US4474962A
Expired / Lapsed
US
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Process for the preparation of pyridyl and quinolyl imidazolinones
Assignee: Wyeth Holdings LLC
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Filing: 1983-05-05
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Granted: 1984-10-02
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Expires: 2003-05-05
Abstract
Abstract There is provided a novel process for the preparation of pyridyl and quinolyl imidazolinones.
Inventors
- 👤 Peter J. Wepplo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 22:11
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/63; C07D213/65
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
223 words
A method for the preparation of a compound of the formula: ##STR15## wherein Z is hydrogen; Y is hydrogen, chlorine, fluorine, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, phenyl or substituted phenyl; A is hydrogen, C 1 -C 6 primary or secondary alkyl or COOR 3 where R 3 is C 1 -C 12 alkyl and R 1 and R 2 are C 1 -C 4 alkyl or when taken together they may represent C 3 -C 6 cycloalkyl optionally substituted with methyl and when R 1 and R 2 are not the same, the optical isomers thereof; and when taken together, Y and Z may form a ring in which YZ is ##STR16## where L, M, Q and R 7 each represent members selected from the group consisting of hydrogen, chlorine, fluorine, methyl, methoxy or phenyl; A, R 1 , R 2 and R 3 are as described above and when R 1 and R 2 are not the same the optical isomers thereof, comprising reacting from 1 to 20 equivalents of a compound of the formula: ##STR17## wherein A, Y and Z are as described above; with at least 3 equivalents of sulfur and about 1 equivalent of an aminocarboxamide of the formula: ##STR18## wherein R 1 and R 2 are as described above; at an elevated temperature.
Claim 2
Independent Claim
223 words
A method for the preparation of a compound of the formula: ##STR15## wherein Z is hydrogen; Y is hydrogen, chlorine, fluorine, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, phenyl or substituted phenyl; A is hydrogen, C 1 -C 6 primary or secondary alkyl or COOR 3 where R 3 is C 1 -C 12 alkyl and R 1 and R 2 are C 1 -C 4 alkyl or when taken together they may represent C 3 -C 6 cycloalkyl optionally substituted with methyl and when R 1 and R 2 are not the same, the optical isomers thereof; and when taken together, Y and Z may form a ring in which YZ is ##STR16## where L, M, Q and R 7 each represent members selected from the group consisting of hydrogen, chlorine, fluorine, methyl, methoxy or phenyl; A, R 1 , R 2 and R 3 are as described above and when R 1 and R 2 are not the same the optical isomers thereof, comprising reacting from 1 to 20 equivalents of a compound of the formula: ##STR17## wherein A, Y and Z are as described above; with at least 3 equivalents of sulfur and about 1 equivalent of an aminocarboxamide of the formula: ##STR18## wherein R 1 and R 2 are as described above; at an elevated temperature.
Claim 3
Dependent Claim
35 words
A method according to claim 1 wherein 1.5 to 10 equivalents of α-picoline is reacted with 3 to 5 equivalents of sulfur and 1 equivalent of aminocarboxamide at a temperature between 100° and 200° C.
Claim 4
Dependent Claim
28 words
A method according to claim 1 wherein A and Z are hydrogen; Y is C 1 -C 6 alkoxy; R 1 is methyl and R 2 is isopropyl.
Claim 5
Dependent Claim
28 words
A method according to claim 1 wherein Y is C 1 -C 6 alkyl; A and Z are hydrogen; R 1 is methyl and R 2 is isopropyl.
Claim 6
Dependent Claim
55 words
A method according to claim 1 wherein Y and Z are taken together and represent ##STR19## where L, M, Q and R 7 each represent members selected from the group consisting of hydrogen, chlorine, fluorine, methyl, methoxy or phenyl; A is as described in claim 1; R 1 is methyl and R 2 is isopropyl.
Claim 7
Dependent Claim
29 words
A method according to claim 1 wherein Y is phenyl; Z is hydrogen; A is as described in claim 1; R 1 is methyl and R 2 is isopropyl.
Claim 8
Dependent Claim
23 words
A method according to claim 1 wherein Y is ethyl, A and Z are hydrogen, R is methyl and R 2 is isopropyl.
Claim 9
Dependent Claim
31 words
A method according to claim 1 wherein Y and Z are hydrogen, A is CH 3 , R 1 is CH 3 , R 2 is CH(CH 3 ) 2 .
Claim 10
Dependent Claim
39 words
A method according to claim 1 wherein Y and Z are hydrogen, A is COOR 3 , R 1 is CH 3 , R 2 is CH(CH 3 ) 2 and R 3 is as described in claim 1.
Claim 11
Dependent Claim
39 words
A method according to claim 1 wherein Y and Z are --CH═CH--CH═CH--, A is COOR 3 , R 1 is CH 3 , R 2 is CH(CH 3 ) 2 and R 3 is as described in claim 1.
Claim 12
Dependent Claim
40 words
A method according to claim 1 wherein 1,5 equivalents of α-picoline or quinaldine is heated to from 100° to 250° C. with 3 equivalents of sulfur and 1 equivalent of the α-aminocarboxamide to obtain the desired pyridyl or quinolyl imidazolinone.
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) | 1987-10-02 | 1988-04-02 | 1988-10-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-10-02 | 1992-04-02 | 1992-10-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-10-02 | 1996-04-02 | 1996-10-02 | $7700.00 | Window Closed / Lapsed |