DE2201991C2 - Verfahren zur Gewinnung von steroidalen Insektenhäutungshormonen - Google Patents
Verfahren zur Gewinnung von steroidalen InsektenhäutungshormonenInfo
- Publication number
- DE2201991C2 DE2201991C2 DE2201991A DE2201991A DE2201991C2 DE 2201991 C2 DE2201991 C2 DE 2201991C2 DE 2201991 A DE2201991 A DE 2201991A DE 2201991 A DE2201991 A DE 2201991A DE 2201991 C2 DE2201991 C2 DE 2201991C2
- Authority
- DE
- Germany
- Prior art keywords
- methanol
- residue
- makisteron
- hormones
- water
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 13
- 230000003637 steroidlike Effects 0.000 title claims description 5
- 239000002428 insect molting hormone Substances 0.000 title description 8
- NKDFYOWSKOHCCO-YPVLXUMRSA-N 20-hydroxyecdysone Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@@](C)(O)[C@H](O)CCC(C)(O)C)CC[C@]33O)C)C3=CC(=O)[C@@H]21 NKDFYOWSKOHCCO-YPVLXUMRSA-N 0.000 claims description 21
- NKDFYOWSKOHCCO-UHFFFAOYSA-N beta-ecdysone Natural products C1C(O)C(O)CC2(C)C(CCC3(C(C(C)(O)C(O)CCC(C)(O)C)CCC33O)C)C3=CC(=O)C21 NKDFYOWSKOHCCO-UHFFFAOYSA-N 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 19
- YXPVYQIMXPYFSF-UHFFFAOYSA-N Makisterone A Natural products CC(C)C(C)(O)CC(O)C(C)(O)C1CCC2(O)C3=CC(=O)C4CC(O)C(O)CC4(C)C3CCC12C YXPVYQIMXPYFSF-UHFFFAOYSA-N 0.000 claims description 18
- UPEZCKBFRMILAV-UHFFFAOYSA-N alpha-Ecdysone Natural products C1C(O)C(O)CC2(C)C(CCC3(C(C(C(O)CCC(C)(C)O)C)CCC33O)C)C3=CC(=O)C21 UPEZCKBFRMILAV-UHFFFAOYSA-N 0.000 claims description 16
- 238000000605 extraction Methods 0.000 claims description 15
- 241000196324 Embryophyta Species 0.000 claims description 14
- 239000013078 crystal Substances 0.000 claims description 14
- IJRBORPEVKCEQD-JMQWOFAPSA-N Makisterone A Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@@](C)(O)[C@H](O)C[C@@H](C)C(C)(C)O)CC[C@]33O)C)C3=CC(=O)[C@@H]21 IJRBORPEVKCEQD-JMQWOFAPSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 239000005556 hormone Substances 0.000 claims description 9
- 229940088597 hormone Drugs 0.000 claims description 9
- SGNLNHWVOICCOZ-UHFFFAOYSA-N Crustecdyson Natural products CC(O)C1(CCC2(O)C3=CC(=O)C4CC(O)C(O)CC4(C)C3CCC12C)C(O)CCC(C)(C)O SGNLNHWVOICCOZ-UHFFFAOYSA-N 0.000 claims description 8
- 241000238631 Hexapoda Species 0.000 claims description 7
- 229930187267 Muristeron Natural products 0.000 claims description 5
- -1 aliphatic chlorinated hydrocarbon Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 241000207782 Convolvulaceae Species 0.000 claims description 2
- 229930182558 Sterol Natural products 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 150000003432 sterols Chemical class 0.000 claims description 2
- 235000003702 sterols Nutrition 0.000 claims description 2
- 235000013312 flour Nutrition 0.000 claims 1
- 235000013311 vegetables Nutrition 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 89
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- UPEZCKBFRMILAV-JNEQICEOSA-N Ecdysone Natural products O=C1[C@H]2[C@@](C)([C@@H]3C([C@@]4(O)[C@@](C)([C@H]([C@H]([C@@H](O)CCC(O)(C)C)C)CC4)CC3)=C1)C[C@H](O)[C@H](O)C2 UPEZCKBFRMILAV-JNEQICEOSA-N 0.000 description 12
- UPEZCKBFRMILAV-JMZLNJERSA-N ecdysone Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@@H]([C@H](O)CCC(C)(C)O)C)CC[C@]33O)C)C3=CC(=O)[C@@H]21 UPEZCKBFRMILAV-JMZLNJERSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 150000003431 steroids Chemical class 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 229930183445 Makisteron Natural products 0.000 description 5
