ES473544A1 - New procedure for synthesis of valerate of diflucortolone. (Machine-translation by Google Translate, not legally binding) - Google Patents
New procedure for synthesis of valerate of diflucortolone. (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES473544A1 ES473544A1 ES473544A ES473544A ES473544A1 ES 473544 A1 ES473544 A1 ES 473544A1 ES 473544 A ES473544 A ES 473544A ES 473544 A ES473544 A ES 473544A ES 473544 A1 ES473544 A1 ES 473544A1
- Authority
- ES
- Spain
- Prior art keywords
- alpha
- difluo
- beta
- methyl
- above compound
- 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 4
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 229960004091 diflucortolone Drugs 0.000 title abstract 2
- OGPWIDANBSLJPC-RFPWEZLHSA-N diflucortolone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)CO)[C@@]2(C)C[C@@H]1O OGPWIDANBSLJPC-RFPWEZLHSA-N 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 229940070710 valerate Drugs 0.000 title 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- HOWBJCLELHJALU-WZBAXQLOSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-3h-cyclopenta[a]phenanthrene Chemical compound C1CC2CCC=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 HOWBJCLELHJALU-WZBAXQLOSA-N 0.000 abstract 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 abstract 2
- HHJIUUAMYGBVSD-YTFFSALGSA-N Diflucortolone valerate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)COC(=O)CCCC)[C@@]2(C)C[C@@H]1O HHJIUUAMYGBVSD-YTFFSALGSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229960003970 diflucortolone valerate Drugs 0.000 abstract 2
- 229960003469 flumetasone Drugs 0.000 abstract 2
- WXURHACBFYSXBI-GQKYHHCASA-N flumethasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]2(C)C[C@@H]1O WXURHACBFYSXBI-GQKYHHCASA-N 0.000 abstract 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 abstract 2
- BMFZXPIZDWRICU-RDQPJNLGSA-N (8R,9S,10R,13S,14S)-17-ethyl-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15-decahydro-3H-cyclopenta[a]phenanthrene Chemical compound CCC1=CC[C@H]2[C@@H]3CCC4CCC=C[C@]4(C)[C@H]3CC[C@]12C BMFZXPIZDWRICU-RDQPJNLGSA-N 0.000 abstract 1
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- -1 alpha-methyl-21-valeryloxy, 1,4-pregnadiene-3, 20 dione Chemical compound 0.000 abstract 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract 1
- 239000004327 boric acid Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 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
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- OPCDHYPGIGFJGH-UHFFFAOYSA-M potassium;pentanoate Chemical compound [K+].CCCCC([O-])=O OPCDHYPGIGFJGH-UHFFFAOYSA-M 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
New procedure for the synthesis of diflucortolone valerate or 6 alpha, 9 alpha-difluo-11 beta-hydroxy, 16 alpha-methyl-21-valeryloxy, 1,4-pregnadiene-3, 20 dione which is obtained in a six-step process. From flumetasone, according to the following process: reaction of flumethasone with ethylene glycol in acid medium to obtain 6 alpha-9 alpha-difluo, 11 beta, 17 alpha, 21-dihydroxy, 16-alpha-methyl, 1-pregnen-3, 20-di (1,3-dioxolone); dehydration of the above compound with boric acid to obtain 6 alpha-9 alpha difluo, 11 beta, 21-dihydroxy, 16-alpha-methyl, 1,16-pregnadiene, 3,20-di (1,3-dioxolane); catalytic hydrogenation of the above compound with hydrogen gas in the presence of palladium or raney nickel with which 6 alpha, 9 alpha-difluo, 11 beta, 21-dihydroxy, 16-alpha-methyl, 1-pregnen, 3,20-di (1,3-dioxolane); acetic hydrolysis of the above compound to obtain 6 alpha, 9 alpha-difluo, 11 beta, hydroxy, 21-acetyloxy, 16-alpha-methyl, 1-pregnen, 3,20-dione; oxidation with selenium dioxide of the above compound to form a double bond in delta 1,2 with which we obtain 6 alpha, 9 alpha-difluo, 11 beta, 21-dihydroxy, 16-alpha-methyl, 1,4-prepnadien, 3,20-dione (dione (diflucortolone acetate); reaction of the above compound with potassium valerate to obtain diflucortolone valerate. (Machine-translation by Google Translate, not legally binding)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES473544A ES473544A1 (en) | 1978-09-21 | 1978-09-21 | New procedure for synthesis of valerate of diflucortolone. (Machine-translation by Google Translate, not legally binding) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES473544A ES473544A1 (en) | 1978-09-21 | 1978-09-21 | New procedure for synthesis of valerate of diflucortolone. (Machine-translation by Google Translate, not legally binding) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES473544A1 true ES473544A1 (en) | 1979-05-16 |
Family
ID=8476793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES473544A Expired ES473544A1 (en) | 1978-09-21 | 1978-09-21 | New procedure for synthesis of valerate of diflucortolone. (Machine-translation by Google Translate, not legally binding) |
Country Status (1)
| Country | Link |
|---|---|
| ES (1) | ES473544A1 (en) |
-
1978
- 1978-09-21 ES ES473544A patent/ES473544A1/en not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 19991209 |