SI8710674B - Postopek za pripravo 10,11,12,13-tetrahidro derivatov tilozina - Google Patents
Postopek za pripravo 10,11,12,13-tetrahidro derivatov tilozina Download PDFInfo
- Publication number
- SI8710674B SI8710674B SI8710674A SI8710674A SI8710674B SI 8710674 B SI8710674 B SI 8710674B SI 8710674 A SI8710674 A SI 8710674A SI 8710674 A SI8710674 A SI 8710674A SI 8710674 B SI8710674 B SI 8710674B
- Authority
- SI
- Slovenia
- Prior art keywords
- stands
- alcohol
- tylosin
- process according
- noh
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 9
- WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical class O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 title claims abstract 6
- 238000002360 preparation method Methods 0.000 title claims abstract 3
- 229930194936 Tylosin Natural products 0.000 claims abstract 4
- 239000004182 Tylosin Substances 0.000 claims abstract 4
- 229960004059 tylosin Drugs 0.000 claims abstract 4
- 235000019375 tylosin Nutrition 0.000 claims abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims 4
- 230000003647 oxidation Effects 0.000 claims 3
- 238000007254 oxidation reaction Methods 0.000 claims 3
- QDAVFUSCCPXZTE-VMXQISHHSA-N (4r,5s,6s,7r,9r,11e,13e,15r,16r)-6-[(2r,3r,4r,5s,6r)-5-[(2s,4r,5s,6s)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-15-[[(2r,3r,4r,5r,6r)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-7 Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CCO)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 QDAVFUSCCPXZTE-VMXQISHHSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 2
- 238000006359 acetalization reaction Methods 0.000 claims 2
- 150000001241 acetals Chemical class 0.000 claims 2
- 125000003172 aldehyde group Chemical group 0.000 claims 2
- 230000003197 catalytic effect Effects 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 229950010526 relomycin Drugs 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000002537 cosmetic Substances 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- QZIQJVCYUQZDIR-UHFFFAOYSA-N mechlorethamine hydrochloride Chemical compound Cl.ClCCN(C)CCCl QZIQJVCYUQZDIR-UHFFFAOYSA-N 0.000 claims 1
- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 150000004681 metal hydrides Chemical class 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910000510 noble metal Inorganic materials 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 239000008363 phosphate buffer Substances 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
Classifications
-
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Claims (5)
17 PATENTNI ZAHTEVKI 1. Postopek za pripravo 10,11,12,13-tetrahidro tilozina in njegovih derivatov s formulo R2 R1
v kateri R stoji za CHO, CH2OH, CH=NOH ali CH(OCH3)2; Rl stoji za H; R^ stoji za OH; ali Rl + R^ stojita za =0 ali =NOH, R^ stoji za mikarozilno skupino ali atom vodika, kjer mikarozil =
a) enojno vez, ali b) dvojno vez, s pridržkom, da R stoji za CH2OH, Rl + R^ stojita za =NOH in R^ stoji za mikarozilno skupino, 18 označen s tem, da obsega A) katalitsko hidrogenacijo tilozina, relomicina, 9-deokso-9-hidroksitilozina in njihovih 4’-demikarozil spojin s plemenito kovino kot katalizatorjem v alkoholu pri sobni temperaturi in pri tlaku vodika 0.2 do 0.5 MPa, in po izbiri B) selektivno redukcijo aldehidne ali keto skupine dobljenega 10,11,12,13-tetrahidrotilozina ali 4’-demikarozil-10,ll,12,13-tetrahidro tilozina s kompleksnim kovinskim hidridom pri sobni temperaturi v zmesi alkohola in fosfatnega pufra, ali, po izbiri, v brezvodnem alkoholu ob začasni zaščiti aldehidne skupine z acetalizacijo in kasneje s hidrolizo acetala in po izbiri C) z oksimiranjem relomicina ali produktov, dobljenih po metodah A) in B), s hidroksilaminom ali z njegovo adicijsko soljo s kislino pri temperaturi od 0-100 °C v prisotnosti organske ali anorganske baze.
2. Postopek po zahtevku 1 stopnja B), označen s tem, da se acetalizacija aldehidne skupine izvede v nižjem alifatskem alkoholu v prisotnosti katalitske količine organske kisline.
3. Postopek po zahtevku 1 stopnja B), označen s tem, da hidrolizo acetala izvedemo v vodni raztopini ob prisotnosti katalitske količine organske ali anorganske kisline.