- LRJUYAVTHIEHAI-LHBNDURVSA-N Muristerone Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H]([C@H](O)C[C@@]3([C@@H]([C@@](C)(O)[C@H](O)CCC(C)C)CC[C@]33O)C)C3=CC(=O)[C@@]21O LRJUYAVTHIEHAI-LHBNDURVSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 4
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DCEFCUHVANGEOE-UHFFFAOYSA-N Ecdysterone Natural products CC(CC(C)(C)O)C(O)C(C)(O)C1CCC2(O)C3=CC(=O)C4CC(O)C(O)CC4(C)C3CCC12C DCEFCUHVANGEOE-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 3
- HXWZQRICWSADMH-SEHXZECUSA-N 20-hydroxyecdysone Natural products CC(C)(C)CC[C@@H](O)[C@@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C HXWZQRICWSADMH-SEHXZECUSA-N 0.000 description 2
- 208000034656 Contusions Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 240000007332 Podocarpus macrophyllus Species 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 208000034526 bruise Diseases 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 210000005239 tubule Anatomy 0.000 description 2
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 2
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 2
- 235000012141 vanillin Nutrition 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241001164374 Calyx Species 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 241001573881 Corolla Species 0.000 description 1
- 244000295277 Cynanchum muricatum Species 0.000 description 1
- VROYHCMGMRXPPB-UHFFFAOYSA-N Ecdysteron Natural products CC(CC(C)(C)O)C(O)C(C)(O)C1CCC2(O)C3CC(=O)C4CC(O)C(O)CC4(C)C3CCC12C VROYHCMGMRXPPB-UHFFFAOYSA-N 0.000 description 1
- 240000007218 Ipomoea hederacea Species 0.000 description 1
- 241000371392 Jasus Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241000255969 Pieris brassicae Species 0.000 description 1
- 244000155172 Podocarpus elatus Species 0.000 description 1
- 235000016408 Podocarpus macrophyllus Nutrition 0.000 description 1
- 241001518143 Polypodium <fern> Species 0.000 description 1
- MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- WTRDCBSIGOAXLO-UHFFFAOYSA-N chloroform;ethanol;hydrate Chemical compound O.CCO.ClC(Cl)Cl WTRDCBSIGOAXLO-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- MJKOCZIZHOHSNY-UHFFFAOYSA-N ecdysterone triacetate Natural products C1C(OC(C)=O)C(OC(C)=O)CC2(C)C(CCC3(C(C(C)(O)C(CCC(C)(C)O)OC(=O)C)CCC33O)C)C3=CC(=O)C21 MJKOCZIZHOHSNY-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000003918 fraction a Anatomy 0.000 description 1
- 210000000540 fraction c Anatomy 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008141 laxative Substances 0.000 description 1
- 230000002475 laxative effect Effects 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000029052 metamorphosis Effects 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G15/00—Hormones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G99/00—Subject matter not provided for in other groups of this subclass
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
-
- 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
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Botany (AREA)
- Microbiology (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Endocrinology (AREA)
- Medical Informatics (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mycology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1946671 | 1971-01-18 | ||
| IT780671A IT997026B (it) | 1971-07-29 | 1971-07-29 | Prodotto insetticida biologico e procedimento per la sua preparazione |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2201991A1 DE2201991A1 (de) | 1972-08-10 |
