GB452238A - Process for purifying progesterone preparations - Google Patents
Process for purifying progesterone preparationsInfo
- Publication number
- GB452238A GB452238A GB23590/35A GB2359035A GB452238A GB 452238 A GB452238 A GB 452238A GB 23590/35 A GB23590/35 A GB 23590/35A GB 2359035 A GB2359035 A GB 2359035A GB 452238 A GB452238 A GB 452238A
- Authority
- GB
- United Kingdom
- Prior art keywords
- progesterone
- ether
- crystallisate
- reacted
- extracted
- 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
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone 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 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 title abstract 14
- 229960003387 progesterone Drugs 0.000 title abstract 7
- 239000000186 progesterone Substances 0.000 title abstract 7
- 238000002360 preparation method Methods 0.000 title abstract 3
- 238000000034 method Methods 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 6
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 2
- -1 nitrobenzoyl Chemical group 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- MPJOJCZVGBOVOV-UHFFFAOYSA-N 2-phenylbenzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1C1=CC=CC=C1 MPJOJCZVGBOVOV-UHFFFAOYSA-N 0.000 abstract 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical class O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000012259 ether extract Substances 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical class O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The hydroxylated impurities are removed from crude progesterone preparations by treatment of the preparations with an acylating agent followed by separation of the portion which has entered into reaction from the non-esterified portion which contains the progesterone. Suitable acylating agents which yield sparingly soluble esters with the oxyketones are benzoyl, nitrobenzoyl, dinitrobenzoyl, and phenylbenzoyl chlorides, phenylisocyanate, diphenylisocyanate, and phosgene. It is preferred, however, to use agents which in addition to the acylating group, contain a salt forming group or a group which can be transformed into a salt forming group such as phthalic and maleic acid anhydrides, oxybenzoic acid chlorides, chlorosulphonic acid, phosphorus oxychloride and alkyl-meta-phosphates. In examples: (1) a crude progesterone crystallisate is reacted with phthalic anhydride in an atmosphere of nitrogen, the aqueous solution extracted with ether, and the ether extract washed with hydrochloric acid and water. Evaporation of the ether and recrystallization of the product yields progesterone in two polymorphous forms. The hydroxylated compounds may also if desired be extracted from the aqueous solution; (2) a crude progesterone crystallisate is reacted with 2 : 4-dinitrobenzoyl chloride in quinoline solution, the product mixed with water, extracted with ether, and worked up to yield the two polymorphous forms as in example 1; (3) a progesterone crystallisate is reacted with phthalic anhydride in pyridine, and worked up as in example 1.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH452238X | 1934-08-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB452238A true GB452238A (en) | 1936-08-19 |
Family
ID=4515510
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23590/35A Expired GB452238A (en) | 1934-08-24 | 1935-08-22 | Process for purifying progesterone preparations |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB452238A (en) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8846648B2 (en) | 2011-11-23 | 2014-09-30 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US8933059B2 (en) | 2012-06-18 | 2015-01-13 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US9180091B2 (en) | 2012-12-21 | 2015-11-10 | Therapeuticsmd, Inc. | Soluble estradiol capsule for vaginal insertion |
| US9289382B2 (en) | 2012-06-18 | 2016-03-22 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US9931349B2 (en) | 2016-04-01 | 2018-04-03 | Therapeuticsmd, Inc. | Steroid hormone pharmaceutical composition |
| US10052386B2 (en) | 2012-06-18 | 2018-08-21 | Therapeuticsmd, Inc. | Progesterone formulations |
| US10206932B2 (en) | 2014-05-22 | 2019-02-19 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US10258630B2 (en) | 2014-10-22 | 2019-04-16 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10286077B2 (en) | 2016-04-01 | 2019-05-14 | Therapeuticsmd, Inc. | Steroid hormone compositions in medium chain oils |
| US10328087B2 (en) | 2015-07-23 | 2019-06-25 | Therapeuticsmd, Inc. | Formulations for solubilizing hormones |
| US10471148B2 (en) | 2012-06-18 | 2019-11-12 | Therapeuticsmd, Inc. | Progesterone formulations having a desirable PK profile |
| US10471072B2 (en) | 2012-12-21 | 2019-11-12 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10537581B2 (en) | 2012-12-21 | 2020-01-21 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10806740B2 (en) | 2012-06-18 | 2020-10-20 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US11246875B2 (en) | 2012-12-21 | 2022-02-15 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US11266661B2 (en) | 2012-12-21 | 2022-03-08 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
-
1935
- 1935-08-22 GB GB23590/35A patent/GB452238A/en not_active Expired
