US3870747A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Intermediates and process for prostaglandin synthesis
Assignee: Merck and Co Inc
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Filing: 1971-11-24
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Granted: 1975-03-11
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Expires: 1991-11-24
Abstract
Abstract A precursor of prostaglandin E1, racemic or optically active 3a, 6,7,7a-tetrahydro-4-methyl-2-oxo-1 Beta -indaneheptanoic acid loweralkyl ester, is synthesized from racemic or optically active precursors in good yield at the various steps from 3 Alpha methyl-4-cyclohexene-1 Alpha ,2 Alpha -dicarboxylic anhydride by a sequence of reactions proceding through 3 Alpha -methyl-4cyclohexene-1 Alpha ,2 Alpha -diacetic acid, 4 Alpha -hydroxy-3 Alpha -methyl-1 Alpha ,2 Alpha -cyclohexene diacetic acid- delta lactone, and 3-methyl-3-cyclohexene-1 Alpha ,2 Alpha -diacetic acid dimethyl ester.
Inventors
- 👤 Norman L Wendler
- 👤 David Taub
- 👤 Harry L Slates
- 👤 Zbigniew S Zelawski
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 14:05
CPC Classifications
C; C07; C07D; C07D311/00; C07C; C07C309/00
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
29 words
3 Alpha ,6,7,7 Alpha -Tetrahydro-1 Alpha -(loweralkoxycarbonyl)-4-methyl-2-oxindaneheptanoic acid and loweralkyl esters or esters with a loweralkyl group substituted with an aromatic group of from 6 to 10 carbon atoms.
Claim 2
Dependent Claim
29 words
3 Alpha ,6,7,7 Alpha -Tetrahydro-1 Alpha -(loweralkoxycarbonyl)-4-methyl-2-oxindaneheptanoic acid and loweralkyl esters or esters with a loweralkyl group substituted with an aromatic group of from 6 to 10 carbon atoms.
Claim 3
Dependent Claim
23 words
3A,6,7,7A,-TETRAHYDRO-LA-(LOWERALKOXYCARBONYL)-4METHYL-2-OXINDANEHEPTONIC ACID AND LOWERALKYL ESTERS OR ESTERS WITH A LOWERALKYL GROUP SUBSTITUTED WITH AN AROMATIC GROUP OF FROM 6 TO 10 CARBON ATOMS.
Claim 4
Dependent Claim
23 words
3A,6,7,7A,-TETRAHYDRO-LA-(LOWERALKOXYCARBONYL)-4METHYL-2-OXINDANEHEPTONIC ACID AND LOWERALKYL ESTERS OR ESTERS WITH A LOWERALKYL GROUP SUBSTITUTED WITH AN AROMATIC GROUP OF FROM 6 TO 10 CARBON ATOMS.
Claim 5
Dependent Claim
22 words
The compound of claim 1 in which the lower-alkyl ester is the methyl ester, and the loweralkoxycarbonyl group is the methoxycarbonyl group.
Claim 6
Dependent Claim
98 words
The process of preparing the compound of claim 1 in which the diloweralkyl ester or diloweralkyl ester substituted with an aromatic group of from 6 to 10 carbon atoms of 3-methyl-3-cyclohexene-1 Alpha ,2 Alpha -diacetic acid is treated with an alkali metal loweralkoxide in a solvent at from 50*C. to the boiling point of the reaction mixture for from 1/2 to 3 hours, and subsequently treated with the loweralkyl ester or loweralkyl ester substituted with an aromatic group of from 6 to 10 carbon atoms of omega -iodoheptanoic acid at from 100*-200*C. for from 10 to 30 hours.
Claim 7
Dependent Claim
92 words
THE PROCESS OF PREPARING THE COMPOUND OF CLAIM 1 IN WHICH THE DILOWERALKYL ESTER OR DILOWERALKYL ESTER SUBSTITUTED WITH AN AROMATIC GROUP OF FROM 6 TO 10 CARBON ATOMS OF 3METHYL-3-CYCLOHEXENE-1A,2A-DIACETIC ACID IS TREATED WITH AN ALKALI METAL LOWERALKOXIDE IN A SOLVENT AT FROM 50*C. TO THE BOILING POINT OF THE REACTION MIXTURE FOR FROM 1/2TO 3 HOURS, AND SUBSEQUENTLY TREATED WITH THE LOWERALKYL ESTER OF LOWERALKYL ESTER SUBSTITUTED WITH AN AROMATIC GROUP OF FROM 6 TO 10 CARBON ATOMS OF W-IODOHEPTANOIC ACID AT FROM 100*-200*C. FOR FROM 10 TO 30 HOURS.
Claim 8
Dependent Claim
13 words
The process of claim 3 in which the alkali metal loweralkoxide is potassium-t-butoxide.
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) | 1978-03-10 | 1978-09-09 | 1979-03-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-03-10 | 1982-09-09 | 1983-03-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-03-10 | 1986-09-09 | 1987-03-11 | $7700.00 | Window Closed / Lapsed |