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US4163801A Expired / Lapsed US ⏱️ 0.0 years remaining

Treatment of animals with 2,6-bis(2-hydroxybenzyl)phenols to eradicate trematodes

Assignee: Orica Ltd
•
Filing: 1977-07-05
•
Granted: 1979-08-07
•
Expires: 1997-07-05
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Abstract

Abstract A process for killing internal parasites of warm blooded animals which process comprises treating the infected animal with an effective amount of a composition comprising as active ingredient a compound of the general formula I: ##STR1## wherein R 1 , R 2 and R 3 , which may be the same or different, are hydrogen, lower alkyl, lower alkenyl, lower alkanoyl, lower alkenoyl, aroyl or CH 2 COOR 4 wherein R 4 is hydrogen or lower alkyl; B, C and D, which may be the same or different, are halogen, optionally substituted lower alkyl, optionally substituted aryl, lower alkenyl, lower alkoxy, hydroxy, cyano, nitro, or COR 5 wherein R 5 is hydroxy, lower alkoxy or NR 6 R 7 wherein R 6 and R 7 , which may be the same or different, are hydrogen or lower alkyl; A, E, X, Y and Z, which may be the same or different, are hydrogen, halogen, optionally substituted lower alkyl, optionally substituted aryl, lower alkenyl, lower alkoxy, hydroxy, cyano, nitro, or COR 5 wherein R 5 is as hereinbefore defined; J and G, which may be the same or different, are hydrogen, lower alkyl, optionally substituted aryl, cyano, nitro or trichloromethyl or, together with the geminal hydrogen, the group ═CCl 2 ; or an optical isomer thereof; or a salt thereof; and wherein lower alkyl and lower alkoxy are defined as groups containing from 1 to 6 carbon atoms, lower alkenyl and lower alkanoyl are defined as groups containing from 2 to 6 carbon atoms and lower alkenoyl is defined as a group containing from 3 to 6 carbon atoms; and an inert carrier therefor.

Inventors

  • 👤 Errol J. McGarry
  • 👤 Bruce A. Forsyth

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 17:27
CPC Classifications
C; C07; C07C; C07C255/00; A; A61; A61K; A61K31/00; A61K31/045; A61K31/05; A61K31/055; A61K31/21; A61K31/215; A61K31/22; A61K31/275; C07C205/00; C07C205/13; C07C205/26; C07C37/00; C07C37/001; C07C37/002; C07C37/11; C07C37/16; C07C37/18; C07C37/20; C07C37/62; C07C41/00; C07C41/01; C07C41/16; C07C45/00; C07C45/51; C07C45/54

