AR036207A1 - 3,5-dihidroxi-2,2-dimetil-valeroamidas protegidas para la sintesis de epotilonas y derivados, un procedimiento para su preparacion y el empleo de las mismas - Google Patents
3,5-dihidroxi-2,2-dimetil-valeroamidas protegidas para la sintesis de epotilonas y derivados, un procedimiento para su preparacion y el empleo de las mismasInfo
- Publication number
- AR036207A1 AR036207A1 ARP020102940A ARP020102940A AR036207A1 AR 036207 A1 AR036207 A1 AR 036207A1 AR P020102940 A ARP020102940 A AR P020102940A AR P020102940 A ARP020102940 A AR P020102940A AR 036207 A1 AR036207 A1 AR 036207A1
- Authority
- AR
- Argentina
- Prior art keywords
- compounds
- group
- preparation
- benzyl
- formula
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- -1 TIP Chemical group 0.000 abstract 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 3
- HESCAJZNRMSMJG-KKQRBIROSA-N epothilone A Chemical class C/C([C@@H]1C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(C)=N1 HESCAJZNRMSMJG-KKQRBIROSA-N 0.000 abstract 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 2
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 abstract 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 abstract 2
- JOCBASBOOFNAJA-UHFFFAOYSA-N N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid Chemical compound OCC(CO)(CO)NCCS(O)(=O)=O JOCBASBOOFNAJA-UHFFFAOYSA-N 0.000 abstract 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 abstract 2
- 125000006241 alcohol protecting group Chemical group 0.000 abstract 2
- 229930013356 epothilone Natural products 0.000 abstract 2
- GQNZGCARKRHPOH-RQIKCTSVSA-N miocamycin Chemical compound C1[C@](OC(C)=O)(C)[C@@H](OC(=O)CC)[C@H](C)O[C@H]1O[C@H]1[C@H](N(C)C)[C@@H](O)[C@H](O[C@@H]2[C@H]([C@H](OC(=O)CC)CC(=O)O[C@H](C)C/C=C/C=C/[C@H](OC(C)=O)[C@H](C)C[C@@H]2CC=O)OC)O[C@@H]1C GQNZGCARKRHPOH-RQIKCTSVSA-N 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 2
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 abstract 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 2
- ZYRUAVNMUFDGQT-UHFFFAOYSA-N 3,5-dihydroxy-2,2-dimethylpentanamide Chemical class NC(=O)C(C)(C)C(O)CCO ZYRUAVNMUFDGQT-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000000470 constituent Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000012634 fragment Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 238000003860 storage Methods 0.000 abstract 1
- 238000006257 total synthesis reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/16—Preparation of optical isomers
- C07C231/18—Preparation of optical isomers by stereospecific synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/16—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/002—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by oxidation/reduction reactions
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Analytical Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Se describen 3,5-dihidroxi-2,2-dimetil-valeroamidas protegidas de fórmula general (1) en donde R1, R2 pueden ser iguales o diferentes y representan, independientemente entre sí, un grupo protector de alcohol tal como, bencilo, 4-metoxibencilo, 3,4-dimetoxibencilo, THP, TBDMS, TMS, TES, TIP, TBDPS, MEM, MOM, alilo, tritilo, o en caso de que R1 y R2 formen un puente, representan un grupo protector cetal tal como, grupo (2); Y representa un grupo -NA1A2, en donde A1 y A2 representan independientemente un radical alquilo C1-6 tal como metilo, etilo, propilo, o un radical arilo o aralquilo tal como fenilo o bencilo, -OH, OMe u -O- bencilo, o representa un resto (3). También se describen antípodas ópticamente puros de los compuestos de fórmula (1), los productos intermedios, ópticamente activos, y compuestos de partida empleados en la preparación de los compuestos de fórmula (1), así como los procedimientos de preparación de todos estos compuestos. También se describe un procedimiento para preparar cetonas de fórmula general (4), donde R1, R2 pueden ser iguales o diferentes y representan independientemente un grupo protector de alcohol tal como, por ejemplo, bencilo, 4-metoxibencilo, 3,4-dimetoxibencilo, THP, TBDMS, TMS, TES, TIP, TBDPS, MEM, MOM, alilo, tritilo, o en caso de que R1 y R2 formen un puente, representan un grupo protector cetal tal como, por ejemplo, grupo (2) y V representa un radical alquilo C1-5 o alquenilo, a partir de compuestos de fórmula (1), ópticamente activos. Asimismo se describe el uso de estos compuestos para la obtención de epotilonas o derivados de epotilonas, en particular para la preparación del fragmento constitutivo (4) en la síntesis total de epotilonas. Los compuestos descriptos más arriba son estables al almacenamiento y pueden ser obtenidos fácilmente a partir de materiales de partida relativamente económicos. En general, son sustancias sólidas cristalinas y pueden purificarse por recristalización. De esta manera se pueden alcanzar elevados rendimientos químicos y ópticos.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10138348A DE10138348A1 (de) | 2001-08-03 | 2001-08-03 | Geschützte 3,5-Dihydroxy-2,2-dimethyl-valeroamide für die Synthese von Epothilonen und Derivaten und Verfahren zur Herstellung und die Verwendung |
