US4338453A
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US
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Aminoalkyl-1,2,4-triazoles
Assignee: Pharmacia and Upjohn Co
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Filing: 1980-09-17
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Granted: 1982-07-06
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Expires: 2000-09-17
Abstract
Abstract Novel aminoalkyl triazoles are provided which are useful for the treatment of sensitized humans and animals for allergies and anaphylactic reactions. Additionally, a number of the compounds are useful in the treatment of hypertension. These compounds are of the formula ##STR1## wherein R 4 is hydrogen, alkyl, alkoxy, aryl, sulfonyl, or sulfinyl, R 5 is aryl, R 6 is hydrogen, hydroxy, alkyl, alkoxy, or alkanoyloxy, and R 1 is piperidinyl or amino.
Inventors
- 👤 Martin Gall
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 04:01
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/64; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D233/56; C07D249/00; C07D249/02; C07D249/08; C07D249/10; C07D249/12
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
333 words
A compound according to formula 1 or a pharmacologically acceptable salt thereof, wherein m is zero, one, 2 or 3; wherein n is zero, one or 2, wherein R 1 is: (a) 1-piperidinyl substituted at the 3 or 4 position by R 15 , wherein R 15 is defined as below; (b) --N(CH 3 )--(CH 2 ) p --R 15 , wherein R 15 and p are defined as below and wherein p is 1, 2, or 3; or (c) --NH--(CH 2 ) p --R 15 wherein R 15 is as defined as below and wherein p is 1, 2, or 3; wherein R 4 is: (a) hydrogen; (b) alkyl of one to three carbon atoms, inclusive; (c) R 54 OCH 2 --, wherein R 54 is as defined below; (d) --CH(R 35 )(OH); (e) --R 35 (f) --SH; (g) S(O) q R 17 , wherein q is zero, one or two; and R 17 is as defined below; (h) 1-hydroxy-1-cyclohexyl; or (i) 1-cyclohexen-1yl; wherein R 5 , R 15 , R 25 , and R 35 are the same or different and are (i) 2, 3, or 4 pyridinyl, or (ii) phenyl substituted by zero to 2 chloro, fluoro, bromo, alkyl of from one to 3 carbon atoms, or alkoxy of from one to 3 carbon atoms, or (iii) phenyl substituted by one trifluoromethyl and zero to one of the previous phenyl substituents; wherein R 6 is: (a) hydrogen; (b) --OR 54 ; (c) alkanoyloxy of from one to 3 carbon atoms; or (d) alkyl of from one to 3 carbon atoms; with the proviso that when m is zero, R 6 does not contain oxygen; and wherein R 17 is methyl, phenyl, benzyl, or 2-phenylethyl; and wherein R 54 is hydrogen or alkyl of one to 3 carbon atoms; or an enantiomer when R 4 is --CH(R 35 )OH or when R 6 is not hydrogen or diastereomer when R 4 is --CH(R 35 )OH and R 6 is not hydrogen
Claim 2
Dependent Claim
333 words
A compound according to formula 1 or a pharmacologically acceptable salt thereof, wherein m is zero, one, 2 or 3; wherein n is zero, one or 2, wherein R 1 is: (a) 1-piperidinyl substituted at the 3 or 4 position by R 15 , wherein R 15 is defined as below; (b) --N(CH 3 )--(CH 2 ) p --R 15 , wherein R 15 and p are defined as below and wherein p is 1, 2, or 3; or (c) --NH--(CH 2 ) p --R 15 wherein R 15 is as defined as below and wherein p is 1, 2, or 3; wherein R 4 is: (a) hydrogen; (b) alkyl of one to three carbon atoms, inclusive; (c) R 54 OCH 2 --, wherein R 54 is as defined below; (d) --CH(R 35 )(OH); (e) --R 35 (f) --SH; (g) S(O) q R 17 , wherein q is zero, one or two; and R 17 is as defined below; (h) 1-hydroxy-1-cyclohexyl; or (i) 1-cyclohexen-1yl; wherein R 5 , R 15 , R 25 , and R 35 are the same or different and are (i) 2, 3, or 4 pyridinyl, or (ii) phenyl substituted by zero to 2 chloro, fluoro, bromo, alkyl of from one to 3 carbon atoms, or alkoxy of from one to 3 carbon atoms, or (iii) phenyl substituted by one trifluoromethyl and zero to one of the previous phenyl substituents; wherein R 6 is: (a) hydrogen; (b) --OR 54 ; (c) alkanoyloxy of from one to 3 carbon atoms; or (d) alkyl of from one to 3 carbon atoms; with the proviso that when m is zero, R 6 does not contain oxygen; and wherein R 17 is methyl, phenyl, benzyl, or 2-phenylethyl; and wherein R 54 is hydrogen or alkyl of one to 3 carbon atoms; or an enantiomer when R 4 is --CH(R 35 )OH or when R 6 is not hydrogen or diastereomer when R 4 is --CH(R 35 )OH and R 6 is not hydrogen
