FI111727B - Förfarande för framställning av antiparasitiska föreningar - Google Patents
Förfarande för framställning av antiparasitiska föreningar Download PDFInfo
- Publication number
- FI111727B FI111727B FI940218A FI940218A FI111727B FI 111727 B FI111727 B FI 111727B FI 940218 A FI940218 A FI 940218A FI 940218 A FI940218 A FI 940218A FI 111727 B FI111727 B FI 111727B
- Authority
- FI
- Finland
- Prior art keywords
- monosaccharide
- cyclohexyl
- dihydroavermectin
- compound
- evaporated
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Tropical Medicine & Parasitology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (7)
1. Förfarande för framställning av nya antiparasitiska föreningar med formeln (I) 5 OCH3 r1 4' ?^3 H /T^R2
10 H3CT o ^ ^-o H R H2° 1 I (I) L | 0H /H 15 °'TY'CH3 N OR4 20 där den streckade linjen i ställningen 22 - 23 :: : representerar en alternativ (dubbel)bindning, varvid i ;··.· molekylen antingen ingär denna bindning och ej R1, eller i :'. J molekylen ingär ej denna bindning och R1 är H eller OH, .···. 25 R2 är en Ci-8 -alkyl- eller C3-8-cykloalkylgrupp, • · R4 är H eller en grupp, som förmär hydrolyseras '!!! under in vivo- betingelser och ästadkomma en förening, där • * > * * * A R4 är H, kännetecknat därav, att : 30 (i) en förening med formeln (II) : 54 111727 ?CH3 Η1 ho. \* /ch3 4' Ί CH3 h 21^/Λ r H3C 0 ^nX R H I J °H L <v° 0H Lh 10 ^V^CHj (II) H I OH 15 där den streckade linjen, R1 och R2 är sä som ovan be-skrivits, oxideras till en förening med formeln (III): OCH3 r1
20 HCV^t ch )^/CH3 4' Ym3 h 22// \ Hscr^o^ H^.0/^r2 ....: H H :/.: H3C^N j[ 25 k °%^° ] ohT/h (III) : ·’ 30 H o :* och (ii) föreningen med formeln (III) bringas att reagera med en förening med formeln R4-0-NH2, där R4 är sä som ovan beskrivits, den bildade föreningen hydrolyseras 35 till en förening med formeln (I), 55 111727 och (iii) vid behov ersätts gruppen R4, da denna är H, med nämnda grupp, som förmär hydrolyseras under in vivo -betingelser och ästadkomma en förening, där R4 är H, varvid 5 förfarandet vid behov ytterligare omfattar ett steg fore eller efter stegen (i), (ii) och (iii), i vilket steg (iv) föreningen hydrogeneras för reducering av dubbelbindningen i ställningen 22-23 till en enkel-10 bindning.
2. Förfarande enligt patentkrav 1, känne-t e c k n a t därav, att nämnda grupp, som förmär hydrolyseras under in vivo -betingelser, är en acetyl-, t-butylkarbonyl-, t-butyloxikarbonyl-, bensoyl-, metylpiper-15 azinkarbonyl-, N-metylkarbamoyl-, N,N-dimetylkarbamoyl-, N—4 — (formylfenyl)karbamoyl-, N-(4-dietylaminofenyl)karb-amoyl-, N-(4-metyl-l-piperazinylmetylfenyl)karbonyl-, N-(3-pridylkarbonyl)karbamoyl-, N-(3-pyridyl)karbamoyl- eller N-allylkarbamoylgrupp. 20 3. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att R2 är cyklohexyl.
4. Förfarande enligt nägot av föregäende patentkrav, kännetecknat därav, att i molekylen ej ingär en alternativ bindning i ställningen 25 22-23 och R1 är H. ,:. 5. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att man framställer • · · 5-oximino-22,23-dihydroavermektin Bla-monosacka- ., . rid, • ·* 30 5-oximino-22,23-dihydro-25-cyklohexylavermektin '··* Bl-monosackarid, ·· 5-oximino-25-cyklohexylavermektin B2-monosackarid, 5-oximino-25-cyklohexylavermektin Bl-monosackarid eller 35 5-oximino-avermektin Bla-monosackarid. 111727 56
6. Förfarande enligt patentkrav 1, känne-t e c k n a t därav, att man framställer 5-oximino-22, 23-dihydro-25-cyklohexylavermektin B1-monosackarid. 5 7. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att man framställer 5-(trimetylacetyloximino)-25-cyklohexyl-22,23-dihydroavermektin Bl-monosackarid, 5-(bensoyloximino)-25-cyklohexyl-22,23-dihydro-10 avermektin Bl-monosackarid, 5-(N-metylkarbamoyloximino)-25-cyklohexyl-22,23-dihydroavermektin Bl-monosackarid, 5-(N,N-dimetylkarbamoyloximino)-25-cyklohexyl- 22.23- dihydroavermektin Bl-monosackarid, 15 5-(4-metylpiperazinyl-l-karbonyloximino)-25- cyklohexyl-22,23-dihydroavermektin Bl-monosackarid, 5- (t-butyloxikarbonyloximino)-25-cyklohexyl-22,23-dihydroavermektin Bl-monosackarid, 5-[N- (4-formylfenyl) karbamoyloximino]-25-cyklo-20 hexyl-22,23-dihydroavermektin Bl-monosackarid, 5-{N-[4- (dietylaminometyl) fenyl]karbamoyloximino}-,* 25-cyklohexyl-22,23-dihydroavermektin Bl-monosackarid, 5-{N-[4-(4-metyl-l-piperazinylmetyl)fenyl]-• karbamoyloximino}-25-cyklohexyl-22,23-dihydroavermektin
