GB1291293A - Steroid carbonates and their preparation - Google Patents
Steroid carbonates and their preparationInfo
- Publication number
- GB1291293A GB1291293A GB2614370A GB2614370A GB1291293A GB 1291293 A GB1291293 A GB 1291293A GB 2614370 A GB2614370 A GB 2614370A GB 2614370 A GB2614370 A GB 2614370A GB 1291293 A GB1291293 A GB 1291293A
- Authority
- GB
- United Kingdom
- Prior art keywords
- steroid
- appropriate
- compounds
- haloformate
- methylbicyclo
- 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
- -1 Steroid carbonates Chemical class 0.000 title abstract 3
- 125000002619 bicyclic group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000003431 steroids Chemical class 0.000 abstract 2
- UDNIMRNTWHDLKM-UHFFFAOYSA-N (1-methyl-4-bicyclo[2.2.2]octanyl)methanol Chemical compound C1CC2(CO)CCC1(C)CC2 UDNIMRNTWHDLKM-UHFFFAOYSA-N 0.000 abstract 1
- VAIOYMYTWWCODC-UHFFFAOYSA-N 1-methylbicyclo[2.2.2]octane-4-carboxylic acid Chemical compound C1CC2(C(O)=O)CCC1(C)CC2 VAIOYMYTWWCODC-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 230000001548 androgenic effect Effects 0.000 abstract 1
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 230000001016 myotrophic effect Effects 0.000 abstract 1
- 229960004719 nandrolone Drugs 0.000 abstract 1
- NPAGDVCDWIYMMC-IZPLOLCNSA-N nandrolone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 NPAGDVCDWIYMMC-IZPLOLCNSA-N 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 230000003637 steroidlike Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- 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
1291293 Steroid carbonates E I DU PONT DE NEMOURS & CO. 29 May 1970 26143/70 Headings C2C and C2U The invention comprises compounds of formula wherein each of R<SP>1</SP> to R<SP>5</SP> is H or Me, and each of the bonds a, b and c is single or double, with the provisos that (i) when R<SP>3</SP> is H, at least one of a and b is a single bond, (ii) when b is a single bond, any 2-methyl group (R<SP>1</SP>) is α-oriented, (iii) when any one of R<SP>1</SP>, R<SP>2</SP> and R<SP>4</SP> is Me, the others are each H, (iv) when R<SP>2</SP> is Me, b is a double bond, and (v) when a is a single bond, the 5-hydrogen atom is α-oriented. Preparation of compounds I is by reacting an appropriate steroid 17-haloformate with an appropriate bicyclic alcohol, or by reacting an appropriate steroid 17-ol with an appropriate bicyclic haloformate. The steroidal and bicyclic haloformate starting compounds are prepared from the corresponding alcohols by reaction with carbonyl halides. 4 - Methylbicyclo[2.2.2]octane- 1 - methanol is prepared from 4 - methylbicyclo[2.2.2]octane- 1-carboxylic acid via the ethyl ester of the latter. The 17 - (4 - methylbicyclo[2.2.2]octane-1. carboxylate) of 19-nortestosterone is disclosed by way of comparison. Compounds I are said to possess myotrophic and androgenic activity, and may be made up with carriers into pharmaceutical compositions for oral and parenteral administration.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2614370A GB1291293A (en) | 1970-05-29 | 1970-05-29 | Steroid carbonates and their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2614370A GB1291293A (en) | 1970-05-29 | 1970-05-29 | Steroid carbonates and their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1291293A true GB1291293A (en) | 1972-10-04 |
Family
ID=10239078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2614370A Expired GB1291293A (en) | 1970-05-29 | 1970-05-29 | Steroid carbonates and their preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1291293A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5208032A (en) * | 1988-07-15 | 1993-05-04 | Rutgers, The State University Of New Jersey | Increasing the growth of turkeys using implant of 19-nortestosterone |
| WO2006083618A1 (en) * | 2005-02-04 | 2006-08-10 | Government Of The United States Of America, Represented By The Secretary, Department Of Health And Human Services | NANDROLONE 17ß-CARBONATES |
-
1970
- 1970-05-29 GB GB2614370A patent/GB1291293A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5208032A (en) * | 1988-07-15 | 1993-05-04 | Rutgers, The State University Of New Jersey | Increasing the growth of turkeys using implant of 19-nortestosterone |
| WO2006083618A1 (en) * | 2005-02-04 | 2006-08-10 | Government Of The United States Of America, Represented By The Secretary, Department Of Health And Human Services | NANDROLONE 17ß-CARBONATES |
| US7820642B2 (en) | 2005-02-04 | 2010-10-26 | The United States Of America As Represented By The Department Of Health And Human Services | Nandrolone 17β-carbonates |
| AU2006211907B2 (en) * | 2005-02-04 | 2011-09-08 | Government Of The United States Of America, Represented By The Secretary, Department Of Health And Human Services | Nandrolone 17beta-carbonates |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |