AR073248A1 - Proceso para la preparacion de (1s, 2r)-3- ((4-aminofenil) sulfonil) ( isobutil) amino)-1- bencil-2- hidroxipropilcarbamato de (3r, 3as,6ar)- hexahidrofuro-(2,3-b) furan-3- ilo (darunavir) y compuestos intermediarios utiles en dicho proceso. - Google Patents
Proceso para la preparacion de (1s, 2r)-3- ((4-aminofenil) sulfonil) ( isobutil) amino)-1- bencil-2- hidroxipropilcarbamato de (3r, 3as,6ar)- hexahidrofuro-(2,3-b) furan-3- ilo (darunavir) y compuestos intermediarios utiles en dicho proceso.Info
- Publication number
- AR073248A1 AR073248A1 ARP090103343A ARP090103343A AR073248A1 AR 073248 A1 AR073248 A1 AR 073248A1 AR P090103343 A ARP090103343 A AR P090103343A AR P090103343 A ARP090103343 A AR P090103343A AR 073248 A1 AR073248 A1 AR 073248A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- darunavir
- furan
- amino
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 13
- CJBJHOAVZSMMDJ-HEXNFIEUSA-N darunavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)C1=CC=CC=C1 CJBJHOAVZSMMDJ-HEXNFIEUSA-N 0.000 title abstract 3
- 229960005107 darunavir Drugs 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- -1 AMINO Chemical class 0.000 title abstract 2
- HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 title 1
- 125000006239 protecting group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000012453 solvate Substances 0.000 abstract 2
- JQUNFHFWXCXPRK-AMMMHQJVSA-N [(3as,4r,6ar)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] n-[(2s,3r)-4-[[2-[(1-cyclopentylpiperidin-4-yl)amino]-1,3-benzothiazol-6-yl]sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical group C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=C2SC(NC3CCN(CC3)C3CCCC3)=NC2=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)C1=CC=CC=C1 JQUNFHFWXCXPRK-AMMMHQJVSA-N 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
- ZELJLECFTLYULH-UHFFFAOYSA-N n-benzyl-2-methylpropan-1-amine Chemical compound CC(C)CNCC1=CC=CC=C1 ZELJLECFTLYULH-UHFFFAOYSA-N 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- 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
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Virology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Abstract
Reivindicacion 1: Un proceso para la preparacion de darunavir de formula (1) o un solvato, sal de adicion o forma polimorfica o pseudopolimorfica del mismo que comprende (i) hacer reaccionar un compuesto de formula (2) en donde PG representa un grupo protector de amino, con N-bencil-isobutilamina, es decir un compuesto de formula (3) para obtener un compuesto de formula (4); (ii) tratar el compuesto de formula (4) para eliminar el grupo protector PG para obtener un compuesto de formula (5); (iii) acoplar el compuesto de formula (5) con un derivado de (3R,3aS,6aR)-hexahidrofuro[2,3-b]furan-3-ilo para obtener un compuesto de formula (6); (iv) eliminar el grupo N-bencilo del compuesto de formula (6) para obtener un compuesto de formula (7); (v) introducir un grupo p-nitrofenilsulfonilo en el compuesto de formula (7) para obtener un compuesto de formula (8); (vi) reducir el grupo nitro del compuesto de formula (8) para formar darunavir o un solvato, sal de adicion o forma polimorfica o pseudopolimorfica del mismo.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08163383 | 2008-09-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR073248A1 true AR073248A1 (es) | 2010-10-20 |
Family
ID=40786641
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP090103343A AR073248A1 (es) | 2008-09-01 | 2009-08-31 | Proceso para la preparacion de (1s, 2r)-3- ((4-aminofenil) sulfonil) ( isobutil) amino)-1- bencil-2- hidroxipropilcarbamato de (3r, 3as,6ar)- hexahidrofuro-(2,3-b) furan-3- ilo (darunavir) y compuestos intermediarios utiles en dicho proceso. |
