FI90243B - Förfarande för framställning av amikacin - Google Patents
Förfarande för framställning av amikacin Download PDFInfo
- Publication number
- FI90243B FI90243B FI885489A FI885489A FI90243B FI 90243 B FI90243 B FI 90243B FI 885489 A FI885489 A FI 885489A FI 885489 A FI885489 A FI 885489A FI 90243 B FI90243 B FI 90243B
- Authority
- FI
- Finland
- Prior art keywords
- derivative
- kanamycin
- amikacin
- process according
- acylation
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
- C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
- C07H15/234—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/12—Acyclic radicals, not substituted by cyclic structures attached to a nitrogen atom of the saccharide radical
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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)
- Crystallography & Structural Chemistry (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Insulating Materials (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Peptides Or Proteins (AREA)
- Steroid Compounds (AREA)
- Financial Or Insurance-Related Operations Such As Payment And Settlement (AREA)
- Silicates, Zeolites, And Molecular Sieves (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Claims (6)
1. Förfarande för framställning av amikacin med formeln
2. Förfarande enligt patentkravet 1, känne-t e c k n a t därav, att pH är 4,5 - 6,5.
3. Förfarande enligt patentkravet 1, känne- , t e c k n a t därav, att det nämnda diskyddade derivatet 5 av kanamycin A är skyddat i 6'- och 3-positioner med acyl-grupper, nämligen bensyloxikarbonyl-, substituerad bensyl-oxikarbonyl-, alkoxikarbonyl-, ftaloyl- eller halogenal-kylkarbonylgrupper.
4. Förfarande enligt patentkravet 3, känne-10 tecknat därav, att acylskyddsgruppen är bensyloxikarbonyl, p-nitrobensyloxikarbonyl och p-metoxibensyloxi-karbonyl.
5. Förfarande enligt patentkravet 1, känne-tecknat därav, att det nämnda aprotiska lösnings- 15 medlet är ett alifatiskt kolväte eller ett halogenerat alifatiskt kolväte.
5 CH2NH2 ΗΟΎ^ο HO Ί NH0 °-Τ^Ά (i) 10 “«-J^s/nhX-nh, CH-OH / g 2 ”»->^0 / ° 15 ° genom acylering av ett diskyddat derivat av kanamycin A med formeln 6· CH-NHR 4< Η°η^-ο
20 HO-ViMl' HO I NHR o 6" N HR" 4„ch2oh / 1 / (11) HO ]/ : O med ett derivat av L-(-)-4-amino-2-hydroxismörsyra (L-HABA), och genom avlägsning av skyddsgrupper p4 i och 30 för sig känt sätt, kännetecknat därav, att det nämnda diskyddade derivatet av kanamycin A suspenderas i vatten, lösningens pH regleras tili ett värde av 3 - 10 och nämnda acylering utföres medelst det nämnda reaktiva derivatet av L-HABA, vilket upplösts i ett aprotiskt lös-35 ningsmedel som är svärlösligt i vatten, medan reaktions-temperaturen är 0 - 60 °C. is 90243
6. Förfarande enligt patentkravet 5, känne-tecknat därav, att det aprotiska lösningsmedlet är metylenklorid, kloroform eller 1,2-dikloretan.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2278387 | 1987-11-27 | ||
| IT8722783A IT1225484B (it) | 1987-11-27 | 1987-11-27 | Procedimento di sintesi dell'amikacina |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI885489A0 FI885489A0 (sv) | 1988-11-25 |
| FI885489A FI885489A (sv) | 1989-05-28 |
| FI90243B true FI90243B (sv) | 1993-09-30 |
| FI90243C FI90243C (sv) | 1994-01-10 |
Family
ID=11200418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI885489A FI90243C (sv) | 1987-11-27 | 1988-11-25 | Förfarande för framställning av amikacin |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US5763587A (sv) |
| EP (1) | EP0317970B1 (sv) |
| JP (1) | JPH0637512B2 (sv) |
| AT (1) | ATE125544T1 (sv) |
| AU (1) | AU608665B2 (sv) |
| BG (1) | BG49048A3 (sv) |
| CA (1) | CA1324375C (sv) |
| CS (1) | CS277017B6 (sv) |
| DD (1) | DD283564A5 (sv) |
| DE (1) | DE3854225T2 (sv) |
| DK (1) | DK170050B1 (sv) |
| ES (1) | ES2074431T3 (sv) |
| FI (1) | FI90243C (sv) |
| HU (1) | HU201771B (sv) |
| IT (1) | IT1225484B (sv) |
| NO (1) | NO171505C (sv) |
| NZ (1) | NZ227113A (sv) |
| PH (1) | PH25818A (sv) |
| PL (1) | PL161416B1 (sv) |
| RO (1) | RO102339B1 (sv) |
| RU (1) | RU1776262C (sv) |
| YU (1) | YU47063B (sv) |
| ZA (1) | ZA888855B (sv) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW465235B (en) | 1998-09-17 | 2001-11-21 | United Video Properties Inc | Electronic program guide with digital storage |
| US7794713B2 (en) | 2004-04-07 | 2010-09-14 | Lpath, Inc. | Compositions and methods for the treatment and prevention of hyperproliferative diseases |
| BRPI0616642A2 (pt) | 2005-09-29 | 2011-06-28 | Nektar Therapeutics | formulações de antibióticos, doses unitárias, kits e métodos |
| ES2707787T3 (es) | 2005-12-02 | 2019-04-05 | Ionis Pharmaceuticals Inc | Análogos antibacterianos de aminoglucósido 4,5-sustituidos que tienen sustituyentes múltiples |
| US7862812B2 (en) | 2006-05-31 | 2011-01-04 | Lpath, Inc. | Methods for decreasing immune response and treating immune conditions |
| US20080300199A1 (en) * | 2007-04-10 | 2008-12-04 | Achaogen Inc. | Antibacterial 1,4,5-substituted aminoglycoside analogs |
| WO2010030704A2 (en) | 2008-09-10 | 2010-03-18 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| WO2010030690A1 (en) | 2008-09-10 | 2010-03-18 | Isis Pharmaceuticals, Inc. | Antibacterial 4,6-substituted 6', 6" and 1 modified aminoglycoside analogs |
| WO2010037179A1 (en) | 2008-10-03 | 2010-04-08 | Glycan Biosciences Pty Ltd | Anionic conjugates of glycosylated bacterial metabolite |
| WO2010042850A1 (en) | 2008-10-09 | 2010-04-15 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| WO2010042851A1 (en) | 2008-10-09 | 2010-04-15 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| EP2486044A2 (en) | 2009-10-09 | 2012-08-15 | Achaogen, Inc. | Antibacterial aminoglycoside analogs |
| AR083879A1 (es) | 2010-11-17 | 2013-03-27 | Achaogen Inc | Analogos de aminoglicosidos antibacterianos, metodos de preparacion y uso como agentes terapeuticos |
| CN103113429B (zh) * | 2013-03-05 | 2015-02-18 | 齐鲁天和惠世制药有限公司 | 一种由阿米卡星制备硫酸阿米卡星的方法 |
| CN105440090B (zh) * | 2014-08-27 | 2018-03-09 | 北大医药重庆大新药业股份有限公司 | 一种阿米卡星的合成方法 |
| CN111233952A (zh) * | 2020-04-02 | 2020-06-05 | 管炫棣 | 一种阿卡米星的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1485450A (en) * | 1973-11-14 | 1977-09-14 | Bristol Myers Co | Process for the preparation of a kanamycin derivative |
| JPS51127045A (en) * | 1975-04-24 | 1976-11-05 | Microbial Chem Res Found | A process for preparing 3'- deoxykanamycin a derivatives. |
| GB1530201A (en) * | 1976-04-14 | 1978-10-25 | Pfizer Ltd | Process for the preparation of aminoglycoside antibiotics and intermediates therefor |
| US4136254A (en) * | 1976-06-17 | 1979-01-23 | Schering Corporation | Process of selectively blocking amino functions in aminoglycosides using transition metal salts and intermediates used thereby |
| IE54288B1 (en) * | 1982-03-05 | 1989-08-16 | Fujisawa Pharmaceutical Co | New 1,4-diaminocyclitol derivatives, processes for their preparation and pharmaceutical compositions containing them |
| JPS6041692A (ja) * | 1983-08-15 | 1985-03-05 | Microbial Chem Res Found | ２′，３′−ジデオキシカナマイシンａ誘導体 |
| IT1200774B (it) * | 1985-10-10 | 1989-01-27 | Pierrel Spa | Procedimento di sentisi dell'amikacina |
-
1987
- 1987-11-27 IT IT8722783A patent/IT1225484B/it active
-
1988
- 1988-11-23 EP EP88119460A patent/EP0317970B1/en not_active Expired - Lifetime
- 1988-11-23 ES ES88119460T patent/ES2074431T3/es not_active Expired - Lifetime
- 1988-11-23 AT AT88119460T patent/ATE125544T1/de not_active IP Right Cessation
- 1988-11-23 DE DE3854225T patent/DE3854225T2/de not_active Expired - Fee Related
- 1988-11-25 ZA ZA888855A patent/ZA888855B/xx unknown
- 1988-11-25 HU HU886072A patent/HU201771B/hu not_active IP Right Cessation
- 1988-11-25 CA CA000584227A patent/CA1324375C/en not_active Expired - Fee Related
- 1988-11-25 DD DD88322213A patent/DD283564A5/de not_active IP Right Cessation
- 1988-11-25 DK DK661588A patent/DK170050B1/da not_active IP Right Cessation
- 1988-11-25 CS CS887779A patent/CS277017B6/cs unknown
- 1988-11-25 FI FI885489A patent/FI90243C/sv not_active IP Right Cessation
- 1988-11-25 PH PH37859A patent/PH25818A/en unknown
- 1988-11-25 RU SU884356995A patent/RU1776262C/ru active
- 1988-11-25 NO NO885270A patent/NO171505C/no unknown
- 1988-11-25 BG BG086218A patent/BG49048A3/xx active Active
- 1988-11-26 JP JP63299382A patent/JPH0637512B2/ja not_active Expired - Lifetime
- 1988-11-28 AU AU25963/88A patent/AU608665B2/en not_active Ceased
- 1988-11-28 PL PL1988276047A patent/PL161416B1/pl unknown
- 1988-11-28 YU YU218888A patent/YU47063B/sh unknown
- 1988-11-28 NZ NZ227113A patent/NZ227113A/en unknown
- 1988-11-28 RO RO88136098A patent/RO102339B1/ro unknown
-
1992
- 1992-02-14 US US07/834,991 patent/US5763587A/en not_active Expired - Fee Related
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB | Publication of examined application | ||
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: PIERREL S.P.A. |