GB744237A - Cyclopentanophenanthrene compounds and process for the production thereof - Google Patents
Cyclopentanophenanthrene compounds and process for the production thereofInfo
- Publication number
- GB744237A GB744237A GB12838/52A GB1283852A GB744237A GB 744237 A GB744237 A GB 744237A GB 12838/52 A GB12838/52 A GB 12838/52A GB 1283852 A GB1283852 A GB 1283852A GB 744237 A GB744237 A GB 744237A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trione
- dione
- acid
- anhydride
- acetoxyallopregnane
- 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 3
- 150000001875 compounds Chemical class 0.000 title 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl 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
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 2
- 229930195729 fatty acid Natural products 0.000 abstract 2
- 239000000194 fatty acid Substances 0.000 abstract 2
- 150000004665 fatty acids Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- WKAVAGKRWFGIEA-DADBAOPHSA-N 11-Ketoprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2=O WKAVAGKRWFGIEA-DADBAOPHSA-N 0.000 abstract 1
- WKAVAGKRWFGIEA-UHFFFAOYSA-N 11-Ketoprogesterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(=O)C)C1(C)CC2=O WKAVAGKRWFGIEA-UHFFFAOYSA-N 0.000 abstract 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 abstract 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- -1 aromatic peracid Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 235000011056 potassium acetate Nutrition 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
- 235000009518 sodium iodide Nutrition 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises: (a) 3b : 17a -dihydroxyallopregnane-11 : 20-dione; (b) the preparation thereof by a combination of the following steps (or the last one or more of them): (i) selectively reducing allopregnane-3 : 11 : 20-trione with hydrogen in the presence of Raney nickel catalyst to 3b -hydroxyallopregnane-11 : 20-dione, (ii) esterifying this with a fatty acid esterifying agent containing not more than 6 carbon atoms in the acyl group, (iii) treating the resulting ester with a fatty acid anhydride containing not more than 6 carbon atoms in the acyl group, in the presence of an aromatic sulphonic acid, to form the corresponding triacylate of D 11,17-allopregnadiene-3b : 11 : 20-triol, and (iv) treating this with an aromatic peracid followed by saponification; (c) treatment of (a) with bromine to produce its 21-bromo derivative; (d) treatment of the product of (c) with sodium iodide and potassium acetate to produce 3b : 17a -dihydroxy-21-acetoxyallopregnane-11 : 20-dione; (e) selective oxidation of the product of (d) with N-bromoacetamide in the presence of pyridine to 17a -hydroxy-21-acetoxyallopregnane-3 : 11 : 20-trione. In an example, step (i) is effected in a 1 : 1 mixture of ethanol and dioxane, step (ii) with acetic (or propionic) anhydride and pyridine, step (iii) with acetic anhydride in the presence of p-toluenesulphonic acid, step (iv) with perbenzoic acid in chloroform followed by methanolic caustic soda, process (c) with a solution of bromine in chloroform, and process (d) by refluxing in acetone. Specification 735,429 is referred to. Allopregnane-3 : 11 : 20-trione is prepared by shaking D 4 - pregnane - 3 : 11 : 20 - trione (11-ketoprogesterone) in an organic solvent (e.g. ethyl acetate) with hydrogen in the presence of a previously reduced 10 per cent palladiumcharcoal catalyst.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MX744237X | 1951-05-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB744237A true GB744237A (en) | 1956-02-01 |
Family
ID=19742989
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12838/52A Expired GB744237A (en) | 1951-05-25 | 1952-05-21 | Cyclopentanophenanthrene compounds and process for the production thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB744237A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3070614A (en) * | 1960-04-22 | 1962-12-25 | Ormonoterapia Richter Spa | 16-methyl-pregnane |
| US3345387A (en) * | 1964-05-25 | 1967-10-03 | Merck & Co Inc | Process for producing 16beta-alkyl and 16beta-alkyl steroids of the pregnane series |
| US3461144A (en) * | 1958-03-19 | 1969-08-12 | Merck & Co Inc | Novel 16beta-alkyl-17-oxygenated steroids and processes |
| USRE35517E (en) * | 1987-08-25 | 1997-05-20 | University Of Southern California | Method, compositions, and compounds for modulating brain excitability |
-
1952
- 1952-05-21 GB GB12838/52A patent/GB744237A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3461144A (en) * | 1958-03-19 | 1969-08-12 | Merck & Co Inc | Novel 16beta-alkyl-17-oxygenated steroids and processes |
| US3070614A (en) * | 1960-04-22 | 1962-12-25 | Ormonoterapia Richter Spa | 16-methyl-pregnane |
| US3345387A (en) * | 1964-05-25 | 1967-10-03 | Merck & Co Inc | Process for producing 16beta-alkyl and 16beta-alkyl steroids of the pregnane series |
| USRE35517E (en) * | 1987-08-25 | 1997-05-20 | University Of Southern California | Method, compositions, and compounds for modulating brain excitability |
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