| ARP200100624A AR119702A2 (es) | 2008-09-01 | 2020-03-06 | Proceso para la preparación de (1s,2r)-3-[[(4-aminofenil)sulfonil](isobutil)amino]-1-bencil-2-hidroxipropilcarbamato de (3r,3as,6ar)-hexahidrofuro[2,3-b]furan-3-ilo |
| ARP200100623A AR118270A2 (es) | 2008-09-01 | 2020-03-06 | PROCESO PARA LA PREPARACIÓN DEL SOLVATO ETANOLATO DE (1S,2R)-3-[[(4-AMINOFENIL)SULFONIL](ISOBUTIL)AMINO]-1-BENCIL-2-HIDROXIPROPILCARBAMATO DE (3R,3aS,6aR)-HEXAHIDROFURO[2,3-B]FURAN-3-ILO |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP200100624A AR119702A2 (es) | 2008-09-01 | 2020-03-06 | Proceso para la preparación de (1s,2r)-3-[[(4-aminofenil)sulfonil](isobutil)amino]-1-bencil-2-hidroxipropilcarbamato de (3r,3as,6ar)-hexahidrofuro[2,3-b]furan-3-ilo |
| ARP200100623A AR118270A2 (es) | 2008-09-01 | 2020-03-06 | PROCESO PARA LA PREPARACIÓN DEL SOLVATO ETANOLATO DE (1S,2R)-3-[[(4-AMINOFENIL)SULFONIL](ISOBUTIL)AMINO]-1-BENCIL-2-HIDROXIPROPILCARBAMATO DE (3R,3aS,6aR)-HEXAHIDROFURO[2,3-B]FURAN-3-ILO |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8580981B2 (es) |
| EP (1) | EP2346877B1 (es) |
| JP (1) | JP5498497B2 (es) |
| CN (1) | CN102131815B (es) |
| AR (3) | AR073248A1 (es) |
| AU (1) | AU2009286619B2 (es) |
| BR (1) | BRPI0917377B1 (es) |
| CA (1) | CA2734814C (es) |
| ES (1) | ES2519115T3 (es) |
| MX (1) | MX2011002259A (es) |
| TW (1) | TWI482775B (es) |
| WO (1) | WO2010023322A1 (es) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8921415B2 (en) | 2009-01-29 | 2014-12-30 | Mapi Pharma Ltd. | Polymorphs of darunavir |
| EP2493891A2 (en) | 2009-10-30 | 2012-09-05 | Lupin Limited | A novel process for preparation of darunavir and darunavir ethanolate of fine particle size |
| BR112012018862A2 (pt) | 2010-01-28 | 2015-10-13 | Mapi Pharma Ltd | processo para a preparação de darunavir e intermediários de darunavir |
| CN102584844B (zh) * | 2011-01-11 | 2016-04-13 | 浙江九洲药业股份有限公司 | 一种达芦那韦晶型及其制备方法 |
| CN102617586B (zh) * | 2011-01-26 | 2016-04-06 | 浙江九洲药业股份有限公司 | 地瑞那韦中间体的制备方法 |
| WO2013011485A1 (en) | 2011-07-20 | 2013-01-24 | Ranbaxy Laboratories Limited | Process for the preparation of sulfonamides useful as retroviral protease inhibitors |
| EP3795572B1 (en) | 2012-07-24 | 2023-11-15 | Laurus Labs Limited | Darunavir propionate solvate |
| CN105315178B (zh) * | 2014-07-09 | 2018-07-06 | 浙江九洲药业股份有限公司 | 达芦那韦相关物质及其制备方法 |
| JP6435907B2 (ja) * | 2015-02-16 | 2018-12-12 | 住友化学株式会社 | ヘキサヒドロフロフラノール誘導体の製造方法 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5968942A (en) | 1992-08-25 | 1999-10-19 | G. D. Searle & Co. | α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors |
| EP0715618B1 (en) | 1993-08-24 | 1998-12-16 | G.D. Searle & Co. | Hydroxyethylamino sulphonamides useful as retroviral protease inhibitors |
| DE69616446T2 (de) | 1995-02-03 | 2002-05-16 | Kaneka Corp., Osaka | Verfahren zur herstellung von alpha-haloketonen, alpha-halohydrinen und epoxiden |
| ES2173480T3 (es) | 1996-08-23 | 2002-10-16 | Gilead Sciences Inc | Preparacion de derivados de ciclohexeno carboxilato. |
| GB9805898D0 (en) | 1998-03-20 | 1998-05-13 | Glaxo Group Ltd | Process for the sythesis of hiv protease inhibitors |
| ATE500823T1 (de) | 1998-06-23 | 2011-03-15 | Us Of America Represented By The Secretary Dept Of Health And Human Services | Arzneimittel zur behandlung von hiv-infizierten säugetieren |
| WO1999067254A2 (en) * | 1998-06-23 | 1999-12-29 | The United States Of America Represented By The Secretary, Department Of Health And Human Services | Multi-drug resistant retroviral protease inhibitors and use thereof |
| DE69918050T2 (de) | 1998-08-25 | 2005-06-30 | Kaneka Corp. | Verfahren zur herstellung von (2r,3s)-3-amino-1,2-oxiran |
