GB868303A - New cyclopentanophenanthrene derivatives and process for the production thereof - Google Patents
New cyclopentanophenanthrene derivatives and process for the production thereofInfo
- Publication number
- GB868303A GB868303A GB27622/57A GB2762257A GB868303A GB 868303 A GB868303 A GB 868303A GB 27622/57 A GB27622/57 A GB 27622/57A GB 2762257 A GB2762257 A GB 2762257A GB 868303 A GB868303 A GB 868303A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- ethylenedioxy
- bis
- lower alkyl
- methyl
- 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 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- DBPWSSGDRRHUNT-CEGNMAFCSA-N 17α-hydroxyprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DBPWSSGDRRHUNT-CEGNMAFCSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- -1 hydrocarbon carboxylic acid Chemical class 0.000 abstract 2
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 abstract 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 229910001623 magnesium bromide Inorganic materials 0.000 abstract 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 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)
- Steroid Compounds (AREA)
Abstract
The invention comprises 6-alkyl steroids of the general formula: <PICT:0868303/IV (b)/1> wherein R represents an alkyl group containing at most five carbon atoms, and R1 is H or the residue from a hydrocarbon carboxylic acid of from 2 to 12 carbon atoms, together with a process for their preparation by reacting 17a -hydroxy-progesterone with ethylene glycol, oxidising the resulting 3,20-bisethylene ketal with a peracid to form the 5a ,6a -epoxide, treating the latter with a lower alkyl magnesium bromide to form a 3,20-bis-ethylenedioxy-6BETA- lower alkyl-pregnane-5a ,17a -diol, hydrolysing the ketal groups with dilute acid to yield a mixture of partially dehydrated material, completing the dehydration and epimerising the alkyl group with alkali metal hydroxide in methanol to form a 6a -lower alkyl-17a -hydroxyprogesterone, and optionally esterifying the 17a -hydroxy group. In Examples (1) to (4), 17a -hydroxyprogesterone, ethylene glycol, and p-toluene sulphonic acid are refluxed in benzene, the resulting diketal treated with perbenzoic acid in chloroform giving 3,20-bis-ethylenedioxy-5a ,6a -oxido-pregnan-17a -ol, which with ethereal methyl magnesium bromide yields 3,20-bis-ethylenedioxy-6BETA-methyl-pregnane-5a ,17a -diol; subsequent hydrolysis with dilute H2SO4 and treatment with methanolic KOH gives 6a -methyl-D 4-pregnene-17a -ol-3,20-dione, which (5) and (6) is esterified with p-toluene sulphonic and the appropriate acid anhydride to the acetate, propionate, caproate and enanthate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MX868303X | 1956-09-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB868303A true GB868303A (en) | 1961-05-17 |
Family
ID=19743116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27622/57A Expired GB868303A (en) | 1956-09-08 | 1957-09-02 | New cyclopentanophenanthrene derivatives and process for the production thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB868303A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4346037A (en) * | 1981-07-10 | 1982-08-24 | The Upjohn Company | Base catalyzed acylation with enol esters |
| WO2007118830A1 (en) | 2006-04-13 | 2007-10-25 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Azaheterocyclyl derivatives of androstanes and androstenes as medicaments for cardiovascular disorders |
| WO2007118832A3 (en) * | 2006-04-13 | 2008-04-17 | Sigma Tau Ind Farmaceuti | Amino derivatives of androstanes and androstenes as medicaments for cardiovascular disorders |
-
1957
- 1957-09-02 GB GB27622/57A patent/GB868303A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4346037A (en) * | 1981-07-10 | 1982-08-24 | The Upjohn Company | Base catalyzed acylation with enol esters |
| WO2007118830A1 (en) | 2006-04-13 | 2007-10-25 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Azaheterocyclyl derivatives of androstanes and androstenes as medicaments for cardiovascular disorders |
| WO2007118832A3 (en) * | 2006-04-13 | 2008-04-17 | Sigma Tau Ind Farmaceuti | Amino derivatives of androstanes and androstenes as medicaments for cardiovascular disorders |
| EA015257B1 (en) * | 2006-04-13 | 2011-06-30 | Сигма-Тау Индустрие Фармасьютике Риуните С.П.А. | Amino derivatives of androstanes and androstenes as medicaments for cardiovascular disorders |
| EA015622B1 (en) * | 2006-04-13 | 2011-10-31 | Сигма-Тау Индустрие Фармасьютике Риуните С.П.А. | Azaheterocyclyl derivatives of androstanes and androstenes as medicaments for cardiovascular disorders |
| US8536160B2 (en) | 2006-04-13 | 2013-09-17 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Azaheterocyclyl derivatives of androstanes and androstenes as medicaments for cardiovascular disorders |
| US8609644B2 (en) | 2006-04-13 | 2013-12-17 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Amino derivatives of androstanes and androstenes as medicaments for cardiovascular disorders |
| CN101466725B (en) * | 2006-04-13 | 2014-06-25 | 西格马-陶工业制药重组有限公司 | Amino derivatives of androstanes and androstenes as medicaments for cardiovascular disorders |
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