Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1998-02-11
2001-07-03
Ramsuer, Robert W. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S110000, C548S364100, C548S365700, C548S370100, C548S371700, C548S372500, C548S374100, C548S375100, C548S376100, C548S377100
Reexamination Certificate
active
06255333
ABSTRACT:
This application is the United States National filing of International Patent Application PCT/EP96/03501, which was a continuation of Great Britain Patent Applications 9516454.7 and 9601128.3, filed Aug. 11, 1995 and Jan. 19, 1996, respectively, now abandoned.
This invention relates to pyrazole derivatives having parasiticidal properties.
Certain parasiticidal pyrazole derivatives are already known. These include fipronil (5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulphinyl-pyrazole) and certain analogues thereof mentioned in International Patent Application WO 87/03781.
EP 0 658 547 A1 discloses a number of 4-alkenyl and 4-alkynyl pyrazoles with H and alkyl at the 1-position, and a carbamate group at position 5 of the pyrazole, as antifungal agents.
A new group of parasiticidal pyrazole derivatives has now been found. Thus, according to the present invention, there is provided a compound of formula I,
wherein
R
1
represents CN, C
1-6
alkoxycarbonyl, NO
2
, CHO, C
1-6
alkanoyl, phenyl optionally substituted by one or more halogen, or C
1-6
alkyl optionally substituted by one or more halogen;
R
2
represents a group of formula II, III or IV,
in which
R
7
represents H, halogen, carbamoyl cyano, tri(C
1-6
alkyl)silyl, C
1-6
alkyl (optionally substituted by one or more halogen, OH or C
1-6
alkoxy), C
1-6
alkoxycarbonyl, phenyl, or a 5- or 6-membered ring heterocycle which is saturated or partially or fully unsaturated and contains up to 4 hetero-atoms independently selected from up to 4 N atoms, up to 2 O atoms and up to 2 S atoms and which is attached to the alkynyl moiety by an available C, S or N atom where the valence allows; and
and R
8
, R
9
and R
10
each independently represent H, halogen, phenyl optionally substituted by one or more halogen, CN or C
1-6
alkyl optionally substituted by one or more halogen;
R
3
represents H, C
1-6
alkyl halogen, NH
2
, NH(C
1-6
alkanoyl), NH(C
1-6
alkoxycarbonyl), N(C
1-6
alkoxycarbonyl)
2
, NH(C
1-6
alkyl), N(C
1-6
alkyl)
2
, NHCONH(C
1-6
alkyl), N-pyrrolyl, NHCONH(phenyl optionally substituted by one or more halogen), N═CH(phenyl), OH, C
1-6
alkoxy, SH or S(O)
n
(C
1-6
alkyl optionally substituted by one or more halogen) where n is 0,1 or 2; and
R
4
, R
5
and R
6
each independently represent H, halogen, C,
4
alkyl optionally substituted by one or more halogen, C
1-6
alkoxy optionally substituted by one or more halogen, S(O)
n
(C
1-6
alkyl optionally substituted by one or more halogen) where n is 0,1 or 2, or CH
3
CO, CN, CONH
2
, CSNH
2
, OCF
3
, SCF
3
or SF
5
;
or a pharmaceutically or vetennarfly acceptable salt thereof (hereinafter referred to together as “the compounds of the invention”).
Alkyl groups may be straight, cyclic or branched, where the number of carbon atoms allows. Halogen means fluoro, chloro, bromo or iodo.
Pharmaceutically and veterinarily acceptable addition salts are well known to those skilled in the art, and for example include those mentioned by Berge et al in
J.Pharm. Sci.,
66,1-19 (1977).
R
1
is preferably CN, optionally substituted phenyl, optionally substituted C
1-6
alkyl, or C
1-6
alkoxycarbonyl.
R
1
is more preferably CN, Ph, CO
2
C
2
H
5
, CH
3
, CF
3
or CO
2
CH
3
.
R
2
is preferably a group of formula II where R
7
is H, tri(C
1-6
alkyl)silyl, C
1-6
alkyl optionally substituted by one or more halogen, OH or C
1-6
alkoxy, or R
7
is C
1-6
alkoxycarbonyl phenyl a 5- or 6-membered zing heterocycle as previously defined, halogen, or a group of formula III in which R
8
, R
9
, and R
10
are each H, or a group of formula III in which two of R
8
, R
9
and R
10
are halogen and the other is H, CN, phenyl optionally substituted by one or more halogen or C
1-6
alkyl optionally substituted by one or more halogen, or a group of formula III in which R
8
, R
9
and R
10
are each independently F, Cl, Br or I, or a group of formula III in which R
8
is H or C
1-6
alkyl optionally substituted by one or more halogen, OH or C
1-6
alkoxy, and R
9
and R
10
are both halogen, or a group of formula III in which R
8
is H and one of R
9
and R
10
is halogen and the other is C
1-6
alkyl optionally substituted by one or more halogen, OH or C
1-6
alkoxy, or a group of formula III in which R
8
is H and one of R
9
and R
10
is H and the other is CN or C
1-6
alkyl optionally substituted by one or more halogen, OH or C
1-6
alkoxy, or a group of formula III in which R
8
is H and R
9
and R
10
are C
1-6
alkyl optionally substituted by one or more halogen, OH or C
1-6
alkoxy, or a group of formula III in which R
8
is C
1-6
alkyl optionally substituted by one or more halogen, OH or C
1-6
alkoxy and R
9
and R
10
are both H, or a group of formula IV.
