CN110938081B - 一种大环内酯类新化合物、药物组合物及其制备方法与应用 - Google Patents
一种大环内酯类新化合物、药物组合物及其制备方法与应用 Download PDFInfo
- Publication number
- CN110938081B CN110938081B CN201911263377.5A CN201911263377A CN110938081B CN 110938081 B CN110938081 B CN 110938081B CN 201911263377 A CN201911263377 A CN 201911263377A CN 110938081 B CN110938081 B CN 110938081B
- Authority
- CN
- China
- Prior art keywords
- compound
- milbemycin
- pharmaceutical composition
- preparation
- application
- 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.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 67
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 14
- 239000003120 macrolide antibiotic agent Substances 0.000 title abstract description 10
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 5
- 239000003814 drug Substances 0.000 claims abstract description 4
- FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Natural products COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 10
- 241000244206 Nematoda Species 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000855 fermentation Methods 0.000 abstract description 25
- 230000004151 fermentation Effects 0.000 abstract description 25
- 241000187747 Streptomyces Species 0.000 abstract description 10
- 238000012258 culturing Methods 0.000 abstract description 8
- 241000238631 Hexapoda Species 0.000 abstract description 2
- 201000010099 disease Diseases 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical class O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 229930006000 Sucrose Natural products 0.000 description 9
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 238000011218 seed culture Methods 0.000 description 9
- 239000005720 sucrose Substances 0.000 description 9
- 239000000287 crude extract Substances 0.000 description 7
- 230000000749 insecticidal effect Effects 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 229940041514 candida albicans extract Drugs 0.000 description 6
- VOZIAWLUULBIPN-LRBNAKOISA-N milbemycin A4 Chemical compound C1C[C@H](C)[C@@H](CC)O[C@@]21O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 VOZIAWLUULBIPN-LRBNAKOISA-N 0.000 description 6
- 238000002703 mutagenesis Methods 0.000 description 6
- 231100000350 mutagenesis Toxicity 0.000 description 6
- 239000000575 pesticide Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000012138 yeast extract Substances 0.000 description 6
- 239000003480 eluent Substances 0.000 description 5
- 239000001963 growth medium Substances 0.000 description 5
- 238000011068 loading method Methods 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 229930000044 secondary metabolite Natural products 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 230000000895 acaricidal effect Effects 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000000039 preparative column chromatography Methods 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000008213 purified water Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 230000001954 sterilising effect Effects 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000005913 Maltodextrin Substances 0.000 description 3
- 229920002774 Maltodextrin Polymers 0.000 description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 241000199504 Streptomyces bingchenggensis Species 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 235000015278 beef Nutrition 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 3
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 229910052564 epsomite Inorganic materials 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 229940035034 maltodextrin Drugs 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000013028 medium composition Substances 0.000 description 3
- 230000001069 nematicidal effect Effects 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000013612 plasmid Substances 0.000 description 3
