CN104083379A - 闭花木酮Cleistanone的二甲胺衍生物在制备抗鼻炎药物中的应用 - Google Patents
闭花木酮Cleistanone的二甲胺衍生物在制备抗鼻炎药物中的应用 Download PDFInfo
- Publication number
- CN104083379A CN104083379A CN201410291216.8A CN201410291216A CN104083379A CN 104083379 A CN104083379 A CN 104083379A CN 201410291216 A CN201410291216 A CN 201410291216A CN 104083379 A CN104083379 A CN 104083379A
- Authority
- CN
- China
- Prior art keywords
- rhinitis
- muell
- miq
- arg
- derivant
- 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.)
- Granted
Links
- 206010039083 rhinitis Diseases 0.000 title claims abstract description 30
- 239000003814 drug Substances 0.000 title claims abstract description 20
- XURLTFUKDPZAPN-QFIPXVFZSA-N Cleistanone Natural products O(C)[C@H]1OC(=O)c2c(-c3cc4OCOc4cc3)c3c(c(O)c12)cc(OC)c(OC)c3 XURLTFUKDPZAPN-QFIPXVFZSA-N 0.000 title claims description 31
- 238000002360 preparation method Methods 0.000 title abstract description 12
- 229940079593 drug Drugs 0.000 title abstract description 7
- -1 Cleistanone dimethylamine derivative Chemical class 0.000 title 1
- GEIFQLXIDUDMNZ-PCJVTFPHSA-N (4aR,4bR,6aR,8S,10aR,10bR,12R,12aR)-12-hydroxy-1,1,1',1',4a,10a,10b-heptamethyl-3'-methylidenespiro[3,4,4b,5,6,6a,7,9,10,11,12,12a-dodecahydrochrysene-8,2'-cyclopentane]-2-one Chemical class CC1(C)CCC(=C)[C@@]11C[C@@H](CC[C@H]2[C@]3(C[C@@H](O)[C@H]4C(C)(C)C(=O)CC[C@@]42C)C)[C@@]3(C)CC1 GEIFQLXIDUDMNZ-PCJVTFPHSA-N 0.000 claims abstract description 34
- 241000785597 Cleistanthus Species 0.000 claims description 30
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 30
- 150000002576 ketones Chemical class 0.000 claims description 28
- 239000002023 wood Substances 0.000 claims description 28
- 241001597008 Nomeidae Species 0.000 claims description 27
- 108010058846 Ovalbumin Proteins 0.000 claims description 16
- 229940092253 ovalbumin Drugs 0.000 claims description 16
- 229960001340 histamine Drugs 0.000 claims description 15
- 210000003928 nasal cavity Anatomy 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 12
- 230000008728 vascular permeability Effects 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 210000001331 nose Anatomy 0.000 claims description 8
- 239000000427 antigen Substances 0.000 claims description 5
- 102000036639 antigens Human genes 0.000 claims description 5
- 108091007433 antigens Proteins 0.000 claims description 5
- 230000000630 rising effect Effects 0.000 claims 2
- 230000000694 effects Effects 0.000 abstract description 5
- 238000002474 experimental method Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 241000700159 Rattus Species 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 206010039085 Rhinitis allergic Diseases 0.000 description 5
- 201000010105 allergic rhinitis Diseases 0.000 description 5
- 208000035126 Facies Diseases 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 235000002639 sodium chloride Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- XBZYWSMVVKYHQN-MYPRUECHSA-N (4as,6as,6br,8ar,9r,10s,12ar,12br,14bs)-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-9-[(sulfooxy)methyl]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid Chemical compound C1C[C@H](O)[C@@](C)(COS(O)(=O)=O)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C XBZYWSMVVKYHQN-MYPRUECHSA-N 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- ZCVMWBYGMWKGHF-UHFFFAOYSA-N Ketotifene Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 ZCVMWBYGMWKGHF-UHFFFAOYSA-N 0.000 description 1
