CZ284818B6 - Nový způsob esterifikace baccatinu III a 10-desacetylbaccatinu - Google Patents
Nový způsob esterifikace baccatinu III a 10-desacetylbaccatinuInfo
- Publication number
- CZ284818B6 CZ284818B6 CZ95839A CZ83995A CZ284818B6 CZ 284818 B6 CZ284818 B6 CZ 284818B6 CZ 95839 A CZ95839 A CZ 95839A CZ 83995 A CZ83995 A CZ 83995A CZ 284818 B6 CZ284818 B6 CZ 284818B6
- Authority
- CZ
- Czechia
- Prior art keywords
- iii
- sub
- deacetylbaccatin
- baccatin
- hydroxy
- Prior art date
Links
- OVMSOCFBDVBLFW-VHLOTGQHSA-N 5beta,20-epoxy-1,7beta,13alpha-trihydroxy-9-oxotax-11-ene-2alpha,4alpha,10beta-triyl 4,10-diacetate 2-benzoate Chemical compound O([C@@H]1[C@@]2(C[C@H](O)C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)O)C(=O)C1=CC=CC=C1 OVMSOCFBDVBLFW-VHLOTGQHSA-N 0.000 title abstract 6
- YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 title abstract 5
- 150000002148 esters Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- -1 10-deacetylbaccatin iii ester Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 229930014667 baccatin III Natural products 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- YWLXLRUDGLRYDR-SKXCCXORSA-N 10-dab iii Chemical compound O([C@H]1C2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-SKXCCXORSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 230000000719 anti-leukaemic effect Effects 0.000 abstract 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 125000003435 aroyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001602 bicycloalkyls Chemical group 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 125000005017 substituted alkenyl group Chemical group 0.000 abstract 1
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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)
- Epoxy Compounds (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Způsob přípravy esterů baccatinu III nebo 10-desacetylbaccatinu III obecného vzorce I spočívá v esterifikací chráněného baccatinu III nebo 10-desacetylbaccatinu III obecného vzorce III aktivovanou kyselinou obecného vzorce III. Estery obecného vzorce I jsou užitečné pro přípravu derivátů taxanu, majících protileukemické a protinádorové vlastnosti. V obecných vzorcích I, II a III Ar znamená aryl, R.sub.1.n. znamená atom vodíku, aroyl nebo skupinu R.sub.4.n.-O-CO-, kde R.sub.4.n. je případně substituovaná alkenylová, alkinylová nebo alkylová skupina, cykloalkylová skupina, cykloalkenylová skupina, bicykloalkylová skupina, fenylová skupina, heterocyklická skupina a R.sub.2.n. znamená atom vodíku a R.sub.3.n. znamená ochrannou skupinu hydroxy-funkce nebo také R.sub.1.n. má výše uvedený význam a R.sub.2.n. a R.sub.3.n. dohromady tvoří 5- nebo 6-členný nasycený herocykl, G.sub.1.n. znamená acetyl nebo ochrannou skupinu hydroxy-funkce, G.sub.2.n. znamená ochrannou skupinu hydroxy-funkce a X zŕ
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9211739A FR2696464B1 (fr) | 1992-10-05 | 1992-10-05 | Nouveau procédé d'estérification de la baccatine III et de la désacétyl-10 baccatine III. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ83995A3 CZ83995A3 (en) | 1995-09-13 |
| CZ284818B6 true CZ284818B6 (cs) | 1999-03-17 |
Family
ID=9434116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ95839A CZ284818B6 (cs) | 1992-10-05 | 1993-10-04 | Nový způsob esterifikace baccatinu III a 10-desacetylbaccatinu |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US5717103A (cs) |
| EP (1) | EP0663905B1 (cs) |
| JP (1) | JP3064419B2 (cs) |
| KR (1) | KR100290663B1 (cs) |
| AT (1) | ATE147734T1 (cs) |
| AU (1) | AU689446B2 (cs) |
| CA (1) | CA2146372C (cs) |
| CZ (1) | CZ284818B6 (cs) |
| DE (1) | DE69307526T2 (cs) |
| DK (1) | DK0663905T3 (cs) |
| ES (1) | ES2096328T3 (cs) |
| FI (1) | FI115909B (cs) |
| FR (1) | FR2696464B1 (cs) |
| GR (1) | GR3022286T3 (cs) |
| HU (1) | HU225973B1 (cs) |
| MX (1) | MX9305764A (cs) |
| NO (1) | NO313141B1 (cs) |
| NZ (1) | NZ256443A (cs) |
| PL (1) | PL178090B1 (cs) |
| RU (1) | RU2123493C1 (cs) |
| SK (1) | SK281035B6 (cs) |
| TW (1) | TW372234B (cs) |
| WO (1) | WO1994007876A1 (cs) |
| ZA (1) | ZA937316B (cs) |
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| FR2698361B1 (fr) * | 1992-11-20 | 1995-01-13 | Rhone Poulenc Rorer Sa | Procédé de préparation d'un acide oxazolidine-1,3 carboxylique-5. |
