HUP0402140A2 - Eljárás hexahidrofuro [2,3-b]furán-3-ol előállítására - Google Patents
Eljárás hexahidrofuro [2,3-b]furán-3-ol előállításáraInfo
- Publication number
- HUP0402140A2 HUP0402140A2 HU0402140A HUP0402140A HUP0402140A2 HU P0402140 A2 HUP0402140 A2 HU P0402140A2 HU 0402140 A HU0402140 A HU 0402140A HU P0402140 A HUP0402140 A HU P0402140A HU P0402140 A2 HUP0402140 A2 HU P0402140A2
- Authority
- HU
- Hungary
- Prior art keywords
- group
- formula
- furan
- alkyl
- converted
- Prior art date
Links
- RCDXYCHYMULCDZ-UHFFFAOYSA-N 2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-ol Chemical compound O1CCC2C(O)COC21 RCDXYCHYMULCDZ-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- LYGJENNIWJXYER-BJUDXGSMSA-N nitromethane Chemical class [11CH3][N+]([O-])=O LYGJENNIWJXYER-BJUDXGSMSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 150000002009 diols Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 abstract 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen atoms
-
- 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)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A találmány tárgya eljárás (7) képletű hexahidrofuro[2,3-b] furán-3-ol előállítására az (1) általános képletű intermedierből kiindulva,azzal jellemezve, hogy az említett (1) általános képletű intermediertegy (3) általános képletű nitrometánszármazékká alakítják, majd azemlített nitrometánszármazékot egy (6) általános képletűtetrahidrofuránszármazékká alakítják, majd a (6) általános képletűintermediert intramolekuláris ciklizációs reakció útján a (7)szerkezeti képletű hexahidro-furo[2,3-b]furán-3-ol-lá alakítják. Atalálmány tárgya továbbá a (3) általános képletű intermedier ahol aképletben P1 és P2 jelentése egymástól függetlenül hidrogénatom,hidroxilvédő csoport vagy együtt egy vicinális diolvédő csoportotképezhetnek, R1 jelentése alkil-, aril- vagy aralkilcsoport, R2jelentése hidrogénatom vagy C(=O)OR3 csoport, R3 jelentése alkil-,aril- vagy aralkilcsoport, vagy - ha jelen van - R3 és R4 együttazokkal az atomokkal, amelyekhez kapcsolódnak, 6-8 tagú gyűrűscsoportot képezhetnek, amely adott esetben alkil-, aralkil- vagyarilcsoporttal lehet helyettesítve; feltéve, hogy amikor R2 jelentésehidrogénatom és P1 és P2 együtt egy izopropilidéncsoportot képez,akkor R1 jelentése metil- vagy etilcsoporttól eltérő. Ó
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01203416 | 2001-09-10 | ||
| PCT/EP2002/010062 WO2003022853A1 (en) | 2001-09-10 | 2002-09-06 | Method for the preparation of hexahydro-furo[2,3-b]furan-3-ol |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HUP0402140A2 true HUP0402140A2 (hu) | 2005-02-28 |
| HUP0402140A3 HUP0402140A3 (en) | 2007-05-29 |
| HU229505B1 HU229505B1 (hu) | 2014-01-28 |
Family
ID=8180908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0402140A HU229505B1 (hu) | 2001-09-10 | 2002-09-06 | Eljárás hexahidrofuro [2,3-b]furán-3-ol elõállítására |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US7126015B2 (hu) |
