JP6474392B2 - リン酸オセルタミビル調製用中間体の調製方法 - Google Patents
リン酸オセルタミビル調製用中間体の調製方法 Download PDFInfo
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- JP6474392B2 JP6474392B2 JP2016520012A JP2016520012A JP6474392B2 JP 6474392 B2 JP6474392 B2 JP 6474392B2 JP 2016520012 A JP2016520012 A JP 2016520012A JP 2016520012 A JP2016520012 A JP 2016520012A JP 6474392 B2 JP6474392 B2 JP 6474392B2
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- VSZGPKBBMSAYNT-RRFJBIMHSA-N oseltamivir Chemical compound CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1 VSZGPKBBMSAYNT-RRFJBIMHSA-N 0.000 title claims description 28
- 229960002194 oseltamivir phosphate Drugs 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 40
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- 238000006243 chemical reaction Methods 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 21
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- 238000003756 stirring Methods 0.000 claims description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 12
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims description 7
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- JAKPEUADUJGESF-YFKTTZPYSA-N tert-butyl N-[(1R,2R,3S,6S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-7-oxabicyclo[4.1.0]heptan-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H]1CC[C@@H]2O[C@@H]2[C@@H]1NC(=O)OC(C)(C)C JAKPEUADUJGESF-YFKTTZPYSA-N 0.000 description 15
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- -1 3-pentylidene Chemical group 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- LHCQMIOUNMKJTE-PMACEKPBSA-N (3aR,8aS)-1,3-dibenzyl-3a,4,6,7,8,8a-hexahydrothiepino[3,4-d]imidazol-2-one Chemical compound C(C1=CC=CC=C1)N1C(N([C@@H]2[C@@H]1CCCSC2)CC1=CC=CC=C1)=O LHCQMIOUNMKJTE-PMACEKPBSA-N 0.000 description 7
- PKUDNKKEEBTESO-PMACEKPBSA-N (3aR,8aS)-1,3-dibenzyl-5,5-dioxo-3a,4,6,7,8,8a-hexahydrothiepino[3,4-d]imidazol-2-one Chemical compound C(C1=CC=CC=C1)N1C(N([C@@H]2[C@@H]1CCCS(C2)(=O)=O)CC1=CC=CC=C1)=O PKUDNKKEEBTESO-PMACEKPBSA-N 0.000 description 7
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- JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 description 6
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- LUIKWJSAVNSSNH-UHFFFAOYSA-N 2h-imidazo[4,5-d][1,3]thiazole 1-oxide Chemical compound N1=CN=C2S(=O)CN=C21 LUIKWJSAVNSSNH-UHFFFAOYSA-N 0.000 description 4
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- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- QPLGKBMWKLWTHG-UHFFFAOYSA-N 3-pentan-3-yloxypentane Chemical compound CCC(CC)OC(CC)CC QPLGKBMWKLWTHG-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- 238000006027 Birch reduction reaction Methods 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
- 238000006646 Dess-Martin oxidation reaction Methods 0.000 description 1
- 238000006228 Dieckmann condensation reaction Methods 0.000 description 1
- 229940126656 GS-4224 Drugs 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- IFQSXNOEEPCSLW-DKWTVANSSA-N L-cysteine hydrochloride Chemical compound Cl.SC[C@H](N)C(O)=O IFQSXNOEEPCSLW-DKWTVANSSA-N 0.000 description 1
- QIJRTFXNRTXDIP-JIZZDEOASA-N L-cysteine hydrochloride hydrate Chemical compound O.Cl.SC[C@H](N)C(O)=O QIJRTFXNRTXDIP-JIZZDEOASA-N 0.000 description 1
- DZLNHFMRPBPULJ-VKHMYHEASA-N L-thioproline Chemical compound OC(=O)[C@@H]1CSCN1 DZLNHFMRPBPULJ-VKHMYHEASA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- 102000018697 Membrane Proteins Human genes 0.000 description 1
- 108010052285 Membrane Proteins Proteins 0.000 description 1
- XTOKJOTZISCFFS-UHFFFAOYSA-N N1=CN=C2S(=O)C(O)N=C21 Chemical compound N1=CN=C2S(=O)C(O)N=C21 XTOKJOTZISCFFS-UHFFFAOYSA-N 0.000 description 1
- 241000712464 Orthomyxoviridae Species 0.000 description 1