4. Postopek po zahtevku 1 stopnja C), označen s tem, da oksimiranje v eni stopnji izvedemo z enim ekvivalentom hidroksilamin hidroklorida v alkoholu s prebitkom piridina in v toku N2·
5. Postopek po zahtevku 1 stopnja C), označen s tem, da izolirani produkt dobljen pri zahtevku 4,podvržemo oksimiranju z enim ekvivalentom hidroksilamin hidroklorida pri temperaturi refluksa. Za: PLIVA farmaceutska, kemijska, prehrambena i kozmetička industrija, d.d. A V RELIJA G 7
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU674/87A YU45033B (en) | 1987-04-14 | 1987-04-14 | Process for preparing 10,11,12,13-tetrahydro derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI8710674A SI8710674A (en) | 1996-08-31 |
| SI8710674B true SI8710674B (sl) | 1998-06-30 |
Family
ID=25550944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI8710674A SI8710674B (sl) | 1987-04-14 | 1987-04-14 | Postopek za pripravo 10,11,12,13-tetrahidro derivatov tilozina |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5023240A (sl) |
| EP (1) | EP0287082B1 (sl) |
| JP (1) | JPS63313797A (sl) |
| CN (1) | CN1022569C (sl) |
| AT (1) | ATE103289T1 (sl) |
| BG (1) | BG49826A3 (sl) |
| CA (1) | CA1325424C (sl) |
| CZ (2) | CZ285278B6 (sl) |
| DD (1) | DD272304A5 (sl) |
| DE (1) | DE3888563T2 (sl) |
| ES (1) | ES2053605T3 (sl) |
| HU (2) | HU201089B (sl) |
| PL (1) | PL155812B1 (sl) |
| RO (2) | RO113349B1 (sl) |
| SI (1) | SI8710674B (sl) |
| SK (1) | SK253488A3 (sl) |
| SU (2) | SU1708158A3 (sl) |
| YU (1) | YU45033B (sl) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2638458A1 (fr) * | 1988-10-27 | 1990-05-04 | Adir | Nouveaux derives de la tylosine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| YU149889A (en) * | 1989-07-26 | 1991-02-28 | Pliva Zagreb | Process for preparing biologically active derivatives of tylozine |
| US5140014A (en) * | 1989-11-13 | 1992-08-18 | Abbott Laboratories | Rosaramicin derivatives and method of treating bacterial infections |
| JPH04164093A (ja) * | 1990-10-25 | 1992-06-09 | Mercian Corp | 新タイロシン誘導体 |
| SI9012363A (sl) * | 1990-12-14 | 1998-04-30 | Pliva | Derivati 10,11,12,13-tetrahidro-desmikozina, postopki za njihovo pripravo in postopki za pripravo farmacevtskih preparatov |
| HRP960509A2 (en) * | 1996-10-30 | 1998-06-30 | Pliva Pharm & Chem Works | Novel polyhydro tylosin derivatives and a process for the preparation thereof |
| CZ211798A3 (cs) * | 1997-07-16 | 1999-02-17 | Pliva, Farmaceutska, Kemijska, Prehrambena I Kozmetička Industrije, Dioničko Društvo | Lineární 8a-sekoazalidy a způsob jejich výroby |
| HRP980496B1 (en) * | 1998-09-10 | 2007-03-31 | GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o. | New thilozine hydroxy derivatives and a process for the preparation thereof |
| HRP990129B1 (en) * | 1999-05-03 | 2003-10-31 | Pliva D D | New compounds of 3-deoxy-desmycosin class and process for the preparation thereof |
| HRP990192A2 (en) * | 1999-06-11 | 2001-04-30 | Pliva D D | 4'-DEMICAROZYL-8a-AZA-8a-HOMOTHILOSINE DERIVATIVES |
| US7247617B2 (en) * | 2004-07-13 | 2007-07-24 | Kosan Biosciences Incorporated | Sixteen-member macrolide antiinfective agents |
| RU2412710C2 (ru) * | 2006-07-13 | 2011-02-27 | Эко Энимал Хелс Лимитед | Применение тилвалосина в качестве противовирусного агента |
| EP2089408B1 (en) | 2006-07-28 | 2011-10-12 | Intervet International B.V. | Macrolide synthesis process |
| CN117510561B (zh) * | 2023-11-30 | 2024-04-02 | 中国农业科学院饲料研究所 | 一种泰乐菌素衍生物及其制备方法与应用 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3910892A (en) * | 1971-03-23 | 1975-10-07 | Hoffmann La Roche | Benzodioxane derivatives |
| CH630391A5 (en) * | 1975-02-28 | 1982-06-15 | Scherico Ltd | Process for preparing derivatives of rosaramicin |
| US4205163A (en) * | 1977-11-08 | 1980-05-27 | Sanraku-Ocean Co., Ltd. | Tylosin derivatives |
| DE2826760A1 (de) * | 1978-06-19 | 1980-01-03 | Hoechst Ag | Derivate des 1,2,4-triazols |
| NL8004922A (nl) * | 1979-09-19 | 1981-03-23 | Toyo Jozo Kk | Deformyltylosinederivaten. |
