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US4408049A Expired / Lapsed US ⏱️ 0.0 years remaining

Substituted piperazinyl-1,2,4-triazoles

Assignee: Pharmacia and Upjohn Co
•
Filing: 1982-03-26
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Granted: 1983-10-04
•
Expires: 2002-03-26
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Abstract

Abstract The present invention provides certain substituted-piperazinyl-1,2,4-triazoles which are useful for the treatment of sensitized humans for allergies and anaphylactic reactions.

Inventors

  • 👤 Martin Gall

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 22:52
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: 30
Claim 1
Independent Claim 293 words
A compound according to formula I ##STR2## or a pharmacologically acceptable salt thereof, wherein m is zero, one, 2 or 3; wherein n is zero, one or 2, wherein R 4 is: (a) hydrogen; (b) alkyl of one to three carbon atoms, inclusive; (c) R 54 OCH 2 --, wherein R 54 is 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-1-yl; 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; wherein R 7 is (i) hydrogen, (ii) methyl, (iii) phenylmethyl, or (iv) 2-phenylethyl, wherein R 8 is: (i) --R 15 ; (ii) --CH 2 R 15 , or (iii) --CHR 15 R 25 ; 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) of such compound.
Claim 2
Dependent Claim 293 words
A compound according to formula I ##STR2## or a pharmacologically acceptable salt thereof, wherein m is zero, one, 2 or 3; wherein n is zero, one or 2, wherein R 4 is: (a) hydrogen; (b) alkyl of one to three carbon atoms, inclusive; (c) R 54 OCH 2 --, wherein R 54 is 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-1-yl; 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; wherein R 7 is (i) hydrogen, (ii) methyl, (iii) phenylmethyl, or (iv) 2-phenylethyl, wherein R 8 is: (i) --R 15 ; (ii) --CH 2 R 15 , or (iii) --CHR 15 R 25 ; 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) of such compound.
Claim 3
Dependent Claim 17 words
A compound of claim 1, wherein n is zero and R 6 and R 7 are hydrogen.
Claim 4
Dependent Claim 6 words
1-(2-Methoxyphenyl)-4-[3-(4-phenyl-4H-1,2,4-triazol-3-yl)propyl]piperazine, a compound of claim 2.
Claim 5
Dependent Claim 9 words
A compound of claim 2, wherein m is 2.
Claim 6
Dependent Claim 6 words
1-[4-Fluorophenyl-4-[3-(4-phenyl-4H-1,2,4-triazol-3-yl)propyl]piperazine, a compound of claim 4.
Claim 7
Dependent Claim 6 words
1-Phenyl-4-[3-(4-phenyl)-4H-1,2,4-triazol-3-yl)propyl]piperazine, a compound of claim 4.
Claim 8
Dependent Claim 6 words
1-(4-Fluorophenyl)-4-[3-(5-methyl-4-phenyl-4H-1,2,4-triazol-3-yl)propyl]piperazine, a compound of claim 4.
Claim 9
Dependent Claim 6 words
1-(4-Chlorophenyl)-4-[3-(4-phenyl-4H-1,2,4-triazol-3-yl)propyl]piperazine, a compound of claim 4.
Claim 10
Dependent Claim 47 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 by zero to 2 chloro, fluoro or bromo.
Claim 11
Dependent Claim 6 words
1-[2-(5-Methyl-4-phenyl-4H-1,2,4-triazol-3-yl)ethyl]-4-phenylpiperazine, a compound of claim 9.
Claim 12
Dependent Claim 6 words
1-(4-Fluorophenyl)-4-[2-(5-methyl-4-phenyl-4H-1,2,4-triazole-3-yl)ethyl]piperazine, a compound of claim 9.
Claim 13
Dependent Claim 6 words
1-(4-Chlorophenyl)-4-[2-(5-methyl-4-phenyl-4H-1,2,4-triazol-3-yl)ethyl]piperazine, a compound of claim 9.
Claim 14
Dependent Claim 10 words
A compound of claim 8, wherein R 5 is phenyl.
Claim 15
Dependent Claim 7 words
1-(2-Chlorophenyl)-4-[3-(4-phenyl-4H-1,2,4-triazol-3-yl)propyl]piperazine, dihydrochloride, a compound of claim 13.
Claim 16
Dependent Claim 6 words
1-(3-Chlorophenyl)-4-[3-(4-phenyl-4H-1,2,4-triazol-3-yl)propyl]piperazine, a compound of claim 13.
Claim 17
Dependent Claim 6 words
1-(4-Methoxyphenyl)-4-[3-(4-phenyl-4H-1,2,4-triazol-3-yl)propyl]piperazine, a compound of claim 13.
Claim 18
Dependent Claim 6 words
1-(2-Methylphenyl)-4-[3-(4-phenyl-4H-1,2,4-triazol-3-yl)propyl]piperazine, a compound of claim 13.
Claim 19
Dependent Claim 10 words
A compound of claim 12, wherein R 4 is methyl.
Claim 20
Dependent Claim 10 words
A compound of claim 12, wherein R 4 is hydrogen.
Claim 21
Dependent Claim 6 words
1-(4-Fluorophenyl)-4-[3-[4-(4-fluorophenyl)-4H-1,2,4-triazol-3-yl]propyl]piperazine, a compound of claim 19.
Claim 22
Dependent Claim 6 words
1-[3-[4-(4-Fluorophenyl)-4H-1,2,4-triazol-3-yl]propyl]-4-phenylpiperazine, a compound of claim 19.
Claim 23
Dependent Claim 6 words
1-(4-Chlorophenyl)-4-[3-[4-(4-fluorophenyl)-4H-1,2,4-triazol-3-yl]propyl]piperazine, a compound of claim 19.
Claim 24
Dependent Claim 6 words
1-[3-[4-(4-Fluorophenyl)-4H-1,2,4-triazol-3-yl]propyl]-4-(4-methoxyphenyl)piperazine, a compound of claim 19.
Claim 25
Dependent Claim 10 words
A compound of claim 13, wherein R 6 is hydrogen.
Claim 26
Dependent Claim 10 words
A compound of claim 1, wherein R 4 is hydrogen.
Claim 27
Dependent Claim 6 words
1-(Phenylmethyl)-4-[3-(4-phenyl-4H-1,2,4-triazol-3-yl)-propyl]piperazine, a compound of claim 25.
Claim 28
Dependent Claim 6 words
1-(Diphenylmethyl)-4-[3-(4-phenyl-4H-1,2,4-triazol-3-yl)propyl]piperazine, a compound of claim 25.
Claim 29
Dependent Claim 12 words
A compound of claim 1, wherein R 4 is methyl or thiomethyl.
Claim 30
Dependent Claim 6 words
1-[3-[5-(Methylthio)-4-phenyl-4H-1,2,4-triazole-3-yl]propyl]-4-phenyl-piperazine, a compound of claim 28.

References Cited (Backward Citations)

US3969366A Cited
US4147700A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-10-03 1987-04-04 1987-10-04 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-10-03 1991-04-04 1991-10-04 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-10-03 1995-04-04 1995-10-04 $7700.00 Window Closed / Lapsed

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