ES2010511B3 - Un procedimiento para la preparacion de forskolina a partir de 9-desoxi-forskolina. - Google Patents
Un procedimiento para la preparacion de forskolina a partir de 9-desoxi-forskolina.Info
- Publication number
- ES2010511B3 ES2010511B3 ES87103939T ES87103939T ES2010511B3 ES 2010511 B3 ES2010511 B3 ES 2010511B3 ES 87103939 T ES87103939 T ES 87103939T ES 87103939 T ES87103939 T ES 87103939T ES 2010511 B3 ES2010511 B3 ES 2010511B3
- Authority
- ES
- Spain
- Prior art keywords
- beta
- alpha
- epoxy
- tetrahydroxylabd
- dehydro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title abstract 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 abstract 3
- SUZLHDUTVMZSEV-WESICCPUSA-N (3R,4aR,5S,6S,6aS,10S,10aS,10bS)-3-ethenyl-6,10-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxododecahydro-1H-benzo[f]chromen-5-yl acetate Chemical compound O=C([C@@H]12)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C SUZLHDUTVMZSEV-WESICCPUSA-N 0.000 abstract 2
- SUZLHDUTVMZSEV-UHFFFAOYSA-N Deoxycoleonol Natural products C12C(=O)CC(C)(C=C)OC2(C)C(OC(=O)C)C(O)C2C1(C)C(O)CCC2(C)C SUZLHDUTVMZSEV-UHFFFAOYSA-N 0.000 abstract 2
- OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 abstract 2
- 150000002084 enol ethers Chemical class 0.000 abstract 2
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- OHCQJHSOBUTRHG-UHFFFAOYSA-N colforsin Natural products OC12C(=O)CC(C)(C=C)OC1(C)C(OC(=O)C)C(O)C1C2(C)C(O)CCC1(C)C OHCQJHSOBUTRHG-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- WPDITXOBNLYZHH-UHFFFAOYSA-N desacetylforskolin Natural products O1C(C)(C=C)CC(=O)C2(O)C3(C)C(O)CCC(C)(C)C3C(O)C(O)C21C WPDITXOBNLYZHH-UHFFFAOYSA-N 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- 230000002194 synthesizing effect Effects 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
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/06—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical being a hydroxyalkyl group esterified by a fatty acid
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Excavating Of Shafts Or Tunnels (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Toys (AREA)
- Auxiliary Devices For And Details Of Packaging Control (AREA)
- Shaping Of Tube Ends By Bending Or Straightening (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
SE DESCRIBE UN METODO PARA SINTETIZAR, REGIOSELECTIVAMENTE Y ESTEREOSELECTIVAMENTE FORSKOLINA (8,13-EPOXI-1ALFA, 6BETA,9ALFA-TETRAHIDROXILABD-14-EN-11ONA) A PARTIR DE 9-DESOXIFORSKOLINA (8,13-EPOXI-1ALFA, 6BETA, 7BETA-TRIHIDROXILABD-14-EN-11-ONA) CON BUEN RENDIMIENTO. EL METODO COMPRENDE UNA FORMACION ENOL ETER A PARTIR DE 8,13-EPOXI 1ALFA, 6BETA, 7BETATRIHIDROXILABD-14-EN-11-ONA-6,7-CARBONATO, OXIDACION DEL ENOL ETER CONUN PEROXIACIDO CONVENIENTE PARA OBTENER 11,12-DEHIDRO-8,13-EPOXI-11-METOXI-1ALFA, 6BETA, 7 BETA, 9BETA-TETRAHIDROLABD-14-ENO-CARBONATO E HIDROLISIS, DEL ULTIMO BAJO CONDICIONES ACIDAS PARA OBTENER 8,13-EPOXI-1ALFA, 6BETA, 7BETA, 9ALFA-TETRAHIDROXILABD14-ENO-6,7-CARBONATO. COMO CAMINO ALTERNATIVO PARA PROTEGER LOS DOS GRUPOS HIDROXI EN EL CARBONO 6 Y EL CARBONO 7, PUEDEN TAMBIEN CONVERTIRSE EN DIMETIL ACETAL DURANTE LA SECUENCIA DE SINTESIS. SE CONSIDERA QUE SON NUEVOS CUATRO COMPUESTOS PRODUCIDOS EN EL ESQUEMA DE SINTESIS COMO PRODUCTOS INTERMEDIOS PRINCIPALMENTE, 9,11-DEHIDRO-8,13-EPOXI-11-METOXI-1ALFA, 6BETA, 7BETATRIHIDROXILABD-14-ENO-6,7-CARBONATO Y 11,12-DEHIDRO-8,13EPOXI-11-METOXI-1ALFA, 6BETA, 7BETA, 9ALFATETRAHIDROXILABD-14-ENO-6,7-CARBONATO Y LOS CORRESPONDIENTES COMPUESTOS DIMETIL ACETALICOS.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/846,550 US4734513A (en) | 1986-03-31 | 1986-03-31 | Method of synthesizing forskolin from 9-deoxyforskolin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2010511B3 true ES2010511B3 (es) | 1989-11-16 |
Family
