HRP20110258T1 - Postupci za dobivanje heksahidrofuro[2,3-b]furan-3-ola - Google Patents
Postupci za dobivanje heksahidrofuro[2,3-b]furan-3-ola Download PDFInfo
- Publication number
- HRP20110258T1 HRP20110258T1 HR20110258T HRP20110258T HRP20110258T1 HR P20110258 T1 HRP20110258 T1 HR P20110258T1 HR 20110258 T HR20110258 T HR 20110258T HR P20110258 T HRP20110258 T HR P20110258T HR P20110258 T1 HRP20110258 T1 HR P20110258T1
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- arylalkyl
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- 238000000034 method Methods 0.000 title claims abstract 15
- 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 claims abstract 3
- RCDXYCHYMULCDZ-HCWXCVPCSA-N (3as,4r,6ar)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-ol Chemical compound O1CC[C@H]2[C@@H](O)CO[C@H]21 RCDXYCHYMULCDZ-HCWXCVPCSA-N 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 28
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims 8
- 238000006243 chemical reaction Methods 0.000 claims 4
- 150000003608 titanium Chemical class 0.000 claims 4
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- 239000007795 chemical reaction product Substances 0.000 claims 3
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical class OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims 3
- 239000010936 titanium Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- 235000011006 sodium potassium tartrate Nutrition 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- ZHOFTVOJICJJNF-UHFFFAOYSA-N 1-(2-propan-2-yloxyoxolan-3-yl)ethane-1,2-diol Chemical compound CC(C)OC1OCCC1C(O)CO ZHOFTVOJICJJNF-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- HYMFICVSTYUSOC-UHFFFAOYSA-N ethyl 2-hydroxy-2-(2-propan-2-yloxyoxolan-3-yl)acetate Chemical compound CCOC(=O)C(O)C1CCOC1OC(C)C HYMFICVSTYUSOC-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- -1 radical halogen Chemical class 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 150000003609 titanium compounds Chemical class 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract 1
Classifications
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Postupak dobivanja spoja formule (V) naznačen time da sadrži reakciju 2,3-dihidrofurana formule (II) sa derivatom glioksilata formule (III) u prisutnosti titanijeve soli formule Ti(Hal)n(ILI)4-n gdje je Hal radikal halogena, n je 0, 1, 2 ili 3 i R je alkil ili arilalkil, te sadrži naknadnu reakciju rezultirajućeg reakcijskog produkta sa alkoholom formule (IV) pri čemu tvore spoj formule (V): pri čemu R1 je alkil ili arilalkil i R2 je alkil ili arilalkil. Patent sadrži još 15 patentnih zahtjeva.
Claims (16)
1. Postupak dobivanja spoja formule (V) naznačen time da sadrži reakciju 2,3-dihidrofurana formule (II) sa derivatom glioksilata formule (III) u prisutnosti titanijeve soli formule Ti(Hal)n(ILI)4-n gdje je Hal radikal halogena, n je 0, 1, 2 ili 3 i R je alkil ili arilalkil, te sadrži naknadnu reakciju rezultirajućeg reakcijskog produkta sa alkoholom formule (IV) pri čemu tvore spoj formule (V):
[image]
pri čemu R1 je alkil ili arilalkil i R2 je alkil ili arilalkil.
2. Postupak prema zahtjevu 1 naznačen time da titanijeva sol je spoj formule Ti(Hal)n(ILI)4-n pri čemu n je 1, 2 ili 3.
3. Postupak prema zahtjevu 1 ili zahtjevu 2 naznačen time da R1 je C1-4 alkil.
4. Postupak prema bilo kojem od prethodnih zahtjeva naznačen time da R2 je C1-4 alkil.
5. Postupak prema bilo kojem od prethodnih zahtjeva naznačen time da je 2,3-dihidrofuran formule (II) u reakciji sa derivatom glioksilata formule (III) u prisutnosti titanijeve soli, te naknadni reakcijski produkt reagira sa alkoholom formule (IV) pri čemu tvore spoj formule (V).
6. Postupak prema bilo kojem od prethodnih zahtjeva naznačen time da je rezultirajuća reakcijska mješavina koja sadrži spoj formule (V) tretirana sa Rochelle soli kako bi se postiglo uklanjanje zaostalih spojeva titana.
7. Postupak prema zahtjevu 6 naznačen time da se tretiranje sa Rochelle soli provodi u alkalnom mediju.
8. Spojevi formule (Va):
[image]
i njihovi stereoizomerni oblici i racematne smjese,
pri čemu R1 je alkil ili arilalkil i R2 je alkil ili arilalkil, pod uvjetom da kada R2 je metil R1 je nije metil ili etil.