| EP (1) | EP1448567B1 (hu) |
| JP (1) | JP4521185B2 (hu) |
| KR (1) | KR100894673B1 (hu) |
| CN (2) | CN100519561C (hu) |
| AP (1) | AP1758A (hu) |
| AR (1) | AR036501A1 (hu) |
| AT (1) | ATE453648T1 (hu) |
| AU (1) | AU2002333809C1 (hu) |
| BR (1) | BRPI0212341B8 (hu) |
| CA (1) | CA2459168C (hu) |
| CY (1) | CY1109974T1 (hu) |
| DE (1) | DE60234952D1 (hu) |
| DK (1) | DK1448567T3 (hu) |
| EA (1) | EA010883B1 (hu) |
| ES (1) | ES2338538T3 (hu) |
| HK (1) | HK1068887A1 (hu) |
| HR (1) | HRP20040320B1 (hu) |
| HU (1) | HU229505B1 (hu) |
| IL (2) | IL160166A0 (hu) |
| MX (1) | MXPA04002247A (hu) |
| NO (1) | NO328934B1 (hu) |
| NZ (1) | NZ531641A (hu) |
| PL (1) | PL224030B1 (hu) |
| PT (1) | PT1448567E (hu) |
| SI (1) | SI21463B (hu) |
| WO (1) | WO2003022853A1 (hu) |
| ZA (1) | ZA200401501B (hu) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1532127B1 (en) * | 2002-06-27 | 2006-09-27 | SmithKline Beecham Corporation | PREPARATION OF STEREOISOMERS OF (3ALPHA, 3ALPHA/BETA, 6ALPHA/BETA) HEXAHYDROFURO(2,3-b) FURAN-3-OL |
| AU2003275675A1 (en) * | 2002-12-27 | 2004-07-29 | Sumitomo Chemical Company, Limited | Process for producing hexahydrofurofuranol derivative, intermediate thereof and process for producing the same |
| JP4818124B2 (ja) | 2003-12-23 | 2011-11-16 | テイボテク・フアーマシユーチカルズ・リミテツド | （３Ｒ，３ａＳ，６ａＲ）−ヘキサヒドロフロ〔２，３−ｂ〕フラン−３−イル（１Ｓ，１Ｒ）−３−〔〔（４−アミノフェニル）スルホニル〕（イソブチル）アミノ〕−１−ベンジル−２−ヒドロキシプロピルカルバマートの製造方法 |
| TWI383975B (zh) * | 2004-03-31 | 2013-02-01 | Tibotec Pharm Ltd | 製備（３Ｒ，３ａＳ，６ａＲ）六氫-呋喃并〔２，３-ｂ〕呋喃-３-醇之方法 |
| JP5549898B2 (ja) * | 2006-03-31 | 2014-07-16 | 独立行政法人産業技術総合研究所 | ５−ヒドロキシメチル−２−フルフラールの製造法 |
| CA2669014C (en) | 2006-11-09 | 2016-01-26 | Tibotec Pharmaceuticals Ltd. | Methods for the preparation of hexahydrofuro[2,3-b]furan-3-ol |
| CN101024646B (zh) * | 2007-02-06 | 2010-07-14 | 启东东岳药业有限公司 | 4-甲氧基呋喃并呋喃-2-酮的纯化方法 |
| MX2009011574A (es) | 2007-04-27 | 2009-11-09 | Tibotec Pharm Ltd | Metodos para la preparacion de derivados de n-isobutil-n-(2-hidrox i-3-amino-4-fenilbutil)-p-nitrobencensulfonilamida. |
| US8592487B2 (en) | 2007-10-26 | 2013-11-26 | Concert Pharmaceuticals, Inc. | Deuterated darunavir |
| TWI482775B (zh) | 2008-09-01 | 2015-05-01 | Tibotec Pharm Ltd | 用於製備（３ｒ，３ａｓ，６ａｒ）－六氫呋喃并〔２，３－ｂ〕呋喃－３－基（１ｓ，２ｒ）－３－〔〔（４－胺基苯基）磺醯基〕（異丁基）胺基〕－１－苯甲基－２－羥基丙基胺基甲酸酯之方法 |
| WO2010047819A1 (en) * | 2008-10-24 | 2010-04-29 | Concert Pharmaceuticals, Inc. | Hydroxyethylamino sulfonamide derivatives |
| US8921415B2 (en) | 2009-01-29 | 2014-12-30 | Mapi Pharma Ltd. | Polymorphs of darunavir |
| WO2011051978A2 (en) | 2009-10-30 | 2011-05-05 | Lupin Limited | A novel process for preparation of darunavir and darunavir ethanolate of fine particle size |
| WO2011092687A1 (en) | 2010-01-28 | 2011-08-04 | Mapi Pharma Hk Limited | Process for the preparation of darunavir and darunavir intermediates |
| EP2643326B1 (en) | 2010-11-23 | 2016-09-14 | Mylan Laboratories, Limited | Process for the preparation of (3R, 3aS, 6aR)-hexahydrofuro[2,3-b]furan-3-ol |
