AR001426A1 - Procedimiento para la preparación de derivados cis-4-0-protegido-2 -ciclopentenol que son intermediarios utiles en la preparación de diversos analogosde ciclopentanil y ciclopentenil purina que son u tiles como inmunosupresores, procedimientos para la preparación de enantiomeros de dichos derivados y de esteres cis-4-o-protegido-2-ciclopentenilicosy procedimientos para la preparación de enantiome ros de cis-4-o-protegido ciclopentanol y esteres cis-4-o-protegido ciclopentanilicos. - Google Patents
Procedimiento para la preparación de derivados cis-4-0-protegido-2 -ciclopentenol que son intermediarios utiles en la preparación de diversos analogosde ciclopentanil y ciclopentenil purina que son u tiles como inmunosupresores, procedimientos para la preparación de enantiomeros de dichos derivados y de esteres cis-4-o-protegido-2-ciclopentenilicosy procedimientos para la preparación de enantiome ros de cis-4-o-protegido ciclopentanol y esteres cis-4-o-protegido ciclopentanilicos.Info
- Publication number
- AR001426A1 AR001426A1 AR33590696A AR33590696A AR001426A1 AR 001426 A1 AR001426 A1 AR 001426A1 AR 33590696 A AR33590696 A AR 33590696A AR 33590696 A AR33590696 A AR 33590696A AR 001426 A1 AR001426 A1 AR 001426A1
- Authority
- AR
- Argentina
- Prior art keywords
- protected
- cis
- preparation
- enantiomers
- esters
- Prior art date
Links
- -1 cyclopentanyl Chemical group 0.000 title abstract 7
- 238000000034 method Methods 0.000 title abstract 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 title abstract 5
- 150000002148 esters Chemical class 0.000 title 2
- JFECIVJLAVYIKP-UHFFFAOYSA-N 2-(cyclopenten-1-yl)-7h-purine Chemical compound C1CCC=C1C1=NC=C(NC=N2)C2=N1 JFECIVJLAVYIKP-UHFFFAOYSA-N 0.000 title 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 title 1
- 229960003444 immunosuppressant agent Drugs 0.000 title 1
- 239000003018 immunosuppressive agent Substances 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 abstract 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000005869 (methoxyethoxy)methanyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])* 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 abstract 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- 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
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- 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
-
- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
El procedimiento para la preparación del compuesto de fórmula (II) donde Pg se selecciona del grupo formado por bencilo, bencilo sustituido, -CH2OCH3,-CH2SCH3, -OCH2OCH2Fenilo, -CH2OCH2CH2OCH3, -CH2OCH2CCl3, -CH(OCH2CH2Cl)2, CH2OCH2CH2Si(CH3)3, -CH(OC2H5)CH3, -C(OCH3)(CH3)2, -CH(CH3)OCH(CH3)2,-CH2CCl3, -C(CH3)3, -CH2CH=CH2, -CH2CH=CHfenilo, -CH(fenilo)2, -C(fenilo)3, tetrahidropiranilo, 4-metoxitetrahidropiranilo, 3-bromotetrahidropiranilo,tetrahidrotiopiranilo, 4-metoxitetrahidrotiopiranilo, tetrahidrofuranilo, tetrahidrotiofuranilo, y SiR1R2R3, donde R1, R2 y R3 son cada unoindependientemente alquilo C1-C4, fenilo, bencilo, fenilo sustituido o bencilo sustituido, a partir de una 4-0-protegida ciclopentenona, dicha ciclopentenonase disuelve en un disolvente orgánico y se trata la solución con un ácido de Lewis y un reductor a una temperatura entre -100°C y 20°C. También sedescriben procedimientos para obtener los enantiómeros de dicho compuesto de fórmula (II) a partir del correspondiente enantiómero de la ciclopentenona,y procedimientos para la obtención de dichos enantiómeros del compuesto de fórmula (II) y de enantiómeros de ésteres cis-4-0-protegido-2-pentenílicos apartir de una mezcla racémica de la ciclopentenona por medio de un agente acilante adecuado.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41113695A | 1995-03-27 | 1995-03-27 | |
