028A (es) |
| PH (1) | PH12014501865A1 (es) |
| PL (2) | PL3312156T3 (es) |
| PT (2) | PT3312156T (es) |
| RS (2) | RS60036B1 (es) |
| RU (1) | RU2632875C2 (es) |
| SG (1) | SG11201405035XA (es) |
| SI (2) | SI3312156T1 (es) |
| SM (2) | SMT201900397T1 (es) |
| TR (1) | TR201910430T4 (es) |
| TW (1) | TW201336815A (es) |
| UA (1) | UA116773C2 (es) |
| WO (1) | WO2013126360A2 (es) |
| ZA (1) | ZA201405892B (es) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR090100A1 (es) | 2012-02-21 | 2014-10-22 | Celgene Corp | Procesos para la preparacion de la (s)-1-(3-etoxi-4-metoxifenil)-2-metanosulfoniletilamina |
| US9126906B2 (en) * | 2012-02-21 | 2015-09-08 | Celgene Corporation | Asymmetric synthetic processes for the preparation of aminosulfone compounds |
| NZ628329A (en) | 2013-06-17 | 2017-12-22 | Celgene Corp | Formulations of (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione |
| IN2014MU01283A (es) | 2014-04-04 | 2015-10-09 | Cadila Healthcare Ltd | |
| US9994522B2 (en) | 2014-05-11 | 2018-06-12 | Mapi Pharma Ltd. | Amorphous form of apremilast |
| EP2949645A1 (en) | 2014-05-28 | 2015-12-02 | LEK Pharmaceuticals d.d. | Processes for the preparation of ß-aminosulfone compounds |
| CN105622380B (zh) * | 2014-10-29 | 2020-06-30 | 南京安源生物医药科技有限公司 | 一种阿普斯特的制备方法及其中间体 |
| CN104447445B (zh) * | 2014-12-05 | 2016-07-06 | 新发药业有限公司 | 一种合成阿普斯特中间体的制备方法 |
| CN104761474B (zh) * | 2015-03-11 | 2016-11-30 | 中山奕安泰医药科技有限公司 | 一种阿普斯特手性胺中间体的合成方法 |
| CN104744323B (zh) * | 2015-03-11 | 2016-08-31 | 中山奕安泰医药科技有限公司 | 一种阿普斯特手性胺中间体的合成工艺 |
| CN104803897A (zh) * | 2015-04-23 | 2015-07-29 | 中山奕安泰医药科技有限公司 | 一种阿普斯特中间体的合成工艺 |
| US10370329B2 (en) * | 2015-04-27 | 2019-08-06 | Mylan Laboratories Limited | Process for the enantiomeric resolution of apremilast intermediates |
| JP2018518489A (ja) * | 2015-06-09 | 2018-07-12 | ドクター レディズ ラボラトリーズ リミテッド | アプレミラスト及びその中間体の調製方法 |
| EP3106457A1 (en) | 2015-06-15 | 2016-12-21 | LEK Pharmaceuticals d.d. | A novel synthetic pathway towards apremilast |
| EP3144393A1 (en) * | 2015-09-18 | 2017-03-22 | LEK Pharmaceuticals d.d. | A synthetic pathway towards apremilast |
| WO2017059040A1 (en) | 2015-09-29 | 2017-04-06 | Pliva Hrvatska D.O.O. | Processes for the preparation of apremilast and intermediates thereof |
| WO2017085568A1 (en) * | 2015-11-19 | 2017-05-26 | Alembic Pharmaceuticals Limited | An improved process and novel polymorphic form of apremilast |
| CN105461602B (zh) * | 2015-11-27 | 2018-01-02 | 东华大学 | 手性S或R‑3‑乙氧基‑4‑甲氧基‑α‑[(甲磺酰基)甲基]苯甲醇的制备方法 |
| CN105330586B (zh) * | 2015-11-27 | 2017-12-22 | 东华大学 | 一种阿普斯特的制备方法 |
