US4577020A
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Aminoalkyl and aminoalkenyl triazoles as anti-psychotic agents
Assignee: Pharmacia and Upjohn Co
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Filing: 1983-01-25
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Granted: 1986-03-18
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Expires: 2003-01-25
Abstract
Abstract The present invention provides certain aminoalkyl and aminoalkenyl triazoles which are useful as anti-psychotics. Certain of these aminoalkyl triazoles were previously known as anti-allergy agents.
Inventors
- 👤 Martin Gall
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 04:02
CPC Classifications
C; C07; C07D; C07D249/00; C07D249/02; C07D249/08
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
326 words
A compound of the Formula I, or an enantiomer or stereoisomer thereof, wherein P 4 is (a) hydrogen, (b) (C 1 -C 3 ) alkyl, (c) --CH 2 OH, (d) --CH 2 OCOCH 3 , (e) --S(O) q CH 3 , (f) --SCH 2 CH 3 , or (g) --R 15 ; wherein R 5 , R 15 , and R 25 are the same or different and are (a) phenyl substituted by zero to 2 chloro, fluoro, bromo, alkyl of from one to 3 carbon atoms, nitro, or alkoxy of from one to 3 carbon atoms, or (b) phenyl substituted by one trifluoromethyl and zero to one of the previous phenyl substituents; wherein W 1 is (a) cis--C(R 3 )═CH--CH 2 NR 1 R 2 , (b) trans--C(R 3 )═CH--CH 2 NR 1 R 2 , (c) --C(CH 3 )(OR 14 )--CH 2 --CH 2 NR 1 R 2 , (d) a substituent of the Formula III, or ##STR2## (e) a substituent of the Formula IV; ##STR3## wherein --NR 1 R 2 is (a) --N(CH 3 )--CH 2 (CH 2 ) m --R 25 , (b) --NH--CH 2 (CH 2 ) m R 25 , (c) a substituent of the Formula V, ##STR4## (d) a substituent of the Formula VI, ##STR5## (e) a substituent of the Formula VII, or ##STR6## (f) --N(CH 3 )--(CH 2 ) 3 --CH(R 51 ) 2 ; wherein R 14 is (a) hydrogen, (b) --COCH 3 , or (c) --COCH 2 CH 3 ; wherein R 51 is (a) phenyl, (b) p-fluorophenyl, or (c) p-chlorophenyl; wherein R 3 is (a) hydrogen or (b) methyl; wherein the dotted line represents a single or double bond; wherein m is an integer of from one to 2, inclusive; wherein n is an integer of from zero to 3, inclusive; and wherein q is an integer of from zero to 2, inclusive; or a pharmacologically acceptable acid addition salt; or solvate or hydrate thereof.
Claim 2
Dependent Claim
326 words
A compound of the Formula I, or an enantiomer or stereoisomer thereof, wherein P 4 is (a) hydrogen, (b) (C 1 -C 3 ) alkyl, (c) --CH 2 OH, (d) --CH 2 OCOCH 3 , (e) --S(O) q CH 3 , (f) --SCH 2 CH 3 , or (g) --R 15 ; wherein R 5 , R 15 , and R 25 are the same or different and are (a) phenyl substituted by zero to 2 chloro, fluoro, bromo, alkyl of from one to 3 carbon atoms, nitro, or alkoxy of from one to 3 carbon atoms, or (b) phenyl substituted by one trifluoromethyl and zero to one of the previous phenyl substituents; wherein W 1 is (a) cis--C(R 3 )═CH--CH 2 NR 1 R 2 , (b) trans--C(R 3 )═CH--CH 2 NR 1 R 2 , (c) --C(CH 3 )(OR 14 )--CH 2 --CH 2 NR 1 R 2 , (d) a substituent of the Formula III, or ##STR2## (e) a substituent of the Formula IV; ##STR3## wherein --NR 1 R 2 is (a) --N(CH 3 )--CH 2 (CH 2 ) m --R 25 , (b) --NH--CH 2 (CH 2 ) m R 25 , (c) a substituent of the Formula V, ##STR4## (d) a substituent of the Formula VI, ##STR5## (e) a substituent of the Formula VII, or ##STR6## (f) --N(CH 3 )--(CH 2 ) 3 --CH(R 51 ) 2 ; wherein R 14 is (a) hydrogen, (b) --COCH 3 , or (c) --COCH 2 CH 3 ; wherein R 51 is (a) phenyl, (b) p-fluorophenyl, or (c) p-chlorophenyl; wherein R 3 is (a) hydrogen or (b) methyl; wherein the dotted line represents a single or double bond; wherein m is an integer of from one to 2, inclusive; wherein n is an integer of from zero to 3, inclusive; and wherein q is an integer of from zero to 2, inclusive; or a pharmacologically acceptable acid addition salt; or solvate or hydrate thereof.
Claim 3
Dependent Claim
9 words
A compound of claim 1, wherein n is zero.
Claim 4
Dependent Claim
42 words
A compound of claim 2, wherein R 4 is hydrogen or methyl and W 1 is trans--CH═CH--CH 2 NR 1 R 2 , --C(CH 3 )(OR 14 )--CH 2 --NR 1 R 2 , or a substituent of the formula III ##STR7##
Claim 5
Dependent Claim
66 words
A compound of claim 3, wherein R 5 is phenyl or ortho-, meta-, or para-halo phenyl, and W 1 is trans--CH═CH--CH 2 NR 1 R 2 wherein --NR 1 R 2 is --N(CH 3 )--CH 2 --CH 2 --phenyl or a substituent of the formula VI ##STR8## or W 1 is a substituent of the formula III ##STR9## and the dotted line represents a double bond.
Claim 6
Dependent Claim
31 words
A compound of claim 4 selected from the group consisting of 4-chloro-N-methyl-N-[3-(5-methyl-4-phenyl-4H-1,2,4-triazol-3-yl)-2-cyclohexen-1-yl]benzeneethanamine, and its (E)-2-butenedioate (1:1), ethyl acetate solvate (2:1), hydrate; α, 5-Dimethyl-α-[2-[methyl-(2-phenylethyl)amino]ethyl]-4-phenyl-4H-1,2,4-triazole-3-methanol; 1-[3-(5-methyl-4-phenyl-4H-1,2,4-triazol-3-yl)-2-propenyl]-4-phenylpiperazine; (E)-3-methyl-5-[3-([methyl(2-phenylethyl)amino]-1-propenyl]-4-phenyl-4H-1,2,4-triazole; N-methyl-N-[3-(5-methyl-4-phenyl-4H-1,2,4-triazol-3-yl)-2-cyclohexen-1-yl]benzeneethanamine; (E)-4-chloro-N-methyl-N-[3-(5-methyl-4-phenyl-4H-1,2,4-triazol-3-yl)-2-propenyl]benzeneethanamine; 4-chloro-N-methyl-N-[3-(5-methyl-4-phenyl-4H-1,2,4-triazol-3-yl)-2-cyclohexen-1-yl]benzeneethanamine; Cis-N-methyl-3-(5-methyl-4-phenyl-4H-1,2,4-triazol-3-yl)-N-(2-phenylethyl)cyclohexamine and Trans-N-methyl-3-(5-methyl-4-phenyl-4H-1,2,4-triazol-3-yl)-N-(2-phenylethyl)cyclohexanamine.
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) | 1989-03-17 | 1989-09-16 | 1990-03-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-03-17 | 1993-09-16 | 1994-03-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-03-17 | 1997-09-16 | 1998-03-18 | $7700.00 | Window Closed / Lapsed |