JPH07505363A - 活性抗寄生虫剤としてのアルキルチオアルキルアベルメクチン - Google Patents
活性抗寄生虫剤としてのアルキルチオアルキルアベルメクチンInfo
- Publication number
- JPH07505363A JPH07505363A JP5516659A JP51665993A JPH07505363A JP H07505363 A JPH07505363 A JP H07505363A JP 5516659 A JP5516659 A JP 5516659A JP 51665993 A JP51665993 A JP 51665993A JP H07505363 A JPH07505363 A JP H07505363A
- Authority
- JP
- Japan
- Prior art keywords
- methylthiomethyl
- aglycone
- tert
- dihydroavermectin
- butyldimethylsilyl
- 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
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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Genetics & Genomics (AREA)
- Public Health (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
Description
Claims (9)
- 1.式: ▲数式、化学式、表等があります▼ (式中、 nは0、1又は2であり; Aは単結合又は二重結合であり; R1はAが単結合である場合にのみ存在し、H、OH、=O、=NOCH3又は ハロゲンであり;R2はC1−6アルキル、C2−6アルケニル、C3−8シク ロアルキル、C4−8シクロアルケニル、フェニル、フリル又はチエニルであり ; R3はOH又は=NOHであり; Bは単結合又は二重結合であり; R5はBが単結合である場合にのみ存在し、H、OH、又はハロゲンであり; R4は ▲数式、化学式、表等があります▼ であり; R6は水素又はC1−3アルキルである)を有する化合物。
- 2.Aが単結合であり、R1がH、OH又は=0であり、R2がC1−6アルキ ル又はC3−8シクロアルキルであり、R3がOHであり、Bが二重結合であり 、R4が上記と同義であり、R6が水素又はメチルである請求項1に記載の化合 物。
- 3.Aが単結合であり、R1がH又はOHであり、R2がC3−4アルキル又は C5−6シクロアルキルであり、R3がOHであり、Bが二重結合であり、R4 が上記と同義であり、R6が水素である請求項2に記載の化合物。
- 4.13−O−メチルチオメチル−22,23−ジヒドロァベルメクチンB1ア グリコン; 13−エピ−O−メチルチオメチル−22,23−ジヒドロアベルメクチンB1 アグリコン; 4′−O−メチルチオメチル−22,23−ジヒドロアベルメクチンB1単糖; 4′−O−メチルチオメチルアベルメクチンB1単糖;13−O−メチルチオメ チルアベルメクチンB1アグリコン; 4′′−O−メチルチオメチル−22,23−ジヒドロアベルメクチンB1; 4′′−O−メチルチオメチルアベルメクチンB1;13−O−メチルチオメチ ル−10,11,22,23−テトラヒドロアベルメクチンB1アグリコン;1 3−O−メチルチオメチル−10−ヒドロキシ−10,11,22,23−テト ラヒドロアベルメクチンB1アグリコン;又は 13−O−メチルチオメチル−10−フメオロ−10,11,22,23−テト ラヒドロアベルメクチンB1アグリコンである請求項1に記載の化合物。
- 5.4′′、4又は13位にヒドロキシを含むアベルメクチン化合物又はその誘 導体を、RCOOH及び(RCO)2O(式中、RはC1−5アルキルである) の存在下で式:R6CH2SOCH2R6(式中、R6は水素又はC1−3アル キルである)を有する化合物で処理することからなる請求項1に記載の化合物の 製造方法。
- 6.RCOOHが酢酸であり、(RCO)2Oが酢酸無水物であり、R6が水素 である請求項5に記載の方法。
- 7.寄生虫に感染した動物に有効量の請求項1に記載の化合物を投与することか らなる動物の寄生虫感染の治療方法。
- 8.寄生虫に感染した植物、土壌又は構内に有効量の請求項1に記載の化合物を 施用することからなる植物、土壌又は構内の寄生虫感染の処置方法。
- 9.不活性キャリヤーと請求項1に記載の化合物とを含有する、動物の寄生虫感 染又は植物、土壌もしくは構内の寄生虫感染の処置に有用な組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US857,035 | 1992-03-24 | ||
US07/857,035 US5229415A (en) | 1992-03-24 | 1992-03-24 | Alkylthio alkyl avermectins are active antiparasitic agents |
PCT/US1993/002362 WO1993018778A1 (en) | 1992-03-24 | 1993-03-16 | Alkylthio alkyl avermectins are active antiparasitic agents |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH07505363A true JPH07505363A (ja) | 1995-06-15 |
JP3135918B2 JP3135918B2 (ja) | 2001-02-19 |
Family
ID=25325031
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP05516659A Expired - Lifetime JP3135918B2 (ja) | 1992-03-24 | 1993-03-16 | 活性抗寄生虫剤としてのアルキルチオアルキルアベルメクチン |
Country Status (9)
Country | Link |
---|---|
US (1) | US5229415A (ja) |
EP (1) | EP0632725B1 (ja) |
JP (1) | JP3135918B2 (ja) |
AT (1) | ATE173738T1 (ja) |
AU (1) | AU669358B2 (ja) |
CA (1) | CA2132429C (ja) |
DE (1) | DE69322265T2 (ja) |
WO (1) | WO1993018778A1 (ja) |
