SI8911498B - Postopek za pripravo derivatov tilozina - Google Patents

Postopek za pripravo derivatov tilozina Download PDF

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Publication number
SI8911498B
SI8911498B SI8911498A SI8911498A SI8911498B SI 8911498 B SI8911498 B SI 8911498B SI 8911498 A SI8911498 A SI 8911498A SI 8911498 A SI8911498 A SI 8911498A SI 8911498 B SI8911498 B SI 8911498B
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Slovenia
Prior art keywords
micarosil
ch2oh
double bond
cho
micarosyl
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SI8911498A
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English (en)
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SI8911498A (sl
Inventor
Nevenka Lopotar
Slobodan Djoki�
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Pliva
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Publication date
Application filed by Pliva filed Critical Pliva
Publication of SI8911498A publication Critical patent/SI8911498A/sl
Publication of SI8911498B publication Critical patent/SI8911498B/sl

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    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (1)

  1. Λ 1. Postopek za pripravo derivatov tilozina s formulo I
    (I) mikarozil
    2, kjer la A = CO-NH, R = CH(OCH3)2. R' = mikarozil, - dvojna vez, Ib A = CO-NH. R = CHO, v R1 = mikarozil, = dvojna vez. le A = CO-NH. R = CH(OCH3)2, R1 = H. = dvojna vez, Id A = CO-NH, R = CHO. R' = H. Λ'~ = dvojna vez, le A = CO-NH. R = CH2OH. Ri = mikarozil, = dvojna vez. le' A = NH-CO. R = CH2OH. R1 = mikarozil. Λ/V , = dvojna vez. lf A = CO-NH. R = CH2OH, R1 = mikarozil, = enojna vez. lf A = NH-CO. R = CH2OH. R1= mikarozil, = enojna vez, ig A = CO-NH, R = CH(OCH3)2. R1 = mikarozil. = enojna vez, Ih A = CO-NH. R = CHO. R1 = mikarozil, = enojna vez, ii A = CO-NH. R = CHO. R1 = H. = enojna vez, ij A = CO-NH. R = CH2OH. R1 = H. = dvojna vez, if A i NH-CO. R = CH2OH. R1 = H. = dvojna vez, lk A = CO-NH. R = CH2OH. I II £ = enojna vez, lk' A = NH-CO. R = CH^H, R1 = H. = enojna vez, . označen s tem, da obsega A/ Beckmannovo premestitev spojin s formulo II
    mikarozil
    Ha R - CH(OCH3)2f R1 * mikarozil, 'srw * dvojna vez, llb R-CHO, R1 * mikarozil, s dvojna vez, Ilc R - CH(OCH3)2. R1 - H. ,srw = dvojna vez, IkJ R * CHO. R1 « H, Λ/V dvojna vez, lle R = CHzOH, Ri „ mikarozil, ~ dvojna vez, llf R = CHiOH. Ri . mikarozil, ,s/s' = enojna vez, «9 R CH(OCH3)2. R1 » mikarozil, 's/>' s enojna vez, lih R = CHO, R1 * mikarozil, 's/s' = enojna vez, z 1-4 moli aromatskih sulfokloridov s formulo 4-R-C6H4-SO2CI, kjer R predstavlja C1-C3 alkil, halo ali acilamino skupino s formulo -NH-COR1, kjer R1 predstavlja metil, v prisotnosti 1-5 molov organske ali anorganske baze, kot so piridin, trietilamin ali NaHC03, NaOH, da dobimo spojine s formulo I
    (i) mikarozil H HO CHj
    OH Rl = la A = CO-NH, R = CH(OCH3)2. R1 = mikarozil, ~~ _ dvojna vez. Ib A = CO-NH, R = CHO. R1 = mikarozil, = dvojna vez, le A = CO-NH, R = CH(OCH3)2. R' = H, ~~ = dvojna vez, Id A = CO-NH. R = CHO. R’ = H. = dvojna vez, le A = CO-NH, R = CH2OH. ri = mikarozil, = dvojna vez, le' A.= NH-CO. R = CH2OH. R' = mikarozil, = dvojna vez, If A = CO-NH, R = CH2OH, R1 = mikarozil, ~~ _ enojna vez, ir A = NH-CO. R = CH2OH. R' = mikarozil, = enojna vez, ig A = CO-NH, R = CH(OCH3)2. R' = mikarozil, ~~ = enojna vez, Ih A = CO-NH. R = CHO, R1 =1 mikarozil, ~~ = enojna vez, B/ hidrolizo spojin s formulo I HjCO OCHj HO
    1-)—0-H2C ° H3C-H2C
    (I) s mikarozil HO CH3
    la A = CO-NH. R = CH(OCH3)2. R1 = mikarozil,. le A = CO-NH. R = CH(OCH3)2, R1 = H, le A = CO-NH, R = CH2OH. R’ = mikarozil, le' A = NH-CO, R = CH2OH, R1 = mikarozil, s katalitsko količino organske kisline, kot je trifluoroocetna kislina v 50% acetonitrilu, ali z anorganskimi kislinami, kot so HCl ali H2SO4, v prisotnosti acetonitrila kot topila, da dobimo spojine s formulo I
    (I) mikarozil HO CH
    € kjer Ib A = CO-NH. R « CHO. R1 s mikarozil, Id A = CO-NH, R = CHO. X n S: lj A = CO-NH. R s.CHzOH, x' 11 5: lj' A = NH-CO. R - CH2OH. R' «H. C/ katalitsko hidrogenacijo spojin s formulo I
    mikarozil (i)
    la A « CO-NH. R - CH(OCH3)2. Ri = mikarozil, Ib A = CO-NH. R - CHO. '' Ri & mikarozil, le A * CO-NH. R - CH2OH. R1 = mikarozil, le' A = NH-CO. R = CHjOH. R1 = mikarozil, lj ' A = CO-NH. R = CH2OH. Ri = H. lj’ A = NH-CO. R « CH2OH. Ri = H. pod tlakom vodika od 0.2 do 2.0 MPa, v prisotnosti plemenitih kovin kot katalizatorjev v inertnih topilih, kot so C1-C4 alkoholi, da dobimo spojine s forrnulo .1
    kjer If A = CO-NH. ir A = NH-CO. ig A = CO-NH. Ih A = CO-NH. li A = CO-NH. lk A = CO-NH. lk' A = NH-CO. R = CHzOH, R = CH2OH, R = CH(OCH3)2, R = CHO, R = CHO. R = CH2OH. R = CH2OH. Ri = mikarozil, R’ = mikarozil, R1 = mikarozil, R1 = mikarozil, R' = H. R1 = H. R’ = H
SI8911498A 1989-07-26 1989-07-26 Postopek za pripravo derivatov tilozina SI8911498B (sl)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
YU01498/89A YU149889A (en) 1989-07-26 1989-07-26 Process for preparing biologically active derivatives of tylozine