9. Spoj prema zahtjevu 8, naznačen time da je navedeni spoj etil hidroksi-(2-izopropoksitetrahidro-3-furanil)acetat.
10. Postupak za dobivanje spojeva formule (VI) naznačen time da sadrži redukciju spoja formule (V) koja tvori spoj formule (VI):
[image]
pri čemu R1 i R2 su kako je definirano u zahtjevu 1.
11. Postupak prema zahtjevu 10 naznačen time da se redukcija provodi sa borohidridnim redukcijskim sredstvom.
12. Spojevi formule (VI):
[image]
pri čemu R2 je kako je definirano u zahtjevu 1.
13. Spoj prema zahtjevu 12, naznačen time da navedeni spoj je 1-(2-izo-propoksitetrahidro-3-furanil)-1,2-etandiol.
14. Postupak za dobivanje spoja formule (I) naznačen time da sadrži spoj formule (VI) koji ciklizira i tvori spoj formule (I):
15. Postupak prema zahtjevu 14 naznačen time da se cikliziranje spoja formule (VI) provodi tretiranjem sa jakom protičkom kiselinom.
16. Postupak za dobivanje heksahidrofuro[2,3-b]furan-3-ola formule (I) naznačen time da sadrži korake:
a) reakciju 2,3-dihidrofurana formule (II) sa derivatom glioksilata formule (III) u prisutnosti titanijeve soli formule Ti(Hal)n(ILI)4-n gdje n je 0, 1, 2 ili 3 i R je alkil ili arilalkil, i naknadnu reakciju dobivenog reakcijskog produkta sa alkoholom formule (IV) da tvori spoj formule (V):
[image]
pri čemu R1 je alkil ili arilalkil i R2 je alkil ili arilalkil; i
b) redukciju rezultirajućeg spoja formule (V) da tvori spoj formule (VI):
[image]
i
c) ciklizacije spoja formule (VI) da tvori spoj formule (I):
[image]
i ako je poželjno naknadnog
(i) podvrgavanja dobivenoga spoja formule (I) kiralnoj separaciji radi izoliranja (3R,3aS,6aR) heksahidrofuro-[2,3-b]furan-3-ola formule (Ia):
[image]
i/ili
(ii) oksidacije rezultirajućeg spoja formule (I) da se dobije spoj formule (I'):
[image]
i naknadne redukcije spoja formule (I') u spoj formule (Ia).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06123752 | 2006-11-09 | ||
| PCT/EP2007/062119 WO2008055970A2 (en) | 2006-11-09 | 2007-11-09 | Methods for the preparation of hexahydrofuro[2,3-b]furan-3-ol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110258T1 true HRP20110258T1 (hr) | 2011-05-31 |
Family
ID=37692659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110258T HRP20110258T1 (hr) | 2006-11-09 | 2011-04-11 | Postupci za dobivanje heksahidrofuro[2,3-b]furan-3-ola |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US8153829B2 (hr) |
| EP (1) | EP2089371B1 (hr) |
| JP (1) | JP5491862B2 (hr) |
| CN (2) | CN101541775B (hr) |
| AT (1) | ATE497499T1 (hr) |
| AU (1) | AU2007316562B2 (hr) |
| BR (1) | BRPI0718706B8 (hr) |
| CA (1) | CA2669014C (hr) |
| CY (1) | CY1111407T1 (hr) |
| DE (1) | DE602007012365D1 (hr) |
| DK (1) | DK2089371T3 (hr) |
| ES (1) | ES2359949T3 (hr) |
| HR (1) | HRP20110258T1 (hr) |
| IL (1) | IL198270A (hr) |
| ME (1) | ME01232B (hr) |
| MX (1) | MX2009004957A (hr) |
| PL (1) | PL2089371T3 (hr) |
| PT (1) | PT2089371E (hr) |
| RS (1) | RS51675B (hr) |
| RU (1) | RU2464266C2 (hr) |
| SI (1) | SI2089371T1 (hr) |
| WO (1) | WO2008055970A2 (hr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010075887A1 (en) * | 2008-12-30 | 2010-07-08 | Oxyrane (Uk) Limited | Methods and intermediates useful in the synthesis of hexahydrofuro[2,3-b]furan-3-ol |
| US8921415B2 (en) | 2009-01-29 | 2014-12-30 | Mapi Pharma Ltd. | Polymorphs of darunavir |
