GB896817A - Improvements in or relating to steroids and the manufacture thereof - Google Patents
Improvements in or relating to steroids and the manufacture thereofInfo
- Publication number
- GB896817A GB896817A GB9500/60A GB950060A GB896817A GB 896817 A GB896817 A GB 896817A GB 9500/60 A GB9500/60 A GB 9500/60A GB 950060 A GB950060 A GB 950060A GB 896817 A GB896817 A GB 896817A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aryl
- alkyl
- pregnadiene
- dione
- compounds
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000003431 steroids Chemical class 0.000 title 1
- -1 acyl radical Chemical class 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 229960004544 cortisone Drugs 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- LGTNVTBMTQCJMS-BYZMTCBYSA-N (8s,9s,10r,13r,14s,17s)-17-ethyl-10,13-dimethyl-2,3,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1=CC2=CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 LGTNVTBMTQCJMS-BYZMTCBYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical compound [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 150000001886 cortisols Chemical class 0.000 abstract 1
- 238000006356 dehydrogenation reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 229960000890 hydrocortisone Drugs 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- 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)
Abstract
The invention comprises compounds having the formula <FORM:0896817/IV (b)/1> wherein R1111 is hydroxy or acyloxy wherein the acyl radical is of a hydrocarbon carboxylic acid containing 1-12 carbon atoms inclusive, R111 is a b -hydroxymethylene or carbonyl group, X1111 is hydrogen, chlorine, bromine or fluorine, R1 is an alkyl or aryl radical and the 1,2-carbon atom linkage represents a single or double bond linkage, compounds having the formula <FORM:0896817/IV (b)/2> wherein R has the same value as R1111, compounds having the formula <FORM:0896817/IV (b)/3> wherein R11 is lower alkyl or aryl and X111 is fluorine chlorine or bromine, and processes for the preparation thereof by dehydrogenating a 6a -alkyl- or aryl-hydrocortisone 21-acylate to produce the corresponding 4,6-pregnadiene II, dehydrating II to obtain a 6-alkyl or aryl-17a ,21-dihydroxy-4,6,9(11)-pregnatriene-3,20-dione 21 ester III, adding hypohalous acid to form the corresponding 9a -halo compound IV, treating IV with a base to obtain a 6-alkyl or aryl-9b ,11b -oxido - 17a ,21 - dihydroxy - 4,6 - pregnadiene - 3,20-dione 21-acylate V, treating V with HF to obtain 6-alkyl or aryl-9a -fluoro-11b ,17a ,21-trihydroxy - 4,6 - pregnadiene - 3, 20 - dione 2I-acylate VI, treating VI with an organic sulphonyl halide to produce a 21-sulphonic acid ester VII and fluorinating VII to obtain a 6-alkyl- or aryl-21 - fluoro - 9a - halo - 11b ,17a - dihydroxy - 4,6 - pregnadiene - 3,20 - dione VIII. The 11-hydroxygroup may be oxidized to an 11-keto group or alternatively the 21-fluoro group may be introduced into an 11-keto compound. A 1,2-double bond may be introduced into either the starting compounds or the products by fermentative dehydrogenation. Examples describe the preparation of 6-dehydro-6-methyl cortisone, 1,6-bis-dehydro-6-methyl cortisone and the corresponding hydrocortisones. Specifications 826,629 and 853,981 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US896817XA | 1959-03-25 | 1959-03-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB896817A true GB896817A (en) | 1962-05-16 |
Family
ID=22219018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9500/60A Expired GB896817A (en) | 1959-03-25 | 1960-03-17 | Improvements in or relating to steroids and the manufacture thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB896817A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1201342B (en) * | 1963-03-05 | 1965-09-23 | Olin Mathieson | Method of making steroids |
-
1960
- 1960-03-17 GB GB9500/60A patent/GB896817A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1201342B (en) * | 1963-03-05 | 1965-09-23 | Olin Mathieson | Method of making steroids |
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