CN104262255A - 一种不对称催化合成γ-硝基吡唑酰胺化合物的方法 - Google Patents
一种不对称催化合成γ-硝基吡唑酰胺化合物的方法 Download PDFInfo
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- CN104262255A CN104262255A CN201410486209.3A CN201410486209A CN104262255A CN 104262255 A CN104262255 A CN 104262255A CN 201410486209 A CN201410486209 A CN 201410486209A CN 104262255 A CN104262255 A CN 104262255A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
- C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/50—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
- C07C205/53—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
- C07D231/16—Halogen atoms or nitro radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
序号 | R,R1,R2,R3 | 收率(%) | 对映选择性(%ee) |
1 | H,C6H5,CH3,H | 99 | 99 |
2 | H,4-FC6H4,CH3,H | 99 | 99 |
3 | H,4-ClC6H4,CH3,H | 98 | 98 |
4 | H,4-BrC6H4,CH3,H | 96 | 98 |
5 | H,4-MeC6H4,CH3,H | 95 | 99 |
6 | H,4-MeOC6H4,CH3,H | 89 | 99 |
7 | H,3-BrC6H4,CH3,H | 98 | 98 |
8 | H,3-MeC6H4,CH3,H | 96 | 99 |
9 | H,2-BrC6H4,CH3,H | 99 | 99 |
10 | H,2-MeOC6H4,CH3,H | 99 | 99 |
11 | H,3,4–Cl2C6H3,CH3,H | 96 | 99 |
12 | H,3,4-(MeO)2C6H3,CH3,H | 83 | 99 |
13 | H,2-Furyl,CH3,H | 56 | 97 |
14 | H,2-Thienyl,CH3,H | 58 | 98 |
15 | H,CH3,CH3,H | 69 | 98 |
16 | H,Pr,CH3,H | 87 | 98 |
17 | H,Pent,CH3,H | 65 | 98 |
18 | H,iBu,CH3,H | 77 | 98 |
19 | H,EtO,CH3,H | 53 | 95 |
20 | H,EtOOC,CH3,H | 67 | 95 |
21 | H,4-ClC6H4,CH3,Cl | 94 | 99 |
22 | H,4-ClC6H4,CH3,Br | 96 | 99 |
23 | H,4-ClC6H4,CH3,I | 97 | 99 |
24 | H,4-ClC6H4,C6H5,H | 39 | 81 |
25 | CH3,4-ClC6H4,CH3,H | 94 | 98/98(d.r.1.6/1) |
26 | Et,4-ClC6H4,CH3,H | 87 | 99/98(d.r.1.2/1) |
27 | PhCH2,4-ClC6H4,CH3,H | 98 | 99/98(d.r.1.1/1) |
Claims (11)
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410486209.3A CN104262255A (zh) | 2014-09-22 | 2014-09-22 | 一种不对称催化合成γ-硝基吡唑酰胺化合物的方法 |
CN201510075076.5A CN105985292B (zh) | 2014-09-22 | 2015-02-12 | 一种不对称催化合成γ-硝基吡唑酰胺化合物的方法 |
CN201510291876.0A CN105418502B (zh) | 2014-09-22 | 2015-06-01 | 一种用于合成帕罗西汀的中间体及其制备方法和用途 |
EP15844037.0A EP3199525A4 (en) | 2014-09-22 | 2015-06-12 | Method for asymmetrically catalyzed synthesis of nitropyrazole amide compound |
JP2017512956A JP2017530956A (ja) | 2014-09-22 | 2015-06-12 | ニトロピラゾールアミド化合物の不斉触媒合成方法 |
US15/511,243 US10464899B2 (en) | 2014-09-22 | 2015-06-12 | Asymmetrically catalyzed synthesis method of nitropyrazole amide compound |
PCT/CN2015/081341 WO2016045415A1 (zh) | 2014-09-22 | 2015-06-12 | 一种不对称催化合成硝基吡唑酰胺化合物的方法 |
US15/511,244 US9796675B1 (en) | 2014-09-22 | 2015-06-15 | Intermediate for synthesizing paroxetine, method for preparing the same, and uses thereof |
EP15844676.5A EP3199526A4 (en) | 2014-09-22 | 2015-06-15 | Intermediate for use in synthesizing paroxetine, preparation method for the intermediate, and uses thereof |
PCT/CN2015/081422 WO2016045416A1 (zh) | 2014-09-22 | 2015-06-15 | 一种用于合成帕罗西汀的中间体及其制备方法和用途 |
JP2017513185A JP2017529343A (ja) | 2014-09-22 | 2015-06-15 | パロキセチンを合成するための中間体およびその製造方法と用途 |
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CN201410486209.3A CN104262255A (zh) | 2014-09-22 | 2014-09-22 | 一种不对称催化合成γ-硝基吡唑酰胺化合物的方法 |
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CN201410486209.3A Pending CN104262255A (zh) | 2014-09-22 | 2014-09-22 | 一种不对称催化合成γ-硝基吡唑酰胺化合物的方法 |
CN201510075076.5A Active CN105985292B (zh) | 2014-09-22 | 2015-02-12 | 一种不对称催化合成γ-硝基吡唑酰胺化合物的方法 |
CN201510291876.0A Active CN105418502B (zh) | 2014-09-22 | 2015-06-01 | 一种用于合成帕罗西汀的中间体及其制备方法和用途 |
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CN201510075076.5A Active CN105985292B (zh) | 2014-09-22 | 2015-02-12 | 一种不对称催化合成γ-硝基吡唑酰胺化合物的方法 |
CN201510291876.0A Active CN105418502B (zh) | 2014-09-22 | 2015-06-01 | 一种用于合成帕罗西汀的中间体及其制备方法和用途 |
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US (2) | US10464899B2 (zh) |
EP (2) | EP3199525A4 (zh) |
