CN104447775A - 一种新的生物碱类化合物、药物组合物和其医药用途 - Google Patents
一种新的生物碱类化合物、药物组合物和其医药用途 Download PDFInfo
- Publication number
- CN104447775A CN104447775A CN201410811159.1A CN201410811159A CN104447775A CN 104447775 A CN104447775 A CN 104447775A CN 201410811159 A CN201410811159 A CN 201410811159A CN 104447775 A CN104447775 A CN 104447775A
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- CN
- China
- Prior art keywords
- ethyl acetate
- hexane
- compound
- extract
- acid
- 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
- 229930013930 alkaloid Natural products 0.000 title claims abstract description 29
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
- -1 alkaloid compound Chemical class 0.000 title description 9
- 229940125904 compound 1 Drugs 0.000 claims abstract description 28
- 239000008280 blood Substances 0.000 claims abstract description 23
- 210000004369 blood Anatomy 0.000 claims abstract description 22
- 238000002360 preparation method Methods 0.000 claims abstract description 20
- 150000003797 alkaloid derivatives Chemical class 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 241001671204 Stemona Species 0.000 claims abstract description 14
- 239000003814 drug Substances 0.000 claims abstract description 12
- 201000010099 disease Diseases 0.000 claims abstract description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
- 239000003937 drug carrier Substances 0.000 claims abstract description 6
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 claims description 30
- 238000010828 elution Methods 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 20
- 239000002024 ethyl acetate extract Substances 0.000 claims description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000287 crude extract Substances 0.000 claims description 10
- 230000006837 decompression Effects 0.000 claims description 10
- 238000011084 recovery Methods 0.000 claims description 10
- 239000000741 silica gel Substances 0.000 claims description 10
- 229910002027 silica gel Inorganic materials 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 9
- 239000000284 extract Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 claims description 5
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
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- 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 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 6
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- 241000283973 Oryctolagus cuniculus Species 0.000 description 7
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- 102000008946 Fibrinogen Human genes 0.000 description 3
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- 238000011534 incubation Methods 0.000 description 3
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- UINUUSQOLRQGNF-KLDYRVGWSA-N stemoninine Chemical class C([C@H]1[C@H]2N3CCC[C@@H]4[C@@H]([C@@H]3CC2)[C@@H]([C@@]2(C=C(C)C(=O)O2)O4)CC)[C@H](C)C(=O)O1 UINUUSQOLRQGNF-KLDYRVGWSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000517307 Pediculus humanus Species 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 1
- JGSARLDLIJGVTE-UHFFFAOYSA-N 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-UHFFFAOYSA-N 0.000 description 1
- 206010053567 Coagulopathies Diseases 0.000 description 1
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- 208000008350 Pruritus Vulvae Diseases 0.000 description 1
- 241001671203 Stemona japonica Species 0.000 description 1
- 241000417534 Stemona sessilifolia Species 0.000 description 1
- 241000411860 Stemona tuberosa Species 0.000 description 1
- POQHFALZNYMCBA-UHFFFAOYSA-N Stemonine Natural products CCC1C2C3CCC(C4CC(C)C(=O)O4)N3CCC(=O)C2OC15OC(=O)C(=C5)C POQHFALZNYMCBA-UHFFFAOYSA-N 0.000 description 1
- GYOGHROCTSEKDY-UHFFFAOYSA-N Tuberostemonine J Natural products C12N3CCCCC1C(CC)C1OC(=O)C(C)C1C2CC3C1CC(C)C(=O)O1 GYOGHROCTSEKDY-UHFFFAOYSA-N 0.000 description 1
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- 230000036772 blood pressure Effects 0.000 description 1
- 238000010241 blood sampling Methods 0.000 description 1
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- 230000002708 enhancing effect Effects 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 1
- 238000005570 heteronuclear single quantum coherence Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 239000002297 parasiticide Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
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- 210000002966 serum Anatomy 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- UINUUSQOLRQGNF-UHFFFAOYSA-N stemonine Chemical compound O1C2(C=C(C)C(=O)O2)C(CC)C(C2CC3)C1CCCN2C3C1CC(C)C(=O)O1 UINUUSQOLRQGNF-UHFFFAOYSA-N 0.000 description 1
- HTLBMAZNGBFLEY-UHFFFAOYSA-N stemonine-C17 Natural products O1C(=O)C(C)CC1C1N2CCCC3OC(=O)C(C)C3C2CC1 HTLBMAZNGBFLEY-UHFFFAOYSA-N 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
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- 238000010998 test method Methods 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/16—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (7)
Priority Applications (1)
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CN201410811159.1A CN104447775B (zh) | 2014-12-22 | 2014-12-22 | 一种新的生物碱类化合物、药物组合物和其医药用途 |
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CN201410811159.1A CN104447775B (zh) | 2014-12-22 | 2014-12-22 | 一种新的生物碱类化合物、药物组合物和其医药用途 |
Publications (2)
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CN104447775A true CN104447775A (zh) | 2015-03-25 |
CN104447775B CN104447775B (zh) | 2016-08-17 |
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CN201410811159.1A Expired - Fee Related CN104447775B (zh) | 2014-12-22 | 2014-12-22 | 一种新的生物碱类化合物、药物组合物和其医药用途 |
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CN (1) | CN104447775B (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104387400A (zh) * | 2014-12-06 | 2015-03-04 | 西宁意格知识产权咨询服务有限公司 | 黄皮中一种新的咔唑生物碱、其制备方法与用途 |
CN104387352A (zh) * | 2014-11-20 | 2015-03-04 | 西宁意格知识产权咨询服务有限公司 | 一种新的倍半萜类化合物、制备方法及其医药用途 |
CN108864123A (zh) * | 2018-07-11 | 2018-11-23 | 山西大学 | 一种百部生物碱的合成方法 |
-
2014
- 2014-12-22 CN CN201410811159.1A patent/CN104447775B/zh not_active Expired - Fee Related
Non-Patent Citations (2)
Title |
---|
李琳等: "直立百部中生物碱的研究现状", 《浙江化工》, vol. 40, no. 3, 31 December 2009 (2009-12-31), pages 17 - 22 * |
邹长英等: "蔓生百部中新生物碱的结构研究", 《山西职工医学院学报》, vol. 10, no. 3, 30 September 2000 (2000-09-30), pages 1 - 3 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104387352A (zh) * | 2014-11-20 | 2015-03-04 | 西宁意格知识产权咨询服务有限公司 | 一种新的倍半萜类化合物、制备方法及其医药用途 |
CN104387400A (zh) * | 2014-12-06 | 2015-03-04 | 西宁意格知识产权咨询服务有限公司 | 黄皮中一种新的咔唑生物碱、其制备方法与用途 |
CN108864123A (zh) * | 2018-07-11 | 2018-11-23 | 山西大学 | 一种百部生物碱的合成方法 |
Also Published As
Publication number | Publication date |
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CN104447775B (zh) | 2016-08-17 |
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Inventor after: Shi Peiqing Inventor before: Hu Wenjie |
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Effective date of registration: 20160705 Address after: 276600 Junan County People's Hospital, 156 Tianqiao Road, Junan, Shandong, Linyi Applicant after: Shi Peiqing Address before: 255400 Shandong City, Zibo province Linzi District, east of the living area of the warriors, building 3, unit 109, 202 Applicant before: Hu Wenjie |
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