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 229940124623 antihistamine drug Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 231100000749 chronicity Toxicity 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 229960004958 ketotifen Drugs 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229960002275 pentobarbital sodium Drugs 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- NZHGWWWHIYHZNX-CSKARUKUSA-N tranilast Chemical compound C1=C(OC)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1C(O)=O NZHGWWWHIYHZNX-CSKARUKUSA-N 0.000 description 1
- 229960005342 tranilast Drugs 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Claims (8)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410291216.8A CN104083379B (zh) | 2014-06-25 | 2014-06-25 | 闭花木酮Cleistanone的二甲胺衍生物在制备抗鼻炎药物中的应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410291216.8A CN104083379B (zh) | 2014-06-25 | 2014-06-25 | 闭花木酮Cleistanone的二甲胺衍生物在制备抗鼻炎药物中的应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104083379A true CN104083379A (zh) | 2014-10-08 |
CN104083379B CN104083379B (zh) | 2016-03-16 |
Family
ID=51631209
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410291216.8A Active CN104083379B (zh) | 2014-06-25 | 2014-06-25 | 闭花木酮Cleistanone的二甲胺衍生物在制备抗鼻炎药物中的应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN104083379B (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104814967A (zh) * | 2015-04-15 | 2015-08-05 | 南京广康协生物医药技术有限公司 | 闭花木酮的o-(1h-四氮唑基)乙基衍生物在制备抗鼻炎药物中的应用 |
CN105168222A (zh) * | 2015-07-23 | 2015-12-23 | 南京赋海澳赛医药科技有限公司 | 组合物及其在抗鼻炎药物中的应用 |
CN105343044A (zh) * | 2015-11-09 | 2016-02-24 | 南京广康协生物医药技术有限公司 | 一种组合物及其在抗鼻炎药物中的应用 |
-
2014
- 2014-06-25 CN CN201410291216.8A patent/CN104083379B/zh active Active
Non-Patent Citations (2)
Title |
---|
VAN TRINH THI THANH 等: "Cleistanone: A Triterpenoid from Cleistanthus indochinensis with a New Carbon Skeleton", 《EUROPEAN JOURNAL ORGANIC CHEMISTRY》 * |
刘丹等: "3种五环三萜类化合物及其衍生物抗艾滋病的研究进展", 《中草药》 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104814967A (zh) * | 2015-04-15 | 2015-08-05 | 南京广康协生物医药技术有限公司 | 闭花木酮的o-(1h-四氮唑基)乙基衍生物在制备抗鼻炎药物中的应用 |
CN105168222A (zh) * | 2015-07-23 | 2015-12-23 | 南京赋海澳赛医药科技有限公司 | 组合物及其在抗鼻炎药物中的应用 |
CN105343044A (zh) * | 2015-11-09 | 2016-02-24 | 南京广康协生物医药技术有限公司 | 一种组合物及其在抗鼻炎药物中的应用 |
Also Published As
Publication number | Publication date |
---|---|
CN104083379B (zh) | 2016-03-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104083379B (zh) | 闭花木酮Cleistanone的二甲胺衍生物在制备抗鼻炎药物中的应用 | |
CN104188980A (zh) | 闭花木酮Cleistanone的O-(吗啉基)乙基衍生物、制备方法及其用途 | |
CN104083383B (zh) | 闭花木酮Cleistanone的O-(哌啶基)乙基衍生物在制备抗急性肾衰药物中的应用 | |
CN105287598A (zh) | 一种组合物及其在抗鼻炎药物中的应用 | |
CN104402964B (zh) | 闭花木酮的o-(咪唑基)乙基衍生物、制备方法及其用途 | |
CN104814967A (zh) | 闭花木酮的o-(1h-四氮唑基)乙基衍生物在制备抗鼻炎药物中的应用 | |
CN104825468A (zh) | 闭花木酮的o-(苯并咪唑基)乙基衍生物在制备抗鼻炎药物中的应用 | |
CN105287568A (zh) | 一种组合物及其在抗鼻炎药物中的应用 | |