Claim 3
Dependent Claim
21 words
A compound of claim 1 selected from the group consisting of N-methyl-4-phenyl-N-(2-phenylethyl)-4H-1,2,4-triazole-3-propanamine, 5-methyl-4-phenyl-N-(2-phenylethyl)-4H-1,2,4-triazole-3-ethaneamine, N,5-dimethyl-4-phenyl-N-(2-phenylethyl)-4H-1,2,4-triazole-3-ethaneamine, N-[2-(4-chlorophenyl)-ethyl]-N-methyl-4-phenyl-4H-1,2,4-triazole-3-propanamine, 4-(Phenylmethyl)-2-[3-(4-phenyl-4H-1,2,4-triazol-3-yl(propyl]-piperidine, N-[2-(3,4-dichlorophenyl)-ethyl]-N-methyl-4-phenyl-4H-1,2,4-triazol-3-propanamine, α-[[[2-(3,4-dichlorophenyl(ethyl]methylamino]methyl]-5-methyl-4-phenyl-4H-1,2,4-triazole-3-methanol, α-[[[2-(4-chlorophenyl)ethyl]methylamino]methyl]-5-methyl-4-phenyl-4H-1,2,4-triazol-3-methanol, and 5-[3-[methyl(phenylethyl)amino]propyl]-α-4-diphenyl-4H-1,2,4-triazol-
Claim 4
Dependent Claim
2 words
N-methyl-4-phenyl-N-(2-phenylethyl)-4H-1,2,4-triazole-3-propanamine, a
Claim 5
Dependent Claim
2 words
N-methyl-4-phenyl-N-(2-phenylethyl)-4H-1,2,4-triazole-3-propanamine, a
Claim 6
Dependent Claim
39 words
A compound of claim 2, wherein m is one or two, and R 4 is hydrogen, methyl, hydroxymethyl, S(O) q R 17 wherein q is zero, or --CH(R 35 )--(OH), wherein R 5 and R 35 are phenyl substituted
Claim 7
Dependent Claim
2 words
5-Methyl-4-phenyl-N-(2-phenylethyl)-4H-1,2,4-triazole-3-ethanamine, a
Claim 8
Dependent Claim
2 words
5-Methyl-4-phenyl-N-(2-phenylethyl)-4H-1,2,4-triazole-3-ethanamine, a
Claim 9
Dependent Claim
1 words
N,5-Dimethyl-4-phenyl-N-(2-phenylethyl)-4H-1,2,4-triazole-3-ethaneamine,
Claim 10
Dependent Claim
1 words
N,5-Dimethyl-4-phenyl-N-(2-phenylethyl)-4H-1,2,4-triazole-3-ethaneamine,
Claim 11
Dependent Claim
4 words
N-[2-(4-chlorophenyl)-ethyl]-N-methyl-4-phenyl-4H-1,2,4-triazole-3-propanamine, a compound of
Claim 12
Dependent Claim
4 words
N-[2-(4-chlorophenyl)-ethyl]-N-methyl-4-phenyl-4H-1,2,4-triazole-3-propanamine, a compound of
Claim 13
Dependent Claim
2 words
4-(Phenylmethyl)-1-[3-(4-phenyl-4H-1,2,4-triazol-3-yl)-propyl]-piperidine, a
Claim 14
Dependent Claim
2 words
4-(Phenylmethyl)-1-[3-(4-phenyl-4H-1,2,4-triazol-3-yl)-propyl]-piperidine, a
Claim 15
Dependent Claim
3 words
N-[2-(3,4-Dichlorophenyl)-ethyl]-N-methyl-4phenyl-4H-1,2,4-triazol-3-propanamine, a compound
Claim 16
Dependent Claim
3 words
N-[2-(3,4-Dichlorophenyl)-ethyl]-N-methyl-4phenyl-4H-1,2,4-triazol-3-propanamine, a compound
Claim 17
Dependent Claim
1 words
α-[[[2-(3,4-Dichlorophenyl)ethyl]methylamino]methyl]-5-methyl-4-phenyl-4H-1,2
Claim 18
Dependent Claim
1 words
α-[[[2-(3,4-Dichlorophenyl)ethyl]methylamino]methyl]-5-methyl-4-phenyl-4H-1,2
Claim 19
Dependent Claim
5 words
α-[[4-(4-Chlorophenyl)-1-piperazinyl]methyl]-5-methyl-4-phenyl-4-1,2,4-triazole-3-methanol, a compound of claim
Claim 20
Dependent Claim
1 words
α-[[[2-(4-Chlorophenyl)ethyl]methylamino]methyl]-5-methyl-4-phenyl-4
Claim 21
Dependent Claim
1 words
α-[[[2-(4-Chlorophenyl)ethyl]methylamino]methyl]-5-methyl-4-phenyl-4
Claim 22
Dependent Claim
1 words
5-[3-[Methyl(phenylethyl)amino]propyl]-α
Claim 23
Dependent Claim
1 words
5-[3-[Methyl(phenylethyl)amino]propyl]-α
Claim 24
Dependent Claim
6 words
4-Phenyl-N-(2-phenylethyl)-4H-1,2,4-triazol-3-propan-amine, a compound of claim 4.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-07-05 | 1986-01-04 | 1986-07-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-07-05 | 1990-01-04 | 1990-07-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-07-05 | 1994-01-04 | 1994-07-06 | $7700.00 | Window Closed / Lapsed |