| US4357325A (en) * | 1981-04-20 | 1982-11-02 | Eli Lilly And Company | Methods of controlling Pasteurella infections |
| AU551142B2 (en) * | 1981-07-09 | 1986-04-17 | Zaidan Hojin Biseibutsu Kagaku Kenkyukai | Tylosin derivatives |
| PT76448B (en) * | 1982-04-05 | 1986-03-20 | Merck Sharp & Dohme | Process for preparing stabilization of unstable drugs or food supplements containing antibiotics mainly ephrotomycin |
| US4443436A (en) * | 1982-09-13 | 1984-04-17 | Eli Lilly And Company | C-20-Modified macrolide derivatives of the macrolide antibiotics tylosin, desmycosin, macrocin, and lactenocin |
| GB8405087D0 (en) * | 1984-02-27 | 1984-04-04 | Omura S | Antibiotic |
| JPS61103890A (ja) * | 1984-10-26 | 1986-05-22 | Taisho Pharmaceut Co Ltd | ６−０−メチルエリスロマイシンａ誘導体 |
| JPS61191692A (ja) * | 1985-02-20 | 1986-08-26 | Toyo Jozo Co Ltd | Ｃ−１９−修飾デホルミルデスマイコシン誘導体 |
| JPS62221695A (ja) * | 1986-03-24 | 1987-09-29 | Microbial Chem Res Found | タイロシンオキシム誘導体およびその製造法 |
| EP0292352A3 (fr) * | 1987-05-06 | 1988-12-28 | Adir Et Compagnie | Nouveaux dérivés macrolides, leur procédé de préparation et les compositions pharmaceutiques les contenant |
| JPH02221695A (ja) * | 1989-02-22 | 1990-09-04 | Hitachi Ltd | ロータリ圧縮機 |
| JP3141148B2 (ja) * | 1995-08-08 | 2001-03-05 | 大鵬薬品工業株式会社 | 縮合インダン誘導体及びその塩 |
-
1987
- 1987-04-14 SI SI8710674A patent/SI8710674B/sl unknown
- 1987-04-14 YU YU674/87A patent/YU45033B/xx unknown
-
1988
- 1988-04-12 RO RO148895A patent/RO113349B1/ro unknown
- 1988-04-12 RO RO133024A patent/RO104952B1/ro unknown
- 1988-04-13 AT AT88105905T patent/ATE103289T1/de not_active IP Right Cessation
- 1988-04-13 HU HU881898A patent/HU201089B/hu not_active IP Right Cessation
- 1988-04-13 SK SK2534-88A patent/SK253488A3/sk unknown
- 1988-04-13 US US07/180,940 patent/US5023240A/en not_active Expired - Fee Related
- 1988-04-13 DE DE3888563T patent/DE3888563T2/de not_active Expired - Fee Related
- 1988-04-13 JP JP63089161A patent/JPS63313797A/ja active Pending
- 1988-04-13 CZ CZ973998A patent/CZ285278B6/cs not_active IP Right Cessation
- 1988-04-13 SU SU884355567A patent/SU1708158A3/ru active
- 1988-04-13 EP EP88105905A patent/EP0287082B1/en not_active Expired - Lifetime
- 1988-04-13 BG BG083745A patent/BG49826A3/xx unknown
- 1988-04-13 CN CN88102128A patent/CN1022569C/zh not_active Expired - Fee Related
- 1988-04-13 DD DD88314704A patent/DD272304A5/de not_active IP Right Cessation
- 1988-04-13 PL PL1988271797A patent/PL155812B1/pl unknown
- 1988-04-13 ES ES88105905T patent/ES2053605T3/es not_active Expired - Lifetime
- 1988-04-13 CZ CS882534A patent/CZ283995B6/cs not_active IP Right Cessation
- 1988-04-13 CA CA000564033A patent/CA1325424C/en not_active Expired - Fee Related
-
1989
- 1989-03-27 SU SU894613684A patent/SU1731063A3/ru active
-
1995
- 1995-06-30 HU HU95P/P00625P patent/HU211975A9/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL271797A1 (en) | 1989-01-23 |
| SK278558B6 (en) | 1997-09-10 |
| HUT46924A (en) | 1988-12-28 |
| CZ285278B6 (cs) | 1999-06-16 |
| YU67487A (en) | 1988-12-31 |
| CZ283995B6 (cs) | 1998-07-15 |
| RO113349B1 (ro) | 1998-06-30 |
| BG49826A3 (en) | 1992-02-14 |
| YU45033B (en) | 1991-06-30 |
| RO104952B1 (en) | 1995-01-23 |
| ES2053605T3 (es) | 1994-08-01 |
| CZ253488A3 (cs) | 1998-06-17 |
| DE3888563T2 (de) | 1994-09-29 |
| US5023240A (en) | 1991-06-11 |
| EP0287082A3 (en) | 1990-04-18 |
| CN88102128A (zh) | 1988-12-21 |
| HU201089B (en) | 1990-09-28 |
| ATE103289T1 (de) | 1994-04-15 |
| DE3888563D1 (de) | 1994-04-28 |
| SK253488A3 (en) | 1997-09-10 |
| CN1022569C (zh) | 1993-10-27 |
| CA1325424C (en) | 1993-12-21 |
| EP0287082B1 (en) | 1994-03-23 |
| PL155812B1 (en) | 1992-01-31 |
| SU1708158A3 (ru) | 1992-01-23 |
| HU211975A9 (en) | 1996-01-29 |
| DD272304A5 (de) | 1989-10-04 |
| SU1731063A3 (ru) | 1992-04-30 |
| JPS63313797A (ja) | 1988-12-21 |
| EP0287082A2 (en) | 1988-10-19 |
| SI8710674A (en) | 1996-08-31 |
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