CN1345728A - Solasodine hydrochlorate and productive method and application in medicine - Google Patents
Solasodine hydrochlorate and productive method and application in medicine Download PDFInfo
- Publication number
- CN1345728A CN1345728A CN 00129122 CN00129122A CN1345728A CN 1345728 A CN1345728 A CN 1345728A CN 00129122 CN00129122 CN 00129122 CN 00129122 A CN00129122 A CN 00129122A CN 1345728 A CN1345728 A CN 1345728A
- Authority
- CN
- China
- Prior art keywords
- ethanol
- hydrochloride
- crystallization
- solasodine
- alcohol
- 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
- 239000003814 drug Substances 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims description 11
- KWVISVAMQJWJSZ-VKROHFNGSA-N solasodine Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CN1 KWVISVAMQJWJSZ-VKROHFNGSA-N 0.000 title description 13
- JXWLYDNHVXFBJA-UHFFFAOYSA-N solasodine Natural products CC1CCC2(NC1)NC3CC4C5CC=C6CC(O)CCC6(C)C5CCC4(C)C3C2C JXWLYDNHVXFBJA-UHFFFAOYSA-N 0.000 title description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 28
- 238000002347 injection Methods 0.000 claims abstract description 14
- 239000007924 injection Substances 0.000 claims abstract description 14
- 208000006673 asthma Diseases 0.000 claims abstract description 10
- -1 compound solasodine hydrochloride Chemical class 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 92
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 78
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 42
- 238000002425 crystallisation Methods 0.000 claims description 40
- 230000008025 crystallization Effects 0.000 claims description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 240000002307 Solanum ptychanthum Species 0.000 claims description 18
- 235000002594 Solanum nigrum Nutrition 0.000 claims description 17
- 229930013930 alkaloid Natural products 0.000 claims description 15
- 235000015203 fruit juice Nutrition 0.000 claims description 13
- 239000006228 supernatant Substances 0.000 claims description 11
- 238000001816 cooling Methods 0.000 claims description 9
- 244000061458 Solanum melongena Species 0.000 claims description 8
- 235000002597 Solanum melongena Nutrition 0.000 claims description 8
- 230000001093 anti-cancer Effects 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 7
- 235000021559 Fruit Juice Concentrate Nutrition 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- 238000007670 refining Methods 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 235000013399 edible fruits Nutrition 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 3
- 230000006837 decompression Effects 0.000 claims description 3
- 239000003480 eluent Substances 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 239000000084 colloidal system Substances 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 230000001741 anti-phlogistic effect Effects 0.000 claims 1
- 238000013375 chromatographic separation Methods 0.000 claims 1
- 235000019628 coolness Nutrition 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 abstract description 3
- 206010028980 Neoplasm Diseases 0.000 abstract description 3
- 230000004054 inflammatory process Effects 0.000 abstract description 3
- 201000011510 cancer Diseases 0.000 abstract 1
- 239000002552 dosage form Substances 0.000 abstract 1
- GSRSOTGLOHUAGA-XBODYBRHSA-N solasodine hydrochloride Chemical compound Cl.O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CN1 GSRSOTGLOHUAGA-XBODYBRHSA-N 0.000 description 53
- 230000000694 effects Effects 0.000 description 17
- 239000007788 liquid Substances 0.000 description 16
- 230000003110 anti-inflammatory effect Effects 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 239000002775 capsule Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000004062 sedimentation Methods 0.000 description 6
- 206010006187 Breast cancer Diseases 0.000 description 4
- 208000026310 Breast neoplasm Diseases 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 4
- 201000007100 Pharyngitis Diseases 0.000 description 4
- 206010035664 Pneumonia Diseases 0.000 description 4
- QCTMYNGDIBTNSK-UHFFFAOYSA-N Solasonin Natural products O1C2(NCC(C)CC2)C(C)C(C2(CCC3C4(C)CC5)C)C1CC2C3CC=C4CC5OC(C1OC2C(C(O)C(O)C(C)O2)O)OC(CO)C(O)C1OC1OC(CO)C(O)C(O)C1O QCTMYNGDIBTNSK-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 230000001088 anti-asthma Effects 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- 238000002386 leaching Methods 0.000 description 4
- 201000007270 liver cancer Diseases 0.000 description 4
- 208000014018 liver neoplasm Diseases 0.000 description 4
- 201000005202 lung cancer Diseases 0.000 description 4
- 208000020816 lung neoplasm Diseases 0.000 description 4
- 208000008128 pulmonary tuberculosis Diseases 0.000 description 4