| US9062065B2 (en) | 2009-10-30 | 2015-06-23 | Lupin Limited | Process for preparation of darunavir and darunavir ethanolate of fine particle size |
| CN102686594A (zh) | 2009-12-16 | 2012-09-19 | 熙德隆研究基金会 | 地瑞那韦的多晶型物 |
| ES2516916T3 (es) | 2010-01-28 | 2014-10-31 | Mapi Pharma Limited | Procedimiento para la preparación de darunavir e intermedios de darunavir |
| EP2571355B1 (en) | 2010-05-20 | 2016-09-07 | Hetero Research Foundation | Crystalline hydrochloride salt of darunavir |
| 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 |
| EP2887807B1 (en) * | 2012-08-22 | 2019-09-18 | Merck Sharp & Dohme Corp. | Benzimidazole hexahydrofuro[3,2-b]furan derivatives useful as amp-activated protein kinase activators |
| 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 |
| CN103896886A (zh) * | 2012-12-31 | 2014-07-02 | 上海迪赛诺化学制药有限公司 | 一种达鲁那韦中间体及其制备方法和应用 |
| TW201514188A (zh) * | 2013-03-13 | 2015-04-16 | Lantheus Medical Imaging Inc | 製備釓磷維塞三鈉單水合物之方法 |
| CN103664976B (zh) * | 2013-12-12 | 2015-11-04 | 惠州市莱佛士制药技术有限公司 | 一种顺式六氢呋喃并[2,3-b]呋喃-3-醇的制备方法 |
| CN113307783B (zh) * | 2016-05-07 | 2023-04-07 | 成都博腾药业有限公司 | 一种制备地瑞那韦中间体的方法 |
| CN112300186B (zh) * | 2019-08-01 | 2024-04-30 | 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 |
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| DE69415326T2 (de) | 1993-08-24 | 1999-06-02 | G.D. Searle & Co., Chicago, Ill. | Hydroxyaminosulfonamide verwendbar als inhibitoren retroviraler proteasen |
| DE69512220T2 (de) | 1994-03-07 | 2000-03-16 | Vertex Pharmaceuticals Inc. | Sulfonamidderivate als aspartylprotease-inhibitoren |
| JP3665343B2 (ja) | 1995-02-03 | 2005-06-29 | 株式会社カネカ | α−ハロケトン、α−ハロヒドリン及びエポキシドの製造法 |
| WO1997018205A1 (en) | 1995-11-15 | 1997-05-22 | G.D. Searle & Co. | Substituted sulfonylalkanoylamino hydroxyethylamino sulfonamide retroviral protease inhibitors |
| US5990313A (en) * | 1996-10-21 | 1999-11-23 | Eastman Chemical Company | Preparation of 3-alkyltetrahydrofurans |
| EP0932607A2 (en) * | 1996-10-21 | 1999-08-04 | Eastman Chemical Company | Preparation of 3-alkyltetrahydrofurans |
| US5856531A (en) * | 1996-10-21 | 1999-01-05 | Eastman Chemical Company | Preparation of 3-methytetra-hydrofuran from 2,3-dihydrofuran |
| DK1086076T3 (da) | 1998-06-19 | 2005-03-29 | Vertex Pharma | Sulfonamidinhibitorer af aspartylprotease |
| WO1999067417A2 (en) | 1998-06-23 | 1999-12-29 | The United States Of America, Represented By The Secretary, Department Of Health And Human Services | Fitness assay and associated methods |
| 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 |
| US6278002B1 (en) | 1998-08-25 | 2001-08-21 | Kaneka Corporation | Process for the preparation of (2r,3s)-3-amino-1,2-oxirane |
| ATE334121T1 (de) | 1999-01-29 | 2006-08-15 | Kaneka Corp | Verfahren zur herstellung von threo-1,2-epoxy-3- amino-4-phenylbutan-derivaten |
| DK1159278T3 (da) | 1999-02-12 | 2006-04-10 | Vertex Pharma | Inhibitorer af aspartylprotease |
| AR031520A1 (es) | 1999-06-11 | 2003-09-24 | Vertex Pharma | Un compuesto inhibidor de aspartilo proteasa, una composicion que lo comprende y un metodo para tratar un paciente con dicha composicion |
| KR100708221B1 (ko) | 1999-08-31 | 2007-04-17 | 아지노모토 가부시키가이샤 | 에폭사이드 결정의 제조방법 |
