ES280806A1 - Steroid esters - Google Patents
Steroid estersInfo
- Publication number
- ES280806A1 ES280806A1 ES0280806A ES280806A ES280806A1 ES 280806 A1 ES280806 A1 ES 280806A1 ES 0280806 A ES0280806 A ES 0280806A ES 280806 A ES280806 A ES 280806A ES 280806 A1 ES280806 A1 ES 280806A1
- Authority
- ES
- Spain
- Prior art keywords
- homo
- acyl
- nortestosterone
- nortestosterones
- acylation
- 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 esters Chemical class 0.000 title abstract 2
- 229960004719 nandrolone Drugs 0.000 abstract 4
- 230000010933 acylation Effects 0.000 abstract 3
- 238000005917 acylation reaction Methods 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 abstract 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 abstract 1
- QDRSJFZQMOOSAF-UHFFFAOYSA-N 9-undecenoic acid Chemical compound CC=CCCCCCCCC(O)=O QDRSJFZQMOOSAF-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 abstract 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 230000001974 anti-anabolic effect Effects 0.000 abstract 1
- 230000001833 anti-estrogenic effect Effects 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 235000001968 nicotinic acid Nutrition 0.000 abstract 1
- 239000011664 nicotinic acid Substances 0.000 abstract 1
- 229940049953 phenylacetate Drugs 0.000 abstract 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000000725 suspension Substances 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
- 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
The invention comprises (1) 17-acyl-18-homo-19-nortestosterones wherein the acyl group contains at least 6 carbon atoms (2) 3-enol acylates of 17-acyl-18-homo-19-nortestosterones (3) 18-homo-19-nortestosterone 17-isovalerate and 17-hemisuccinate and (4) the preparation of 17-acyl-18-homo-19-nortestosterones and their 3-enol acylates by esterifying 18-homo-19-nortestosterone with an acylating agent. The claims are stated to include all states of resolution except the fully resolved 13a -enantiomers. Suitable agents are carboxylic acids or their anhydrides or halides, or esters with lower alcohols. Thus, acylation at the 17-position may be achieved with an acid chloride in presence of a base and acylation at the 3-position simultaneously or subsequent to acylation at the 17-position can be carried out by heating with an acid anhydride or chloride and a catalytic amount of toluene-p-sulphonic acid. A 17-acyl-3-enolacylate can be selectively hydrolysed to the 17-acyl-18-homo-19-nortestosterone. Examples describe the preparation of the acetate, isovalerate, n-decanoate, n - undec - 9 - enoate, b - cyclopentylpropionate, hemisuccinate, benzoate, phenylacetate, b -phenylpropionate and nicotinate of 18-homo-19-nortestosterone, and of 3,17-diacetoxy-18-homo-oestra-3,5-diene. Other esterifying acids are also referred to. The steroid esters of the invention, which are stated to have anti-oestrogenic and anabolic properties, may be made up into liquid injectable preparations in solution, suspension or emulsion with a suitable carrier. A dispersion of the n-decanoate is described.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3325161A GB1041276A (en) | 1961-09-15 | 1961-09-15 | Steroid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES280806A1 true ES280806A1 (en) | 1963-02-01 |
Family
ID=10350497
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0280806A Expired ES280806A1 (en) | 1961-09-15 | 1962-09-14 | Steroid esters |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT256353B (en) |
| CH (1) | CH427784A (en) |
| DK (1) | DK103939C (en) |
| ES (1) | ES280806A1 (en) |
| GB (1) | GB1041276A (en) |
| IT (1) | IT1061784B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20230227492A1 (en) * | 2020-06-11 | 2023-07-20 | The Usa As Represented By The Secretary, Department Of Health And Human Services | Monomeric and oligomeric compound embodiments as contraceptives and therapies and methods of making and using the same |
-
1961
- 1961-09-15 GB GB3325161A patent/GB1041276A/en not_active Expired
-
1962
- 1962-08-29 CH CH1027662A patent/CH427784A/en unknown
- 1962-09-12 AT AT726062A patent/AT256353B/en active
- 1962-09-14 ES ES0280806A patent/ES280806A1/en not_active Expired
- 1962-09-14 DK DK403062A patent/DK103939C/en active
- 1962-09-14 IT IT1816162A patent/IT1061784B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| IT1061784B (en) | 1983-04-30 |
| GB1041276A (en) | 1966-09-01 |
| DK103939C (en) | 1966-03-14 |
| AT256353B (en) | 1967-08-25 |
| CH427784A (en) | 1967-01-15 |
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