- 206010044008 tonsillitis Diseases 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- QCTMYNGDIBTNSK-XEAAVONHSA-N α-Solamarine Chemical group O([C@H]1[C@@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@H](O)[C@@H](O)[C@H](C)O1)O)O[C@@H]1CC2=CC[C@H]3[C@@H]4C[C@H]5[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@@H]([C@]1(NC[C@H](C)CC1)O5)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O QCTMYNGDIBTNSK-XEAAVONHSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- MBWUSSKCCUMJHO-ZGXDEBHDSA-N Solamargine Chemical compound O([C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O[C@H]1[C@@H]([C@H](O)[C@@H](O)[C@H](C)O1)O)O[C@@H]1CC2=CC[C@H]3[C@@H]4C[C@H]5[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@@H]([C@]1(NC[C@H](C)CC1)O5)C)[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O MBWUSSKCCUMJHO-ZGXDEBHDSA-N 0.000 description 3
- MBWUSSKCCUMJHO-DVDUUUGDSA-N Solamargine Natural products O([C@@H]1[C@@H](O)[C@@H](O[C@H]2[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O2)[C@H](CO)O[C@@H]1O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]5[C@@H](C)[C@@]6(O[C@H]5C4)NC[C@H](C)CC6)CC3)CC=2)CC1)[C@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](C)O1 MBWUSSKCCUMJHO-DVDUUUGDSA-N 0.000 description 3
- KNLOWJPFLKGYGQ-UHFFFAOYSA-N Solasodine 3-O-??-L-rhamnopyranosyl (1‘Â∆2)-O-[??-D-glucopyranosyl (1‘Â∆4)]-??-D-glucopyranoside Natural products O1C2(NCC(C)CC2)C(C)C(C2(CCC3C4(C)CC5)C)C1CC2C3CC=C4CC5OC(C(C1O)OC2C(C(O)C(O)C(C)O2)O)OC(CO)C1OC1OC(CO)C(O)C(O)C1O KNLOWJPFLKGYGQ-UHFFFAOYSA-N 0.000 description 3
- QCTMYNGDIBTNSK-QCNFCIKQSA-N Solasonine Natural products O([C@@H]1[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@H](C)O2)[C@@H](O[C@@H]2CC=3[C@@](C)([C@@H]4[C@H]([C@H]5[C@@](C)([C@H]6[C@@H](C)[C@@]7(O[C@H]6C5)NC[C@H](C)CC7)CC4)CC=3)CC2)O[C@@H](CO)[C@@H]1O)[C@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 QCTMYNGDIBTNSK-QCNFCIKQSA-N 0.000 description 3
- 230000003187 abdominal effect Effects 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- RCTKRNCKOYYRIO-UHFFFAOYSA-N alpha-Solamarine Natural products O1C2(NCC(C)CC2)C(C)C(C2(CCC3C4(C)CC5)C)C1CC2C3CC=C4CC5OC(C1O)OC(CO)C(O)C1OC1OC(CO)C(O)C(O)C1OC1OC(C)C(O)C(O)C1O RCTKRNCKOYYRIO-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 208000000059 Dyspnea Diseases 0.000 description 2
- 206010013975 Dyspnoeas Diseases 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 102000011759 adducin Human genes 0.000 description 2
- 108010076723 adducin Proteins 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 150000003797 alkaloid derivatives Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000001387 anti-histamine Effects 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 239000000739 antihistaminic agent Substances 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 235000019219 chocolate Nutrition 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 231100000135 cytotoxicity Toxicity 0.000 description 2
- 230000003013 cytotoxicity Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002481 ethanol extraction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 230000004992 fission Effects 0.000 description 2
- 238000013467 fragmentation Methods 0.000 description 2
- 238000006062 fragmentation reaction Methods 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002547 new drug Substances 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 206010011224 Cough Diseases 0.000 description 1
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000037656 Respiratory Sounds Diseases 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
- 240000007776 Solanum aviculare Species 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 206010047924 Wheezing Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000009837 dry grinding Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- WUEXFSVOXPGVML-UHFFFAOYSA-N ethanol;pentane Chemical compound CCO.CCCCC WUEXFSVOXPGVML-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Images
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 00129122 CN1107680C (en) | 2000-09-29 | 2000-09-29 | Solasodine hydrochlorate and productive method and application in medicine |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 00129122 CN1107680C (en) | 2000-09-29 | 2000-09-29 | Solasodine hydrochlorate and productive method and application in medicine |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1345728A true CN1345728A (en) | 2002-04-24 |
CN1107680C CN1107680C (en) | 2003-05-07 |
Family
ID=4593304
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 00129122 Expired - Fee Related CN1107680C (en) | 2000-09-29 | 2000-09-29 | Solasodine hydrochlorate and productive method and application in medicine |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN1107680C (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1329038C (en) * | 2003-06-20 | 2007-08-01 | 德英生物科技股份有限公司 | Water soluble nightshade extract, its preparation method and pharmaceutical compositions |
CN100340570C (en) * | 2003-11-29 | 2007-10-03 | 刘良 | Solasodine salt of organic acid, its preparation method and application in medicine |
CN102643326A (en) * | 2012-04-25 | 2012-08-22 | 广东固升医药科技有限公司 | 3,6-dihydroxyl-22(27)imino-4-furan sterene and preparation method and application thereof |