| OA12053A (en) | 1999-10-06 | 2006-05-02 | Tibotec Pharm Ltd | HexahydrofuroÄ2,3-bÜfuran-3-yl-N-ä3-Ä(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)aminoÜ-1-benzyl-2-hydroxypropylücarbamate as retroviral protease inhibitor. |
| WO2002060905A2 (en) | 2000-10-24 | 2002-08-08 | Glaxo Group Ltd | METHOD FOR PREPARING HIV PROTEASE INHIBITOR INTERMEDIATES |
| US6764545B2 (en) | 2000-12-12 | 2004-07-20 | Ajinomoto Co., Inc. | Production method of epoxide crystal |
| DE60234952D1 (de) * | 2001-09-10 | 2010-02-11 | Tibotec Pharm Ltd | VERFAHREN ZUR HERSTELLUNG VON HEXAHYDROFUROc2,3-BÜFURAN-3-OL |
| DE60213874T2 (de) | 2001-09-20 | 2007-10-18 | Smithkline Beecham Corp. | Verfahren zur herstellung von protease hemmenden zwischenprodukten |
| DK2767539T3 (en) * | 2002-05-16 | 2017-09-11 | Janssen Sciences Ireland Uc | Pseudopolymorphic forms of an HIV protease inhibitor |
| US20050261507A1 (en) * | 2002-06-27 | 2005-11-24 | Doan Brian D | Preparation of stereoisomers of (3alpha/beta, 6alpha/beta)hexahydrofuro[2,3-b]furan-3-ol |
| WO2004033462A2 (en) | 2002-10-09 | 2004-04-22 | The Board Of Trustees Of The University Of Illinois | METHOD OF PREPARING (3R, 3aS, 6aR) -3- HYDROXYHEXAHYDROFURO [2, 3-b] FURAN AND RELATED COMPOUNDS |
| WO2004060895A1 (ja) | 2002-12-27 | 2004-07-22 | Sumitomo Chemical Company, Limited | ヘキサヒドロフロフラノール誘導体の製造方法、その中間体及びその製造方法 |
| PL1725566T3 (pl) * | 2003-12-23 | 2009-11-30 | Janssen Sciences Ireland Uc | Sposób wytwarzania (1s,2r)-3-[[(4-aminofenylo)sulfonylo](izobutylo)amino]-1-benzylo-2-hydroksypropylokarbaminianu (3r,3as,6ar)-heksahydrofuro-[2,3-b]furan-3-ylu |
| 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 |
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- 2007-11-09 SI SI200730567T patent/SI2089371T1/sl unknown
- 2007-11-09 MX MX2009004957A patent/MX2009004957A/es active IP Right Grant
- 2007-11-09 PL PL07822416T patent/PL2089371T3/pl unknown
- 2007-11-09 BR BRPI0718706A patent/BRPI0718706B8/pt active IP Right Grant
- 2007-11-09 US US12/447,537 patent/US8153829B2/en active Active
- 2007-11-09 CN CN2007800418345A patent/CN101541775B/zh active Active
- 2007-11-09 JP JP2009535738A patent/JP5491862B2/ja active Active
- 2007-11-09 RU RU2009121792/04A patent/RU2464266C2/ru active
- 2007-11-09 PT PT07822416T patent/PT2089371E/pt unknown
- 2007-11-09 WO PCT/EP2007/062119 patent/WO2008055970A2/en active Application Filing
- 2007-11-09 DK DK07822416.9T patent/DK2089371T3/da active
- 2007-11-09 AT AT07822416T patent/ATE497499T1/de active
- 2007-11-09 AU AU2007316562A patent/AU2007316562B2/en active Active
- 2007-11-09 ME MEP-2011-65A patent/ME01232B/me unknown
- 2007-11-09 EP EP07822416A patent/EP2089371B1/en active Active
- 2007-11-09 ES ES07822416T patent/ES2359949T3/es active Active
- 2007-11-09 RS RS20110169A patent/RS51675B/en unknown
- 2007-11-09 CA CA2669014A patent/CA2669014C/en active Active
- 2007-11-09 CN CN201110342987.1A patent/CN102432621B/zh active Active
- 2007-11-09 DE DE602007012365T patent/DE602007012365D1/de active Active
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- 2009-04-21 IL IL198270A patent/IL198270A/en active IP Right Grant
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- 2011-04-11 HR HR20110258T patent/HRP20110258T1/hr unknown
- 2011-05-02 CY CY20111100423T patent/CY1111407T1/el unknown
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