| DE2201991C2 true DE2201991C2 (de) | 1983-03-17 |
Family
ID=26325925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2201991A Expired DE2201991C2 (de) | 1971-01-18 | 1972-01-17 | Verfahren zur Gewinnung von steroidalen Insektenhäutungshormonen |
Country Status (17)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1118225B (it) * | 1977-08-12 | 1986-02-24 | Simes | Procedimento per l'ottenimento di steroidi poliossidrilati,lisergolo ed alcaloidi ergolici |
| FR2695035A1 (fr) * | 1992-08-25 | 1994-03-04 | Lvmh Rech Gie | Utilisation d'un ecdystéroïde pour la préparation de compositions cosmétiques ou dermatologiques destinées notamment à renforcer la fonction protectrice de la peau, et compositions ainsi obtenues. |
| AU746878B2 (en) | 1996-12-20 | 2002-05-02 | Novo Nordisk A/S | Meiosis regulating compounds |
| FR3065644B1 (fr) * | 2017-04-28 | 2020-02-21 | Biophytis | Extrait de 20-hydroxyecdysone de qualite pharmaceutique, son utilisation et sa preparation |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH485692A (de) * | 1966-10-19 | 1970-02-15 | Rohto Pharma | Verfahren zur Herstellung von Inokosteron und/oder Isoinokosteron für nicht therapeutische Zwecke |
| US3527777A (en) * | 1968-03-05 | 1970-09-08 | Ceskoslovenska Akademie Ved | Method for obtaining ecdysterones |
-
1972
- 1972-01-11 IL IL38540A patent/IL38540A0/xx unknown
- 1972-01-14 GB GB191372A patent/GB1382682A/en not_active Expired
- 1972-01-14 US US00217842A patent/US3828082A/en not_active Expired - Lifetime
- 1972-01-15 OA OA54468A patent/OA04070A/xx unknown
- 1972-01-17 AT AT37072A patent/AT314726B/de not_active IP Right Cessation
- 1972-01-17 BE BE778139A patent/BE778139A/xx unknown
- 1972-01-17 CH CH65672A patent/CH613213A5/xx not_active IP Right Cessation
- 1972-01-17 NL NL727200655A patent/NL146027B/xx unknown
- 1972-01-17 DK DK21972A patent/DK130701B/da unknown
- 1972-01-17 AU AU37972/72A patent/AU462750B2/en not_active Expired
- 1972-01-17 DE DE2201991A patent/DE2201991C2/de not_active Expired
- 1972-01-18 FR FR7201595A patent/FR2122498B1/fr not_active Expired
- 1972-01-18 HU HUDA000291 patent/HU164403B/hu unknown
- 1972-01-18 CA CA132,696A patent/CA983018A/en not_active Expired
- 1972-01-18 BR BR29072A patent/BR7200290D0/pt unknown
- 1972-01-18 JP JP671772A patent/JPS5720320B1/ja active Pending
- 1972-01-18 DD DD16040172A patent/DD95564A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3828082A (en) | 1974-08-06 |
| GB1382682A (en) | 1975-02-05 |
| IL38540A0 (en) | 1972-03-28 |
| BR7200290D0 (pt) | 1973-09-20 |
| NL146027B (nl) | 1975-06-16 |
| DD95564A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-02-12 |
| FR2122498B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-09-13 |
| DK130701B (da) | 1975-04-01 |
| NL7200655A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-07-20 |
| AT314726B (de) | 1974-04-25 |
| OA04070A (fr) | 1979-10-30 |
| CH613213A5 (en) | 1979-09-14 |
| DK130701C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-09-01 |
| FR2122498A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-09-01 |
| BE778139A (fr) | 1972-05-16 |
| AU3797272A (en) | 1973-07-19 |
| HU164403B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-02-28 |
| JPS5720320B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-04-27 |
| AU462750B2 (en) | 1975-07-03 |
| DE2201991A1 (de) | 1972-08-10 |
| CA983018A (en) | 1976-02-03 |
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