Cited By (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9248136B2 (en) | 2011-11-23 | 2016-02-02 | Therapeuticsmd, Inc. | Transdermal hormone replacement therapies |
| US8846649B2 (en) | 2011-11-23 | 2014-09-30 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US10675288B2 (en) | 2011-11-23 | 2020-06-09 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US8987237B2 (en) | 2011-11-23 | 2015-03-24 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US11103516B2 (en) | 2011-11-23 | 2021-08-31 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US8846648B2 (en) | 2011-11-23 | 2014-09-30 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US11793819B2 (en) | 2011-11-23 | 2023-10-24 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US9006222B2 (en) | 2012-06-18 | 2015-04-14 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US11166963B2 (en) | 2012-06-18 | 2021-11-09 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US9289382B2 (en) | 2012-06-18 | 2016-03-22 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US9301920B2 (en) | 2012-06-18 | 2016-04-05 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US9012434B2 (en) | 2012-06-18 | 2015-04-21 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US10052386B2 (en) | 2012-06-18 | 2018-08-21 | Therapeuticsmd, Inc. | Progesterone formulations |
| US11529360B2 (en) | 2012-06-18 | 2022-12-20 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US11865179B2 (en) | 2012-06-18 | 2024-01-09 | Therapeuticsmd, Inc. | Progesterone formulations having a desirable PK profile |
| US10639375B2 (en) | 2012-06-18 | 2020-05-05 | Therapeuticsmd, Inc. | Progesterone formulations |
| US11110099B2 (en) | 2012-06-18 | 2021-09-07 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US8987238B2 (en) | 2012-06-18 | 2015-03-24 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US10471148B2 (en) | 2012-06-18 | 2019-11-12 | Therapeuticsmd, Inc. | Progesterone formulations having a desirable PK profile |
| US11033626B2 (en) | 2012-06-18 | 2021-06-15 | Therapeuticsmd, Inc. | Progesterone formulations having a desirable pk profile |
| US10806740B2 (en) | 2012-06-18 | 2020-10-20 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US8933059B2 (en) | 2012-06-18 | 2015-01-13 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US11116717B2 (en) | 2012-12-21 | 2021-09-14 | Therapeuticsmd, Inc. | Soluble estradiol capsule for vaginal insertion |
| US11266661B2 (en) | 2012-12-21 | 2022-03-08 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US9180091B2 (en) | 2012-12-21 | 2015-11-10 | Therapeuticsmd, Inc. | Soluble estradiol capsule for vaginal insertion |
| US10537581B2 (en) | 2012-12-21 | 2020-01-21 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US11622933B2 (en) | 2012-12-21 | 2023-04-11 | Therapeuticsmd, Inc. | Soluble estradiol capsule for vaginal insertion |
| US10806697B2 (en) | 2012-12-21 | 2020-10-20 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10835487B2 (en) | 2012-12-21 | 2020-11-17 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10888516B2 (en) | 2012-12-21 | 2021-01-12 | Therapeuticsmd, Inc. | Soluble estradiol capsule for vaginal insertion |
| US11497709B2 (en) | 2012-12-21 | 2022-11-15 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10471072B2 (en) | 2012-12-21 | 2019-11-12 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US11065197B2 (en) | 2012-12-21 | 2021-07-20 | Therapeuticsmd, Inc. | Soluble estradiol capsule for vaginal insertion |
| US11351182B2 (en) | 2012-12-21 | 2022-06-07 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US11304959B2 (en) | 2012-12-21 | 2022-04-19 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10568891B2 (en) | 2012-12-21 | 2020-02-25 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US11246875B2 (en) | 2012-12-21 | 2022-02-15 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US11123283B2 (en) | 2012-12-21 | 2021-09-21 | Therapeuticsmd, Inc. | Soluble estradiol capsule for vaginal insertion |
| US11241445B2 (en) | 2012-12-21 | 2022-02-08 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US11103513B2 (en) | 2014-05-22 | 2021-08-31 | TherapeuticsMD | Natural combination hormone replacement formulations and therapies |
| US10206932B2 (en) | 2014-05-22 | 2019-02-19 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US10258630B2 (en) | 2014-10-22 | 2019-04-16 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10398708B2 (en) | 2014-10-22 | 2019-09-03 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10668082B2 (en) | 2014-10-22 | 2020-06-02 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10328087B2 (en) | 2015-07-23 | 2019-06-25 | Therapeuticsmd, Inc. | Formulations for solubilizing hormones |
| US10912783B2 (en) | 2015-07-23 | 2021-02-09 | Therapeuticsmd, Inc. | Formulations for solubilizing hormones |
| US10286077B2 (en) | 2016-04-01 | 2019-05-14 | Therapeuticsmd, Inc. | Steroid hormone compositions in medium chain oils |
| US10532059B2 (en) | 2016-04-01 | 2020-01-14 | Therapeuticsmd, Inc. | Steroid hormone pharmaceutical composition |
| US9931349B2 (en) | 2016-04-01 | 2018-04-03 | Therapeuticsmd, Inc. | Steroid hormone pharmaceutical composition |
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