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US4351948A Expired / Lapsed US ⏱️ 0.0 years remaining

Imidazole hydrazone derivatives

Assignee: GD Searle LLC
•
Filing: 1981-01-16
•
Granted: 1982-09-28
•
Expires: 2001-01-16
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Abstract

Abstract Compounds corresponding to the following general formula: ##STR1## wherein Ar and Ar 1 , which may be the same or different, each represents an aromatic radical which may be substituted one or more times by halogen and/or nitro and/or lower alkyl and/or trihalomethyl and/or cyano and/or lower alkoxy and/or di-lower alkyl-amino, the alkyl groups optionally completing a ring optionally incorporating a further heteroatom, and/or lower alkyl sulphonyl; Alk 1 and Alk 2 , which may be the same or different, each represents an alkylene group containing from one to eight carbon atoms which may be substituted one or more times by aryl and/or cycloalkyl and/or lower alkyl and if two such alkyl groups are present, they may complete a ring optionally containing a heteroatom and in which imidazole ring may be further substituted; and m represents 0 or 1; provided that not both Ar and Ar 1 represent phenyl; and acid addition salts thereof. Such compounds are prepared by reaction of a compound corresponding to the following general formula: ##STR2## with a compound of the formula: Ar.sup.1 --NH--NH.sub.2 The compounds have an anti-fungal activity as well as an antianaerobic and anti-thrombotic activity.

Inventors

  • 👤 Peter J. Fellner
  • 👤 Brendan J. Hamill
  • 👤 Paul W. Manley

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 19:07
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/56; C07D233/60; A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/41; A61K31/415; A61K31/435; A61K31/44; A61K31/4427; A61K31/443; A61K31/4433; C07D233/61; C07D401/00; C07D401/02; C07D401/06; C07D401/12; C07D405/00; C07D405/02; C07D405/06; C07D405/12; C07D409/00; C07D409/02; C07D409/06

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 91 words
A compound of the formula ##STR6## or a pharmacologically acceptable salt thereof wherein: Ar is phenyl, thienyl or a mono, di or trisubstituted form thereof wherein the mono, di or trisubstituent is F, Cl, Br, CF 3 , C 1 -C 3 alkyl, C 1 -C 3 alkoxy, CN, or NO 2 ; Ar 1 is C 6 H 5-n X n ; X is F, Cl or CF 3 ; R is H, CH 3 or CH 2 CH 3 ; and n is an integer from 1 to 5.
Claim 2
Dependent Claim 91 words
A compound of the formula ##STR6## or a pharmacologically acceptable salt thereof wherein: Ar is phenyl, thienyl or a mono, di or trisubstituted form thereof wherein the mono, di or trisubstituent is F, Cl, Br, CF 3 , C 1 -C 3 alkyl, C 1 -C 3 alkoxy, CN, or NO 2 ; Ar 1 is C 6 H 5-n X n ; X is F, Cl or CF 3 ; R is H, CH 3 or CH 2 CH 3 ; and n is an integer from 1 to 5.
Claim 3
Dependent Claim 24 words
A compound according to claim 1 wherein Ar 1 is chloro or fluorophenyl, dichloro or difluorophenyl, 2,4,6-trichloro or trifluorophenyl, pentachloro or pentafluorophenyl, or trifluoromethylphenyl.
Claim 4
Dependent Claim 32 words
A compound according to claim 1 or 2 wherein Ar is phenyl, thienyl, chloro or fluorophenyl, di or tri (chloro or fluoro) phenyl, 2 or 4-methylphenyl, 2 or 4-methoxyphenyl, trifluoromethylphenyl, or cyanophenyl.
Claim 5
Dependent Claim 15 words
A compound according to claim 1 wherein Ar is 4-chlorophenyl and Ar 1 is 2,4-dichlorophenyl.
Claim 6
Dependent Claim 15 words
A compound according to claim 1 wherein Ar is 4-chlorophenyl and Ar 1 is 2,6-dichlorophenyl.
Claim 7
Dependent Claim 15 words
A compound according to claim 1 wherein Ar is 2-chlorophenyl and Ar 1 is 2,4-dichlorophenyl.
Claim 8
Dependent Claim 15 words
A compound according to claim 1 wherein Ar is 4-chlorophenyl and Ar 1 is pentafluorophenyl.
Claim 9
Dependent Claim 15 words
A compound according to claim 1 wherein Ar is 2,4-dichlorophenyl and Ar 1 is 2,4,6-trichlorophenyl.
Claim 10
Dependent Claim 15 words
A compound according to claim 1 wherein Ar is 4-chlorophenyl and Ar 1 is 2-chlorophenyl.
Claim 11
Dependent Claim 15 words
A compound according to claim 1 wherein Ar is 5-chlorothien-2-yl and Ar 1 is 2,6-dichlorophenyl.
Claim 12
Dependent Claim 15 words
A compound according to claim 1 wherein Ar is phenyl and Ar 1 is 2,4-dichlorophenyl.
Claim 13
Dependent Claim 8 words
(E)-1-(4-chlorophenyl)-2-(1H-imidazol-1-yl) ethanone, 2,4-dichlorophenylhydrazone, hydrochloride according to claim 1.
Claim 14
Dependent Claim 8 words
(Z)-1-(4-chlorophenyl)-2-(1H-imidazol-1-yl) ethanone, 2,6-dichlorophenylhydrazone, hydrochloride according to claim 1.
Claim 15
Dependent Claim 8 words
(E)-1-(5-chlorothienyl-2-yl)-2-(1H-imidazol-1-yl) ethanone, 2,6-dichlorophenylhydrazone, hydrochloride according to claim 1.
Claim 16
Dependent Claim 8 words
(Z)-1-(4-chlorophenyl)-1-(1H-imidazol-1-yl) ethanone, 2-chlorophenylhydrazone, hydrochloride according to claim 1.
Claim 17
Dependent Claim 8 words
1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl) ethanone, 2,4,6-trichlorophenylhydrazone, hydrochloride according to claim 1.
Claim 18
Dependent Claim 11 words
(Z)-1-(4-chlorophenyl)-2-(1H-imidazol-1-yl) ethanone, 2, 3, 4, 5,6-pentafluorophenylhydrazone, hydrochloride according to claim 1.

References Cited (Backward Citations)

US3830642A Cited
US3927017A Cited
GB1533748A Cited
GB1533705A Cited
GB1533706A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-09-27 1986-03-29 1986-09-28 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-09-27 1990-03-29 1990-09-28 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-09-27 1994-03-29 1994-09-28 $7700.00 Window Closed / Lapsed

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