JP2020203856A (en) * | 2019-06-17 | 2020-12-24 | 株式会社ダイセル | Method for producing tomatidine-containing extract |
CN114848663A (en) * | 2022-05-09 | 2022-08-05 | 河南省人民医院 | Application of natural compound Solamargine and anti-HBV (hepatitis B virus) pharmaceutical composition |
-
2000
- 2000-09-29 CN CN 00129122 patent/CN1107680C/en not_active Expired - Fee Related
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1329038C (en) * | 2003-06-20 | 2007-08-01 | 德英生物科技股份有限公司 | Water soluble nightshade extract, its preparation method and pharmaceutical compositions |
CN100340570C (en) * | 2003-11-29 | 2007-10-03 | 刘良 | Solasodine salt of organic acid, its preparation method and application in medicine |
CN102643326A (en) * | 2012-04-25 | 2012-08-22 | 广东固升医药科技有限公司 | 3,6-dihydroxyl-22(27)imino-4-furan sterene and preparation method and application thereof |
CN102643326B (en) * | 2012-04-25 | 2014-03-26 | 广东固升医药科技有限公司 | 3,6-dihydroxyl-22(27)imino-4-furan sterene and preparation method and application thereof |
JP2020203856A (en) * | 2019-06-17 | 2020-12-24 | 株式会社ダイセル | Method for producing tomatidine-containing extract |
CN114848663A (en) * | 2022-05-09 | 2022-08-05 | 河南省人民医院 | Application of natural compound Solamargine and anti-HBV (hepatitis B virus) pharmaceutical composition |
Also Published As
Publication number | Publication date |
---|---|
CN1107680C (en) | 2003-05-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN100545164C (en) | The preparation technology of disodium cantharidinate | |
CN101919913B (en) | Composition with effect of treating rheumatoid arthritis | |
CN101926801A (en) | Medicinal composition | |
CN1241574C (en) | Medicine for relieving spasm and pain and preparation process thereof | |
CN102786417B (en) | The brilliant type III of chlorogenic acid characterizes and preparation method and applying in medicine and healthcare products | |
CN1382478A (en) | Extract of mulberry twig and its extracting process and novel usage | |
CN1107680C (en) | Solasodine hydrochlorate and productive method and application in medicine | |
CN102526349A (en) | Gel ointment as well as preparation method and application thereof | |
CN102228547B (en) | Application of traditional Chinese medicine composition in preparing medicaments treating pancreatitis and/or cholecystitis | |
CN101411779B (en) | Chinese medicine effective component composition for treating liver cancer and method for preparing the same | |
CN1312170C (en) | Technique of preparing extract product of Radde Anemone Rhizome extract, and its application in preparing medication of treating cancer | |
CN1193766C (en) | Gardenia total glycoside composite for curing hepatitis and its preparation method | |
CN102786418A (en) | Chlorogenic acid crystal II characterization and preparation methods, and applications of chlorogenic acid crystal II in medicines and healthcare products | |
CN101633661B (en) | Process for preparing sodium cantharidinate | |
CN1298705A (en) | Chinese medicine for treating hepatitis B and its preparing process | |
CN1426783A (en) | Application of evodiamine in the preparation of medicine | |
CN102552383A (en) | Compound jellyfish antihypertensive dispersible tablet and preparation method thereof | |
CN1679797A (en) | Anti-cancer Tengli root extract and its making method and use | |
CN111714521B (en) | Periplaneta americana intestinal flora metabolite extract, preparation method thereof and application thereof in preparing anti-inflammatory or anti-ulcer products | |
CN1079396A (en) | Intelligence-enhancing pharmaceutical preparation | |
CN115364179B (en) | Traditional Chinese medicine composition for reducing blood uric acid as well as preparation method and application thereof | |
CN102499913A (en) | Preparation method for refined and purified paeonol preparation | |
CN1182151C (en) | Method for purifying Huanweihuangyangxing D and preparation thereof | |
CN102070700A (en) | Marsdenia tenacissima saponins H and preparation method and application thereof | |
CN100421685C (en) | Chinese material medica preparation in use for treating infection of influenza virus, and preparation method |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C06 | Publication | ||
PB01 | Publication | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: JILIN ZHUOYIKANGNA PHARMACEUTICAL CO., LTD. Free format text: FORMER OWNER: LIU LIANG Effective date: 20031219 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20031219 Address after: 132013 No. 7-1, Xiamen street, hi tech Zone, Jilin, Jilin, Jilin Patentee after: Jilin City Zhuoyikangna pharmaceutical Co., Ltd. Address before: 1 Department of organic chemistry, School of medicine, Beihua University, Beijing Road, Jilin, Jilin 132011, China Patentee before: Liu Liang |
|
DD01 | Delivery of document by public notice |
Addressee: Jilin City Zhuoyikangna pharmaceutical Co., Ltd. Document name: Notification of Termination of Patent Right |
|
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20030507 Termination date: 20150929 |
|
EXPY | Termination of patent right or utility model |