- 238000010472 Ramberg-Bäcklund reaction Methods 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000007247 aza-Henry reaction Methods 0.000 description 1
- 150000001541 aziridines Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 150000001925 cycloalkenes Chemical group 0.000 description 1
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- YWWZCHLUQSHMCL-UHFFFAOYSA-N diphenyl diselenide Chemical compound C=1C=CC=CC=1[Se][Se]C1=CC=CC=C1 YWWZCHLUQSHMCL-UHFFFAOYSA-N 0.000 description 1
- 229940042406 direct acting antivirals neuraminidase inhibitors Drugs 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 241001493065 dsRNA viruses Species 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 230000009456 molecular mechanism Effects 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 229940061374 relenza Drugs 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 239000002911 sialidase inhibitor Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229960001028 zanamivir Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/36—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing at least two amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN2956/DEL/2013 | 2013-10-04 | ||
| IN2956DE2013 IN2013DE02956A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2013-10-04 | 2014-10-07 | |
| PCT/IN2014/000645 WO2015049700A1 (en) | 2013-10-04 | 2014-10-07 | A process for the preparation of intermediate for the preparation of oseltamivir phosphate |
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| Publication Number | Publication Date |
|---|---|
| JP2016537315A JP2016537315A (ja) | 2016-12-01 |
| JP6474392B2 true JP6474392B2 (ja) | 2019-02-27 |
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| JP2016520012A Expired - Fee Related JP6474392B2 (ja) | 2013-10-04 | 2014-10-07 | リン酸オセルタミビル調製用中間体の調製方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110506045B (zh) * | 2017-04-12 | 2023-01-13 | 帝斯曼知识产权资产管理有限公司 | 制备咪唑并噻唑酮化合物的方法 |
| CN109890790B (zh) * | 2017-06-20 | 2020-04-21 | 广东东阳光药业有限公司 | 一种奥司他韦及其异构体的制备方法 |
| US10385010B1 (en) * | 2018-03-28 | 2019-08-20 | Georgia State University Research Foundation, Inc. | Expedient synthesis of oseltamivir and related compounds via direct olefin diazidation-diamidation reaction |
| CN111349059B (zh) * | 2018-12-20 | 2023-03-31 | 中国科学院上海药物研究所 | 一类手性环氧化合物的制备方法 |
| CN113307744A (zh) * | 2021-05-29 | 2021-08-27 | 弘健制药(上海)有限公司 | 一种磷酸奥司他韦的制备方法 |
| CN114478290A (zh) * | 2022-01-24 | 2022-05-13 | 广东中润药物研发有限公司 | 奥司他韦中间体的合成方法 |
| CN116396306A (zh) * | 2023-04-13 | 2023-07-07 | 华东理工大学 | 一种d-生物素关键中间体硫内酯的制备方法 |
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| US6486328B1 (en) * | 2000-10-12 | 2002-11-26 | Council Of Scientific And Industrial Research | Substituted 2-[-6-benzyl-5-oxo-3-phenyl-(3s,7s, 7aR)-perhydroimidazol[1,5-c][1,3]thiazol-7yl] compounds |
| JPWO2007099843A1 (ja) | 2006-02-23 | 2009-07-16 | 国立大学法人 東京大学 | α，β−不飽和シクロヘキサノン誘導体及びその製造方法、並びにその中間体の製造方法 |
| JP2008081489A (ja) | 2006-08-31 | 2008-04-10 | Univ Of Tokyo | 環状ウレタン化合物及びその製造方法 |
-
2014
- 2014-10-07 IN IN2956DE2013 patent/IN2013DE02956A/en unknown
- 2014-10-07 EP EP14811991.0A patent/EP3052473B1/en not_active Not-in-force
- 2014-10-07 WO PCT/IN2014/000645 patent/WO2015049700A1/en active Application Filing
- 2014-10-07 US US15/026,376 patent/US9522922B2/en not_active Expired - Fee Related
- 2014-10-07 JP JP2016520012A patent/JP6474392B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20160222029A1 (en) | 2016-08-04 |
| EP3052473B1 (en) | 2018-01-17 |
| WO2015049700A1 (en) | 2015-04-09 |
| IN2013DE02956A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2015-04-10 |
| JP2016537315A (ja) | 2016-12-01 |
| EP3052473A1 (en) | 2016-08-10 |
| US9522922B2 (en) | 2016-12-20 |
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