JP2015523337A5 - - Google Patents
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- JP2015523337A5 JP2015523337A5 JP2015514142A JP2015514142A JP2015523337A5 JP 2015523337 A5 JP2015523337 A5 JP 2015523337A5 JP 2015514142 A JP2015514142 A JP 2015514142A JP 2015514142 A JP2015514142 A JP 2015514142A JP 2015523337 A5 JP2015523337 A5 JP 2015523337A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- contacted
- solution
- tms
- acetonitrile
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 23
- 238000000034 method Methods 0.000 claims 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 10
- 239000000243 solution Substances 0.000 claims 10
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 8
- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 claims 6
- VIMMECPCYZXUCI-MIMFYIINSA-N (4s,6r)-6-[(1e)-4,4-bis(4-fluorophenyl)-3-(1-methyltetrazol-5-yl)buta-1,3-dienyl]-4-hydroxyoxan-2-one Chemical compound CN1N=NN=C1C(\C=C\[C@@H]1OC(=O)C[C@@H](O)C1)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VIMMECPCYZXUCI-MIMFYIINSA-N 0.000 claims 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- 229940125782 compound 2 Drugs 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- RWWYLEGWBNMMLJ-YSOARWBDSA-N remdesivir Chemical compound NC1=NC=NN2C1=CC=C2[C@]1([C@@H]([C@@H]([C@H](O1)CO[P@](=O)(OC1=CC=CC=C1)N[C@H](C(=O)OCC(CC)CC)C)O)O)C#N RWWYLEGWBNMMLJ-YSOARWBDSA-N 0.000 claims 6
- 229940126214 compound 3 Drugs 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 4
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 claims 4
- 238000006227 trimethylsilylation reaction Methods 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 claims 3
- VSTXCZGEEVFJES-UHFFFAOYSA-N 1-cycloundecyl-1,5-diazacycloundec-5-ene Chemical compound C1CCCCCC(CCCC1)N1CCCCCC=NCCC1 VSTXCZGEEVFJES-UHFFFAOYSA-N 0.000 claims 2
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 claims 2
- WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical group CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 claims 1
- 239000004367 Lipase Substances 0.000 claims 1
- 102000004882 Lipase Human genes 0.000 claims 1
- 108090001060 Lipase Proteins 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 claims 1
- 235000019421 lipase Nutrition 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261650553P | 2012-05-23 | 2012-05-23 | |
| US61/650,553 | 2012-05-23 | ||
| PCT/US2013/042150 WO2013177243A1 (en) | 2012-05-23 | 2013-05-22 | Sulfilimine and sulphoxide methods for producing festinavir |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015523337A JP2015523337A (ja) | 2015-08-13 |
| JP2015523337A5 true JP2015523337A5 (enExample) | 2016-07-07 |
Family
ID=48534517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015514142A Pending JP2015523337A (ja) | 2012-05-23 | 2013-05-22 | フェスチナビルを製造するためのスルフィリミンおよびスルホキシド方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9249171B2 (enExample) |
| EP (1) | EP2852583A1 (enExample) |
| JP (1) | JP2015523337A (enExample) |
| CN (1) | CN104379571A (enExample) |
| WO (1) | WO2013177243A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014172264A1 (en) | 2013-04-16 | 2014-10-23 | Bristol-Myers Squibb Company | Method for producing festinavir using 5-methyluridine as starting material |
| US20160130260A1 (en) | 2013-06-13 | 2016-05-12 | Bristol-Myers Squibb Company | Tert-butyl sulphoxide method for producing festinavir |
| US10301624B2 (en) | 2014-06-25 | 2019-05-28 | The General Hospital Corporation | Targeting human satellite II (HSATII) |
| WO2020032152A1 (ja) * | 2018-08-09 | 2020-02-13 | ヤマサ醤油株式会社 | ４'－置換ヌクレオシド誘導体の立体選択的合成法 |
| PH12021551734A1 (en) | 2019-01-25 | 2022-07-25 | Univ Brown | Compositions and methods for treating, preventing or reversing age-associated inflammation and disorders |
| IL316425A (en) * | 2022-04-22 | 2024-12-01 | Rome Therapeutics Inc | Dihydro-3'-deoxy-4'-ethynylthymidines and related compounds and their uses in the treatment of medical conditions |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0454193A (ja) * | 1990-05-25 | 1992-02-21 | Japan Tobacco Inc | ２’，３’―ジデオキシ―２’，３’―ジデヒドロ―β―リボヌクレオシドの製造方法 |
| US7589078B2 (en) * | 2003-02-19 | 2009-09-15 | Yale University | Anti-viral nucleoside analogs and methods for treating viral infections, especially HIV infections |
| EP3159351A3 (en) | 2005-09-26 | 2017-05-17 | Gilead Pharmasset LLC | Modified 3'-azido-4'-ethynyl-nucleosides as antiviral agents |
| CA2692460A1 (en) | 2007-06-29 | 2009-01-08 | Korea Research Institute Of Chemical Technology | Hiv reverse transcriptase inhibitors |
| US20090318380A1 (en) | 2007-11-20 | 2009-12-24 | Pharmasset, Inc. | 2',4'-substituted nucleosides as antiviral agents |
| JP5511389B2 (ja) * | 2007-12-27 | 2014-06-04 | オンコリスバイオファーマ株式会社 | ４’−エチニルｄ４Ｔの製造方法 |
| JP5485138B2 (ja) | 2008-03-28 | 2014-05-07 | 浜理薬品工業株式会社 | エチニルチミジン化合物の精製方法 |
| WO2009125841A1 (ja) | 2008-04-10 | 2009-10-15 | 浜理薬品工業株式会社 | ５－メチルウリジンを出発原料とするエチニルチミジン化合物の製造方法 |
| DE102009034346B4 (de) | 2009-07-23 | 2013-01-24 | Kone Corp. | Antriebssystem für eine Personenförderanlage |
| EP2537851B1 (en) | 2010-02-15 | 2015-06-10 | Nissan Chemical Industries, Ltd. | Process for preparation of b-glycoside compounds |
| WO2011099443A1 (ja) * | 2010-02-15 | 2011-08-18 | 日産化学工業株式会社 | β－ジヒドロフラン誘導化合物、β－ジヒドロフラン誘導化合物またはβ－テトラヒドロフラン誘導化合物の製造方法、β－グリコシド化合物、β－グリコシド化合物の製造方法、並びに、４'－エチニルｄ４Ｔ及びその類縁化合物の製造方法 |
-
2013
- 2013-05-22 JP JP2015514142A patent/JP2015523337A/ja active Pending
- 2013-05-22 US US14/402,231 patent/US9249171B2/en active Active
- 2013-05-22 CN CN201380027023.5A patent/CN104379571A/zh active Pending
- 2013-05-22 WO PCT/US2013/042150 patent/WO2013177243A1/en not_active Ceased
- 2013-05-22 EP EP13725545.1A patent/EP2852583A1/en not_active Withdrawn
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