US3931282A
Expired / Lapsed
US
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11α-Hydroxymethyl prostaglandins
Assignee: Syntex USA LLC
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Filing: 1974-02-21
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Granted: 1976-01-06
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Expires: 1994-02-21
Abstract
Abstract Novel process for the preparation of 11α-hydroxymethyl derivatives of natural (8R-) and racemic 9-keto-15α-hydroxy- and 9,15α-dihydroxy-prosta-5-cis,13-trans-dienoic and prost-13-transenoic acids, and the novel 15-methyl and ethyl substituted derivatives thereof, as well as the esters of the primary and secondary hydroxy groups and the non-toxic, pharmaceutically acceptable salts of the novel compounds.
Inventors
- 👤 Joseph M. Muchowski
- 👤 Angel Guzman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 22:05
CPC Classifications
C; C07; C07C; C07C405/00; C07C405/0008; C07C405/0041; C07D; C07D309/00; C07D309/02; C07D309/08; C12; C12P; C12P31/00
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
141 words
An 8R-antimeric or racemic compound selected from the group of those represented by the following formula: ##SPC7## wherein R is the grouping ##EQU2## each of R 1 and R 2 is hydrogen or a hydrocarbon carboxylic group of 1 to 6 carbon atoms; R 3 is methyl or ethyl; R 4 is hydrogen, a lower alkyl group of 1 to 6 carbon atoms or the pharmaceutically acceptable, non-toxic salts of compounds in which R 4 is hydrogen; Z is a cis double bond and the wavy lines ( ) indicate the α or β configuration or mixtures thereof, provided that when R 3 is α, the hydroxyl group, attached to the same carbon atom as R 3 , is β; and when R 3 is β, the hydroxyl group, attached to the same carbon atom as R 3 , is α.
Claim 2
Dependent Claim
141 words
An 8R-antimeric or racemic compound selected from the group of those represented by the following formula: ##SPC7## wherein R is the grouping ##EQU2## each of R 1 and R 2 is hydrogen or a hydrocarbon carboxylic group of 1 to 6 carbon atoms; R 3 is methyl or ethyl; R 4 is hydrogen, a lower alkyl group of 1 to 6 carbon atoms or the pharmaceutically acceptable, non-toxic salts of compounds in which R 4 is hydrogen; Z is a cis double bond and the wavy lines ( ) indicate the α or β configuration or mixtures thereof, provided that when R 3 is α, the hydroxyl group, attached to the same carbon atom as R 3 , is β; and when R 3 is β, the hydroxyl group, attached to the same carbon atom as R 3 , is α.
Claim 3
Dependent Claim
18 words
A compound according to claim 1 wherein R is α-hydroxy-β-hydrogen and R 2 and R 4 are hydrogen.
Claim 4
Dependent Claim
18 words
A compound according to claim 1 wherein R is β-hydroxy-α-hydrogen and R 2 and R 4 are hydrogen.
Claim 5
Dependent Claim
14 words
A compound according to claim 1 wherein R 2 and R 4 are hydrogen.
Claim 6
Dependent Claim
19 words
A compound according to claim 1 wherein R 3 is methyl and R 2 and R 4 are hydrogen.
Claim 7
Dependent Claim
12 words
A compound according to claim 1 wherein said compound is an 8R-antimer.
Claim 8
Dependent Claim
36 words
A compound according to claim 6 wherein R is α-hydroxy-β-hydrogen, R 2 and R 4 are hydrogen, R 3 is β-methyl and Z is a cis-double bond, 8R-11α-hydroxymethyl-15β-methyl-9α,15α-dihydroxyprosta-5-cis,13-trans-dienoic acid and the non-toxic, pharmaceutically acceptable salts thereof.
Claim 9
Dependent Claim
32 words
A compound according to claim 6 wherein R is α-hydroxy-β-hydrogen, R 2 is hydrogen, R 3 is β-methyl, R 4 is methyl and Z is a cis-double bond, 8R-11α-hydroxymethyl-15β-methyl-9α,15α-dihydroxyprosta-5-cis,13-trans-dienoic acid methyl ester.
Claim 10
Dependent Claim
37 words
A compound according to claim 6 wherein R is β-hydroxy-α-hydrogen, R 2 and R 4 are hydrogen, R 3 is β-methyl and Z is a cis double bond, 8R-11α-hydroxymethyl-15β-methyl-9β,15α-dihydroxyprosta-5-cis,13-trans-dienoic acid and the non-toxic, pharmaceutically acceptable salts thereof.
Claim 11
Dependent Claim
33 words
A compound according to claim 6 wherein R is β-hydroxy-α-hydrogen, R 2 is hydrogen, R 3 is β-methyl, R 4 is methyl and Z is a cis double bond, 8R-11α-hydroxymethyl-15β-methyl-9β,15α-dihydroxyprosta-5-cis,13-trans-dienoic acid methyl ester.
Claim 12
Dependent Claim
13 words
A compound according to claim 1 wherein said compound is a racemic compound.
Claim 13
Dependent Claim
38 words
A compound according to claim 11 wherein R is α-hydroxy-β-hydrogen, R 2 and R 4 are hydrogen, R 3 is methyl and Z is a cis-double bond, 11α-hydroxymethyl-15 -methyl-9α,15 -dihydroxyprosta-5-cis,13-trans-dienoic acid and the nontoxic, pharmaceutically acceptable salts thereof.
Claim 14
Dependent Claim
33 words
A compound according to claim 11 wherein R is α-hydroxy-β-hydrogen, R 2 is hydrogen, R 3 and R 4 are methyl and Z is a cis-double bond, 11α-hydroxymethyl-15 -methyl-9α,15 -dihydroxyprosta-5-cis,13-trans-dienoic acid methyl ester.
Claim 15
Dependent Claim
39 words
A compound according to claim 11 wherein R is β-hydroxy-α-hydrogen, R 2 and R 4 are hydrogen, R 3 is methyl and Z is a cis double bond, 11α-hydroxymethyl-15 -methyl-9β,15 -dihydroxyprosta-5-cis,13-trans-dienoic acid and the nontoxic, pharmaceutically acceptable salts thereof.
Claim 16
Dependent Claim
34 words
A compound according to claim 11, wherein R is β-hydroxy-α-hydrogen, R 2 is hydrogen, R 3 and R 4 are methyl and Z is a cis double bond, 11α-hydroxymethyl-15 -methyl-9β,15 -dihydroxyprosta-5-cis,13-trans-dienoic acid methyl ester.
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) | 1979-01-05 | 1979-07-07 | 1980-01-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-01-05 | 1983-07-07 | 1984-01-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-01-05 | 1987-07-07 | 1988-01-06 | $7700.00 | Window Closed / Lapsed |