US4348327A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the preparation of 17α-hydroxy- and 17aα-hydroxy-D-homoetiocarboxylic acids
Assignee: Bayer Pharma AG
•
Filing: 1981-06-23
•
Granted: 1982-09-07
•
Expires: 2001-06-23
Abstract
Abstract 17α-hyroxy- and 17aα-hydroxy-D-homoetiocarboxylic acids of the formula ##STR1## wherein n is 1 or 2, A is ##STR2## and R 1 is H or CH 3 are prepared by hydrating the corresponding 17-nitriles with a mixture of a lower carboxylic acid and its anhydride in the presence of perchloric acid. The resultant 17β-N-acylcarboxamide is then treated with an alkali metal hydroxide in a polyhydric alcohol at an elevated temperature. The product acids are intermediates, e.g., for the production of steroids having antiinflammatory activity.
Inventors
- 👤 Robert Nickolson
- 👤 Ulrich Kerb
- 👤 Rudolf Wiechert
- 👤 Leo Alig
- 👤 Andor Furst
- 👤 Marcel Muller
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 11:31
CPC Classifications
C; C07; C07J; C07J63/00; C07J63/008; C07J3/00; C07J3/005; C07J41/00; C07J41/0033; C07J41/0066; C07J41/0094
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
103 words
A process for preparing a 17α-hydroxy- or 17aα-hydroxy-D-homoetiocarboxylic acid of the formula ##STR7## wherein n is 1 or 2, A is ##STR8## and R 1 is H or CH 3 , comprising hydrating the corresponding nitrile of the formula ##STR9## wherein R 1 and n are as defined above and B is ##STR10## wherein R 2 is hydrogen or C 1-6 alkanoyl, with a mixture of a lower alkane carboxylic acid and its anhydride in the presence of perchloric acid, and subsequently treating the thus-formed 17β-N-acylcarboxamide in a polyhydric alcohol with an alkali metal hydroxide at a temperature of 100° C. or higher.
Claim 2
Dependent Claim
103 words
A process for preparing a 17α-hydroxy- or 17aα-hydroxy-D-homoetiocarboxylic acid of the formula ##STR7## wherein n is 1 or 2, A is ##STR8## and R 1 is H or CH 3 , comprising hydrating the corresponding nitrile of the formula ##STR9## wherein R 1 and n are as defined above and B is ##STR10## wherein R 2 is hydrogen or C 1-6 alkanoyl, with a mixture of a lower alkane carboxylic acid and its anhydride in the presence of perchloric acid, and subsequently treating the thus-formed 17β-N-acylcarboxamide in a polyhydric alcohol with an alkali metal hydroxide at a temperature of 100° C. or higher.
Claim 3
Dependent Claim
14 words
A process of claim 1 wherein the hydration step is conducted at room temperature.
Claim 4
Dependent Claim
36 words
A process of claim 1 or 2 wherein the molar ratio in the hydration step is 0.1:100 and the total quantity of such acid and anhydride is 1.1-10 molar equivalents per equivalent of starting steroidal acid.
Claim 5
Dependent Claim
26 words
A process of claim 3 wherein the amount of perchloric acid in the hydration step is 0.001-0.1 molar equivalents per molar equivalent of starting steroidal acid.
Claim 6
Dependent Claim
23 words
A process of claim 1 or 2 wherein the lower alkane carboxylic acid is acetic acid and the corresponding anhydride is acetic anhydride.
Claim 7
Dependent Claim
33 words
A process of claim 1 wherein prior to the treatment with polyhydric alcohol and alkali metal hydroxide, the 17β-N-acylcarboxamide is first treated with methanolic alkali metal hydroxide to deacylate any blocked OH groups.
Claim 8
Dependent Claim
14 words
A process of claim 1 wherein the polyhydric alcohol is ethylene glycol or glycerine.
Claim 9
Dependent Claim
97 words
A process for preparing a etiocarboxylic acid or a D-homo-counterpart of the formula ##STR11## wherein n is 1 or 2, A is ##STR12## R 1 is H or CH 3 , and R 3 and R 4 independently each are C 1-6 -alkanoyl comprising hydrating the corresponding nitrile of the formula ##STR13## wherein R 1 and n are as defined above and B is ##STR14## wherein R 2 is hydrogen or C 1-6 alkanoyl, with a mixture of the corresponding C 1-6 alkane carboxylic acid and its anhydride in the presence of perchloric acid at room temperature.
Claim 10
Dependent Claim
97 words
A process for preparing a etiocarboxylic acid or a D-homo-counterpart of the formula ##STR11## wherein n is 1 or 2, A is ##STR12## R 1 is H or CH 3 , and R 3 and R 4 independently each are C 1-6 -alkanoyl comprising hydrating the corresponding nitrile of the formula ##STR13## wherein R 1 and n are as defined above and B is ##STR14## wherein R 2 is hydrogen or C 1-6 alkanoyl, with a mixture of the corresponding C 1-6 alkane carboxylic acid and its anhydride in the presence of perchloric acid at room temperature.
Claim 11
Dependent Claim
12 words
A process of claim 1 wherein R 1 is CH 3 .
Claim 12
Dependent Claim
10 words
A process of claim 1 wherein R 1 is H.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-09-06 | 1986-03-08 | 1986-09-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-09-06 | 1990-03-08 | 1990-09-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-09-06 | 1994-03-08 | 1994-09-07 | $7700.00 | Window Closed / Lapsed |