Publications (1)
Publication Number | Publication Date |
---|---|
AR036207A1 true AR036207A1 (es) | 2004-08-18 |
Family
ID=7694415
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ARP020102940A AR036207A1 (es) | 2001-08-03 | 2002-08-02 | 3,5-dihidroxi-2,2-dimetil-valeroamidas protegidas para la sintesis de epotilonas y derivados, un procedimiento para su preparacion y el empleo de las mismas |
Country Status (16)
Country | Link |
---|---|
EP (1) | EP1412322A2 (es) |
JP (1) | JP2004537589A (es) |
KR (1) | KR20040029394A (es) |
CN (2) | CN1538952A (es) |
AR (1) | AR036207A1 (es) |
BR (1) | BR0211649A (es) |
CA (1) | CA2456255A1 (es) |
DE (1) | DE10138348A1 (es) |
IL (1) | IL160159A0 (es) |
MX (1) | MXPA04000954A (es) |
NO (1) | NO20040912L (es) |
PE (1) | PE20030345A1 (es) |
PL (1) | PL367430A1 (es) |
RU (1) | RU2004106530A (es) |
WO (1) | WO2003014063A2 (es) |
ZA (1) | ZA200401727B (es) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6867305B2 (en) | 1996-12-03 | 2005-03-15 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
EP0977563B1 (en) | 1996-12-03 | 2005-10-12 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto, analogues and uses thereof |
WO2003029195A1 (fr) | 2001-09-28 | 2003-04-10 | Sumika Fine Chemicals Co., Ltd. | Intermediaires pour l'elaboration d'un derive de l'epothilone, et leur procede de production |
DE10326195A1 (de) * | 2003-06-07 | 2004-12-23 | Schering Ag | Geschützte 5,7-Dihydroxy-4,4-dimethyl-3-oxoheptansäureester und 5,7-Dihydroxy-2-alkyl-4,4-dimethyl-3-oxoheptansäureester für die Synthese von Epothilonen- und Derivaten und Verfahren zur Herstellung dieser Ester |
CN110857276B (zh) * | 2018-08-22 | 2021-03-02 | 中国科学院化学研究所 | 一类手性β-羟基酰胺类化合物及其制备方法与应用 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4824980A (en) * | 1988-09-02 | 1989-04-25 | Dow Corning Corporation | Process to produce O-silyl O,N-ketene acetals |
US6211412B1 (en) * | 1999-03-29 | 2001-04-03 | The University Of Kansas | Synthesis of epothilones |
-
2001
- 2001-08-03 DE DE10138348A patent/DE10138348A1/de not_active Withdrawn
-
2002
- 2002-08-02 PE PE2002000704A patent/PE20030345A1/es not_active Application Discontinuation
- 2002-08-02 AR ARP020102940A patent/AR036207A1/es unknown
- 2002-08-05 KR KR10-2004-7001710A patent/KR20040029394A/ko not_active Application Discontinuation
- 2002-08-05 MX MXPA04000954A patent/MXPA04000954A/es unknown
- 2002-08-05 WO PCT/EP2002/008726 patent/WO2003014063A2/de active Application Filing
- 2002-08-05 CN CNA028152379A patent/CN1538952A/zh active Pending
- 2002-08-05 BR BR0211649-9A patent/BR0211649A/pt not_active IP Right Cessation
- 2002-08-05 CA CA002456255A patent/CA2456255A1/en not_active Abandoned
- 2002-08-05 IL IL16015902A patent/IL160159A0/xx unknown
- 2002-08-05 JP JP2003519015A patent/JP2004537589A/ja active Pending
- 2002-08-05 EP EP02774500A patent/EP1412322A2/de not_active Withdrawn
- 2002-08-05 CN CNA2005100764590A patent/CN1807403A/zh active Pending
- 2002-08-05 RU RU2004106530/04A patent/RU2004106530A/ru not_active Application Discontinuation
- 2002-08-05 PL PL02367430A patent/PL367430A1/xx unknown
-
2004
- 2004-03-02 NO NO20040912A patent/NO20040912L/no not_active Application Discontinuation
- 2004-03-02 ZA ZA200401727A patent/ZA200401727B/xx unknown
Also Published As
Publication number | Publication date |
---|---|
JP2004537589A (ja) | 2004-12-16 |
EP1412322A2 (de) | 2004-04-28 |
BR0211649A (pt) | 2004-07-13 |
WO2003014063A2 (de) | 2003-02-20 |
ZA200401727B (en) | 2005-04-12 |
NO20040912L (no) | 2004-03-02 |
MXPA04000954A (es) | 2004-04-20 |
CN1538952A (zh) | 2004-10-20 |
DE10138348A1 (de) | 2003-02-27 |
PL367430A1 (en) | 2005-02-21 |
CA2456255A1 (en) | 2003-02-20 |
KR20040029394A (ko) | 2004-04-06 |
RU2004106530A (ru) | 2005-07-27 |
IL160159A0 (en) | 2004-07-25 |
CN1807403A (zh) | 2006-07-26 |
WO2003014063A3 (de) | 2003-05-01 |
PE20030345A1 (es) | 2003-04-10 |
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