SI8911498B - Postopek za pripravo derivatov tilozina - Google Patents
Postopek za pripravo derivatov tilozina Download PDFInfo
- 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
- Authority
- SI
- Slovenia
- Prior art keywords
- micarosil
- ch2oh
- double bond
- cho
- micarosyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 3
- 238000002360 preparation method Methods 0.000 title claims abstract 3
- 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 3
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims abstract 25
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910005948 SO2Cl Inorganic materials 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- -1 aromatic sulfochlorides Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 238000006073 displacement reaction Methods 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 239000010970 precious metal Substances 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 235000011149 sulphuric acid Nutrition 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 238000003786 synthesis reaction 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
-
- 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
Landscapes
- 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)
- Λ 1. Postopek za pripravo derivatov tilozina s formulo I(I) mikarozil2, 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 IImikarozilHa 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 CHjOH 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 HO1-)—0-H2C ° H3C-H2C(I) s mikarozil HO CH3la 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 Imikarozil (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 .1kjer 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
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 |
Family
ID=25554392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI8911498A SI8911498B (sl) | 1989-07-26 | 1989-07-26 | Postopek za pripravo derivatov tilozina |
Country Status (6)
| Country | Link |
|---|---|
| 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)
| 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 |
| CA2068951A1 (en) * | 1991-05-20 | 1992-11-21 | Robert R. Wilkening | 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 |
| WO2005019238A1 (ja) | 2003-08-22 | 2005-03-03 | Meiji Seika Kaisha, Ltd. | 新規アザライド及びアザラクタム誘導体とその製造法 |
| 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)
| 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 |
| YU45033B (en) * | 1987-04-14 | 1991-06-30 | Pliva Zagreb | Process for preparing 10,11,12,13-tetrahydro derivative |
-
1989
- 1989-07-26 SI SI8911498A patent/SI8911498B/sl unknown
- 1989-07-26 YU YU01498/89A patent/YU149889A/xx unknown
-
1990
- 1990-07-25 EP EP90114291A patent/EP0410433B1/en not_active Expired - Lifetime
- 1990-07-25 ES ES90114291T patent/ES2086334T3/es not_active Expired - Lifetime
- 1990-07-25 DE DE69025505T patent/DE69025505T2/de not_active Expired - Fee Related
- 1990-07-25 AT AT90114291T patent/ATE134642T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| YU149889A (en) | 1991-02-28 |
| DE69025505T2 (de) | 1996-09-19 |
| ES2086334T3 (es) | 1996-07-01 |
| EP0410433A2 (en) | 1991-01-30 |
| ATE134642T1 (de) | 1996-03-15 |
| EP0410433B1 (en) | 1996-02-28 |
| DE69025505D1 (de) | 1996-04-04 |
| SI8911498A (sl) | 1998-02-28 |
| EP0410433A3 (en) | 1991-11-06 |
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