US4144254A
Expired / Lapsed
US
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Process for the purification of steroids
Assignee: Mitsubishi Chemical Corp
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Filing: 1977-11-29
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Granted: 1979-03-13
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Expires: 1997-11-29
Abstract
Abstract 19-Norethisterone or 19-norandrost-4-ene-3,17-dione is purified by passing its solution in an aromatic hydrocarbon, an alkyl halide or an ester of acetic acid through a column packed with basic alumina and then crystallizing it.
Inventors
- 👤 Haruo Imai
- 👤 Tadashi Oohama
- 👤 Ryozo Yamaguchi
- 👤 Kunihiro Ninomiya
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 14:30
CPC Classifications
C; C07; C07J; C07J1/00; C07J1/0051; C07J1/0081; C07J1/0088; C07J1/0096; C07J1/0059
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
179 words
A process for the purification of 19-norandrost-4-ene-3,17-dione or 19-norethisterone which comprises the steps of: (a) dissolving crude 19-norandrost-4-ene-3,17-dione or 19-norethisterone in at least one solvent selected from the group consisting of an aromatic hydrocarbon optionally having one or more alkyl side chains and having from 6 to 20 carbon atoms, an alkyl halide having from 1-10 carbon atoms and an alkyl ester of acetic acid having from 3 to 10 carbon atoms; (b) passing the resulting solution in its entirety through a column packed with basic alumina and collecting the total effluent as a single fraction; and (c) crystallizing pure 19-norandrost-4-ene-3,17-dione or 19-norethisterone from the alumina-treated solution using as the crystallization solvent at least one member selected from the group consisting of an aromatic hydrocarbon optionally having one or more alkyl side chains and having from 6 to 20 carbon atoms, an alkyl halide having from 1 to 10 carbon atoms, a ketone having from 3 to 10 carbon atoms, an alkanol having from 1 to 10 carbon atoms and an alkane having from 5 to 10 carbon atoms.
Claim 2
Dependent Claim
179 words
A process for the purification of 19-norandrost-4-ene-3,17-dione or 19-norethisterone which comprises the steps of: (a) dissolving crude 19-norandrost-4-ene-3,17-dione or 19-norethisterone in at least one solvent selected from the group consisting of an aromatic hydrocarbon optionally having one or more alkyl side chains and having from 6 to 20 carbon atoms, an alkyl halide having from 1-10 carbon atoms and an alkyl ester of acetic acid having from 3 to 10 carbon atoms; (b) passing the resulting solution in its entirety through a column packed with basic alumina and collecting the total effluent as a single fraction; and (c) crystallizing pure 19-norandrost-4-ene-3,17-dione or 19-norethisterone from the alumina-treated solution using as the crystallization solvent at least one member selected from the group consisting of an aromatic hydrocarbon optionally having one or more alkyl side chains and having from 6 to 20 carbon atoms, an alkyl halide having from 1 to 10 carbon atoms, a ketone having from 3 to 10 carbon atoms, an alkanol having from 1 to 10 carbon atoms and an alkane having from 5 to 10 carbon atoms.
Claim 3
Dependent Claim
14 words
The process of claim 1, wherein said crude 19-norethisterone is prepared by: ethynylating 19-norandrost-4-ene-3,17-dione.
Claim 4
Dependent Claim
40 words
The process of claim 1, wherein said solvent in step (a) is selected from the group consisting of benzene, toluene, xylene, ethylbenzene, carbon tetrachloride, chloroform, methylene dichloride, 1,2-dichloroethane, 1,1-dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,1,2-trichloroethylene, 1,1,2,2-tetrachloroethane, ethyl acetate, propyl acetate and butyl acetate.
Claim 5
Dependent Claim
35 words
The process of claim 1, wherein in said step (a), said crude 19-norethisterone is dissolved in at least one solvent selected from the group consisting of toluene, xylene, ethylbenzene, 1,2-dichloroethane, 1,1,2-trichloroethylene, toluene-chloroform and toluene-methylene dichloride.