CN104887662A (zh) | Daphmalenine A衍生物在制备抗鼻炎药物中的应用 | |
CN105343080A (zh) | 组合物及其在抗鼻炎药物中的应用 | |
CN105343044A (zh) | 一种组合物及其在抗鼻炎药物中的应用 | |
CN104095856A (zh) | 闭花木酮Cleistanone的二乙胺衍生物在制备抗急性肾衰药物中的应用 | |
CN104083376B (zh) | 闭花木酮Cleistanone的二甲胺衍生物在制备抗缺氧药物中的应用 | |
CN105250271A (zh) | 一种组合物及其在抗鼻炎药物中的应用 | |
US9266852B2 (en) | Daidzein derivative, pharmaceutically acceptable salt and preparation method thereof, and pharmaceutical composition containing same | |
CN104873506A (zh) | Daphmalenine A的O-(二乙胺基)乙基衍生物在制备抗鼻炎药物中的应用 | |
CN105232535A (zh) | 组合物及其在抗鼻炎药物中的应用 | |
CN105168222A (zh) | 组合物及其在抗鼻炎药物中的应用 | |
CN104188982A (zh) | 闭花木酮Cleistanone的O-(吗啉基)乙基衍生物在制备抗缺氧药物中的应用 | |
CN104188983A (zh) | 闭花木酮Cleistanone的O-(吗啉基)乙基衍生物在制备抗心衰药物中的应用 | |
CN105287557A (zh) | 一种组合物及其在抗鼻炎药物中的应用 | |
CN104434929B (zh) | 闭花木酮的o-(哌嗪基)乙基衍生物在制备抗急性肾衰药物中的应用 | |
CN105343091A (zh) | 组合物及其在抗鼻炎药物中的应用 | |
CN105434413A (zh) | 一种组合物及其在抗鼻炎药物中的应用 | |
CN105055410A (zh) | 组合物16080301030537及其在抗鼻炎药物中的应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C41 | Transfer of patent application or patent right or utility model | ||
CB03 | Change of inventor or designer information |
Inventor after: Yang Hua Inventor after: Fan Wensheng Inventor after: Fan Shanshan Inventor after: Wang Qin Inventor after: Zhuang Yan Inventor after: Guan Enling Inventor before: Luo Dongjun Inventor before: Jiang Chunping Inventor before: Wu Junhua |
|
COR | Change of bibliographic data | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20160217 Address after: 266000 Hainan Island Road, Huangdao District, Shandong, No. 158, No. Applicant after: Yang Hua Address before: Metro Technology Building No. 69 Olympic Avenue in Jianye District of Nanjing city in Jiangsu province 210019 01 5 storey buildings Applicant before: Nanjing Guangkangxie Biomedical Technology Co., Ltd. |
|
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CB03 | Change of inventor or designer information |
Inventor after: Pei Bin Inventor before: Yang Hua Inventor before: Fan Wensheng Inventor before: Fan Shanshan Inventor before: Wang Qin Inventor before: Zhuang Yan Inventor before: Guan Enling |
|
CB03 | Change of inventor or designer information | ||
TR01 | Transfer of patent right |
Effective date of registration: 20170816 Address after: 043600 Shanxi city of Yuncheng province Jiangxian Jiang Ancient Town Street No. 51 Patentee after: Pei Bin Address before: 266000 Hainan Island Road, Huangdao District, Shandong, No. 158, No. Patentee before: Yang Hua |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20180129 Address after: Henan city of Xinyang province Xixian County Zhang Tao Xiang Cao Lin Cun Nan Chen Zhuang group Patentee after: Hou Xiulan Address before: 043600 Shanxi city of Yuncheng province Jiangxian Jiang Ancient Town Street No. 51 Patentee before: Pei Bin |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20180607 Address after: 226000 No. 998 Century Avenue, Nantong high tech Zone, Jiangsu Patentee after: Nantong Xiang Xiang biological medicine technology Co., Ltd. Address before: Henan city of Xinyang province Xixian County Zhang Tao Xiang Cao Lin Cun Nan Chen Zhuang group Patentee before: Hou Xiulan |
|
TR01 | Transfer of patent right |