JP (2) | JP2017530956A (zh) |
CN (3) | CN104262255A (zh) |
WO (1) | WO2016045416A1 (zh) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016045415A1 (zh) * | 2014-09-22 | 2016-03-31 | 浙江九洲药业股份有限公司 | 一种不对称催化合成硝基吡唑酰胺化合物的方法 |
WO2016045416A1 (zh) * | 2014-09-22 | 2016-03-31 | 浙江九洲药业股份有限公司 | 一种用于合成帕罗西汀的中间体及其制备方法和用途 |
CN106748949A (zh) * | 2017-01-13 | 2017-05-31 | 厦门大学 | 一种合成α,β不饱和酰胺化合物的方法 |
CN112876328A (zh) * | 2021-01-15 | 2021-06-01 | 四川大学 | 一种不对称催化合成γ-氰基酰胺化合物及采用该化合物手性药物的方法 |
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DE3680184D1 (de) * | 1985-08-10 | 1991-08-14 | Beecham Group Plc | Verfahren zur herstellung von arylpiperidincarbinol. |
WO2009005647A2 (en) * | 2007-06-27 | 2009-01-08 | Bioverdant, Inc. | Compounds and process to prepare chiral intermediates for synthesis of paroxetine |
CN102531825B (zh) * | 2010-12-29 | 2014-04-23 | 中国科学院大连化学物理研究所 | 一种促进丙烷转化制芳烃的方法 |
CN102531815B (zh) * | 2011-12-22 | 2014-04-16 | 四川大学 | 一种不对称催化α,β-不饱和羰基化合物环氧化反应方法 |
CN104262255A (zh) * | 2014-09-22 | 2015-01-07 | 四川大学 | 一种不对称催化合成γ-硝基吡唑酰胺化合物的方法 |
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2014
- 2014-09-22 CN CN201410486209.3A patent/CN104262255A/zh active Pending
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2015
- 2015-02-12 CN CN201510075076.5A patent/CN105985292B/zh active Active
- 2015-06-01 CN CN201510291876.0A patent/CN105418502B/zh active Active
- 2015-06-12 EP EP15844037.0A patent/EP3199525A4/en not_active Withdrawn
- 2015-06-12 US US15/511,243 patent/US10464899B2/en active Active
- 2015-06-12 JP JP2017512956A patent/JP2017530956A/ja active Pending
- 2015-06-15 JP JP2017513185A patent/JP2017529343A/ja active Pending
- 2015-06-15 EP EP15844676.5A patent/EP3199526A4/en not_active Withdrawn
- 2015-06-15 US US15/511,244 patent/US9796675B1/en active Active
- 2015-06-15 WO PCT/CN2015/081422 patent/WO2016045416A1/zh active Application Filing
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016045415A1 (zh) * | 2014-09-22 | 2016-03-31 | 浙江九洲药业股份有限公司 | 一种不对称催化合成硝基吡唑酰胺化合物的方法 |
WO2016045416A1 (zh) * | 2014-09-22 | 2016-03-31 | 浙江九洲药业股份有限公司 | 一种用于合成帕罗西汀的中间体及其制备方法和用途 |
CN105985292A (zh) * | 2014-09-22 | 2016-10-05 | 浙江九洲药业股份有限公司 | 一种不对称催化合成γ-硝基吡唑酰胺化合物的方法 |
JP2017529343A (ja) * | 2014-09-22 | 2017-10-05 | 浙江九洲▲藥▼▲業▼股▲ふぇん▼有限公司Zhejiang Jiuzhou Pharmaceutical Co., Ltd. | パロキセチンを合成するための中間体およびその製造方法と用途 |
CN105985292B (zh) * | 2014-09-22 | 2019-05-10 | 浙江九洲药业股份有限公司 | 一种不对称催化合成γ-硝基吡唑酰胺化合物的方法 |
CN106748949A (zh) * | 2017-01-13 | 2017-05-31 | 厦门大学 | 一种合成α,β不饱和酰胺化合物的方法 |
CN106748949B (zh) * | 2017-01-13 | 2019-04-09 | 厦门大学 | 一种合成α,β不饱和酰胺化合物的方法 |
CN112876328A (zh) * | 2021-01-15 | 2021-06-01 | 四川大学 | 一种不对称催化合成γ-氰基酰胺化合物及采用该化合物手性药物的方法 |
Also Published As
Publication number | Publication date |
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CN105418502B (zh) | 2018-12-14 |
US20170291876A1 (en) | 2017-10-12 |
JP2017530956A (ja) | 2017-10-19 |
EP3199526A4 (en) | 2018-02-14 |
EP3199526A1 (en) | 2017-08-02 |
EP3199525A4 (en) | 2018-02-14 |
US20170283380A1 (en) | 2017-10-05 |
CN105985292A (zh) | 2016-10-05 |
WO2016045416A1 (zh) | 2016-03-31 |
US9796675B1 (en) | 2017-10-24 |
CN105418502A (zh) | 2016-03-23 |
US10464899B2 (en) | 2019-11-05 |
EP3199525A1 (en) | 2017-08-02 |
JP2017529343A (ja) | 2017-10-05 |
CN105985292B (zh) | 2019-05-10 |
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Effective date of registration: 20150129 Address after: Jiaojiang District of Taizhou City, Zhejiang province 318000 road outside No. 99 Applicant after: Jiuzhou Pharmaceutical Co., Ltd., Zhejiang Address before: 610065 Wuhou District, Chengdu, South Ring Road, No. 1, No. 1, Sichuan Applicant before: Sichuan University |
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C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20150107 |