More preferably R
2
is a group of formula II in which R
7
is Si(CH
3
)
3
, H, CH
3
, CH(CH
3
)
2
, CH
2
OH, (CH
2
)
2
OH, CO
2
CH
3
, Ph, thien-2-yl CH
2
OCH
3
, Br, Cl, or CF
3
, or a group of formula III in which R
8
, R
9
and R
10
are each H, or a group of formula III in which R
8
, R
9
and R
10
are each Cl or a group of formula III in which R
8
and R
9
are Br and R
10
is H, or a group of formula III in which R
8
and R
10
are Br and R
9
is H, or a group of formula III in which R
8
and R
9
are Br and R
10
is CH
3
, or a group of formula III in which R
8
and R
10
are Br and R
9
is CH
3
, or a group of formula III in which R
8
and R
10
are Br and R
9
is Ph, or a group of formula III in which R
8
and R
9
are Br and R
10
is Ph, or a group of formula III in which R
8
and R
10
are Cl and R
9
is Ph, or a group of formula III in which R
8
and R
9
are Cl and R
10
is Ph, or a group of formula III in which R
8
and R
10
are Cl and R
9
is Br, or a group of formula III in which R
8
and R
9
are Cl and R
10
is Br, or a group of formula III in which R
8
is H and R
10
and R
9
are Br, or a group of formula III in which R
8
is H and R
10
and R
9
are Cl, or a group of formula III in which R
8
is H and R
10
and R
9
are F, or a group of formula III in which R
8
is H and R
10
is CF
3
and R
9
is Cl, or a group of formula III in which R
8
is H and R
9
is CF
3
and R
10
is Cl, or a group of formula III in which R
8
is H and R
10
is CF
3
and R
9
is Br, or a group of formula III in which R
8
is H and R
9
is CF
3
and R
10
is Br, or a group of formula III in which R
8
is H and R
10
is CF
3
and R
9
is F, or a group of formula III in which R
8
is H and R
9
is CF
3
and R
10
is F, or a group of formula III in which R
8
and R
10
are H and R
9
is CN, or a group of formula III in which R
8
and R
9
are Br and R
10
is CF
3
, or a group of formula III in which R
8
and R
10
are Br and R
9
is CF
3
, or a group of formula III in which R
8
is Br, R
9
is Br and R
9
is Cl, or a group of formula III in which R
8
is Br, R
10
is Br and R
9
is Cl, or a group of formula III in which R
8
is CH
3
, R
9
and R
10
are Br, or a group of formula III in which R
8
is CH
3
, R
9
and R
10
are F, or a group of formula II in which R
8
is CH
3
, R
9
and R
10
are H, or a group of formula III in which R
8
is H, R
9
and R
10
are CH
3
, or a group of formula III in which R
8
, R
9
and R
10
are each Br, or a group of formula IV.
R
3
is preferably H, C
1-6
alkyL NH
2
, NH(C
1-6
alkanoyl), NH(C
1-6
alkoxycarbonyl), N(C
1-6
alkoxycarbonyl)
2
, N(C
1-6
alkyl)
2
, N-pyrrolyl halogen or S(O)
n
(C
1-6
alkyl optionally substituted by one or more halogen) where n is 0, 1 or 2.
R
3
is more preferably H, CH
3
, NH
2
, N-pyrrolyl, N(CH
3
)
2
, NH(CO
2
(t-butyl)), N(CO
2
(t-butyl))
2
, NHCOCH
3
, Br, Cl SCH
3
or SCF
3
.
R
4
and R
6
are preferably halogen.
R
4
and R
6
are more preferably Cl.
R
5
is preferably C
1-6
alkyl optionally substituted by one or more halogen, C
1-6
alkoxy optionally substituted by one or more halogen, C
1-6
alkylthio optionally substituted by one or more halogen, SF
5
or halogen.
R
5
is more preferably CF
3
, OCF
3
, SCF
3
or SF
5
.
The compounds (and salts thereof) which are most preferred are:
3-cyano-1-(2,6-dichloro-4-trifluoromethylphen
Benson Gregg C.
Creagan B. Timothy
Pfizer Inc.
Ramsuer Robert W.
Richardson Peter C.
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