ZA (1) | ZA932048B (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012097092A (ja) * | 2000-08-09 | 2012-05-24 | Kitasato Institute | エバーメクチン誘導体 |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5691320A (en) | 1987-10-28 | 1997-11-25 | Pro-Neuron, Inc. | Acylated pyrimidine nucleosides for treatment of systemic inflammation and inflammatory hepatitis |
GB9205007D0 (en) * | 1992-03-07 | 1992-04-22 | Pfizer Ltd | Antiparasitic agents |
US5229416A (en) * | 1992-04-29 | 1993-07-20 | Merck & Co., Inc. | Avermectin difluoro derivatives |
ES2138090T3 (es) * | 1993-10-05 | 2000-01-01 | Pfizer | Procedimiento e intermedios para doramectina. |
SE521031C2 (sv) | 1999-05-05 | 2003-09-23 | Srinivas Uppugunduri | Nya specifika inhibitorer av akut och kronisk inflammation |
AU2001277712A1 (en) * | 2000-08-09 | 2002-02-18 | The Kitasato Institute | Avermectin derivatives |
EG23124A (en) * | 2001-02-27 | 2004-04-28 | Syngenta Participations Ag | Avermectins substituted in the 4-position having pesticidal properties |
CR6574A (es) * | 2001-02-27 | 2004-10-28 | Syngenta Participations Ag | Sales de avermectinas substituidas en la posicion 4 con propiedades plaguicidas |
AR036486A1 (es) * | 2001-08-28 | 2004-09-15 | Syngenta Participations Ag | Derivados 4"-desoxi-4"-(s)-amino avermectina, composicion plaguicida, procedimiento para la preparacion de esa composicion, metodo para controlar plagas, y uso de estos derivados para preparar una composicion |
TW200407330A (en) * | 2002-05-07 | 2004-05-16 | Syngenta Participations Ag | 4"-Deoxy-4"-(S)-amido avermectin derivatives |
GB0302309D0 (en) * | 2003-01-31 | 2003-03-05 | Syngenta Participations Ag | Avermectin monosaccharide derivatives substituted in the 4 -position having pesticidal properties |
GB0302308D0 (en) * | 2003-01-31 | 2003-03-05 | Syngenta Participations Ag | Avermectin and avermectin monosaccharide derivatives substituted in the 4"- or 4'-position having pesticidal properties |
GB0302310D0 (en) * | 2003-01-31 | 2003-03-05 | Syngenta Participations Ag | Avermectin- and avermectin monosaccharide derivatives substituted in the 4"- or 4' - positionhaving pesticidal properties |
GB0302547D0 (en) * | 2003-02-04 | 2003-03-12 | Syngenta Participations Ag | Avermectins and avermectin monosaccharide substituted in the 4'- and 4" position having pesticidal properties |
GB0320176D0 (en) * | 2003-08-28 | 2003-10-01 | Syngenta Participations Ag | Avermectins and avermectin monosaccharides substitued in the 4'-and 4"-positionhaving pesticidal properties |
DE102007007750A1 (de) * | 2006-08-17 | 2008-02-21 | Bayer Cropscience Ag | Avermectinderivate |
JP2011522515A (ja) | 2008-04-10 | 2011-08-04 | マサチューセッツ インスティテュート オブ テクノロジー | 癌幹細胞を標的とする薬剤を同定する方法およびその使用 |
WO2014074805A1 (en) | 2012-11-08 | 2014-05-15 | Whitehead Institute For Biomedical Research | Selective targeting of cancer stem cells |
WO2015168255A1 (en) | 2014-04-29 | 2015-11-05 | Whitehead Institute For Biomedical Research | Methods and compositions for targeting cancer stem cells |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE434277B (sv) * | 1976-04-19 | 1984-07-16 | Merck & Co Inc | Sett att framstella nya antihelmintiskt verkande foreningar genom odling av streptomyces avermitilis |
