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US4404382A Expired / Lapsed US ⏱️ 0.0 years remaining

Piperazinyl-substituted imidazoles

Assignee: Pharmacia and Upjohn Co
•
Filing: 1982-03-26
•
Granted: 1983-09-13
•
Expires: 2002-03-26
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Abstract

Abstract The present invention provides certain piperazinyl-substituted imidazoles 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 2026-11-09 04:20
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/64; C07D249/00; C07D249/02; C07D249/08; C07D249/10; C07D249/12

Claims Analysis

Total Claims: 16
Claim 1
Independent Claim 278 words
A compound according to formula I ##STR2## or a pharmacologically acceptable salt thereof, wherein X 1 is (a) ═CH--; or (b) ═C(CH 3 )--; 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); or (e) --R 35 ; 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) 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 278 words
A compound according to formula I ##STR2## or a pharmacologically acceptable salt thereof, wherein X 1 is (a) ═CH--; or (b) ═C(CH 3 )--; 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); or (e) --R 35 ; 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) 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 9 words
A compound of claim 2, wherein m is 2.
Claim 5
Dependent Claim 39 words
A compound of claim 2, wherein m is one or 2, and R 4 is hydrogen, methyl, hydroxymethyl, or --CH(R 35 )(OH), wherein R 5 and R 35 are phenyl substituted by zero to 2 chloro, fluoro or bromo.
Claim 6
Dependent Claim 6 words
1-[2-(5-Methyl-1-phenyl-1H-imidazole-2-yl)-ethyl]-4-phenylpiperazine, a compound of claim 4.
Claim 7
Dependent Claim 6 words
1-(4-Chlorophenyl)-4-[2-(5-methyl-1-phenyl-1H-imidazole-2-yl)-ethyl]piperazine, a compound of claim 4.
Claim 8
Dependent Claim 10 words
A compound of claim 4, wherein R 4 is methyl.
Claim 9
Dependent Claim 6 words
1-(4-Fluorophenyl)-4-[2-[1-(4-fluorophenyl)-5-methyl-1H-imidazole-2-yl]ethyl]piperazine, a compound of claim 7.
Claim 10
Dependent Claim 6 words
1-(4-Chlorophenyl)-4-[2-[1-(4-fluorophenyl)-5-methyl-1H-imidazol-2-yl]ethyl]piperazine, a compound of claim 7.
Claim 11
Dependent Claim 6 words
1-[2-[1-(4-Fluorophenyl)-5-methyl-1H-imidazol-2-yl]ethyl]-4-phenylpiperazine, a compound of claim 7.
Claim 12
Dependent Claim 10 words
A compound of claim 4, wherein R 6 is hydrogen.
Claim 13
Dependent Claim 10 words
A compound of claim 1, wherein X 1 is ═CH--.
Claim 14
Dependent Claim 12 words
A compound of claim 1, wherein X 1 is ═C(CH 3 )--.
Claim 15
Dependent Claim 10 words
A compound of claim 1, wherein R 4 is hydrogen.
Claim 16
Dependent Claim 12 words
A compound of claim 1, wherein R 4 is methyl or thiomethyl.

References Cited (Backward Citations)

US3423413A Cited
US3362956A Cited
US3491098A Cited
US3927011A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-09-12 1987-03-14 1987-09-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-09-12 1991-03-14 1991-09-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-09-12 1995-03-14 1995-09-13 $7700.00 Window Closed / Lapsed

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