AR044694A1 - Proceso y compuestos intermedios para la preparacion de (1r, 2s,5s) - 3 azabiciclo [3,1,0] hexano-2- carboxamida, n- [3- amino-1- (ciclobutilmetil) - 2, 3 - dioxopropil] -3- [ (2s) - 2 - [[ [ 1,1- dimetiletil] amino] carbonilamino] -3,3-dimetil -1- oxobutil]-6,6 dimetilo - Google Patents
Proceso y compuestos intermedios para la preparacion de (1r, 2s,5s) - 3 azabiciclo [3,1,0] hexano-2- carboxamida, n- [3- amino-1- (ciclobutilmetil) - 2, 3 - dioxopropil] -3- [ (2s) - 2 - [[ [ 1,1- dimetiletil] amino] carbonilamino] -3,3-dimetil -1- oxobutil]-6,6 dimetiloInfo
- Publication number
- AR044694A1 AR044694A1 ARP040102058A ARP040102058A AR044694A1 AR 044694 A1 AR044694 A1 AR 044694A1 AR P040102058 A ARP040102058 A AR P040102058A AR P040102058 A ARP040102058 A AR P040102058A AR 044694 A1 AR044694 A1 AR 044694A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- dimethyl
- amino
- preparation
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- 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
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Virology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Reivindicación 1: Un proceso para la preparación de un compuesto de la fórmula (1) que comprende: a) acoplar un compuesto de la fórmula (2) con un compuesto de la fórmula (3), o sales de los mismos, para obtener un compuesto de la fórmula (4), en donde Z+ representa el catión de una amina o metal, y R es seleccionado del grupo que consiste en alquilo, arilo y aralquilo; b) oxidar el grupo hidroxilo de un compuesto de la fórmula (5) para obtener un compuesto de la fórmula (6), en donde P representa un grupo N-protector; c) desproteger el compuesto de la fórmula (6) para obtener un compuesto de la fórmula (7); d) generar un compuesto de ácido libre de la fórmula (8) a partir del compuesto de la fórmula (4); e) acoplar el compuesto de la fórmula (7) con un compuesto de la fórmula (8) para obtener el compuesto de la fórmula (1).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47951703P | 2003-06-17 | 2003-06-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR044694A1 true AR044694A1 (es) | 2005-09-21 |
Family
ID=33539185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP040102058A AR044694A1 (es) | 2003-06-17 | 2004-06-14 | Proceso y compuestos intermedios para la preparacion de (1r, 2s,5s) - 3 azabiciclo [3,1,0] hexano-2- carboxamida, n- [3- amino-1- (ciclobutilmetil) - 2, 3 - dioxopropil] -3- [ (2s) - 2 - [[ [ 1,1- dimetiletil] amino] carbonilamino] -3,3-dimetil -1- oxobutil]-6,6 dimetilo |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7326795B2 (es) |
| EP (1) | EP1641754B1 (es) |
| JP (1) | JP5219368B2 (es) |
| CN (2) | CN1805932B (es) |
| AR (1) | AR044694A1 (es) |
| AT (1) | ATE390412T1 (es) |
| CA (1) | CA2526629C (es) |
| DE (1) | DE602004012746T2 (es) |
| ES (1) | ES2299850T3 (es) |
| MX (1) | MXPA05013753A (es) |
| WO (1) | WO2004113294A1 (es) |
| ZA (1) | ZA200509100B (es) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050249702A1 (en) * | 2004-05-06 | 2005-11-10 | Schering Corporation | (1R,2S,5S)-N-[(1S)-3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3-[(2S)-2-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide as inhibitor of hepatitis C virus NS3/NS4a serine protease |
