LV10503B - Method for producing of ll-f-28249 23-(c1-c6-alkyloxime) - Google Patents
Method for producing of ll-f-28249 23-(c1-c6-alkyloxime) Download PDFInfo
- Publication number
- LV10503B LV10503B LVP-93-697A LV930697A LV10503B LV 10503 B LV10503 B LV 10503B LV 930697 A LV930697 A LV 930697A LV 10503 B LV10503 B LV 10503B
- Authority
- LV
- Latvia
- Prior art keywords
- mmojih
- dimethylsulfoxide
- nitrobenzoyl
- okco
- npn
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract 8
- 230000003647 oxidation Effects 0.000 claims abstract 4
- 238000007254 oxidation reaction Methods 0.000 claims abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 8
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims 4
- 230000001590 oxidative effect Effects 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 238000001953 recrystallisation Methods 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- NKRJRPDCNYYXEZ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxyalumane Chemical compound CC(C)(C)O[AlH2] NKRJRPDCNYYXEZ-UHFFFAOYSA-N 0.000 claims 1
- WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical compound O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 claims 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 claims 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 1
- SYNHCENRCUAUNM-UHFFFAOYSA-N Nitrogen mustard N-oxide hydrochloride Chemical compound Cl.ClCC[N+]([O-])(C)CCCl SYNHCENRCUAUNM-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- INGGGNUCWJHFKD-UHFFFAOYSA-N chromium;pyridine Chemical group [Cr].C1=CC=NC=C1 INGGGNUCWJHFKD-UHFFFAOYSA-N 0.000 claims 1
- NKRNGKIEDAVMHL-UHFFFAOYSA-L dihydroxy(dioxo)chromium;pyridine Chemical compound O[Cr](O)(=O)=O.C1=CC=NC=C1 NKRNGKIEDAVMHL-UHFFFAOYSA-L 0.000 claims 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 claims 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 101100397240 Arabidopsis thaliana ISPD gene Proteins 0.000 description 1
- 101000622010 Crotalus atrox Snake venom metalloproteinase atrolysin-B Proteins 0.000 description 1
- 241001669680 Dormitator maculatus Species 0.000 description 1
- 101100013145 Drosophila melanogaster Flo2 gene Proteins 0.000 description 1
- 101100168745 Emericella nidulans (strain FGSC A4 / ATCC 38163 / CBS 112.46 / NRRL 194 / M139) csnG gene Proteins 0.000 description 1
- WDWFRIMNWVDXGF-YQERLSOISA-N LL-F28249 beta Chemical compound C1[C@H](O)[C@H](C)[C@@H](C(/C)=C/C)O[C@]11O[C@H](C\C=C(C)\C[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 WDWFRIMNWVDXGF-YQERLSOISA-N 0.000 description 1
- 229910006561 Li—F Inorganic materials 0.000 description 1
- 102000004213 Neuropilin-2 Human genes 0.000 description 1
- 108090000770 Neuropilin-2 Proteins 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 101150078969 acoB gene Proteins 0.000 description 1
- WDWFRIMNWVDXGF-UHFFFAOYSA-N nemadectin beta Natural products C1C(O)C(C)C(C(C)=CC)OC11OC(CC=C(C)CC(C)C=CC=C2C3(C(C(=O)O4)C=C(C)C(O)C3OC2)O)CC4C1 WDWFRIMNWVDXGF-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fats And Perfumes (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyridine Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
- Liquid Crystal Substances (AREA)
- Cosmetics (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Lubricants (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/405,793 US4988824A (en) | 1989-09-11 | 1989-09-11 | Process for the preparation of 23-(C1-C6 alkyloxime)-LL-F28249 compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LV10503A LV10503A (lv) | 1995-02-20 |