Claims Analysis

Total Claims: 20
Claim 1
Independent Claim 207 words
A method of treating warm blooded animals to eradicate trematodes which method comprises administering to the animal an effective amount of a composition comprising as active ingredient a compound of formula I: ##STR6## wherein R 1 , R 2 and R 3 are independently chosen from the group consisting of hydrogen, C 1 to C 6 alkyl and C 2 to C 6 alkenyl; B, c and D are independently chosen from the group consisting of halogen, C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 2 to C 6 alkoxy, hydroxy, cyano, nitro and the group COR 5 wherein R 5 is hydroxy or C 1 to C 6 alkoxy; A, e, x, y and Z are independently chosen from the group consisting of hydrogen, C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 2 to C 6 alkoxy, hydroxy, cyano, nitro and the group COR 5 wherein R 5 is hydroxy or C 1 to C 6 alkoxy; J and G are independently chosen from the group consisting of hydrogen, C 1 to C 6 alkyl, trichloromethyl and, together with the geminal hydrogen, the group =CCl 2 ; or an optical isomer thereof; or a salt thereof.
Claim 2
Independent Claim 207 words
A method of treating warm blooded animals to eradicate trematodes which method comprises administering to the animal an effective amount of a composition comprising as active ingredient a compound of formula I: ##STR6## wherein R 1 , R 2 and R 3 are independently chosen from the group consisting of hydrogen, C 1 to C 6 alkyl and C 2 to C 6 alkenyl; B, c and D are independently chosen from the group consisting of halogen, C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 2 to C 6 alkoxy, hydroxy, cyano, nitro and the group COR 5 wherein R 5 is hydroxy or C 1 to C 6 alkoxy; A, e, x, y and Z are independently chosen from the group consisting of hydrogen, C 1 to C 6 alkyl, C 2 to C 6 alkenyl, C 2 to C 6 alkoxy, hydroxy, cyano, nitro and the group COR 5 wherein R 5 is hydroxy or C 1 to C 6 alkoxy; J and G are independently chosen from the group consisting of hydrogen, C 1 to C 6 alkyl, trichloromethyl and, together with the geminal hydrogen, the group =CCl 2 ; or an optical isomer thereof; or a salt thereof.
Claim 3
Dependent Claim 124 words
A method according to claim 1 wherein: R 1 , R 2 and R 3 are independently chosen from the group consisting of hydrogen and C 1 to C 6 alkyl; B, c and D are independently chosen from the group consisting of halogen, C 1 to C 6 alkyl, nitro, cyano and the group COR 5 wherein R 5 is hydroxy or C 1 to C 6 alkoxy; A and E are independently chosen from the group consisting of hydrogen, halogen, C 1 to C 6 alkyl and nitro; X, y and Z are independently chosen from the group consisting of hydrogen and halogen; J and G are independently chosen from the group consisting of hydrogen and C 1 to C 6 alkyl.
Claim 4
Dependent Claim 36 words
A method according to claim 1 wherein A, B, C, D and E are independently selected from halogen, X, Y and Z are each hydrogen and J and G are independently selected from hydrogen and methyl.
Claim 5
Dependent Claim 39 words
A method according to claim 3 wherein: A and E are independently chosen from the group consisting of chlorine, bromine and iodine and B, C and D are independently chosen from the group consisting of fluorine, chlorine and bromine.
Claim 6
Dependent Claim 34 words
A method according to claim 1 wherein the animal is treated by parenteral administration of a sterile injectible composition comprising from 5 to 70% w/w of the active ingredient in a pharmaceutically acceptable carrier.
Claim 7
Dependent Claim 19 words
A method according to claim 5 wherein the composition comprises from 5 to 50% w/w of the active ingredient.
Claim 8
Dependent Claim 34 words
A method according to claim 1 wherein the animal is treated by external application of a composition comprising from 1 to 70% w/w of the active ingredient and a pharmaceutically acceptable liquid as carrier.
Claim 9
Dependent Claim 19 words
A method according to claim 7 wherein the composition comprises from 1 to 10% w/w of the active ingredient.
Claim 10
Dependent Claim 36 words
A method according to claim 1 wherein the animal is treated by orally drenching with a composition comprising from 10 to 50% w/w of dry ingredients which comprise 30 to 95% w/w of the active ingredient.
Claim 11
Dependent Claim 18 words
A method according to claim 9 wherein the dry ingredients comprise 15 to 30% w/w of the composition.
Claim 12
Dependent Claim 17 words
A process according to claim 2 wherein R 1 , R 2 and R 3 are hydrogen.
Claim 13
Dependent Claim 14 words
A method according to claim 1 wherein the compound of formula I is 2,6-bis(2-hydroxy-3-bromo-5-fluorobenzyl)-4-chlorophenol.
Claim 14
Dependent Claim 14 words
A method according to claim 1 wherein the compound of formula 2 is 2,6-bis(2-hydroxy-3-bromo-5-chlorobenzyl)-4-fluorophenol.
Claim 15
Dependent Claim 14 words
A method according to claim 1 wherein the compound of formula I is 2-(2-hydroxy-3-bromo-5-fluoro-α-methylbenzyl)-6-(2-hydroxy-3-bromo-5-fluorobenzyl)-4-chlorophenol.
Claim 16
Dependent Claim 14 words
A method according to claim 1 wherein the compound of formula I is 2,6-bis(2-hydroxy-3-bromo-5-fluorobenzyl)-4-fluorophenol.
Claim 17
Dependent Claim 14 words
A method according to claim 1 wherein the compound of formula I is 2,6-bis(2-hydroxy-3-iodo-5-chlorobenzyl)-4-fluorophenol.
Claim 18
Dependent Claim 14 words
A method according to claim 1 wherein the compound of formula I is 2,6-bis(2-hydroxy-3-iodo-5-fluorobenzyl)-4-fluorophenol.
Claim 19
Dependent Claim 15 words
A process according to claim 1 wherein the nematode is the liver fluke (Fasciola hepatica).
Claim 20
Dependent Claim 23 words
A process according to claim 1 wherein the composition comprises from 1 to 20 mg active ingredient per kg of animal body weight.

References Cited (Backward Citations)

US2598234A Cited
US2730551A Cited
US2798046A Cited
US2783279A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-08-06 1983-02-05 1983-08-07 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-08-06 1987-02-05 1987-08-07 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-08-06 1991-02-05 1991-08-07 $7700.00 Window Closed / Lapsed

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