| US8802724B2 (en) | 2010-11-30 | 2014-08-12 | Purdue Research Foundation | Processes and intermediates for preparing substituted hexahydrofuro [2,3-b] furans |
| ES2969589T3 (es) | 2012-07-24 | 2024-05-21 | Laurus Labs Ltd | Solvato de Propionato de Darunavir |
| WO2014024898A1 (ja) * | 2012-08-09 | 2014-02-13 | 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 |
| CN103864813B (zh) * | 2012-12-18 | 2017-02-22 | 上海迪赛诺化学制药有限公司 | 一种合成六氢呋喃并[2,3‑b]呋喃‑3‑醇及其对映体的方法 |
| US10633390B2 (en) * | 2015-06-25 | 2020-04-28 | Msn Laboratories Private Limited | Process for the preparation of [(1S,2R)-3-[[(4-aminophenyl)sulfonyl] (2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-carbamic acid (3R,3AS,6AR)hexahydro furo [2,3-B]furan-3-YL ester and its amorphous form |
| WO2017041228A1 (zh) * | 2015-09-08 | 2017-03-16 | 浙江九洲药业股份有限公司 | 六氢呋喃并呋喃醇衍生物的制备方法、其中间体及其制备方法 |
| CN107043385B (zh) * | 2016-02-05 | 2019-07-09 | 成都博腾药业有限公司 | 一种制备地瑞那韦中间体的方法 |
| WO2018081292A1 (en) | 2016-10-27 | 2018-05-03 | Gilead Sciences, Inc. | Crystalline forms of darunavir free base, hydrate, solvates and salts |
| CN106928248B (zh) * | 2017-02-04 | 2019-01-04 | 青岛科技大学 | 一种制备(3R,3aS,6aR)六氢呋喃并[2,3-b]呋喃-3-醇的方法 |
| CN116103348A (zh) | 2018-03-16 | 2023-05-12 | 江苏瑞科医药科技有限公司 | 六氢呋喃并呋喃醇衍生物的制备方法、其中间体及其制备方法 |
| CN114853774A (zh) * | 2022-06-24 | 2022-08-05 | 盐城迪赛诺制药有限公司 | 一种达卢那韦关键中间体的制备方法 |
| CN115557964A (zh) * | 2022-10-18 | 2023-01-03 | 启东东岳药业有限公司 | 一种药物化合物的制备方法 |
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|---|---|---|---|---|
| CU35543A1 (es) * | 1980-10-09 | 1983-05-05 | Hoffmann La Roche | Prostaglandines |
| NZ224497A (en) * | 1987-05-18 | 1990-04-26 | Janssen Pharmaceutica Nv | Pharmaceutical composition comprising flunarizine |
| US5281420A (en) * | 1992-05-19 | 1994-01-25 | The Procter & Gamble Company | Solid dispersion compositions of tebufelone |
| WO1994026749A1 (en) * | 1993-05-14 | 1994-11-24 | Merck & Co., Inc. | Hiv protease inhibitors |
| ATE174587T1 (de) | 1993-08-24 | 1999-01-15 | Searle & Co | Hydroxyaminosulfonamide verwendbar als inhibitoren retroviraler proteasen |
| RU2089545C1 (ru) * | 1994-09-28 | 1997-09-10 | Ярославский государственный технический университет | Способ получения 2-метил-2-этил-1,3-диоксолан-4-ил-метилметакрилата |
| DE19510566A1 (de) * | 1995-03-23 | 1996-09-26 | Kali Chemie Pharma Gmbh | Benzazepin-, Benzoxazepin- und Benzothiazepin-N-essigsäurederivate sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE19638020A1 (de) * | 1996-09-18 | 1998-03-19 | Solvay Pharm Gmbh | Die gastrointestinale Durchblutung fördernde Arzneimittel |
| KR20050084502A (ko) * | 1997-01-30 | 2005-08-26 | 노파르티스 아게 | 오일을 함유하지 않은 사이클로스포린 ａ 함유 제약 조성물 |
| AU4828199A (en) * | 1998-06-23 | 2000-01-10 | Board Of Trustees Of The University Of Illinois, The | Multi-drug resistant retroviral protease inhibitors and associated methods |
