SK281684B6 - Hemihydrát kryštalickej soli 4''-deoxy-4''-epimetylaminoavermektínu b1a/b1b s kyselinou benzoovou, spôsob jeho výroby a prostriedok s jeho obsahom - Google Patents
Hemihydrát kryštalickej soli 4''-deoxy-4''-epimetylaminoavermektínu b1a/b1b s kyselinou benzoovou, spôsob jeho výroby a prostriedok s jeho obsahom Download PDFInfo
- Publication number
- SK281684B6 SK281684B6 SK209-96A SK20996A SK281684B6 SK 281684 B6 SK281684 B6 SK 281684B6 SK 20996 A SK20996 A SK 20996A SK 281684 B6 SK281684 B6 SK 281684B6
- Authority
- SK
- Slovakia
- Prior art keywords
- deoxy
- benzoic acid
- crystalline
- mixture
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 13
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 150000003839 salts Chemical class 0.000 title claims abstract description 12
- 239000005711 Benzoic acid Substances 0.000 title claims abstract description 6
- 235000010233 benzoic acid Nutrition 0.000 title claims abstract description 6
- 239000013078 crystal Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000005660 Abamectin Substances 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 241000607479 Yersinia pestis Species 0.000 abstract description 9
- 239000000126 substance Substances 0.000 abstract description 9
- 241000238631 Hexapoda Species 0.000 abstract description 5
- 244000045947 parasite Species 0.000 abstract description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 241000254032 Acrididae Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- 241000254086 Tribolium <beetle> Species 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 244000078703 ectoparasite Species 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000001617 migratory effect Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- -1 polypropylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- 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)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Molecular Biology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10918993A | 1993-08-19 | 1993-08-19 | |
| PCT/US1994/009207 WO1995005390A1 (en) | 1993-08-19 | 1994-08-15 | THERMODYNAMICALLY STABLE CRYSTAL FORM OF 4'-DEOXY-4'-EPI-METHYLAMINO AVERMECTIN B1a/B1b BENZOIC ACID SALT AND PROCESSES FOR ITS PREPARATION |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK20996A3 SK20996A3 (en) | 1996-06-05 |
| SK281684B6 true SK281684B6 (sk) | 2001-06-11 |
Family
ID=22326282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK209-96A SK281684B6 (sk) | 1993-08-19 | 1994-08-15 | Hemihydrát kryštalickej soli 4''-deoxy-4''-epimetylaminoavermektínu b1a/b1b s kyselinou benzoovou, spôsob jeho výroby a prostriedok s jeho obsahom |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP0714400B1 (cs) |
| JP (3) | JP3954093B2 (cs) |
| KR (1) | KR100370697B1 (cs) |
| CN (1) | CN1041523C (cs) |
| AT (1) | ATE187735T1 (cs) |
| AU (1) | AU684828B2 (cs) |
| BR (1) | BR9407300A (cs) |
| CA (1) | CA2168843C (cs) |
| CY (1) | CY2181B1 (cs) |
| CZ (1) | CZ287929B6 (cs) |
| DE (1) | DE69422182T2 (cs) |
| DK (1) | DK0714400T3 (cs) |
| ES (1) | ES2139753T3 (cs) |
| FI (2) | FI110783B (cs) |