| US20060276404A1 (en) * | 2005-06-02 | 2006-12-07 | Anima Ghosal | Medicaments and methods combining a HCV protease inhibitor and an AKR competitor |
| US20070237818A1 (en) * | 2005-06-02 | 2007-10-11 | Malcolm Bruce A | Controlled-release formulation of HCV protease inhibitor and methods using the same |
| NZ563365A (en) * | 2005-06-02 | 2011-02-25 | Schering Corp | Combination of HCV protease inhibitors with a surfactant |
| NZ563361A (en) * | 2005-06-02 | 2011-02-25 | Schering Corp | HCV protease inhibitors in combination with food |
| KR20080059270A (ko) * | 2005-09-30 | 2008-06-26 | 싸이넥시스, 인크. | C형 간염 감염의 치료 및 예방을 위한 방법 및 제약조성물 |
| AR056805A1 (es) * | 2005-11-14 | 2007-10-24 | Schering Corp | Un proceso para oxidacion para la preparcion de n- (3- amino-1- ( ciclobutilmetil) -2,3- dioxopropil ) -3-(n-(( ter-butilamino) carbonil )-3- metil- l- valil) -6,6- dimetil-3- azabiciclo (3.1.0) hexano -2- carboxamida y compuestos ralacionados |
| JP5247466B2 (ja) * | 2005-12-22 | 2013-07-24 | メルク・シャープ・アンド・ドーム・コーポレーション | 6,6−ジメチル−3−アザビシクロ−[3.1.0]−ヘキサン化合物およびその鏡像異性体塩を調製するプロセス |
| JP5092289B2 (ja) * | 2006-06-13 | 2012-12-05 | 三菱瓦斯化学株式会社 | 光学活性N−tert−ブチルカルバモイル−L−tert−ロイシンの製造方法 |
| CN101610999A (zh) * | 2006-12-15 | 2009-12-23 | 先灵公司 | α-酮酰胺的亚硫酸氢盐纯化方法 |
| JP2010513492A (ja) | 2006-12-19 | 2010-04-30 | シェーリング コーポレイション | 3−(アミノ)−3−(シクロブチルメチル)−2−(ヒドロキシ)−プロピオンアミド塩酸塩の調製 |
| JP4955779B2 (ja) * | 2006-12-20 | 2012-06-20 | シェーリング コーポレイション | (1r,2s,5s)−n−[(1s)−3−アミノ−1−(シクロブチルメチル)−2,3−ジオキソプロピル]−3−[(2s)−2−[[[(1,1−ジメチルエチル)アミノ]カルボニル]−アミノ]−3,3−ジメチル−1−オキソブチル]−6,6−ジメチル−3−アザビシクロ[3.1.0]ヘキサン−2−カルボキサミドを調製するための方法 |
| MX2009006865A (es) * | 2006-12-20 | 2009-08-20 | Schering Corp | Proceso para la preparacion de compuestos 6,6-dimetil-3-aza-bicicl o-[3.1.0]-hexano utilizando intermediario bisulfitico. |
| WO2009039361A2 (en) * | 2007-09-20 | 2009-03-26 | Virobay, Inc. | Process for the preparation of (s)-2-(3-tert-butylureido)-3,3-dimethylbutanoic acid |
| JP5647790B2 (ja) | 2007-11-16 | 2015-01-07 | 株式会社カネカ | N−カルバモイル−tert−ロイシンの製造法 |
| WO2009067225A2 (en) * | 2007-11-20 | 2009-05-28 | Concert Pharmaceuticals, Inc. | Boceprevir derivatives for the treatment of hcv infections |
| JP2011504929A (ja) * | 2007-11-28 | 2011-02-17 | シェーリング コーポレイション | 6,6−ジメチル−3−アザビシクロ[3.1.0]ヘキサンを提供するのに有用な中間体調製のための脱塩化水素化プロセス |
| CA2710236A1 (en) * | 2007-12-21 | 2009-07-09 | Schering Corporation | Process for the synthesis of 3-amino-3-cyclobutylmethyl-2-hydroxypropionamide or salts thereof |
| AU2009266318A1 (en) * | 2008-07-03 | 2010-01-07 | Vertex Pharmaceuticals Incorporated | Preparation of protected alpha-keto beta-amino esters and amides |
| US8188137B2 (en) | 2008-08-15 | 2012-05-29 | Avila Therapeutics, Inc. | HCV protease inhibitors and uses thereof |
| US20120244122A1 (en) | 2009-05-28 | 2012-09-27 | Masse Craig E | Peptides for the Treatment of HCV Infections |
| CN103501608A (zh) * | 2011-05-04 | 2014-01-08 | 默沙东公司 | 药用物质、药物组合物和制备它们的方法 |
| CN104470914A (zh) * | 2012-06-20 | 2015-03-25 | 桑多斯股份公司 | 替拉瑞韦和波普瑞韦或者其药学上可接受的盐或溶剂合物和中间产物包括经Mukaiyama羟醛加成制备的β-氨基酸的合成 |
| WO2014061034A1 (en) * | 2012-10-18 | 2014-04-24 | Msn Laboratories Limited | Process for preparation of boceprevir and intermediates thereof |