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Inorganic materials [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 3
- 108010009004 proteose-peptone Proteins 0.000 description 3
- 239000012488 sample solution Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000008223 sterile water Substances 0.000 description 3
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000219977 Vigna Species 0.000 description 2
- 235000010726 Vigna sinensis Nutrition 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000012262 fermentative production Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000004896 high resolution mass spectrometry Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 238000007790 scraping Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000001026 1H--1H correlation spectroscopy Methods 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241001600407 Aphis <genus> Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000243770 Bursaphelenchus Species 0.000 description 1
- 241001414987 Strepsiptera Species 0.000 description 1
- 241000970979 Streptomyces griseochromogenes Species 0.000 description 1
- 241000187391 Streptomyces hygroscopicus Species 0.000 description 1
- 241000344246 Tetranychus cinnabarinus Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000012272 crop production Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000009313 farming Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001052 heteronuclear multiple bond coherence spectrum Methods 0.000 description 1
- 238000000990 heteronuclear single quantum coherence spectrum Methods 0.000 description 1
- 244000000053 intestinal parasite Species 0.000 description 1
- 229940041033 macrolides Drugs 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- -1 pH 7.0-7.2 Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
Claims (5)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201911263377.5A CN110938081B (zh) | 2019-12-11 | 2019-12-11 | 一种大环内酯类新化合物、药物组合物及其制备方法与应用 |
CN202110192320.1A CN112961168B (zh) | 2019-12-11 | 2019-12-11 | 一种大环内酯类新化合物及其制备方法与应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201911263377.5A CN110938081B (zh) | 2019-12-11 | 2019-12-11 | 一种大环内酯类新化合物、药物组合物及其制备方法与应用 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202110192320.1A Division CN112961168B (zh) | 2019-12-11 | 2019-12-11 | 一种大环内酯类新化合物及其制备方法与应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN110938081A CN110938081A (zh) | 2020-03-31 |
CN110938081B true CN110938081B (zh) | 2021-03-26 |
Family
ID=69910093
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201911263377.5A Active CN110938081B (zh) | 2019-12-11 | 2019-12-11 | 一种大环内酯类新化合物、药物组合物及其制备方法与应用 |
CN202110192320.1A Active CN112961168B (zh) | 2019-12-11 | 2019-12-11 | 一种大环内酯类新化合物及其制备方法与应用 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202110192320.1A Active CN112961168B (zh) | 2019-12-11 | 2019-12-11 | 一种大环内酯类新化合物及其制备方法与应用 |
Country Status (1)
Country | Link |
---|---|
CN (2) | CN110938081B (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114634518B (zh) * | 2022-04-02 | 2023-10-24 | 台州职业技术学院 | 两种大环内酯类新化合物、药物组合物及其制备方法和应用 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007246462A (ja) * | 2006-03-17 | 2007-09-27 | Sankyo Agro Kk | 3,4−ジヒドロミルベマイシン誘導体及びその製造方法 |
CN101679451A (zh) * | 2007-05-03 | 2010-03-24 | 梅瑞尔有限公司 | 包含c-13烷氧基醚大环内酯类化合物和苯基吡唑类化合物的组合物 |
CN103242338A (zh) * | 2013-05-07 | 2013-08-14 | 东北农业大学 | 一种大环内酯类化合物及其制备方法和应用 |
CN104098585A (zh) * | 2014-07-07 | 2014-10-15 | 浙江海正药业股份有限公司 | 米尔贝霉素类似物、其制备方法和应用 |
CN105906650A (zh) * | 2016-04-27 | 2016-08-31 | 东北农业大学 | 大环内酯类新化合物及其制备方法与应用 |
CN106432264A (zh) * | 2016-09-06 | 2017-02-22 | 东北农业大学 | 两种大环内酯类化合物及其制备方法与应用 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101012194A (zh) * | 2006-12-27 | 2007-08-08 | 浙江大学 | 2,3,5-三甲基吡啶的制备方法 |
FR3069244B1 (fr) * | 2017-07-20 | 2020-03-06 | IFP Energies Nouvelles | Procede d’hydrogenolyse pour une production amelioree de paraxylene |