| IL107950A (en) | 1992-12-15 | 2001-04-30 | Upjohn Co | 7β, 8β - METHANO-TAXOLS, THEIR PREPARATION AND ANTINEOPLASTIC PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| DE69424166T2 (de) * | 1993-06-11 | 2000-10-05 | Pharmacia & Upjohn Co., Kalamazoo | Delta 6, 7-taxolen, antineoplastische verwendung und diese enthaltende pharmazeutische zusammenstellungen |
| DE69403966T3 (de) | 1993-07-19 | 2008-04-17 | Angiotech Pharmaceuticals, Inc., Vancouver | Anti-angiogene mittel und verfahren zu deren verwendung |
| EP0728130A1 (en) * | 1993-11-12 | 1996-08-28 | PHARMACIA & UPJOHN COMPANY | Pyrimidine-thioalkyl and alkylether compounds |
| IL127598A (en) * | 1994-01-28 | 2003-04-10 | Upjohn Co | Process for preparing isotaxol analogs |
| AU716005B2 (en) | 1995-06-07 | 2000-02-17 | Cook Medical Technologies Llc | Implantable medical device |
| DE69715417T2 (de) * | 1996-05-08 | 2003-06-05 | Pharmacia & Upjohn Co., Kalamazoo | Oxazolidinester |
| US6150537A (en) | 1997-12-12 | 2000-11-21 | Emory University | Methods for the esterification of alcohols and compounds useful therefor as potential anticancer agents |
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| CA3251059A1 (en) | 2022-05-02 | 2023-11-09 | The Board Of Trustees Of The Leland Stanford Junior University | Compositions, systems and methods for modulating a target gene |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US34277A (en) * | 1862-01-28 | Improvement in lamps | ||
| US4942184A (en) * | 1988-03-07 | 1990-07-17 | The United States Of America As Represented By The Department Of Health And Human Services | Water soluble, antineoplastic derivatives of taxol |
| FR2629818B1 (fr) * | 1988-04-06 | 1990-11-16 | Centre Nat Rech Scient | Procede de preparation du taxol |
| USRE34277E (en) * | 1988-04-06 | 1993-06-08 | Centre National De La Recherche Scientifique | Process for preparing taxol |
| MX9102128A (es) * | 1990-11-23 | 1992-07-08 | Rhone Poulenc Rorer Sa | Derivados de taxano,procedimiento para su preparacion y composicion farmaceutica que los contiene |
| FR2696460B1 (fr) * | 1992-10-05 | 1994-11-25 | Rhone Poulenc Rorer Sa | Procédé de préparation de dérivés du taxane. |
| FR2696458B1 (fr) * | 1992-10-05 | 1994-11-10 | Rhone Poulenc Rorer Sa | Procédé de préparation de dérivés du taxane. |
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1992
- 1992-10-05 FR FR9211739A patent/FR2696464B1/fr not_active Expired - Fee Related
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1993
- 1993-09-21 MX MX9305764A patent/MX9305764A/es unknown
- 1993-10-01 ZA ZA937316A patent/ZA937316B/xx unknown
- 1993-10-02 TW TW082108116A patent/TW372234B/zh not_active IP Right Cessation
- 1993-10-04 AU AU51148/93A patent/AU689446B2/en not_active Expired
- 1993-10-04 WO PCT/FR1993/000965 patent/WO1994007876A1/fr not_active Ceased
- 1993-10-04 RU RU95110766A patent/RU2123493C1/ru active
- 1993-10-04 HU HU9500970A patent/HU225973B1/hu unknown
- 1993-10-04 KR KR1019950701300A patent/KR100290663B1/ko not_active Expired - Lifetime
- 1993-10-04 SK SK438-95A patent/SK281035B6/sk not_active IP Right Cessation
- 1993-10-04 CZ CZ95839A patent/CZ284818B6/cs not_active IP Right Cessation
- 1993-10-04 DE DE69307526T patent/DE69307526T2/de not_active Expired - Lifetime
- 1993-10-04 US US08/411,691 patent/US5717103A/en not_active Expired - Lifetime
- 1993-10-04 EP EP93921980A patent/EP0663905B1/fr not_active Expired - Lifetime
- 1993-10-04 NZ NZ256443A patent/NZ256443A/en not_active IP Right Cessation
- 1993-10-04 AT AT93921980T patent/ATE147734T1/de active
- 1993-10-04 JP JP6508785A patent/JP3064419B2/ja not_active Expired - Lifetime
- 1993-10-04 ES ES93921980T patent/ES2096328T3/es not_active Expired - Lifetime
- 1993-10-04 DK DK93921980.4T patent/DK0663905T3/da active
- 1993-10-04 CA CA002146372A patent/CA2146372C/fr not_active Expired - Lifetime
- 1993-10-04 PL PL93308239A patent/PL178090B1/pl unknown
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1995
- 1995-03-29 NO NO19951200A patent/NO313141B1/no not_active IP Right Cessation
- 1995-04-04 FI FI951593A patent/FI115909B/fi not_active IP Right Cessation
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1997
- 1997-01-16 GR GR960402654T patent/GR3022286T3/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| IF00 | In force as of 2000-06-30 in czech republic | ||
| MK4A | Patent expired |
Effective date: 20131004 |