MX3325E - PROCEDURE TO PREPARE USEFUL DICYCLIC LACTONES IN THE PREPARATION OF PROSTAGLANDIN-TYPE COMPOUNDS - Google Patents
PROCEDURE TO PREPARE USEFUL DICYCLIC LACTONES IN THE PREPARATION OF PROSTAGLANDIN-TYPE COMPOUNDSInfo
- Publication number
- MX3325E MX3325E MX000033U MX3376U MX3325E MX 3325 E MX3325 E MX 3325E MX 000033 U MX000033 U MX 000033U MX 3376 U MX3376 U MX 3376U MX 3325 E MX3325 E MX 3325E
- Authority
- MX
- Mexico
- Prior art keywords
- see
- fluorine
- different
- same
- inclusive
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 150000002596 lactones Chemical class 0.000 title abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 4
- 239000011737 fluorine Substances 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- -1 bicyclic lactones Chemical class 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000203 mixture 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
- 239000011591 potassium Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 230000002997 prostaglandinlike Effects 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
La presente invención se refiere a procedimiento para preparar lactonas bicíclicas útiles en la preparación de compuestos tipo prostaglandina por reducción de manera altamente estereoselectiva de la mitad oxo de la cadena lateral de una lactona de la fórmula: (VER FIGURA) en donde L1 es (VER FIGURA) o una mezcla de (VER FIGURA) en donde R3 y R4 son hidrógeno, metilo, o flúor siendo iguales o diferentes, con la condición de que uno de R3 y R4 es flúor sólo cuando el otro es hidrógeno o flúor; en dondr R7 es 3(1)-(CH2)k-CH3, en donde k es 2 a 6 inclusive; (VER VFIGURA) en donde T es cloro, flúor, trifluorometilo, alquilo de 1 a 3 átomos de carbono, inclusive, y s es cero, uno, 2 ó 3, con la condición de que no más de dos T son otra cosa que alquilo, siendo las varias T iguales o diferentes, (VER FIGURA) en donde T y s son como se han definido arriba, ó (4) cis-CHCH2-CH2-CH3, con la condición de que R7 es (VER FIGURA) sólo cuando R3 y R4 son hidrógeno o metilo, siendo iguales o diferentes; y en donde R13 es un grupo directo de la fórmula (VER FIGURA) en donde R1 y R2 son hidrógeno, cloro fluor, bromo, alquilo de uno a 3 átomos de carbono, inclusive, o alcoxi de uno a 3 átomos de carbono, inclusive, siendo iguales o diferentes ó (VER FIGURA) en donde R1 y R2 son como se han definido arriba, siendo iguales o diferentes para cada anillo de fenilo; que comprende: reducir la lectona citada con un trialquil borohidruro de potasio de la fórmula (VER FIGURA) en donde m es cero, uno, 3 ó 3, con lo que se prepara un alcohol de la fórmula (VER FIGURA) en donde L1, R7 y R13 son como se ha definido arriba.The present invention relates to a process for preparing bicyclic lactones useful in the preparation of prostaglandin-like compounds by highly stereoselectively reducing the oxo half of the side chain of a lactone of the formula: (SEE FIGURE) where L1 is (SEE FIGURE) or a mixture of (SEE FIGURE) wherein R3 and R4 are hydrogen, methyl, or fluorine being the same or different, with the proviso that one of R3 and R4 is fluorine only when the other is hydrogen or fluorine; where R7 is 3 (1) - (CH2) k-CH3, where k is 2 to 6 inclusive; (SEE FIGURE) where T is chlorine, fluorine, trifluoromethyl, alkyl of 1 to 3 carbon atoms, inclusive, and s is zero, one, 2 or 3, with the proviso that not more than two T are anything other than alkyl , the various T being the same or different, (SEE FIGURE) where T and s are as defined above, or (4) cis-CHCH2-CH2-CH3, with the condition that R7 is (SEE FIGURE) only when R3 and R4 are hydrogen or methyl, being the same or different; and where R13 is a direct group of the formula (SEE FIGURE) where R1 and R2 are hydrogen, chloro fluorine, bromine, alkyl of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive , being the same or different or (SEE FIGURE) where R1 and R2 are as defined above, being the same or different for each phenyl ring; comprising: reducing the lectone mentioned with a potassium trialkyl borohydride of the formula (SEE FIGURE) where m is zero, one, 3 or 3, whereby an alcohol of the formula is prepared (SEE FIGURE) where L1, R7 and R13 are as defined above.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56596275A | 1975-04-07 | 1975-04-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX3325E true MX3325E (en) | 1980-09-26 |
Family
ID=24260841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX000033U MX3325E (en) | 1975-04-07 | 1976-03-03 | PROCEDURE TO PREPARE USEFUL DICYCLIC LACTONES IN THE PREPARATION OF PROSTAGLANDIN-TYPE COMPOUNDS |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS6028835B2 (en) |
| BE (1) | BE840477A (en) |
| CA (1) | CA1069520A (en) |
| CH (1) | CH621548A5 (en) |
| DE (1) | DE2613306A1 (en) |
| DK (1) | DK163076A (en) |
| FR (1) | FR2306985A1 (en) |
| GB (1) | GB1498764A (en) |
| HU (1) | HU174651B (en) |
| MX (1) | MX3325E (en) |
| NL (1) | NL7603568A (en) |
| PL (1) | PL104354B1 (en) |
| SE (1) | SE424866B (en) |
| ZA (1) | ZA761506B (en) |
-
1976
- 1976-02-25 SE SE7602349A patent/SE424866B/en not_active IP Right Cessation
- 1976-03-03 MX MX000033U patent/MX3325E/en unknown
- 1976-03-05 CA CA247,329A patent/CA1069520A/en not_active Expired
- 1976-03-10 GB GB9505/76A patent/GB1498764A/en not_active Expired
- 1976-03-11 ZA ZA761506A patent/ZA761506B/en unknown
- 1976-03-22 CH CH355576A patent/CH621548A5/en not_active IP Right Cessation
- 1976-03-23 JP JP51030920A patent/JPS6028835B2/en not_active Expired
- 1976-03-29 DE DE19762613306 patent/DE2613306A1/en active Granted
- 1976-04-06 FR FR7609952A patent/FR2306985A1/en active Granted
- 1976-04-06 HU HU76UO117A patent/HU174651B/en not_active IP Right Cessation
- 1976-04-06 NL NL7603568A patent/NL7603568A/en not_active Application Discontinuation
- 1976-04-06 DK DK163076A patent/DK163076A/en not_active IP Right Cessation
- 1976-04-07 PL PL1976188562A patent/PL104354B1/en unknown
- 1976-04-07 BE BE165923A patent/BE840477A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK163076A (en) | 1976-10-08 |
| HU174651B (en) | 1980-02-28 |
| SE424866B (en) | 1982-08-16 |
| PL104354B1 (en) | 1979-08-31 |
| JPS6028835B2 (en) | 1985-07-06 |
| DE2613306C2 (en) | 1987-08-13 |
| SE7602349L (en) | 1976-10-08 |
| BE840477A (en) | 1976-10-07 |
| GB1498764A (en) | 1978-01-25 |
| AU1198676A (en) | 1977-09-22 |
| JPS51118758A (en) | 1976-10-18 |
| FR2306985A1 (en) | 1976-11-05 |
| NL7603568A (en) | 1976-10-11 |
| FR2306985B1 (en) | 1980-01-25 |
| CH621548A5 (en) | 1981-02-13 |
| ZA761506B (en) | 1977-03-30 |
| CA1069520A (en) | 1980-01-08 |
| DE2613306A1 (en) | 1976-10-21 |
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