CN107365248A - 二氟甲氧基取代的二苯乙烷及反式二苯乙烯衍生物及其制备方法和应用 - Google Patents
二氟甲氧基取代的二苯乙烷及反式二苯乙烯衍生物及其制备方法和应用 Download PDFInfo
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- DWRVHDWKWKFSAI-UHFFFAOYSA-N methyl 3,4-difluorobenzoate Chemical compound COC(=O)C1=CC=C(F)C(F)=C1 DWRVHDWKWKFSAI-UHFFFAOYSA-N 0.000 description 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 238000003032 molecular docking Methods 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 208000017708 myomatous neoplasm Diseases 0.000 description 1
- 208000009091 myxoma Diseases 0.000 description 1
- 208000014761 nasopharyngeal type undifferentiated carcinoma Diseases 0.000 description 1
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- 210000005036 nerve Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
化合物编号 | IC50(μmol/L) |
CA-4 | 0.27 |
VIa-Z | 0.24 |
VIa-E | 0.069 |
Ia | 0.19 |
VIb-Z | 0.53 |
VIb-E | 0.26 |
Ib | 0.18 |
VIc-Z | 0.12 |
VIc-E | 0.60 |
Ic | 0.13 |
Id | 0.11 |
Ie | 0.07 |
Claims (8)
Priority Applications (4)
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CN201710610751.9A CN107365248A (zh) | 2017-07-25 | 2017-07-25 | 二氟甲氧基取代的二苯乙烷及反式二苯乙烯衍生物及其制备方法和应用 |
PCT/CN2018/096836 WO2019020016A1 (zh) | 2017-07-25 | 2018-07-24 | 一种ca-4类抗肿瘤药物、合成方法及其应用 |
PCT/CN2018/096862 WO2019020026A1 (zh) | 2017-07-25 | 2018-07-24 | 二氟甲氧基取代的二苯乙烷及反式二苯乙烯衍生物及其制备方法和应用 |
US16/638,355 US20200163913A1 (en) | 2017-07-25 | 2018-07-24 | CA-4 Antitumour Drug, Synthesis Method and Use Thereof |
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Country Status (2)
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WO (1) | WO2019020026A1 (zh) |
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WO2019020026A1 (zh) * | 2017-07-25 | 2019-01-31 | 上海华理生物医药股份有限公司 | 二氟甲氧基取代的二苯乙烷及反式二苯乙烯衍生物及其制备方法和应用 |
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GB202002417D0 (en) * | 2020-02-21 | 2020-04-08 | Johnson Matthey Plc | Process |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101085743A (zh) * | 2006-06-06 | 2007-12-12 | 浙江大德药业集团有限公司 | 含氟烷氧基康普立停衍生物及制法和用途 |
CN104470924A (zh) * | 2012-07-13 | 2015-03-25 | Ucb生物制药私人有限公司 | 作为tnf活性调节剂的咪唑并吡嗪衍生物 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101723813A (zh) * | 2008-10-15 | 2010-06-09 | 上海华理生物医药有限公司 | 一种乙氧基二苯乙烷衍生物及其制备方法和用途 |
CN103012248B (zh) * | 2013-01-11 | 2014-11-05 | 浙江大德药业集团有限公司 | 氨基康普立停衍生物的合成及其作为口服抗肿瘤药物的应用 |
CN107021980B (zh) * | 2016-04-25 | 2019-04-19 | 上海华理生物医药股份有限公司 | 一种二苯乙烯和二苯乙烷类化合物的磷酰氨基酸及其衍生物的制备与用途 |
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CN107365248A (zh) * | 2017-07-25 | 2017-11-21 | 上海应用技术大学 | 二氟甲氧基取代的二苯乙烷及反式二苯乙烯衍生物及其制备方法和应用 |
CN108101795A (zh) * | 2017-12-25 | 2018-06-01 | 上海应用技术大学 | 一种氨基取代的二苯乙烯衍生物及其制备方法和应用 |
-
2017
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101085743A (zh) * | 2006-06-06 | 2007-12-12 | 浙江大德药业集团有限公司 | 含氟烷氧基康普立停衍生物及制法和用途 |
CN104470924A (zh) * | 2012-07-13 | 2015-03-25 | Ucb生物制药私人有限公司 | 作为tnf活性调节剂的咪唑并吡嗪衍生物 |
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Effective date of registration: 20180627 Address after: 200231 room 319, block A, 1305 lane, 1305 Huajing Road, Xuhui District, Shanghai. Applicant after: SHANGHAI HUALI BIOMEDICAL Co.,Ltd. Address before: 200235 Caobao Road, Xuhui District, Shanghai, No. 120-121 Applicant before: Shanghai Institute of Technology Applicant before: SHANGHAI HUALI BIOMEDICAL Co.,Ltd. |
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Application publication date: 20171121 |