HRP20110186T1 - Postupak glikozidacije kolhicina i tiokolhicina - Google Patents
Postupak glikozidacije kolhicina i tiokolhicina Download PDFInfo
- Publication number
- HRP20110186T1 HRP20110186T1 HR20110186T HRP20110186T HRP20110186T1 HR P20110186 T1 HRP20110186 T1 HR P20110186T1 HR 20110186 T HR20110186 T HR 20110186T HR P20110186 T HRP20110186 T HR P20110186T HR P20110186 T1 HRP20110186 T1 HR P20110186T1
- Authority
- HR
- Croatia
- Prior art keywords
- reaction
- formula
- acetyl
- carried out
- groups
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 13
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 title 2
- 229960001338 colchicine Drugs 0.000 title 1
- 238000005858 glycosidation reaction Methods 0.000 title 1
- CMEGANPVAXDBPL-INIZCTEOSA-N n-[(7s)-1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-6,7-dihydro-5h-benzo[a]heptalen-7-yl]acetamide Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(SC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC CMEGANPVAXDBPL-INIZCTEOSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 3
- 238000006243 chemical reaction Methods 0.000 claims 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 239000002841 Lewis acid Substances 0.000 claims 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims 2
- 125000004185 ester group Chemical group 0.000 claims 2
- 150000007517 lewis acids Chemical class 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical group CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims 1
- 229910015900 BF3 Inorganic materials 0.000 claims 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 1
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
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
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/248—Colchicine radicals, e.g. colchicosides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
- C07C2603/34—Benzoheptalenes; Hydrogenated benzoheptalenes
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08157069A EP2128170B1 (fr) | 2008-05-28 | 2008-05-28 | Procédé pour la glycosidation de la colchicine et de la thiocolchicine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110186T1 true HRP20110186T1 (hr) | 2011-04-30 |
Family
ID=39637699
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110186T HRP20110186T1 (hr) | 2008-05-28 | 2011-03-14 | Postupak glikozidacije kolhicina i tiokolhicina |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US8742080B2 (fr) |
| EP (1) | EP2128170B1 (fr) |
| JP (1) | JP5478612B2 (fr) |
| KR (1) | KR101625161B1 (fr) |
| CN (2) | CN102046644A (fr) |
| AT (1) | ATE492556T1 (fr) |
| AU (1) | AU2009253483B2 (fr) |
| BR (1) | BRPI0912287A2 (fr) |
| CA (1) | CA2725842C (fr) |
| CO (1) | CO6290769A2 (fr) |
| DE (1) | DE602008004113D1 (fr) |
| DK (1) | DK2128170T3 (fr) |
| ES (1) | ES2356494T3 (fr) |
| HR (1) | HRP20110186T1 (fr) |
| MX (1) | MX2010012884A (fr) |
| PL (1) | PL2128170T3 (fr) |
| PT (1) | PT2128170E (fr) |
| RU (1) | RU2488589C2 (fr) |
| SI (1) | SI2128170T1 (fr) |
| WO (1) | WO2009143930A1 (fr) |
| ZA (1) | ZA201008480B (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ747657A (en) | 2012-11-02 | 2019-12-20 | Murray And Poole Entpr Ltd | Treatment or prevention of cardiovascular events via the administration of a colchicine derivative |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2112131A1 (en) | 1970-11-06 | 1972-06-16 | Roussel Uclaf | 2-and 3-glucose-2-yl-demethylthiololchicines - antimitotic agents,prepared from colchicine |