| GR (1) | GR3032164T3 (cs) |
| HU (1) | HU217769B (cs) |
| LV (1) | LV12571B (cs) |
| NO (1) | NO305658B1 (cs) |
| NZ (1) | NZ273129A (cs) |
| PL (1) | PL176300B1 (cs) |
| PT (1) | PT714400E (cs) |
| RU (1) | RU2133753C1 (cs) |
| SK (1) | SK281684B6 (cs) |
| WO (1) | WO1995005390A1 (cs) |
| ZA (1) | ZA946203B (cs) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6486195B1 (en) * | 1993-08-19 | 2002-11-26 | Merck & Co., Inc. | Thermodynamically stable crystal form of 4″-deoxy-4″-epi-methylamino avermectin B1a/B1b benzoic acid salt and processes for its preparation |
| 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 |
| GB0229804D0 (en) * | 2002-12-20 | 2003-01-29 | Syngenta Participations Ag | Avermection b1 and avermectin b1 monosaccharide derivatives having an alkoxymethyl substituent in the 4"- or 4'-position |
| DE102004057195A1 (de) * | 2004-11-26 | 2006-06-01 | Wilex Ag | Kristalline Modifikationen von N-Alpha-(2,4,6-Triisopropylphenylsulfonyl)-3-hydroxyamidino-(L)-phenylalanin-4-ethoxycarbonylpiperazid und/oder Salzen davon |
| RU2545094C2 (ru) * | 2010-02-23 | 2015-03-27 | Ниппон Каяку Ко., Лтд. | Стабильная кристаллическая форма 2-этил-3,7-диметил-6-(трифторметокси)фенокси)хинолин-4-илметилкарбоната, способ ее получения и агрохимическая композиция, содержащая данную кристаллическую форму |
| CN106995476B (zh) * | 2017-05-16 | 2018-03-13 | 河北美荷药业有限公司 | 一种甲氨基阿维菌素b2苯甲酸盐的制备方法 |
| CN108840893A (zh) * | 2018-07-01 | 2018-11-20 | 李万强 | 一种甲氨基阿维菌素苯甲酸盐的新晶型及其制备方法 |
| CN109912671B (zh) * | 2019-04-12 | 2022-04-26 | 宁夏泰益欣生物科技有限公司 | 一种利用阿维菌素结晶母液提取阿维菌素B2a的方法 |
Family Cites Families (18)
| 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 |
| JPS57212200A (en) * | 1981-06-23 | 1982-12-27 | Takeda Chem Ind Ltd | Preparation of echinoside a |
| US4423209A (en) * | 1982-02-26 | 1983-12-27 | Merck & Co., Inc. | Processes for the interconversion of avermectin compounds |
| 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 |
| GB8518422D0 (en) * | 1985-07-22 | 1985-08-29 | Beecham Group Plc | Compounds |
| SU1678210A3 (ru) * | 1986-06-13 | 1991-09-15 | Санкио Компани Лимитед (Фирма) | Способ получени макролидных соединений |
| AR243528A1 (es) * | 1986-12-11 | 1993-08-31 | Sankyo Co | Procedimiento para preparar compuestos de macrolida y un procedimiento para producir con los mismos una composicion parasiticida. |
| US4874749A (en) * | 1987-07-31 | 1989-10-17 | Merck & Co., Inc. | 4"-Deoxy-4-N-methylamino avermectin Bla/Blb |
| DE3727648A1 (de) * | 1987-08-19 | 1989-03-02 | Bayer Ag | Neue avermectin derivate, verfahren zu ihrer herstellung und ihre verwendung |
| IT1216059B (it) * | 1988-03-11 | 1990-02-22 | Crc Ricerca Chim | Procedimento per la separazione di diastereomeri macrociclici. |
| JPH0631302B2 (ja) * | 1988-11-16 | 1994-04-27 | 日本化薬株式会社 | エトポシド−２−ジメチルアミノ体塩酸二水和結晶及びその製造法 |
| US4897383A (en) * | 1989-02-13 | 1990-01-30 | Merck & Co., Inc. | Avermectin derivatives |
| JPH0615557B2 (ja) * | 1990-02-19 | 1994-03-02 | ヤマサ醤油株式会社 | ２’―デオキシ―２’―メチリデンシチジンの２水和物結晶 |
| JPH0446192A (ja) * | 1990-06-12 | 1992-02-17 | Nippon Kayaku Co Ltd | オキセタノシンｇ無水物結晶及びその製造法 |