| WO2017094031A2 (en) * | 2015-12-04 | 2017-06-08 | Sun Pharmaceutical Industries Limited | Novel process for preparation of apremilast |
| CN106866475B (zh) * | 2015-12-11 | 2018-03-30 | 北大方正集团有限公司 | 一种阿普斯特中间体及其制备方法 |
| WO2017179065A1 (en) | 2016-04-15 | 2017-10-19 | Davuluri Ramamohan Rao | Improved process for the preparation of apremilast |
| US10196355B2 (en) | 2016-06-20 | 2019-02-05 | Johnson Matthey Public Limited Company | Forms of apremilast |
| CN106543050B (zh) * | 2016-09-28 | 2018-04-10 | 中南大学湘雅医院 | 一种阿普斯特中间体的合成工艺 |
| WO2018061034A1 (en) * | 2016-09-30 | 2018-04-05 | Sun Pharmaceutical Industries Limited | Novel process for the preparation of 1-(3-ethoxy-4-methoxy-phenyl)-2-methylsulfonyl-ethanamine |
| JP6684968B2 (ja) | 2016-11-10 | 2020-04-22 | エス・エム・エス・グループ・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 連続鋳造圧延設備内において、金属的なストリップを製造するための方法 |
| CN107445875A (zh) * | 2017-03-22 | 2017-12-08 | 陕西科技大学 | 一种用于制备阿普斯特的高纯度中间体的手性拆分方法 |
| SI3606908T1 (sl) | 2017-04-04 | 2020-10-30 | Quimica Sintetica, S.A. | Delitev racemičnih beta-aminosulfonskih spojin |
| WO2018184933A1 (en) | 2017-04-04 | 2018-10-11 | Quimica Sintetica, S. A. | Racemic beta-aminosulfone compounds |
| CN107827722B (zh) * | 2017-11-23 | 2021-02-19 | 中山奕安泰医药科技有限公司 | 一种3-乙氧基-4-甲氧基苯甲醛的合成方法 |
| CN108008035B (zh) * | 2017-11-23 | 2020-07-07 | 中山奕安泰医药科技有限公司 | 3-乙氧基-4-甲氧基苯甲醛纯度的检测方法 |
| CN107966509B (zh) * | 2017-11-23 | 2020-06-23 | 中山奕安泰医药科技有限公司 | 一种(s)-1-(3-乙氧基-4-甲氧基苯基)-2-(甲基磺酰基)乙胺的检测方法 |
| CN107976501B (zh) * | 2017-11-23 | 2020-08-25 | 中山奕安泰医药科技有限公司 | 一种1-(3-乙氧基-4-甲氧基苯基)-2-(甲基磺酰基)乙胺的检测方法 |
| CN107941945B (zh) * | 2017-11-23 | 2020-12-22 | 中山奕安泰医药科技有限公司 | 一种3-乙氧基-4-甲氧基苯甲腈的检测方法 |
| CN108084066A (zh) * | 2017-12-12 | 2018-05-29 | 中山大学 | 一种阿普斯特及对映异构体的合成方法 |
| JP6673614B1 (ja) * | 2018-10-16 | 2020-03-25 | 東芝エレベータ株式会社 | 防音装置 |
| CN113896674B (zh) * | 2021-09-01 | 2023-10-27 | 深圳华中科技大学研究院 | 一种阿普斯特的合成方法 |
| JP2024545712A (ja) | 2021-12-21 | 2024-12-10 | ガンチョウ ヘメイ ファーマシューティカル カンパニー リミテッド | チオフェン誘導体の調製 |
| CN115850129B (zh) * | 2023-02-28 | 2023-05-16 | 凯莱英生命科学技术(天津)有限公司 | （s）-1-(3-乙氧基-4-甲氧基苯基)-2-（甲磺酰基）乙胺的制备方法 |
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| US9045417B2 (en) | 2011-01-14 | 2015-06-02 | Celgene Corporation | Isotopologues of isoindole derivatives |
| AR090100A1 (es) * | 2012-02-21 | 2014-10-22 | Celgene Corp | Procesos para la preparacion de la (s)-1-(3-etoxi-4-metoxifenil)-2-metanosulfoniletilamina |
| US9126906B2 (en) * | 2012-02-21 | 2015-09-08 | Celgene Corporation | Asymmetric synthetic processes for the preparation of aminosulfone compounds |
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