| US10238771B2 (en) | 2012-11-08 | 2019-03-26 | Edwards Lifesciences Corporation | Methods for treating bioprosthetic tissue using a nucleophile/electrophile in a catalytic system |
| CN103936627B (zh) * | 2013-01-18 | 2016-08-31 | 上海医药工业研究院 | 抗丙肝药物Boceprevir的中间体Ⅶ及其制备方法和应用 |
| US20140256698A1 (en) * | 2013-03-11 | 2014-09-11 | Virobay, Inc. | Cathepsin inhibitors |
| WO2015004685A2 (en) | 2013-07-12 | 2015-01-15 | Mylan Laboratories Ltd | An improved process for the purification of boceprevir |
| DK3054936T5 (da) | 2013-10-10 | 2024-03-18 | Eastern Virginia Medical School | 4-((2-hydroxy-3-methoxybenzyl)amino) benzensulfonamid derivater som 12-lipoxygenase inhibitorer |
| CN104744291B (zh) * | 2015-02-13 | 2017-01-11 | 宁波九胜创新医药科技有限公司 | N-苄基-4-环丁基-2-羟基-3-硝基丁酰胺及其用途 |
| US20220025424A1 (en) * | 2016-08-16 | 2022-01-27 | Imago Biosciences, Inc. | Compositions and methods for producing stereoisomerically pure aminocyclopropanes |
| CN115784968A (zh) * | 2022-12-20 | 2023-03-14 | 黄冈鲁班药业股份有限公司 | Paxlovid和波普瑞韦中间体的合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100330553B1 (ko) * | 1993-10-01 | 2002-11-27 | 노파르티스 아게 | 약물학적활성피리딘유도체및그의제조방법 |
| US7244721B2 (en) * | 2000-07-21 | 2007-07-17 | Schering Corporation | Peptides as NS3-serine protease inhibitors of hepatitis C virus |
| CN1498224A (zh) | 2000-07-21 | 2004-05-19 | ���鹫˾ | 用作丙型肝炎病毒ns3-丝氨酸蛋白酶抑制剂的新型肽 |
-
2004
- 2004-06-14 AR ARP040102058A patent/AR044694A1/es not_active Application Discontinuation
- 2004-06-15 DE DE602004012746T patent/DE602004012746T2/de not_active Expired - Lifetime
- 2004-06-15 WO PCT/US2004/018914 patent/WO2004113294A1/en not_active Ceased
- 2004-06-15 ES ES04755225T patent/ES2299850T3/es not_active Expired - Lifetime
- 2004-06-15 JP JP2006517263A patent/JP5219368B2/ja not_active Expired - Fee Related
- 2004-06-15 CN CN2004800166406A patent/CN1805932B/zh not_active Expired - Fee Related
- 2004-06-15 US US10/867,600 patent/US7326795B2/en not_active Expired - Fee Related
- 2004-06-15 CA CA2526629A patent/CA2526629C/en not_active Expired - Fee Related
- 2004-06-15 EP EP04755225A patent/EP1641754B1/en not_active Expired - Lifetime
- 2004-06-15 AT AT04755225T patent/ATE390412T1/de not_active IP Right Cessation
- 2004-06-15 CN CN2011100739344A patent/CN102199111B/zh not_active Expired - Fee Related
- 2004-06-15 MX MXPA05013753A patent/MXPA05013753A/es active IP Right Grant
-
2005
- 2005-11-10 ZA ZA2005/09100A patent/ZA200509100B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2526629C (en) | 2012-10-02 |
| EP1641754A1 (en) | 2006-04-05 |
| CA2526629A1 (en) | 2004-12-29 |
| DE602004012746T2 (de) | 2009-04-09 |
| CN1805932B (zh) | 2011-05-18 |
| DE602004012746D1 (de) | 2008-05-08 |
| EP1641754B1 (en) | 2008-03-26 |
| WO2004113294A1 (en) | 2004-12-29 |
| JP5219368B2 (ja) | 2013-06-26 |
| MXPA05013753A (es) | 2006-03-08 |
| ZA200509100B (en) | 2011-06-29 |
| CN102199111B (zh) | 2012-07-04 |
| CN102199111A (zh) | 2011-09-28 |
| US20050059800A1 (en) | 2005-03-17 |
| ATE390412T1 (de) | 2008-04-15 |
| ES2299850T3 (es) | 2008-06-01 |
| HK1084387A1 (en) | 2006-07-28 |
| JP2006528133A (ja) | 2006-12-14 |
| CN1805932A (zh) | 2006-07-19 |
| US7326795B2 (en) | 2008-02-05 |
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