PT90106B - Processo para a preparacao de derivados de avermectina antiparasiticos - Google Patents
Processo para a preparacao de derivados de avermectina antiparasiticos Download PDFInfo
- Publication number
- PT90106B PT90106B PT90106A PT9010689A PT90106B PT 90106 B PT90106 B PT 90106B PT 90106 A PT90106 A PT 90106A PT 9010689 A PT9010689 A PT 9010689A PT 90106 B PT90106 B PT 90106B
- Authority
- PT
- Portugal
- Prior art keywords
- formula
- double bond
- compounds
- compound
- avermectin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title claims description 14
- 239000003096 antiparasitic agent Substances 0.000 title abstract description 7
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical class C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[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 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 title description 5
- 230000002141 anti-parasite Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- -1 cyano, aminosulphonyl Chemical group 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 239000011737 fluorine Substances 0.000 claims abstract description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 239000005660 Abamectin Substances 0.000 claims description 20
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- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
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- 150000003457 sulfones Chemical class 0.000 claims description 6
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 5
- 150000001503 aryl iodides Chemical class 0.000 claims description 5
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- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
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- RTUDBROGOZBBIC-UHFFFAOYSA-N 1-iodo-4-(trifluoromethoxy)benzene Chemical group FC(F)(F)OC1=CC=C(I)C=C1 RTUDBROGOZBBIC-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
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- 238000005481 NMR spectroscopy Methods 0.000 description 15
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- JVGWUGTWQIAGHJ-DRBFDSOZSA-N avermectin a2 Chemical compound C1C(O)[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](OC2OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](OC)[C@H]3OC\2)O)C[C@H]4C1 JVGWUGTWQIAGHJ-DRBFDSOZSA-N 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
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- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 235000020997 lean meat Nutrition 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229940100892 mercury compound Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- XYMVZPOXZCDCNP-UHFFFAOYSA-N sulfamoyl cyanide Chemical compound NS(=O)(=O)C#N XYMVZPOXZCDCNP-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229940035024 thioglycerol Drugs 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
-
- 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
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/195—Antibiotics
-
- 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
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Plant Pathology (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Dentistry (AREA)
- Animal Husbandry (AREA)
- Pest Control & Pesticides (AREA)
- Veterinary Medicine (AREA)
- Environmental Sciences (AREA)
- Food Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB888807280A GB8807280D0 (en) | 1988-03-26 | 1988-03-26 | Antiparasitic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT90106A PT90106A (pt) | 1989-11-10 |
| PT90106B true PT90106B (pt) | 1994-06-30 |
Family
ID=10634193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT90106A PT90106B (pt) | 1988-03-26 | 1989-03-23 | Processo para a preparacao de derivados de avermectina antiparasiticos |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4992424A (OSRAM) |
| EP (1) | EP0335541B1 (OSRAM) |
| JP (1) | JP2686311B2 (OSRAM) |
| AT (1) | ATE78486T1 (OSRAM) |
| CA (1) | CA1325208C (OSRAM) |
| DE (1) | DE68902157T2 (OSRAM) |
| DK (1) | DK170932B1 (OSRAM) |
| ES (1) | ES2041985T3 (OSRAM) |
| GB (1) | GB8807280D0 (OSRAM) |
| GR (1) | GR3005725T3 (OSRAM) |
| IE (1) | IE62750B1 (OSRAM) |
| PT (1) | PT90106B (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9205007D0 (en) * | 1992-03-07 | 1992-04-22 | Pfizer Ltd | Antiparasitic agents |
| IT1255135B (it) * | 1992-05-05 | 1995-10-20 | Principio attivo a base di avermectine, ceppo e procedimento per la sua preparazione e composizione veterinaria che lo contiene. | |
| KR100186946B1 (ko) * | 1993-10-05 | 1999-04-01 | 알렌 제이.스피겔 | 도라멕틴의 구충활성 중간체 및 도라멕틴의 제조방법 |
| GB9825402D0 (en) * | 1998-11-19 | 1999-01-13 | Pfizer Ltd | Antiparasitic formulations |
| DE19913534A1 (de) * | 1999-03-25 | 2000-10-05 | Bayer Ag | Avermectinderivate |
| NZ531787A (en) | 2001-09-17 | 2006-12-22 | Lilly Co Eli | Pesticidal formulations for controlling pests in domestic animals |
| MX2012004523A (es) | 2009-10-19 | 2012-05-08 | Intervet Int Bv | Metodo y formulacion para el control de parasitos. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES8800986A1 (es) * | 1985-07-27 | 1987-12-01 | Pfizer | Un procedimiento para la produccion de un nuevo derivado de avermectina |
| DE3750495T2 (de) * | 1986-07-24 | 1995-02-23 | Beecham Group Plc | Milbemycin-Derivate mit parasitenabtötender Aktivität, ein Verfahren zu ihrer Herstellung und die sie enthaltenden Zusammensetzungen. |
| EP0284176B1 (en) * | 1987-01-23 | 1993-08-25 | Pfizer Inc. | Process for production of avermectins and cultures therefor |
| IN167980B (OSRAM) * | 1987-01-23 | 1991-01-19 | Pfizer |
-
1988
- 1988-03-26 GB GB888807280A patent/GB8807280D0/en active Pending
-
1989
- 1989-03-07 US US07/320,209 patent/US4992424A/en not_active Expired - Fee Related
- 1989-03-17 DE DE8989302680T patent/DE68902157T2/de not_active Expired - Lifetime
- 1989-03-17 AT AT89302680T patent/ATE78486T1/de active
- 1989-03-17 ES ES198989302680T patent/ES2041985T3/es not_active Expired - Lifetime
- 1989-03-17 EP EP89302680A patent/EP0335541B1/en not_active Expired - Lifetime
- 1989-03-22 DK DK142889A patent/DK170932B1/da not_active IP Right Cessation
- 1989-03-23 IE IE94889A patent/IE62750B1/en not_active IP Right Cessation
- 1989-03-23 PT PT90106A patent/PT90106B/pt not_active IP Right Cessation
- 1989-03-23 CA CA000594739A patent/CA1325208C/en not_active Expired - Fee Related
- 1989-03-27 JP JP1074775A patent/JP2686311B2/ja not_active Expired - Lifetime
-
1992
- 1992-09-17 GR GR920402048T patent/GR3005725T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01283298A (ja) | 1989-11-14 |
| DK142889A (da) | 1989-09-27 |
| IE62750B1 (en) | 1995-02-22 |
| EP0335541A3 (en) | 1991-01-30 |
| JP2686311B2 (ja) | 1997-12-08 |
| ATE78486T1 (de) | 1992-08-15 |
| ES2041985T3 (es) | 1993-12-01 |
| GR3005725T3 (OSRAM) | 1993-06-07 |
| DE68902157D1 (de) | 1992-08-27 |
| EP0335541A2 (en) | 1989-10-04 |
| IE890948L (en) | 1989-09-26 |
| PT90106A (pt) | 1989-11-10 |
| US4992424A (en) | 1991-02-12 |
| DK142889D0 (da) | 1989-03-22 |
| DE68902157T2 (de) | 1992-12-17 |
| CA1325208C (en) | 1993-12-14 |
| EP0335541B1 (en) | 1992-07-22 |
| GB8807280D0 (en) | 1988-04-27 |
| DK170932B1 (da) | 1996-03-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG3A | Patent granted, date of granting |
Effective date: 19931207 |
|
| MM3A | Annulment or lapse |
Free format text: LAPSE DUE TO NON-PAYMENT OF FEES Effective date: 20000630 |