Publications (2)

Publication Number Publication Date
SI8911498A SI8911498A (sl) 1998-02-28
SI8911498B true SI8911498B (sl) 1998-10-31

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SI8911498A SI8911498B (sl) 1989-07-26 1989-07-26 Postopek za pripravo derivatov tilozina

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EP (1) EP0410433B1 (sl)
AT (1) ATE134642T1 (sl)
DE (1) DE69025505T2 (sl)
ES (1) ES2086334T3 (sl)
SI (1) SI8911498B (sl)
YU (1) YU149889A (sl)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CA2064634C (en) * 1991-04-04 1998-08-04 James V. Heck 9-deoxo-8a-aza-8a-homoerythromycin a derivatives modified at the 4"- and8a-positions
CA2065222A1 (en) * 1991-04-09 1992-10-10 Robert R. Wilkening Process for the preparation of 8a-aza-8a-homoerythromycin cyclic iminoethers
EP0515141A1 (en) * 1991-05-20 1992-11-25 Merck & Co. Inc. Novel process for the preparation of 8A-aza-8A-homoerythromycin cyclic lactams
DE69615919T2 (de) * 1995-06-06 2002-06-20 Fina Technology, Inc. Bifunktionelle Elektrondonore für die Olefinpolymerisation
CZ211798A3 (cs) * 1997-07-16 1999-02-17 Pliva, Farmaceutska, Kemijska, Prehrambena I Kozmetička Industrije, Dioničko Društvo Lineární 8a-sekoazalidy a způsob jejich výroby
HRP990192A2 (en) * 1999-06-11 2001-04-30 Pliva D D 4'-DEMICAROZYL-8a-AZA-8a-HOMOTHILOSINE DERIVATIVES
EP1661904A1 (en) 2003-08-22 2006-05-31 Meiji Seika Kaisha Ltd. Novel azalide and azalactam derivatives and process for the production of the same
US7247617B2 (en) 2004-07-13 2007-07-24 Kosan Biosciences Incorporated Sixteen-member macrolide antiinfective agents
GB201608236D0 (en) * 2016-05-11 2016-06-22 Fidelta D O O Seco macrolide compounds

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3178341A (en) * 1960-06-27 1965-04-13 Lilly Co Eli Antibiotics tylosin and desmycosin and derivatives thereof
PH19293A (en) * 1982-11-15 1986-03-04 Pfizer Epimeric azahomoerythromycin,pharmaceutical composition containing the same and method of use thereof
SI8710674B (sl) * 1987-04-14 1998-06-30 Pliva Postopek za pripravo 10,11,12,13-tetrahidro derivatov tilozina

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Publication number Publication date
ATE134642T1 (de) 1996-03-15
DE69025505T2 (de) 1996-09-19
ES2086334T3 (es) 1996-07-01
EP0410433A2 (en) 1991-01-30
EP0410433A3 (en) 1991-11-06
YU149889A (en) 1991-02-28
SI8911498A (sl) 1998-02-28
DE69025505D1 (de) 1996-04-04
EP0410433B1 (en) 1996-02-28

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