25 Bl-monosackarid, 5-[N-(3-pyridylkarbonyl)karbamoyloximino]-25-, : , cyklohexvl-22,23-dihydroavermektin Bl-monosackarid, 5-[N- (3-pyridyl) karbamoyloximino]-25-cyklohexyl- 22.23- dihydroavermektin Bl-monosackarid, eller 30 5-(N-allylkarbamoyloximino]-25-cyklohexyl-22,23- dihydroavermektin Bl-monosackarid. » » * t
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939300883A GB9300883D0 (en) | 1993-01-18 | 1993-01-18 | Antiparasitic agents |
| GB9300883 | 1993-01-18 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI940218A0 FI940218A0 (sv) | 1994-01-17 |
| FI940218A FI940218A (sv) | 1994-07-19 |
| FI111727B true FI111727B (sv) | 2003-09-15 |
Family
ID=10728869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI940218A FI111727B (sv) | 1993-01-18 | 1994-01-17 | Förfarande för framställning av antiparasitiska föreningar |
Country Status (35)
| Country | Link |
|---|---|
| EP (1) | EP0677054B1 (sv) |
| JP (1) | JP2732548B2 (sv) |
| KR (1) | KR0185480B1 (sv) |
| CN (1) | CN1043768C (sv) |
| AP (1) | AP522A (sv) |
| AT (1) | ATE164586T1 (sv) |
| AU (1) | AU679033B2 (sv) |
| BR (2) | BR9405811A (sv) |
| CA (1) | CA2152819C (sv) |
| CZ (1) | CZ284849B6 (sv) |
| DE (2) | DE10075003I1 (sv) |
| DK (1) | DK0677054T3 (sv) |
| EG (1) | EG20582A (sv) |
| ES (1) | ES2113639T3 (sv) |
| FI (1) | FI111727B (sv) |
| GB (1) | GB9300883D0 (sv) |
| GR (1) | GR3026710T3 (sv) |
| HR (1) | HRP940110B1 (sv) |
| HU (1) | HU221505B (sv) |
| IL (1) | IL108306A (sv) |
| LU (1) | LU90518I2 (sv) |
| MA (1) | MA23091A1 (sv) |
| MY (1) | MY141106A (sv) |
| NL (1) | NL300003I2 (sv) |
| NO (2) | NO304835B1 (sv) |
| NZ (1) | NZ259868A (sv) |
| OA (1) | OA10223A (sv) |
| PL (1) | PL176733B1 (sv) |
| RU (1) | RU2125059C1 (sv) |
| SG (1) | SG45131A1 (sv) |
| SK (1) | SK282031B6 (sv) |
| UA (1) | UA42707C2 (sv) |
| WO (1) | WO1994015944A1 (sv) |
| YU (1) | YU49169B (sv) |
| ZA (1) | ZA94310B (sv) |
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| GB0108485D0 (en) * | 2001-04-04 | 2001-05-23 | Pfizer Ltd | Combination therapy |
| US20040077703A1 (en) | 2002-10-02 | 2004-04-22 | Soll Mark D. | Nodulisporic acid derivative spot-on formulations for combating parasites |
| AU2004209401A1 (en) | 2003-01-30 | 2004-08-19 | Applied Biosystems, Llc. | Methods, mixtures, kits and compositions pertaining to analyte determination |
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| WO2024132895A1 (en) | 2022-12-19 | 2024-06-27 | Syngenta Crop Protection Ag | Microbiocidal dihydrooxadiazinyl pyridazinone compounds |
| WO2024132901A1 (en) | 2022-12-19 | 2024-06-27 | Syngenta Crop Protection Ag | Microbiocidal pyridazine dihydrooxadiazine derivatives |
| WO2024135828A1 (ja) * | 2022-12-23 | 2024-06-27 | Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 | エバーメクチン誘導体 |
| WO2024156886A1 (en) | 2023-01-27 | 2024-08-02 | Syngenta Crop Protection Ag | Microbiocidal pyrazole derivatives |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5015630A (en) * | 1989-01-19 | 1991-05-14 | Merck & Co., Inc. | 5-oxime avermectin derivatives |
| US5023241A (en) * | 1989-07-31 | 1991-06-11 | Merck & Co., Inc. | Avermectin derivatives |
| US5055454A (en) * | 1989-10-30 | 1991-10-08 | Merck & Co., Inc. | 13-epi-avermectin derivatives useful as antiparasitic agents |
| US5830875A (en) * | 1989-10-30 | 1998-11-03 | Merck & Co., Inc. | 24-and 25-substituted avermectin and milbemycin derivatives |
| CA2052860A1 (en) * | 1990-10-11 | 1992-04-12 | Thomas L. Shih | Avermectin degradation products and derivatives |
| US5208222A (en) * | 1991-03-28 | 1993-05-04 | Merck & Co., Inc. | 4"-and 4'-alkylthio avermectin derivatives |
| US5262400A (en) * | 1991-06-20 | 1993-11-16 | Merck & Co., Inc. | 4α-substituted avermectin derivatives |
| DK0535734T3 (da) * | 1991-09-30 | 1999-08-09 | Merck & Co Inc | Langtidsvirkende injicerbare formuleringer indeholdende hydrogeneret castorolie |
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1993
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- 1994-01-12 AT AT94905061T patent/ATE164586T1/de active
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- 1994-01-12 WO PCT/EP1994/000095 patent/WO1994015944A1/en active IP Right Grant
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- 1994-02-15 HR HR9300883.7 patent/HRP940110B1/xx not_active IP Right Cessation
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