DE1618028A1 - Verfahren zur Herstellung von Methylacyloxymethylketalen aus Prednisolonderivaten mit 3 bis 5 C-Atomen in der Acylgruppe - Google Patents
Verfahren zur Herstellung von Methylacyloxymethylketalen aus Prednisolonderivaten mit 3 bis 5 C-Atomen in der AcylgruppeInfo
- Publication number
- DE1618028A1 DE1618028A1 DE19671618028 DE1618028A DE1618028A1 DE 1618028 A1 DE1618028 A1 DE 1618028A1 DE 19671618028 DE19671618028 DE 19671618028 DE 1618028 A DE1618028 A DE 1618028A DE 1618028 A1 DE1618028 A1 DE 1618028A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- ketals
- methylacyloxymethyl
- acyl group
- preparation
- 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.)
- Pending
Links
- 125000004432 carbon atom Chemical group C* 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims 5
- 125000002252 acyl group Chemical group 0.000 title description 5
- 150000003116 prednisolone derivatives Chemical class 0.000 title 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001887 cortisones Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 229960005294 triamcinolone Drugs 0.000 description 8
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000003246 corticosteroid Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 206010018691 Granuloma Diseases 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- -1 butyroyloxyacetonide Chemical compound 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229940043075 fluocinolone Drugs 0.000 description 2
- FEBLZLNTKCEFIT-VSXGLTOVSA-N fluocinolone acetonide 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]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O FEBLZLNTKCEFIT-VSXGLTOVSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HGTYBQOCNLPOHZ-UHFFFAOYSA-N 2-oxopropyl hexanoate Chemical compound CCCCCC(=O)OCC(C)=O HGTYBQOCNLPOHZ-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001249696 Senna alexandrina Species 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 125000005257 alkyl acyl group Chemical group 0.000 description 1
- 229940051868 antimigraine drug corticosteroid derivative Drugs 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE1048/66A SE307576B (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) | 1966-01-27 | 1966-01-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1618028A1 true DE1618028A1 (de) | 1970-10-29 |
Family
ID=20257516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671618028 Pending DE1618028A1 (de) | 1966-01-27 | 1967-01-05 | Verfahren zur Herstellung von Methylacyloxymethylketalen aus Prednisolonderivaten mit 3 bis 5 C-Atomen in der Acylgruppe |
Country Status (11)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2278122C1 (ru) * | 2004-12-27 | 2006-06-20 | Институт Молекулярной Генетики Российской Академии Наук (Имг Ран) | Высокомеченный тритием [3h]-ацетонид 9альфа-фторо-16альфа-гидроксипреднизолона |
| WO2011029547A2 (en) * | 2009-09-11 | 2011-03-17 | Chiesi Farmaceutici S.P.A. | Pregnane derivatives condensed in the 16, 17 position with an n-substituted isoxazolidine ring as anti-inflammatory agents |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3048581A (en) * | 1960-04-25 | 1962-08-07 | Olin Mathieson | Acetals and ketals of 16, 17-dihydroxy steroids |
| US3341526A (en) * | 1965-01-12 | 1967-09-12 | Bofors Ab | Acyloxyacetals of fluoro-16alpha-hydroxyprednisolones |
-
1966
- 1966-01-27 SE SE1048/66A patent/SE307576B/xx unknown
-
1967
- 1967-01-05 DE DE19671618028 patent/DE1618028A1/de active Pending
- 1967-01-12 NL NL6700465A patent/NL6700465A/xx unknown
- 1967-01-18 US US610010A patent/US3524850A/en not_active Expired - Lifetime
- 1967-01-19 AT AT52967A patent/AT269385B/de active
- 1967-01-20 BE BE692983D patent/BE692983A/xx unknown
- 1967-01-24 ES ES336470A patent/ES336470A1/es not_active Expired
- 1967-01-24 CH CH101267A patent/CH487872A/de not_active IP Right Cessation
- 1967-01-25 GR GR670133327A patent/GR33327B/el unknown
- 1967-01-26 GB GB3976/67A patent/GB1120337A/en not_active Expired
- 1967-01-26 FR FR92659A patent/FR6257M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3524850A (en) | 1970-08-18 |
| SE307576B (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) | 1969-01-13 |
| NL6700465A (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) | 1967-07-28 |
| BE692983A (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) | 1967-07-03 |
| GR33327B (el) | 1967-11-23 |
| CH487872A (de) | 1970-03-31 |
| ES336470A1 (es) | 1970-04-01 |
| AT269385B (de) | 1969-03-10 |
| GB1120337A (en) | 1968-07-17 |
| FR6257M (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) | 1968-08-19 |
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