| US08/588,584 US5728899A (en) | 1995-03-27 | 1996-02-01 | Preparation of cis-4-O-protected-2-cyclopentenol derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR001426A1 true AR001426A1 (es) | 1997-10-22 |
Family
ID=27021289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AR33590696A AR001426A1 (es) | 1995-03-27 | 1996-03-26 | Procedimiento para la preparación de derivados cis-4-0-protegido-2 -ciclopentenol que son intermediarios utiles en la preparación de diversos analogosde ciclopentanil y ciclopentenil purina que son u tiles como inmunosupresores, procedimientos para la preparación de enantiomeros de dichos derivados y de esteres cis-4-o-protegido-2-ciclopentenilicosy procedimientos para la preparación de enantiome ros de cis-4-o-protegido ciclopentanol y esteres cis-4-o-protegido ciclopentanilicos. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5808112A (es) |
| EP (1) | EP0817764A1 (es) |
| JP (1) | JPH11502841A (es) |
| AR (1) | AR001426A1 (es) |
| AU (1) | AU704196B2 (es) |
| CA (1) | CA2216245C (es) |
| HU (1) | HUP9801983A3 (es) |
| IL (1) | IL117639A0 (es) |
| NO (1) | NO974458L (es) |
| NZ (1) | NZ303618A (es) |
| WO (1) | WO1996030320A1 (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007027189A1 (de) * | 2007-06-13 | 2008-12-18 | Archimica Gmbh | Verfahren zur Herstellung von Cyclopent-4-en-1,3-diol oder Cyclopent-4-en-1,3-diol-Derivaten |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5244896A (en) * | 1990-09-14 | 1993-09-14 | Marion Merrell Dow Inc. | Carbocyclic adenosine analogs useful as immunosuppressants |
-
1996
- 1996-03-01 CA CA002216245A patent/CA2216245C/en not_active Expired - Fee Related
- 1996-03-01 HU HU9801983A patent/HUP9801983A3/hu unknown
- 1996-03-01 WO PCT/US1996/002801 patent/WO1996030320A1/en not_active Application Discontinuation
- 1996-03-01 AU AU49983/96A patent/AU704196B2/en not_active Ceased
- 1996-03-01 JP JP8529399A patent/JPH11502841A/ja not_active Abandoned
- 1996-03-01 EP EP96906658A patent/EP0817764A1/en not_active Withdrawn
- 1996-03-01 NZ NZ303618A patent/NZ303618A/xx unknown
- 1996-03-24 IL IL11763996A patent/IL117639A0/xx not_active IP Right Cessation
- 1996-03-26 AR AR33590696A patent/AR001426A1/es not_active Application Discontinuation
-
1997
- 1997-06-17 US US08/877,364 patent/US5808112A/en not_active Expired - Fee Related
- 1997-09-26 NO NO974458A patent/NO974458L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU4998396A (en) | 1996-10-16 |
| HUP9801983A2 (hu) | 1999-03-29 |
| NO974458D0 (no) | 1997-09-26 |
| AU704196B2 (en) | 1999-04-15 |
| CA2216245A1 (en) | 1996-10-03 |
| EP0817764A1 (en) | 1998-01-14 |
| WO1996030320A1 (en) | 1996-10-03 |
| CA2216245C (en) | 2002-10-08 |
| NO974458L (no) | 1997-11-27 |
| IL117639A0 (en) | 1996-07-23 |
| MX9707400A (es) | 1997-11-29 |
| NZ303618A (en) | 1999-03-29 |
| HUP9801983A3 (en) | 1999-08-30 |
| JPH11502841A (ja) | 1999-03-09 |
| US5808112A (en) | 1998-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |