US4096274A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Pyrrolidones and process for their manufacture
Assignee: Hoechst AG
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Filing: 1976-12-16
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Granted: 1978-06-20
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Expires: 1996-12-16
Abstract
Abstract The present invention relates to novel pyrrolidone derivatives as well as to a process of preparing the same. The novel compounds have a pharmaceutical action similar to that of prostaglandins and can therefore be used as medicaments.
Inventors
- 👤 Dieter-Bernd Reuschling
- 👤 Klaus Kuhlein
- 👤 Adolf Linkies
- 👤 Rudolf Kunstmann
- 👤 Josef Musil
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 19:22
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/18; C07D207/22; C07D207/24; C07D207/26; C07D207/273
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
173 words
A compound of the formula or a physiologically tolerable metal or amine salt of the free acid form thereof, wherein R 1 is α-branched alkyl having 3 to 6 carbon atoms or cycloalkyl having 3 to 7 carbon atoms in the ring; R 2 is hydrogen, lower alkyl, or cycloalkyl or aralkyl having 3 to 8 carbon atoms; R 3 is straight-chain or branched alkyl having 1 to 10 carbon atoms, or such alkyl substituted by O-alkyl havng 1 to 5 carbon atoms, by phenyl, by phenoxy, by cycloalkyl, by cycloalkyl in turn substituted by alkyl having 1 to 3 carbon atoms, or phenyl or phenoxy each in turn substituted by halogen, alkyl having 1 to 3 carbon atoms, or haloalkyl having 1 to 3 carbon atoms; R 4 is alkyl having 1 to 4 carbon atoms; and A is --C.tbd.C--, --CH═CH--(cis), or --CH 2 --CH 2 --, in which compound or salt the chains in the 3- and 4- positions of the pyrrolidone ring are in trans-position with respect to each other.
Claim 2
Dependent Claim
173 words
A compound of the formula or a physiologically tolerable metal or amine salt of the free acid form thereof, wherein R 1 is α-branched alkyl having 3 to 6 carbon atoms or cycloalkyl having 3 to 7 carbon atoms in the ring; R 2 is hydrogen, lower alkyl, or cycloalkyl or aralkyl having 3 to 8 carbon atoms; R 3 is straight-chain or branched alkyl having 1 to 10 carbon atoms, or such alkyl substituted by O-alkyl havng 1 to 5 carbon atoms, by phenyl, by phenoxy, by cycloalkyl, by cycloalkyl in turn substituted by alkyl having 1 to 3 carbon atoms, or phenyl or phenoxy each in turn substituted by halogen, alkyl having 1 to 3 carbon atoms, or haloalkyl having 1 to 3 carbon atoms; R 4 is alkyl having 1 to 4 carbon atoms; and A is --C.tbd.C--, --CH═CH--(cis), or --CH 2 --CH 2 --, in which compound or salt the chains in the 3- and 4- positions of the pyrrolidone ring are in trans-position with respect to each other.
Claim 3
Dependent Claim
98 words
The method of making a compound as in claim 1 wherein R 2 is other than hydrogen which method comprises (a) oxidizing a compound of the formula ##STR80## wherein R 2 is other than hydrogen, to form an aldehyde of the formula ##STR81## wherein R 2 is other than hydrogen; (b) reacting said aldehyde with a phosphonate of the formula ##STR82## wherein R 5 is alkyl having 1 to 4 carbon atoms, to form a ketone of the formula ##STR83## wherein R 2 is other than hydrogen; and then (c) reducing the keto group to an hydroxy group.
Claim 4
Dependent Claim
38 words
A pharmaceutical composition useful for inducing luteolysis or bronchospasmolysis, for inhibiting gastric juice secretion or for combatting hypertension, which composition comprises a pharmaceutical carrier and a therapeutically effective amount of a compound or salt as in claim 1.
Claim 5
Dependent Claim
31 words
The method of effecting brochodilation in a patient which comprises administering to said patient from 0.1 mg. to 10 mg. per day of a compound or salt as in claim 1.
Claim 6
Dependent Claim
31 words
The method of combatting hypertension in a patient which comprises administering to said patient from 1 mg. to 10 mg. per day of a compound or salt as in claim 1.
Claim 7
Dependent Claim
35 words
The method of inhibiting the secretion of gastric juice in a patient which comprises administering to said patient from 1 mg. to 10 mg. per day of a compound or salt as in claim 8.
Claim 8
Dependent Claim
65 words
A compound of the formula ##STR84## wherein R 1 is α-branched alkyl having 3 to 6 carbon atoms or cycloalkyl having 3 to 7 carbon atoms in the ring; R 2 is lower alkyl, or cycloalkyl or aralkyl having 3 to 8 carbon atoms; R 4 is alkyl having 1 to 4 carbon atoms; and A is --C.tbd.C--, --CH═CH--(cis), or --CH 2 --CH 2 --.
Claim 9
Dependent Claim
65 words
A compound of the formula ##STR84## wherein R 1 is α-branched alkyl having 3 to 6 carbon atoms or cycloalkyl having 3 to 7 carbon atoms in the ring; R 2 is lower alkyl, or cycloalkyl or aralkyl having 3 to 8 carbon atoms; R 4 is alkyl having 1 to 4 carbon atoms; and A is --C.tbd.C--, --CH═CH--(cis), or --CH 2 --CH 2 --.
Claim 10
Dependent Claim
135 words
A compound of the formula ##STR85## wherein R 1 is α-branched alkyl having 3 to 6 carbon atoms or cycloalkyl having 3 to 7 carbon atoms in the ring; R 2 is lower alkyl, or cycloalkyl or aralkyl having 3 to 8 carbon items; R 3 is straight-chain or branched alkyl having 1 to 10 carbon atoms, or such alkyl substituted by O-alkyl having 1 to 5 carbon atoms, by phenyl, by phenoxy, by cycloalkyl, by cycloalkyl in turn substituted by alkyl having 1 to 3 carbon atoms, or phenyl or phenoxy each in turn substituted by halogen, alkyl having 1 to 3 carbon items, or haloalkyl having 1 to 3 carbon atoms; R 4 is alkyl having 1 to 4 carbon atoms; and A is --C.tbd.C, -- CH--CH--(cis), or --CH 2 --CH 2 --.
Claim 11
Dependent Claim
135 words
A compound of the formula ##STR85## wherein R 1 is α-branched alkyl having 3 to 6 carbon atoms or cycloalkyl having 3 to 7 carbon atoms in the ring; R 2 is lower alkyl, or cycloalkyl or aralkyl having 3 to 8 carbon items; R 3 is straight-chain or branched alkyl having 1 to 10 carbon atoms, or such alkyl substituted by O-alkyl having 1 to 5 carbon atoms, by phenyl, by phenoxy, by cycloalkyl, by cycloalkyl in turn substituted by alkyl having 1 to 3 carbon atoms, or phenyl or phenoxy each in turn substituted by halogen, alkyl having 1 to 3 carbon items, or haloalkyl having 1 to 3 carbon atoms; R 4 is alkyl having 1 to 4 carbon atoms; and A is --C.tbd.C, -- CH--CH--(cis), or --CH 2 --CH 2 --.
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) | 1981-06-19 | 1981-12-19 | 1982-06-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-19 | 1985-12-19 | 1986-06-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-19 | 1989-12-19 | 1990-06-20 | $7700.00 | Window Closed / Lapsed |