| IL98599A (en) * | 1990-06-28 | 1995-06-29 | Merck & Co Inc | Stable salts of 4"-deoxy-4"-epi-methylamino avermectin b1a/b1b and insecticidal compositions containing them |
| JP2652272B2 (ja) * | 1990-12-31 | 1997-09-10 | 住化ファインケム株式会社 | １−（４−アミノ−６，７−ジメトキシ−２−キナゾリニル）−４−（２−テトラヒドロフロイル）ピペラジン塩酸塩の新規な結晶体および該結晶体の製造方法 |
| RU2057132C1 (ru) * | 1991-05-15 | 1996-03-27 | Яманоути Фармасьютикал Ко., Лтд. | Моногидрат (-)-(s)-2,8-диметил-3-метилен-1-окса-8-азаспиро[4,5]-декана l-тартрата и способ его получения |
| JP2848721B2 (ja) * | 1991-08-09 | 1999-01-20 | 森永乳業株式会社 | 結晶ラクチュロース三水和物とその製造法 |
-
1994
- 1994-08-15 DE DE69422182T patent/DE69422182T2/de not_active Expired - Lifetime
- 1994-08-15 WO PCT/US1994/009207 patent/WO1995005390A1/en not_active Ceased
- 1994-08-15 JP JP50713095A patent/JP3954093B2/ja not_active Expired - Lifetime
- 1994-08-15 RU RU96107041A patent/RU2133753C1/ru active
- 1994-08-15 HU HU9600345A patent/HU217769B/hu unknown
- 1994-08-15 EP EP94926502A patent/EP0714400B1/en not_active Expired - Lifetime
- 1994-08-15 PL PL94313043A patent/PL176300B1/pl unknown
- 1994-08-15 CZ CZ1996459A patent/CZ287929B6/cs not_active IP Right Cessation
- 1994-08-15 NZ NZ273129A patent/NZ273129A/en not_active IP Right Cessation
- 1994-08-15 CA CA002168843A patent/CA2168843C/en not_active Expired - Lifetime
- 1994-08-15 BR BR9407300A patent/BR9407300A/pt not_active IP Right Cessation
- 1994-08-15 ES ES94926502T patent/ES2139753T3/es not_active Expired - Lifetime
- 1994-08-15 CN CN94193136A patent/CN1041523C/zh not_active Expired - Lifetime
- 1994-08-15 AU AU76319/94A patent/AU684828B2/en not_active Expired
- 1994-08-15 PT PT94926502T patent/PT714400E/pt unknown
- 1994-08-15 KR KR1019960700754A patent/KR100370697B1/ko not_active Expired - Lifetime
- 1994-08-15 AT AT94926502T patent/ATE187735T1/de active
- 1994-08-15 SK SK209-96A patent/SK281684B6/sk not_active IP Right Cessation
- 1994-08-15 DK DK94926502T patent/DK0714400T3/da active
- 1994-08-17 ZA ZA946203A patent/ZA946203B/xx unknown
-
1996
- 1996-02-16 FI FI960725A patent/FI110783B/fi not_active IP Right Cessation
- 1996-02-16 NO NO960618A patent/NO305658B1/no not_active IP Right Cessation
-
1999
- 1999-12-16 GR GR990403202T patent/GR3032164T3/el unknown
-
2000
- 2000-08-10 CY CY0000041A patent/CY2181B1/xx unknown
- 2000-09-07 LV LVP-00-120A patent/LV12571B/en unknown
-
2002
- 2002-06-11 FI FI20021120A patent/FI111165B/fi not_active IP Right Cessation
-
2007
- 2007-02-09 JP JP2007030096A patent/JP2007176946A/ja not_active Withdrawn
-
2011
- 2011-05-25 JP JP2011117141A patent/JP2011207899A/ja active Pending
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TC4A | Change of owner's name |
Owner name: MERCK SHARP & DOHME CORP., RAHWAY, NJ, US Effective date: 20100202 |
|
| PC4A | Assignment and transfer of rights |
Owner name: SCHERING CORPORATION, KENILWORTH, NEW JERSEY, US Free format text: FORMER OWNER: MERCK SHARP & DOHME CORP., RAHWAY, NJ, US Effective date: 20121122 |
|
| TC4A | Change of owner's name |
Owner name: MERCK SHARP & DOHME CORP., RAHWAY, NJ, US Effective date: 20121122 |
|
| MK4A | Patent expired |
Expiry date: 20140815 |