| PT1088098E (pt) * | 1998-06-23 | 2011-05-25 | Univ Illinois | Medicamento para tratar mam?feros infectados com hiv |
| KR100336090B1 (ko) * | 1998-06-27 | 2002-05-27 | 윤승원 | 오일, 지방산 또는 이들의 혼합물을 함유한 난용성 약물의 고형분산제제 |
| DE19906310A1 (de) * | 1999-02-16 | 2000-08-17 | Solvay Pharm Gmbh | Arzneimittel zur Behandlung von Bluthochdruck |
| DE19932555A1 (de) * | 1999-07-13 | 2001-01-18 | Solvay Pharm Gmbh | Arzneimittel mit protektiver Wirkung gegen oxidativ-toxische und insbesondere gegen kardiotoxische Substanzen |
| BR0014602A (pt) * | 1999-10-06 | 2002-06-11 | Tibotec Pharm Ltd | Hexaidrofluoro'2,3-bifuran-3-il-n-{3'(1,3-benzodioxol- 5ilsulfonil)(isobutil)amino-1 -benzil-2-hidroxipropil}carbamato como inibidor da protease retroviral |
-
2002
- 2002-09-06 CA CA2459168A patent/CA2459168C/en not_active Expired - Lifetime
- 2002-09-06 HU HU0402140A patent/HU229505B1/hu unknown
- 2002-09-06 IL IL16016602A patent/IL160166A0/xx unknown
- 2002-09-06 NZ NZ531641A patent/NZ531641A/en not_active IP Right Cessation
- 2002-09-06 WO PCT/EP2002/010062 patent/WO2003022853A1/en active IP Right Grant
- 2002-09-06 AP APAP/P/2004/002981A patent/AP1758A/en active
- 2002-09-06 CN CNB028176391A patent/CN100519561C/zh not_active Expired - Lifetime
- 2002-09-06 JP JP2003526927A patent/JP4521185B2/ja not_active Expired - Lifetime
- 2002-09-06 DK DK02797968.1T patent/DK1448567T3/da active
- 2002-09-06 CN CN200710186668XA patent/CN101172980B/zh not_active Expired - Lifetime
- 2002-09-06 PT PT02797968T patent/PT1448567E/pt unknown
- 2002-09-06 MX MXPA04002247A patent/MXPA04002247A/es active IP Right Grant
- 2002-09-06 EP EP02797968A patent/EP1448567B1/en not_active Expired - Lifetime
- 2002-09-06 BR BRPI0212341A patent/BRPI0212341B8/pt not_active IP Right Cessation
- 2002-09-06 KR KR1020047002113A patent/KR100894673B1/ko active IP Right Grant
- 2002-09-06 AT AT02797968T patent/ATE453648T1/de active
- 2002-09-06 ES ES02797968T patent/ES2338538T3/es not_active Expired - Lifetime
- 2002-09-06 EA EA200400430A patent/EA010883B1/ru not_active IP Right Cessation
- 2002-09-06 AU AU2002333809A patent/AU2002333809C1/en not_active Expired
- 2002-09-06 SI SI200220026A patent/SI21463B/sl active Search and Examination
- 2002-09-06 PL PL367817A patent/PL224030B1/pl unknown
- 2002-09-06 US US10/489,059 patent/US7126015B2/en not_active Expired - Lifetime
- 2002-09-06 DE DE60234952T patent/DE60234952D1/de not_active Expired - Lifetime
- 2002-09-09 AR ARP020103403A patent/AR036501A1/es active IP Right Grant
-
2004
- 2004-02-02 IL IL160166A patent/IL160166A/en active IP Right Grant
- 2004-02-24 ZA ZA2004/01501A patent/ZA200401501B/en unknown
- 2004-04-05 HR HRP20040320AA patent/HRP20040320B1/hr not_active IP Right Cessation
- 2004-04-06 NO NO20041434A patent/NO328934B1/no not_active IP Right Cessation
-
2005
- 2005-02-23 HK HK05101515.9A patent/HK1068887A1/xx not_active IP Right Cessation
-
2010
- 2010-03-30 CY CY20101100296T patent/CY1109974T1/el unknown
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