US4119625A
Expired / Lapsed
US
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Process for the manufacture of steroid carboxylic acids and the esters thereof
Assignee: Novartis Corp
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Filing: 1977-04-08
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Granted: 1978-10-10
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Expires: 1997-04-08
Abstract
Abstract The present invention provides a novel process for the manufacture of 17- and 17a-carboxylic acids of the androstane and D-homo-androstane series respectively, of the following partial formula of the ring D ##STR1## wherein R represents a hydrogen atom or an unsubstituted or substituted hydrocarbon radical or a free or functionally modified hydroxyl group, and wherein the carboxyl group can be in the α- or β-position, and of the salts and functional acid derivatives thereof, in particular their esters. The new process consists in the oxidative degradation of the side chain of corrsponding 20, 21-ketoaldehydes of the pregnane or D-homopregnane series or of the 17α-pregnane or 17aα-D-homopregnane series with an organic peracid in an inert solvent, preferably at temperatures between -20 and +30° C, and optionally converting free functional groups present into their derivatives or setting free functional groups from substituents which are derivatives of such groups.
Inventors
- 👤 Julius Schmidlin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 11:53
CPC Classifications
C; C07; C07J; C07J3/00; C07J3/005; A; A61; A61P; A61P29/00; C07J1/00; C07J1/0003; C07J1/0033; C07J63/00; C07J63/008; C07J7/00; C07J7/008; C07J7/009; C07J71/00; C07J71/0005; C07J71/0026; C07J71/0031
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
131 words
A process for the manufacture of steroid carboxylic acids selected from the group consisting of those having the formula l ##STR5## wherein R represents a hydrogen atom, an unsubstituted or substituted hydrocarbon radical, or a free or conventionally esteritied or etheritied hydroxyl group, and wherein the carboxyl group and the 5H-atom can be in the alpha or beta position, R ' represents hydrogen or methyl, and its derivatives having expanded or contracted A-, B-and C-rings, an expanded D-ring having R and COOH in 17a-position, one or more than one double bond and/or conventional steroid-substituents in any of the positions different from 17 or 17a; which process comprises oxidising a corresponding 20,21-ketoaldehyde having the group CO-CHO instead of COOH in said 17- or 17a-positions, wih an organic peracid in an inert solvent.
Claim 2
Dependent Claim
131 words
A process for the manufacture of steroid carboxylic acids selected from the group consisting of those having the formula l ##STR5## wherein R represents a hydrogen atom, an unsubstituted or substituted hydrocarbon radical, or a free or conventionally esteritied or etheritied hydroxyl group, and wherein the carboxyl group and the 5H-atom can be in the alpha or beta position, R ' represents hydrogen or methyl, and its derivatives having expanded or contracted A-, B-and C-rings, an expanded D-ring having R and COOH in 17a-position, one or more than one double bond and/or conventional steroid-substituents in any of the positions different from 17 or 17a; which process comprises oxidising a corresponding 20,21-ketoaldehyde having the group CO-CHO instead of COOH in said 17- or 17a-positions, wih an organic peracid in an inert solvent.
Claim 3
Dependent Claim
21 words
A process according to claim 1, wherein peracetic acid, perbenzoic acid, monoperoxyphthalic acid or 3-chloroperoxy-benzoic acid is used as organic peracid.
Claim 4
Dependent Claim
30 words
A process according to claim 1, wherein a lower aliphatic chlorinated hydrocarbon, an aromatic or chlorinated aromatic hydrocarbon, an ether or a lower aliphatic dialkylamide is used as inert solvent.
Claim 5
Dependent Claim
22 words
A process according to claim 1, wherein the oxidation with the peracid is carried out at temperatures between -20° and +30° C.
Claim 6
Dependent Claim
18 words
A process according to claim 1, wherein the starting materials are compounds of the pregnane or D-homopregnane series.
Claim 7
Dependent Claim
25 words
A process according to claim 5, wherein the starting material is said pregnane or D-homopregnane in which R represents an esterified or acetalised hydroxyl group.
Claim 8
Dependent Claim
60 words
A process according to claim 5, wherein the starting material is said pregnane or D-homopregnane with the following partial formula of the ring D ##STR6## wherein P and Q individually or together represent a hydrocarbon radical, containing 1 to 7 carbon atoms, which is unsubstituted or substituted by halogen atoms, free hydroxyl groups or by esterified or etherified hydroxyl groups.
Claim 9
Dependent Claim
92 words
A process according to claim 1, wherein a starting material of the formula ##STR7## is used wherein R has the same meaning as in claim 1, R 2 is a hydroxy or an oxo group, any of the substituents R 3 ,R 4 , and R 5 represents hydrogen or halogen, R 6 represents 2 hydrogen atoms or hydrogen togehter with a methyl group in either the alpha- or beta-position, or a methylene group or, together with R, a hydrogen atom together with a 16alpha, 17alpha-dihydroxy-acetonide grouping; or the 1,2-dehydro derivative thereof.
Claim 10
Dependent Claim
21 words
A process according to claim 8, which comprises the use of said starting material wherein R is an esterified hydroxyl group.
Claim 11
Dependent Claim
21 words
A process according to claim 1, wherein resultant carboxylic acids of formula I are converted into their conventional salts or esters.
Claim 12
Dependent Claim
33 words
A process according to claim 1, wherein the resultant carboxylic acids of formula I are converted into their conventional esters, which latter are isolated and re-converted into the carboxylic acids of formula I.
Claim 13
Dependent Claim
34 words
A process according to claim 1, wherein in any resultant carboxylic acid of formula I with R being a free hydroxyl group, the latter is converted into a conventionally estrified or acetalised hydroxyl group.
Claim 14
Dependent Claim
33 words
A process according to claim 1, wherein in any resultant carboxylic acid of formula I with R being an esterified or acetalised hydroxyl group, the latter is converted into a free hydroxyl group.
References Cited (Backward Citations)
US3636010A
Cited
US3875194A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-10-09 | 1982-04-10 | 1982-10-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-10-09 | 1986-04-10 | 1986-10-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-10-09 | 1990-04-10 | 1990-10-10 | $7700.00 | Window Closed / Lapsed |