-
2019
- 2019-12-11 CN CN201911263377.5A patent/CN110938081B/zh active Active
- 2019-12-11 CN CN202110192320.1A patent/CN112961168B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007246462A (ja) * | 2006-03-17 | 2007-09-27 | Sankyo Agro Kk | 3,4−ジヒドロミルベマイシン誘導体及びその製造方法 |
CN101679451A (zh) * | 2007-05-03 | 2010-03-24 | 梅瑞尔有限公司 | 包含c-13烷氧基醚大环内酯类化合物和苯基吡唑类化合物的组合物 |
CN103242338A (zh) * | 2013-05-07 | 2013-08-14 | 东北农业大学 | 一种大环内酯类化合物及其制备方法和应用 |
CN104098585A (zh) * | 2014-07-07 | 2014-10-15 | 浙江海正药业股份有限公司 | 米尔贝霉素类似物、其制备方法和应用 |
CN105906650A (zh) * | 2016-04-27 | 2016-08-31 | 东北农业大学 | 大环内酯类新化合物及其制备方法与应用 |
CN106432264A (zh) * | 2016-09-06 | 2017-02-22 | 东北农业大学 | 两种大环内酯类化合物及其制备方法与应用 |
Non-Patent Citations (1)
Title |
---|
新化合物天维菌素的杀虫杀螨活性;杨波等;《农药学学报》;20161231;第18卷(第1期);第124-129页 * |
Also Published As
Publication number | Publication date |
---|---|
CN112961168A (zh) | 2021-06-15 |
CN110938081A (zh) | 2020-03-31 |
CN112961168B (zh) | 2022-07-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR940004098B1 (ko) | 신규 항생제 화합물의 제조 방법 | |
CS207397B2 (en) | Method of preparation of the new anthelmintic compounds | |
CN106432264B (zh) | 两种大环内酯类化合物及其制备方法与应用 | |
CZ390592A3 (en) | Process for preparing 4,5-dihydrogendanamycin and hydroquinone thereof and the use of such compounds | |
CN111303184B (zh) | 一种大环内酯类化合物及其制备方法与应用 | |
CN111004252B (zh) | 一种十六元大环内酯类化合物及其制备方法与应用 | |
EP1373290B1 (en) | Pesticidal spinosyn derivatives | |
DK169738B1 (da) | Macrolid-forbindelser, fremgangsmåde til fremstilling af macrolid-forbindelser og biologisk ren mikroorganismekultur til anvendelse ved fremgangsmåden samt præparater indeholdende macrolid-forbindelserne og ikke-terapeutisk fremgangsmåde til bekæmpelse af parasitinfektioner | |
CN105906650B (zh) | 大环内酯类新化合物及其制备方法与应用 | |
CN110938081B (zh) | 一种大环内酯类新化合物、药物组合物及其制备方法与应用 | |
An et al. | Isolation, purification and identification of biological compounds from Beauveria sp. and their evaluation as insecticidal effectiveness against Bemisia tabaci | |
CN113248516B (zh) | 一种十七元大环内酯类化合物及其制备方法与应用 | |
CN105503780B (zh) | 具有抗细菌活性的Pestalotic acid化合物及其应用 | |
CN114634518B (zh) | 两种大环内酯类新化合物、药物组合物及其制备方法和应用 | |
ES2920198B2 (es) | Cepa de aspergillus tubingensis y su uso para el aislamiento de compuestos nematicidas | |
EP0298423A2 (en) | Antibiotic KSB-1939 compounds and production process thereof as well as pesticidal agents containing same | |
CN105968122B (zh) | 十六元环大环内酯类化合物及其制备方法与应用 | |
EP1412346B1 (de) | Verfahren zum herstellen von neuen spinosyn-derivaten | |
CN113817008A (zh) | 新型琥珀酰基十六元大环内酯的制备方法及用途 | |
CN115124582B (zh) | 一种抗立枯丝核菌的含2,9-二甲基十六元大环内酰胺母核的衍生物及其制备方法与应用 | |
CN111909166B (zh) | 两个新的米尔贝霉素类化合物、其制备方法及用途 | |
US4385065A (en) | Novel substances and process for their production | |
CN113200995A (zh) | 化合物Sterigmatocystin及其制备方法和在杀虫农药中的应用 | |
US20040097377A1 (en) | Pesticidal spinosyn derivates | |
CN112010870A (zh) | 新的十六元大环内酯类化合物、其制备方法及用途 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
EE01 | Entry into force of recordation of patent licensing contract | ||
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20200331 Assignee: Taizhou Yongshang Trading Co.,Ltd. Assignor: TAIZHOU VOCATIONAL & TECHNICAL College Contract record no.: X2023980044891 Denomination of invention: A novel macrolide compound, pharmaceutical composition, preparation method and application thereof Granted publication date: 20210326 License type: Common License Record date: 20231030 Application publication date: 20200331 Assignee: Taizhou Yier Technology Co.,Ltd. Assignor: TAIZHOU VOCATIONAL & TECHNICAL College Contract record no.: X2023980044675 Denomination of invention: A novel macrolide compound, pharmaceutical composition, preparation method and application thereof Granted publication date: 20210326 License type: Common License Record date: 20231027 |