US4201861A (en) * | 1977-10-03 | 1980-05-06 | Merck & Co., Inc. | Acyl derivatives of C-076 compounds |
US4199569A (en) * | 1977-10-03 | 1980-04-22 | Merck & Co., Inc. | Selective hydrogenation products of C-076 compounds and derivatives thereof |
US4200581A (en) * | 1978-08-04 | 1980-04-29 | Merck & Co., Inc. | Alkyl derivatives of C-076 compounds |
US4289760A (en) * | 1980-05-02 | 1981-09-15 | Merck & Co., Inc. | 23-Keto derivatives of C-076 compounds |
US4427663A (en) * | 1982-03-16 | 1984-01-24 | Merck & Co., Inc. | 4"-Keto-and 4"-amino-4"-deoxy avermectin compounds and substituted amino derivatives thereof |
CH666690A5 (de) * | 1984-09-14 | 1988-08-15 | Glaxo Group Ltd | Antibiotisch wirkende verbindungen der makrolidgruppe aus streptomyces-mikroorganismen, ihre herstellung und verwendung. |
US4587247A (en) * | 1985-02-25 | 1986-05-06 | Merck & Co., Inc. | Substituted and unsubstituted 13-(alkoxy)methoxy derivatives of the avermectin aglycones, compositions and use |
DE3778768D1 (de) * | 1986-07-02 | 1992-06-11 | Ciba Geigy Ag | Pestizide. |
US4897416A (en) * | 1987-02-18 | 1990-01-30 | Ciba-Geigy Corporation | Insecticides and parasiticides |
GB8714413D0 (en) * | 1987-06-19 | 1987-07-22 | Erba Farmitalia | 6-substituted penem esters |
US4895837A (en) * | 1988-01-29 | 1990-01-23 | Merck & Co., Inc. | Avermectin derivatives |
US4906619A (en) * | 1988-07-22 | 1990-03-06 | Merck & Co., Inc. | Alkyl avermectin 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 |
EP0530901A1 (en) * | 1991-09-04 | 1993-03-10 | Merck & Co. Inc. | 13-beta-O-methoxymethyl-22,23-dihydro avermectin B1A/B1B aglycone |
-
1992
- 1992-03-24 US US07/857,035 patent/US5229415A/en not_active Expired - Lifetime
-
1993
- 1993-03-16 EP EP93907512A patent/EP0632725B1/en not_active Expired - Lifetime
- 1993-03-16 WO PCT/US1993/002362 patent/WO1993018778A1/en active IP Right Grant
- 1993-03-16 JP JP05516659A patent/JP3135918B2/ja not_active Expired - Lifetime
- 1993-03-16 DE DE69322265T patent/DE69322265T2/de not_active Expired - Lifetime
- 1993-03-16 AU AU38092/93A patent/AU669358B2/en not_active Expired
- 1993-03-16 CA CA002132429A patent/CA2132429C/en not_active Expired - Lifetime
- 1993-03-16 AT AT93907512T patent/ATE173738T1/de not_active IP Right Cessation
- 1993-03-23 ZA ZA932048A patent/ZA932048B/xx unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012097092A (ja) * | 2000-08-09 | 2012-05-24 | Kitasato Institute | エバーメクチン誘導体 |
Also Published As
Publication number | Publication date |
---|---|
US5229415A (en) | 1993-07-20 |
EP0632725A4 (en) | 1997-03-19 |
ATE173738T1 (de) | 1998-12-15 |
CA2132429A1 (en) | 1993-09-30 |
ZA932048B (en) | 1993-10-19 |
EP0632725B1 (en) | 1998-11-25 |
EP0632725A1 (en) | 1995-01-11 |
AU669358B2 (en) | 1996-06-06 |
DE69322265D1 (en) | 1999-01-07 |
WO1993018778A1 (en) | 1993-09-30 |
CA2132429C (en) | 2003-05-20 |
AU3809293A (en) | 1993-10-21 |
JP3135918B2 (ja) | 2001-02-19 |
DE69322265T2 (de) | 1999-06-24 |
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