Claim 6
Dependent Claim
10 words
The process of claim 4, wherein said solvent is 1,2-dichloroethane.
Claim 7
Dependent Claim
36 words
The process of claim 1, wherein said step (a), said crude 19-norandrost-4-ene-3,17-dione is dissolved in at least one solvent selected from the group consisting of benzene, toluene, xylene, ethylbenzene, 1,2-dichloroethane, 1,1,2-trichloroethane, 1,1,2-trichloroethylene, 1,1,2,2-tetrachloroethane and butyl acetate.
Claim 8
Dependent Claim
10 words
The process of claim 6, wherein said solvent is benzene.
Claim 9
Dependent Claim
24 words
The process of claim 1, wherein said step (c) is accomplished by sufficiently cooling said alumina-treated solution to precipitate said pure 19-norandrost-4-ene-3,17-dione or 19-norethisterone.
Claim 10
Dependent Claim
24 words
The process of claim 1, wherein said step (c) is accomplished by sufficiently concentrating said alumina-treated solution to precipitate said pure 19-norandrost-4-ene-3,17-dione or 19-norethisterone.
Claim 11
Dependent Claim
39 words
The process of claim 1, wherein said step (c) is accomplished by partially or completely evaporating the solvent from said alumina-treated solution, adding said crystallization solvent, heating to achieve dissolution, and cooling to precipitate said pure 19-norandrost-4-ene-3,17-dione or 19-norethisterone.
Claim 12
Dependent Claim
45 words
The process of claim 1, wherein said crystallization solvent is selected from the group consisting of benzene, toluene, xylene, ethylbenzene, carbon tetrachloride, chloroform, methylene dichloride, 1,2dichloroethane, 1,1-dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,1,2-trichloroethylene, 1,1,2,2-tetrachloroethane, acetone, methyl ethyl ketone, methyl isobutyl ketone, isopropyl alcohol, n-hexane, n-heptane, n-octane, and n-decane.
Claim 13
Dependent Claim
33 words
The process of claim 1, wherein in said step (c), said pure 19-norethisterone is crystallized from at least one crystallization solvent selected from the group consisting of toluene, 1,1,2-trichloroethylene and methyl isobutyl ketone.
Claim 14
Dependent Claim
34 words
The process of claim 1, wherein in said step (c), said pure 19-norandrost-4-ene-3,17-dione is crystallized from at least one crystallization solvent selected from the group consisting of toluene, 1,1,2-trichloroethylene, methyl isobutyl ketone and n-octane.
Claim 15
Dependent Claim
17 words
The process of claim 1, wherein said basic alumina has been calcined at above about 400° C.
Claim 16
Dependent Claim
16 words
The process of claim 1, wherein said basic alumina contains more than about 0.2% sodium oxide.
Claim 17
Dependent Claim
19 words
The process of claim 1, wherein said basic alumina has a particle size of from 10 to 100 mesh.
Claim 18
Dependent Claim
15 words
The process of claim 16, wherein said particle size is from 30 to 60 mesh.
Claim 19
Dependent Claim
20 words
The process of claim 1, wherein said step (b) is carried out at a temperature not higher than 70° C.
Claim 20
Dependent Claim
14 words
The process of claim 18, wherein said temperature is from 10° to 30° C.
Claim 21
Dependent Claim
21 words
The process of claim 1, wherein said step (b) is carried out at a linear velocity not greater than 5 m/hr.
Claim 22
Dependent Claim
15 words
The process of claim 20, wherein said linear velocity is not greater than 3 m/hr.
Claim 23
Dependent Claim
47 words
The process of claim 1, wherein in said step (b) after said resulting solution from step (a) has been passed through said column, the column is then washed with an additional portion of the same solvent used in step (a), the combined effluents constituting said alumina-treated solution.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-03-12 | 1982-09-11 | 1983-03-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-03-12 | 1986-09-11 | 1987-03-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-03-12 | 1990-09-11 | 1991-03-13 | $7700.00 | Window Closed / Lapsed |