ID=25298260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES87103939T Expired ES2010511B3 (es) | 1986-03-31 | 1987-03-18 | Un procedimiento para la preparacion de forskolina a partir de 9-desoxi-forskolina. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4734513A (es) |
| EP (1) | EP0243646B1 (es) |
| JP (1) | JPS62249981A (es) |
| KR (1) | KR900007626B1 (es) |
| AT (1) | ATE45353T1 (es) |
| AU (1) | AU585143B2 (es) |
| DE (1) | DE3760422D1 (es) |
| DK (1) | DK159987A (es) |
| ES (1) | ES2010511B3 (es) |
| GR (1) | GR3000203T3 (es) |
| IL (1) | IL82047A (es) |
| PT (1) | PT84584B (es) |
| ZA (1) | ZA872266B (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5008407A (en) * | 1986-03-31 | 1991-04-16 | Hoechst-Roussel Pharmaceuticals Inc. | Method of synthesizing forskolin from 9-deoxyforskolin |
| US5023344A (en) * | 1986-11-20 | 1991-06-11 | Hoechst-Roussel Pharmaceuticals Incorporated | 12-halogenated forskolin derivatives |
| US4978678A (en) * | 1986-11-20 | 1990-12-18 | Hoechst-Roussel Pharmaceuticals Inc. | 12-halogenated forskolin derivatives |
| US5070209A (en) * | 1986-11-20 | 1991-12-03 | Hoechst Roussel Pharmaceuticals Inc. | 12-halogenated forskolin derivatives |
| US4999351A (en) * | 1989-01-11 | 1991-03-12 | Hoechst-Roussel Pharmaceuticals, Inc. | 7-aryl and heteroaryl ethers of desacetylforskolin |
| JP3557095B2 (ja) * | 1998-04-20 | 2004-08-25 | 高砂香料工業株式会社 | メラニン産生抑制剤 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2654796A1 (de) * | 1976-12-03 | 1978-06-08 | Hoechst Ag | Polyoxygenierte labdan-derivate |
| US4517200A (en) * | 1982-12-27 | 1985-05-14 | Schering-Plough Corporation | Method for treating allergic reactions with forskolin |
| US4564626A (en) * | 1983-04-01 | 1986-01-14 | Schering Corporation | Methods of inducing bronchodilation |
| DE3407514A1 (de) * | 1984-03-01 | 1985-09-26 | Hoechst Ag, 6230 Frankfurt | Verwendung von polyoxygenierten labdanderivaten zur behandlung von konstriktionen der atemwege |
| EP0191166B1 (en) * | 1984-12-14 | 1991-02-06 | Hoechst-Roussel Pharmaceuticals Incorporated | Aminoacyllabdanes, a process and intermediates for their preparation and their use as medicaments |
| US4639443A (en) * | 1985-03-01 | 1987-01-27 | Hoechst-Roussel Pharmaceuticals Inc. | Labdane compounds, pharmaceutical compositions and use |
-
1986
- 1986-03-31 US US06/846,550 patent/US4734513A/en not_active Expired - Lifetime
-
1987
- 1987-03-18 ES ES87103939T patent/ES2010511B3/es not_active Expired
- 1987-03-18 AT AT87103939T patent/ATE45353T1/de not_active IP Right Cessation
- 1987-03-18 EP EP87103939A patent/EP0243646B1/en not_active Expired
- 1987-03-18 DE DE8787103939T patent/DE3760422D1/de not_active Expired
- 1987-03-27 ZA ZA872266A patent/ZA872266B/xx unknown
- 1987-03-30 JP JP62074581A patent/JPS62249981A/ja active Pending
- 1987-03-30 IL IL82047A patent/IL82047A/xx unknown
- 1987-03-30 KR KR1019870002930A patent/KR900007626B1/ko not_active Expired
- 1987-03-30 PT PT84584A patent/PT84584B/pt not_active IP Right Cessation
- 1987-03-30 AU AU70765/87A patent/AU585143B2/en not_active Ceased
- 1987-03-30 DK DK159987A patent/DK159987A/da not_active IP Right Cessation
-
1989
- 1989-11-01 GR GR89400227T patent/GR3000203T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US4734513A (en) | 1988-03-29 |
| PT84584A (en) | 1987-04-01 |
| KR900007626B1 (ko) | 1990-10-17 |
| AU585143B2 (en) | 1989-06-08 |
| PT84584B (pt) | 1989-11-30 |
| IL82047A0 (en) | 1987-10-20 |
| ATE45353T1 (de) | 1989-08-15 |
| DE3760422D1 (en) | 1989-09-14 |
| KR870008908A (ko) | 1987-10-21 |
| IL82047A (en) | 1992-02-16 |
| DK159987D0 (da) | 1987-03-30 |
| JPS62249981A (ja) | 1987-10-30 |
| DK159987A (da) | 1987-10-01 |
| EP0243646A1 (en) | 1987-11-04 |
| GR3000203T3 (en) | 1990-12-31 |
| AU7076587A (en) | 1987-10-08 |
| ZA872266B (en) | 1987-11-25 |
| EP0243646B1 (en) | 1989-08-09 |
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