| SU508204A3 (ru) * | 1972-05-05 | 1976-03-25 | Руссель-Уклаф (Фирма) | Способ получени 3-глюкоз-2-ил3-деметилтиоколхицина или 2-глюкоз2-ил-2-деметилтиоколхицина |
| IT1270124B (it) * | 1994-10-05 | 1997-04-28 | Indena Spa | Derivati della colchicina e loro impiego terapeutico |
| IT1282584B1 (it) | 1996-02-08 | 1998-03-31 | Indena Spa | Processo di glicosidazione di derivati colchicinici e prodotti ottenuti |
| IT1285777B1 (it) | 1996-10-07 | 1998-06-18 | Indena Spa | Processo di biotrasformazione di composti colchicinoidi nei corrispondenti 3-glicosilderivati |
| FR2779147B1 (fr) * | 1998-05-27 | 2000-06-30 | Synthelabo | Derive de thiocolchicoside sa preparation et son application en therapeutique |
| ITMI20031144A1 (it) * | 2003-06-06 | 2004-12-07 | Indena Spa | Analoghi del colchicoside. |
-
2008
- 2008-05-28 PT PT08157069T patent/PT2128170E/pt unknown
- 2008-05-28 EP EP08157069A patent/EP2128170B1/fr active Active
- 2008-05-28 DK DK08157069.9T patent/DK2128170T3/da active
- 2008-05-28 AT AT08157069T patent/ATE492556T1/de active
- 2008-05-28 ES ES08157069T patent/ES2356494T3/es active Active
- 2008-05-28 DE DE602008004113T patent/DE602008004113D1/de active Active
- 2008-05-28 PL PL08157069T patent/PL2128170T3/pl unknown
- 2008-05-28 SI SI200830169T patent/SI2128170T1/sl unknown
-
2009
- 2009-04-09 AU AU2009253483A patent/AU2009253483B2/en active Active
- 2009-04-09 CA CA2725842A patent/CA2725842C/fr active Active
- 2009-04-09 RU RU2010147934/04A patent/RU2488589C2/ru active
- 2009-04-09 MX MX2010012884A patent/MX2010012884A/es active IP Right Grant
- 2009-04-09 CN CN2009801191319A patent/CN102046644A/zh active Pending
- 2009-04-09 US US12/994,485 patent/US8742080B2/en active Active
- 2009-04-09 CN CN201610052127.7A patent/CN105713054A/zh active Pending
- 2009-04-09 KR KR1020107026481A patent/KR101625161B1/ko active IP Right Grant
- 2009-04-09 JP JP2011510851A patent/JP5478612B2/ja active Active
- 2009-04-09 BR BRPI0912287-7A patent/BRPI0912287A2/pt not_active Application Discontinuation
- 2009-04-09 WO PCT/EP2009/002623 patent/WO2009143930A1/fr active Application Filing
-
2010
- 2010-11-16 CO CO10143051A patent/CO6290769A2/es active IP Right Grant
- 2010-11-25 ZA ZA2010/08480A patent/ZA201008480B/en unknown
-
2011
- 2011-03-14 HR HR20110186T patent/HRP20110186T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE602008004113D1 (de) | 2011-02-03 |
| MX2010012884A (es) | 2010-12-14 |
| US8742080B2 (en) | 2014-06-03 |
| CN102046644A (zh) | 2011-05-04 |
| RU2010147934A (ru) | 2012-05-27 |
| CA2725842A1 (fr) | 2009-12-03 |
| BRPI0912287A2 (pt) | 2015-08-04 |
| WO2009143930A1 (fr) | 2009-12-03 |
| JP2011520995A (ja) | 2011-07-21 |
| CO6290769A2 (es) | 2011-06-20 |
| ES2356494T3 (es) | 2011-04-08 |
| CA2725842C (fr) | 2016-11-22 |
| AU2009253483A1 (en) | 2009-12-03 |
| CN105713054A (zh) | 2016-06-29 |
| PL2128170T3 (pl) | 2011-05-31 |
| SI2128170T1 (sl) | 2011-04-29 |
| DK2128170T3 (da) | 2011-02-28 |
| KR101625161B1 (ko) | 2016-05-27 |
| EP2128170B1 (fr) | 2010-12-22 |
| PT2128170E (pt) | 2011-02-23 |
| EP2128170A1 (fr) | 2009-12-02 |
| US20110130554A1 (en) | 2011-06-02 |
| RU2488589C2 (ru) | 2013-07-27 |
| KR20110010739A (ko) | 2011-02-07 |
| ZA201008480B (en) | 2012-02-29 |
| AU2009253483B2 (en) | 2013-08-22 |
| ATE492556T1 (de) | 2011-01-15 |
| JP5478612B2 (ja) | 2014-04-23 |
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