US3875194A
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Process for the preparation of pregnanoic acid derivatives
Assignee: Bayer Pharma AG
•
Filing: 1973-12-05
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Granted: 1975-04-01
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Expires: 1993-12-05
Abstract
Abstract Topical anti-inflammatory pregnanoic acid derivatives of the formula WHEREIN -A-B- is -CH2-CH2-, -CH CH-, or -CCl CH-; X is a hydrogen atom, a halogen atom, or methyl; Y is a hydrogen atom or a halogen atom; Z is a hydroxy or a halogen atom having an atomic weight the same as or lower than Y; R1 is a hydrogen atom or methyl; and R2 is hydrocarbon, are produced in two steps by first converting a 21-hydroxy steroid of the formula WHEREIN -A-B, X, Y, Z, and R1 have the values given above, into the corresponding 20-keto-21-aldehyde, or hydrate or hemiacetal thereof, with an alcohol in the presence of a copper (II) salt, and then converting the thus-produced steroid, with an oxidizing heavy metal oxide in the presence of an alcohol and cyanide ions, into the pregnanoic acid derivative.
Inventors
- 👤 Henry Laurent
- 👤 Rudolf Wiechert
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 12:27
CPC Classifications
C; C07; C07J; C07J5/00; C07J5/0007; C07J5/0023; C07J5/003; C07J5/0038
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
12 words
A PROCESS FOR THE PRODUCTION OF PREGNANOIC ACID DERIVATIVES OF THE FORMULA
Claim 2
Dependent Claim
12 words
A PROCESS FOR THE PRODUCTION OF PREGNANOIC ACID DERIVATIVES OF THE FORMULA
Claim 3
Dependent Claim
14 words
A process according to claim 1, wherein R2 is alkyl or 1-8 carbon atoms.
Claim 4
Dependent Claim
18 words
A process according to claim 1, wherein the copper(II) salt is the salt of a lower carboxylic acid.
Claim 5
Dependent Claim
16 words
A process according to claim 3, wherein the salt is copper(II) formate, acetate, propionate or butyrate.
Claim 6
Dependent Claim
17 words
A process according to claim 1, wherein the alcohol R2OH is a primary or secondary aliphatic alcohol.
Claim 7
Dependent Claim
29 words
A process according to claim 1, wherein the oxidizing oxide is selected from the group consisting of silver oxide, lead(IV) oxide, minium, vanadium(V) oxide, manganese(IV) oxide and chromium(VI) oxide.
Claim 8
Dependent Claim
14 words
A process according to claim 1, wherein the cyanide is sodium or potassium cyanide.
Claim 9
Dependent Claim
17 words
A process according to claim 1, wherein the reaction medium further comprises an alkali-neutralizing amount of acid.
Claim 10
Dependent Claim
31 words
A process according to claim 8, wherein the copper(II) acid salt is the salt of a lower carboxylic acid and wherein the alcohol R2OH is a primary or secondary aliphatic alcohol.
Claim 11
Dependent Claim
12 words
A process for the production of pregnanoic acid derivatives of the formula
Claim 12
Dependent Claim
12 words
A process for the production of pregnanoic acid derivatives of the formula
Claim 13
Dependent Claim
60 words
A process according to claim 8 wherein the copper(II) salt is copper(II) formate, acetate, propionate or butyrate, wherein the alcohol R2OH is a primary or secondary aliphatic alcohol, wherein the oxidizing oxide is selected from the group consisting of silver oxide, lead(IV) oxide, minium, vanadium(V) oxide, manganese(IV) oxide and chromium(VI) oxide, and wherein the cyanide is sodium or potassium cyanide.
Claim 14
Dependent Claim
16 words
A process according to claim 10 wherein the salt is copper(II) formate, acetate, propionate or butyrate.
Claim 15
Dependent Claim
16 words
A process according to claim 10 wherein the alcohol is a primary or secondary aliphatic alcohol.
Claim 16
Dependent Claim
30 words
A process according to claim 10, wherein the oxidizing oxide is selected from the group consisting of silver oxide, lead(IV) oxide, minium, vanadium(V) oxide, manganese(IV) oxide and chromium (VI) oxide.
Claim 17
Dependent Claim
13 words
A process according to claim 10 wherein the cyanide is sodium or potassium.
Claim 18
Dependent Claim
17 words
A process according to claim 10, wherein the reaction medium further comprises an alkali-neutralizing amount of acid.
Claim 19
Dependent Claim
60 words
A process according to claim 10, wherein the copper(II) salt is copper(II) formate, acetate, propionate or butyrate, wherein the alcohol R2OH is a primary or secondary aliphatic alcohol, wherein the oxidizing oxide is selected from the group consisting of silver oxide, lead(IV) oxide, minium, vanadium(V) oxide, manganese(IV) oxide and chromium(VI) oxide, and wherein the cyanide is sodium or potassium cyanide.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-03-31 | 1978-09-30 | 1979-04-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-03-31 | 1982-09-30 | 1983-04-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-03-31 | 1986-09-30 | 1987-04-01 | $7700.00 | Window Closed / Lapsed |