GB732286A - New stilbestrol derivatives and preparation thereof - Google Patents
New stilbestrol derivatives and preparation thereofInfo
- Publication number
- GB732286A GB732286A GB9447/53A GB944753A GB732286A GB 732286 A GB732286 A GB 732286A GB 9447/53 A GB9447/53 A GB 9447/53A GB 944753 A GB944753 A GB 944753A GB 732286 A GB732286 A GB 732286A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ester
- sodium salt
- diethylstilboestrol
- salt
- phosphorus oxychloride
- 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
- RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical class C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 title 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 6
- 150000002148 esters Chemical class 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 4
- 159000000000 sodium salts Chemical class 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 2
- 150000003014 phosphoric acid esters Chemical class 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical class OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- -1 pyridine Chemical class 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Arc-Extinguishing Devices That Are Switches (AREA)
Abstract
Phosphoric acid esters of diethylstilboestrol and water-soluble salts of said esters are obtained by recting diethylstilboestrol with phosphorus oxychloride by heating, preferably to the b.p. of the phosphorus oxychloride, in the presence of an organic base, e.g. pyridine, capable of binding the hydrogen chloride developed during the reaction, the proportion of the base employed being just sufficient to bind the whole of the hydrogen chloride developed, and the phosphoric acid ester formed is separated from the reaction mixture, purified via a readily soluble ether adduct, and if required is converted into a water-soluble salt, for example its sodium salt. To obtain the mono and diphosphoric acid esters 1 and 2 mols. of phosphorus oxychloride per mol. of diethylstilboestrol respectively are employed. The desired ester in analytically pure form may be obtained from the ether adducts by heating in vacuo. Salts of the ester, e.g. the sodium salt, are produced by dissolving the ester in sodium hydroxide solution and precipitating the sodium salt from this solution by the addition of an organic liquid, e.g. acetone. Alternatively the salt of the ester may be obtained by treating in absolute ethanol with sodium and isolating the sodium salt thus formed. Specification 539,506 is referred to.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE318635X | 1952-04-07 | ||
DES29789A DE1018503B (en) | 1952-04-07 | 1952-04-07 | Spark chamber for arc-extinguishing devices without external magnetic blowing |
DE80952X | 1952-09-08 | ||
AT41252X | 1952-12-04 | ||
DE270253X | 1953-02-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB732286A true GB732286A (en) | 1955-06-22 |
Family
ID=27506402
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB9447/53A Expired GB732286A (en) | 1952-04-07 | 1953-04-07 | New stilbestrol derivatives and preparation thereof |
GB22624/53A Expired GB739735A (en) | 1952-04-07 | 1953-08-17 | Improvements in or relating to arc-quenching chambers for electric switches |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB22624/53A Expired GB739735A (en) | 1952-04-07 | 1953-08-17 | Improvements in or relating to arc-quenching chambers for electric switches |
Country Status (5)
Country | Link |
---|---|
BE (1) | BE518690A (en) |
CH (2) | CH318635A (en) |
DE (1) | DE1018503B (en) |
FR (2) | FR1091655A (en) |
GB (2) | GB732286A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2840498A (en) * | 1953-06-08 | 1958-06-24 | Parker Rust Proof Co | Composition and method for producing combination corrosion resistant and lubricatingcoatings on metals |
WO2014060364A1 (en) | 2012-10-15 | 2014-04-24 | Chamaeleo Pharma Bvba | Sulfestrol for treating cancer |
WO2014060358A1 (en) | 2012-10-15 | 2014-04-24 | Chamaeleo Pharma Bvba | Fosfestrol for use in curative or palliative treatment of cancer in female mammals |
WO2014060347A1 (en) | 2012-10-15 | 2014-04-24 | Chamaeleo Pharma Bvba | Fosfestrol for use in curative or palliative treatment of prostate cancer |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1150734B (en) * | 1957-11-06 | 1963-06-27 | Sachsenwerk Licht & Kraft Ag | Arc extinguishing chamber |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE348396C (en) * | 1919-07-04 | 1922-02-07 | Krupp Ag | Electrical switch in which the interrupting arc is driven away from the contact point by a magnetic field |
DE445969C (en) * | 1923-05-14 | 1927-06-21 | Bbc Brown Boveri & Cie | Switch with sparks and magnetic blowing |
DE480802C (en) * | 1926-03-13 | 1929-08-12 | Siemens Schuckertwerke Akt Ges | Switching contact arranged between two insulating walls |
NL66733C (en) * | 1947-01-06 |
-
0
- BE BE518690D patent/BE518690A/xx unknown
-
1952
- 1952-04-07 DE DES29789A patent/DE1018503B/en active Pending
-
1953
- 1953-03-07 CH CH318635D patent/CH318635A/en unknown
- 1953-03-23 FR FR1091655D patent/FR1091655A/en not_active Expired
- 1953-04-07 GB GB9447/53A patent/GB732286A/en not_active Expired
- 1953-08-06 CH CH320095D patent/CH320095A/en unknown
- 1953-08-10 FR FR1082234D patent/FR1082234A/en not_active Expired
- 1953-08-17 GB GB22624/53A patent/GB739735A/en not_active Expired
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2840498A (en) * | 1953-06-08 | 1958-06-24 | Parker Rust Proof Co | Composition and method for producing combination corrosion resistant and lubricatingcoatings on metals |
WO2014060364A1 (en) | 2012-10-15 | 2014-04-24 | Chamaeleo Pharma Bvba | Sulfestrol for treating cancer |
WO2014060358A1 (en) | 2012-10-15 | 2014-04-24 | Chamaeleo Pharma Bvba | Fosfestrol for use in curative or palliative treatment of cancer in female mammals |
WO2014060347A1 (en) | 2012-10-15 | 2014-04-24 | Chamaeleo Pharma Bvba | Fosfestrol for use in curative or palliative treatment of prostate cancer |
US20150283155A1 (en) * | 2012-10-15 | 2015-10-08 | Chamaeleo Pharma Bvba | Fosfestrol for use in curative or palliative treatment of prostate cancer |
US20150283108A1 (en) * | 2012-10-15 | 2015-10-08 | Chamaeleo Pharma Bvba | Sulfestrol for treating cancer |
Also Published As
Publication number | Publication date |
---|---|
FR1091655A (en) | 1955-04-14 |
BE518690A (en) | |
CH320095A (en) | 1957-03-15 |
CH318635A (en) | 1957-01-15 |
DE1018503B (en) | 1957-10-31 |
GB739735A (en) | 1955-11-02 |
FR1082234A (en) | 1954-12-28 |
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