| LV10503B true LV10503B (en) | 1996-04-20 |
Family
ID=23605260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LVP-93-697A LV10503B (en) | 1989-09-11 | 1993-06-28 | Method for producing of ll-f-28249 23-(c1-c6-alkyloxime) |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4988824A (pt) |
| EP (1) | EP0421081B1 (pt) |
| JP (1) | JP2939312B2 (pt) |
| KR (1) | KR0160977B1 (pt) |
| CN (1) | CN1028428C (pt) |
| AT (1) | ATE107650T1 (pt) |
| AU (1) | AU634579B2 (pt) |
| BG (1) | BG60620B1 (pt) |
| BR (1) | BR9004493A (pt) |
| CA (1) | CA2024919C (pt) |
| DE (1) | DE69010129T2 (pt) |
| DK (1) | DK0421081T3 (pt) |
| ES (1) | ES2057291T3 (pt) |
| GE (1) | GEP19981003B (pt) |
| HK (1) | HK1000095A1 (pt) |
| HU (1) | HU206721B (pt) |
| IE (1) | IE66030B1 (pt) |
| IL (1) | IL95303A (pt) |
| LV (1) | LV10503B (pt) |
| MD (1) | MD425C2 (pt) |
| NZ (1) | NZ235151A (pt) |
| PL (1) | PL165332B1 (pt) |
| PT (1) | PT95242B (pt) |
| RU (1) | RU2030416C1 (pt) |
| SI (1) | SI9011711A (pt) |
| UA (1) | UA26907C2 (pt) |
| YU (1) | YU47520B (pt) |
| ZA (1) | ZA907186B (pt) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU660205B2 (en) | 1991-12-23 | 1995-06-15 | Virbac, Inc | Systemic control of parasites |
| US5439924A (en) * | 1991-12-23 | 1995-08-08 | Virbac, Inc. | Systemic control of parasites |
| US5478951A (en) | 1994-06-22 | 1995-12-26 | American Cyanamid Company | Method for the purification of 23-E isomers of 23-imino derivatives of LL-F28249 compounds |
| PT810823E (pt) * | 1995-02-24 | 2001-09-28 | Novartis Ag | Composicao para controlo de parasitas |
| EP0750907B1 (en) * | 1995-06-30 | 2002-03-20 | American Cyanamid Company | Stable macrolide and macrolide vaccine compositions |
| WO1999017760A2 (en) | 1997-10-02 | 1999-04-15 | Microcide Pharmaceuticals, Inc. | Fungal or mammalian cell efflux pump inhibitors for enhancing susceptibility of the cell to a drug |
| US6762327B2 (en) * | 2002-04-29 | 2004-07-13 | Wyeth | Selective oxidation process with enhanced safety |
| US7348417B2 (en) * | 2003-08-07 | 2008-03-25 | Wyeth | Method of purifying moxidectin through crystallization |
| AU2006100658C4 (en) * | 2006-05-08 | 2009-07-23 | Wyeth | Process |
| AU2006100662B4 (en) * | 2006-05-08 | 2006-10-05 | Wyeth | Intermediates and processes using them |
| AU2006100660B4 (en) * | 2006-06-22 | 2006-10-05 | Wyeth | Improved oxidation process with enhanced safety and use thereof |
| DK3351546T5 (da) | 2011-12-02 | 2024-08-12 | Boehringer Ingelheim Vetmedica Gmbh | Langtidsvirkende injicerbare moxidectinformuleringer |
| CN104277050B (zh) * | 2013-07-04 | 2016-05-04 | 北大方正集团有限公司 | 一种制备莫西克汀的方法 |
| CN104017001B (zh) * | 2014-06-18 | 2016-01-13 | 大连九信生物化工科技有限公司 | 一种化学合成莫西克汀的方法 |
| CN104292239A (zh) * | 2014-09-30 | 2015-01-21 | 大连九信生物化工科技有限公司 | 一种消除莫西克汀生产过程中副产物二甲基硫醚的方法 |
| CN104628740B (zh) * | 2015-02-13 | 2017-06-16 | 河北圣雪大成制药有限责任公司 | 一种化学合成及纯化莫西克汀的方法 |
| CN104860961B (zh) * | 2015-04-10 | 2017-08-04 | 新宇药业股份有限公司 | 一种制备5‑氧（对‑硝基苯甲酰）‑尼莫克汀的方法 |
| CN105085540B (zh) * | 2015-08-12 | 2017-07-07 | 内蒙古佳瑞米精细化工有限公司 | 一种制备高含量尼莫克汀的方法 |
| CN114591347B (zh) * | 2022-03-29 | 2023-03-24 | 河北美荷药业有限公司 | 莫西菌素中间体及制备方法、莫西菌素的制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4201861A (en) * | 1977-10-03 | 1980-05-06 | Merck & Co., Inc. | Acyl derivatives of C-076 compounds |
| ES8802229A1 (es) * | 1985-04-30 | 1988-04-16 | Glaxo Group Ltd | Un procedimiento para preparar nuevos derivados lactonicos macrociclicos. |
| CA1296329C (en) * | 1986-06-06 | 1992-02-25 | Derek R. Sutherland | Macrolide compounds |
| ES2058082T3 (es) * | 1986-09-12 | 1994-11-01 | American Cyanamid Co | Derivados 23-oxo (ceto) y 23-imino de compuestos ll-f28249. |
| US4916154A (en) * | 1986-09-12 | 1990-04-10 | American Cyanamid Company | 23-Imino derivatives of LL-F28249 compounds |
| US4855317A (en) * | 1987-03-06 | 1989-08-08 | Ciba-Geigy Corporation | Insecticides and parasiticides |
| GB8721377D0 (en) * | 1987-09-11 | 1987-10-21 | Glaxo Group Ltd | Chemical compounds |
| GB8721376D0 (en) * | 1987-09-11 | 1987-10-21 | Glaxo Group Ltd | Chemical compounds |
| US5057536A (en) * | 1988-05-10 | 1991-10-15 | American Cyanamid Company | Macrolide compounds |
| GB8813150D0 (en) * | 1988-06-03 | 1988-07-06 | American Cyanamid Co | Chemical compounds |
| US4900758A (en) * | 1989-05-11 | 1990-02-13 | Ici Americas Inc. | Novel insecticides |
| DE69023454T2 (de) * | 1989-09-11 | 1996-06-05 | American Cyanamid Co., Wayne, N.J. | 13-Alkyl-23-Imino und 13-Halo-23-Imino-Derivate von LL-F28249-Verbindungen und ihre Verwendung als Endo- und Ectoparasitizide, Insektizide, Akarizide und Nematozide Mittel. |
-
1989
- 1989-09-11 US US07/405,793 patent/US4988824A/en not_active Expired - Lifetime
-
1990
- 1990-08-03 DK DK90114919.5T patent/DK0421081T3/da active
- 1990-08-03 EP EP90114919A patent/EP0421081B1/en not_active Expired - Lifetime
- 1990-08-03 AT AT90114919T patent/ATE107650T1/de not_active IP Right Cessation
- 1990-08-03 DE DE69010129T patent/DE69010129T2/de not_active Expired - Lifetime
- 1990-08-03 ES ES90114919T patent/ES2057291T3/es not_active Expired - Lifetime
- 1990-08-06 IL IL9530390A patent/IL95303A/en unknown
- 1990-09-03 NZ NZ235151A patent/NZ235151A/en unknown
- 1990-09-07 JP JP2235958A patent/JP2939312B2/ja not_active Expired - Lifetime
- 1990-09-07 CA CA002024919A patent/CA2024919C/en not_active Expired - Lifetime
- 1990-09-07 PT PT95242A patent/PT95242B/pt not_active IP Right Cessation
- 1990-09-10 KR KR1019900014281A patent/KR0160977B1/ko not_active IP Right Cessation
- 1990-09-10 PL PL90286824A patent/PL165332B1/pl unknown
- 1990-09-10 CN CN90107676A patent/CN1028428C/zh not_active Expired - Lifetime
- 1990-09-10 IE IE327390A patent/IE66030B1/en not_active IP Right Cessation
- 1990-09-10 RU SU904831093A patent/RU2030416C1/ru active
- 1990-09-10 YU YU171190A patent/YU47520B/sh unknown
- 1990-09-10 BG BG92810A patent/BG60620B1/bg unknown
- 1990-09-10 UA UA4831093A patent/UA26907C2/uk unknown
- 1990-09-10 AU AU62362/90A patent/AU634579B2/en not_active Expired
- 1990-09-10 HU HU905842A patent/HU206721B/hu unknown
- 1990-09-10 BR BR909004493A patent/BR9004493A/pt not_active IP Right Cessation
- 1990-09-10 ZA ZA907186A patent/ZA907186B/xx unknown
- 1990-09-10 SI SI9011711A patent/SI9011711A/sl unknown
-
1993
- 1993-06-28 LV LVP-93-697A patent/LV10503B/lv unknown
- 1993-07-31 GE GEAP19931302A patent/GEP19981003B/en unknown
-
1994
- 1994-07-12 MD MD95-0307A patent/MD425C2/ro unknown
-
1997
- 1997-07-09 HK HK97101524A patent/HK1000095A1/xx not_active IP Right Cessation
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