US3969391A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Preparation of prostaglandin precursors
Assignee: GDS NEWCO Inc A CORP OF DE
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Filing: 1974-05-08
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Granted: 1976-07-13
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Expires: 1994-05-08
Abstract
Abstract 2-Alkoxy-4-hydroxy-5-oxocyclopent-1-eneheptanoic acid and its lower alkyl esters are reduced with metallic hydrides to yield the corresponding 3-hydroxy-5-oxo-cyclopent-1-eneheptanoic acid and its esters. The latter compounds are valuable intermediates in the preparation of pharmacologically active prostaglandin derivatives.
Inventors
- 👤 Raphael Pappo
- 👤 Christopher Jung
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 23:13
CPC Classifications
C; C07; C07C; C07C51/00
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
130 words
The process of producing a compound of the formula ##SPC3## which comprises contacting, in an inert solvent at a temperature between about -90° to +10°C., a compound of the formula ##SPC4## wherein R is lower alkyl, R' is lower alkyl, (lower alkoxy) lower alkoxy and m is an integer greater than 4 and less than 8 with a hydride reducing agent selected from compounds of the formula ##EQU2## wherein M is an alkali metal and R 1 and R 2 are hydrogen, lower alkyl or lower alkoxy, or from aluminum hydride, borane or zinc borohydride, to form, as an unisolated intermediate, a compound of the formula ##SPC5## and contacting, at about the same temperature, said unisolated intermediate with an acidic agent comprising a mineral acid or a strong organic acid.
Claim 2
Dependent Claim
130 words
The process of producing a compound of the formula ##SPC3## which comprises contacting, in an inert solvent at a temperature between about -90° to +10°C., a compound of the formula ##SPC4## wherein R is lower alkyl, R' is lower alkyl, (lower alkoxy) lower alkoxy and m is an integer greater than 4 and less than 8 with a hydride reducing agent selected from compounds of the formula ##EQU2## wherein M is an alkali metal and R 1 and R 2 are hydrogen, lower alkyl or lower alkoxy, or from aluminum hydride, borane or zinc borohydride, to form, as an unisolated intermediate, a compound of the formula ##SPC5## and contacting, at about the same temperature, said unisolated intermediate with an acidic agent comprising a mineral acid or a strong organic acid.
Claim 3
Dependent Claim
32 words
The process of claim 1, wherein the hydride reducing agent is aluminum hydride, lithium aluminum hydride, sodium dihydro bis(2-methoxyethoxy)-aluminate, sodium borohydride or borane and the acidic agent is an aqueous mineral acid.
Claim 4
Dependent Claim
37 words
The process of claim 1, wherein m is the integer 6, R' is methyl, the hydride reducing agent is aluminum hydride, lithium aluminum hydride or sodium dihydro bis(2-methoxyethoxy)aluminate and the acidic agent is an aqueous mineral acid.
Claim 5
Dependent Claim
29 words
The process of claim 1, wherein m is the integer 6, R' is methyl, the hydride reducing agent is sodium bis(methoxyethoxy)aluminate and the acidic agent is aqueous hydrochloric acid.
Claim 6
Dependent Claim
32 words
The process of claim 1, wherein m is the integer 6, R and R' are methyl, the hydride reducing agent is sodium dihydro bis(methoxyethoxy)aluminate and the acidic agent is aqueous hydrochloric acid.
Claim 7
Dependent Claim
113 words
The process of producing a compound of the formula ##SPC6## which comprises contacting, in an inert solvent, a compound of the formula ##SPC7## wherein R' is lower alkyl, (lower alkoxy) lower alkoxy and m is an integer greater than 4 and less than 8, with a hydride reducing agent selected from compounds of the formula ##EQU3## wherein M is an alkali metal and R 1 and R 2 are hydrogen, lower alkyl or lower alkoxy, or from aluminum hydride, borane or zinc borohydride, to form, as an unisolated intermediate, a compound of the formula ##SPC8## and contacting said unisolated intermediate with an acidic agent comprising a mineral acid or a strong organic acid.
Claim 8
Dependent Claim
113 words
The process of producing a compound of the formula ##SPC6## which comprises contacting, in an inert solvent, a compound of the formula ##SPC7## wherein R' is lower alkyl, (lower alkoxy) lower alkoxy and m is an integer greater than 4 and less than 8, with a hydride reducing agent selected from compounds of the formula ##EQU3## wherein M is an alkali metal and R 1 and R 2 are hydrogen, lower alkyl or lower alkoxy, or from aluminum hydride, borane or zinc borohydride, to form, as an unisolated intermediate, a compound of the formula ##SPC8## and contacting said unisolated intermediate with an acidic agent comprising a mineral acid or a strong organic acid.
Claim 9
Dependent Claim
32 words
The process of claim 6 wherein the hydride reducing agent is aluminum hydride, lithium aluminum hydride, sodium dihydro bis(2-methoxyethoxy)aluminate, sodium borohydride or borane and the acidic agent is an aqueous mineral acid.
Claim 10
Dependent Claim
29 words
The process of claim 6 wherein the hydride reducing agent is aluminum hydride, lithium aluminum hydride or sodium dihydro bis(2-methoxyethoxy)aluminate and the acidic agent is an aqueous mineral acid.
Claim 11
Dependent Claim
27 words
The process of claim 6 wherein the hydride reducing agent is sodium dihydro bis(2-methoxyethoxy)aluminate, m is the integer 6 and the acidic agent is aqueous hydrochloric acid.
Claim 12
Dependent Claim
30 words
The process of claim 6 wherein the hydride reducing agent is sodium dihydro bis(2-methoxyethoxy)aluminate, R' is methyl, m is the integer 6 and the acidic agent is aqueous hydrochloric acid.
References Cited (Backward Citations)
DE2321984A1
Cited
FR2187754A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-07-13 | 1980-01-12 | 1980-07-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-07-13 | 1984-01-12 | 1984-07-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-07-13 | 1988-01-12 | 1988-07-13 | $7700.00 | Window Closed / Lapsed |