| ATE334121T1 (de) | 1999-01-29 | 2006-08-15 | Kaneka Corp | Verfahren zur herstellung von threo-1,2-epoxy-3- amino-4-phenylbutan-derivaten |
| KR100708221B1 (ko) | 1999-08-31 | 2007-04-17 | 아지노모토 가부시키가이샤 | 에폭사이드 결정의 제조방법 |
| US6455738B1 (en) | 2000-07-13 | 2002-09-24 | Rhodia Chimie | Process for the sulfonation of an aromatic compound |
| KR20020046948A (ko) | 2000-12-12 | 2002-06-21 | 에가시라 구니오 | 에폭사이드 결정의 제조방법 |
| WO2003022853A1 (en) | 2001-09-10 | 2003-03-20 | Tibotec Pharmaceuticals Ltd. | Method for the preparation of hexahydro-furo[2,3-b]furan-3-ol |
| JPWO2003057665A1 (ja) | 2001-12-28 | 2005-05-19 | 味の素株式会社 | ベンゼンスルホンアミド誘導体結晶の製造方法、およびその中間体の新規結晶とその製造方法 |
| HRP20041061B1 (hr) | 2002-05-16 | 2015-02-27 | Tibotec Pharmaceuticals Ltd. | Pseudopolimorfni oblici inhibitora hiv proteaze |
| JP4681296B2 (ja) | 2002-08-14 | 2011-05-11 | テイボテク・フアーマシユーチカルズ・リミテツド | スペクトルの広い置換オキシインドールスルホンアミドｈｉｖプロテアーゼ阻害剤 |
| AU2004309122B2 (en) * | 2003-12-23 | 2011-07-21 | Janssen Sciences Ireland Unlimited Company | Process for the preparation of (3R,3aS,6AR)-hexahydrofuro [2,3-b] furan-3-yl (1S,2R)-3-[[(4-aminophenyl) sulfonyl] (isobutyl) amino]-1-benzyl-2-hydroxypropylcarbamate |
| ME01059B (me) * | 2003-12-23 | 2012-10-20 | Janssen Sciences Ireland Uc | Proces za pripremanje (3r,3as,6ar)-heksahidrofuro [2,3-b] furan-3-il (1s,2r)-3-[[(4-aminofenil) sulfonil] (izobutil) amino]-1-benzil-2- hidroksipropilkarbamata |
| CA2559328A1 (en) | 2004-03-11 | 2005-09-22 | Sequoia Pharmaceuticals, Inc. | Resistance-repellent retroviral protease inhibitors |
| EP1750696B1 (en) | 2004-05-07 | 2013-06-26 | Sequoia Pharmaceuticals Inc | RETROVIRAL PROTEASE INHIBITORS RESISTING THEIR RESISTANCE |
| TWI432438B (zh) | 2005-11-28 | 2014-04-01 | Tibotec Pharm Ltd | 作為ｈｉｖ蛋白酶抑制劑之經取代的胺基苯基磺醯胺化合物及衍生物 |
| TWI385173B (zh) | 2005-11-28 | 2013-02-11 | Tibotec Pharm Ltd | 作為ｈｉｖ蛋白酶抑制劑之經取代的胺基苯基磺醯胺化合物 |
-
2009
- 2009-08-31 TW TW098129186A patent/TWI482775B/zh not_active IP Right Cessation
- 2009-08-31 AR ARP090103343A patent/AR073248A1/es active IP Right Grant
- 2009-09-01 BR BRPI0917377-3A patent/BRPI0917377B1/pt active IP Right Grant
- 2009-09-01 CN CN200980133649.8A patent/CN102131815B/zh active Active
- 2009-09-01 WO PCT/EP2009/061253 patent/WO2010023322A1/en not_active Ceased
- 2009-09-01 CA CA2734814A patent/CA2734814C/en active Active
- 2009-09-01 MX MX2011002259A patent/MX2011002259A/es active IP Right Grant
- 2009-09-01 US US13/060,942 patent/US8580981B2/en active Active
- 2009-09-01 ES ES09782438.7T patent/ES2519115T3/es active Active
- 2009-09-01 AU AU2009286619A patent/AU2009286619B2/en active Active
- 2009-09-01 EP EP09782438.7A patent/EP2346877B1/en active Active
- 2009-09-01 JP JP2011524412A patent/JP5498497B2/ja active Active
-
2020
- 2020-03-06 AR ARP200100624A patent/AR119702A2/es unknown
- 2020-03-06 AR ARP200100623A patent/AR118270A2/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2346877B1 (en) | 2014-08-20 |
| US20110160468A1 (en) | 2011-06-30 |
| CA2734814A1 (en) | 2010-03-04 |
| AR119702A2 (es) | 2022-01-05 |
| BRPI0917377B1 (pt) | 2022-04-19 |
| CA2734814C (en) | 2017-03-07 |
| MX2011002259A (es) | 2011-04-12 |
| TW201022276A (en) | 2010-06-16 |
| US8580981B2 (en) | 2013-11-12 |
| AR118270A2 (es) | 2021-09-22 |
| CN102131815A (zh) | 2011-07-20 |
| JP2012501316A (ja) | 2012-01-19 |
| JP5498497B2 (ja) | 2014-05-21 |
| WO2010023322A1 (en) | 2010-03-04 |
| TWI482775B (zh) | 2015-05-01 |
| AU2009286619B2 (en) | 2015-05-14 |
| CN102131815B (zh) | 2014-10-15 |
| AU2009286619A1 (en) | 2010-03-04 |
| BRPI0917377A2 (pt) | 2015-12-01 |
| EP2346877A1 (en) | 2011-07-27 |
| ES2519115T3 (es) | 2014-11-06 |
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