Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
1985-10-11
2003-05-20
Killos, Paul J. (Department: 1623)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C560S011000, C560S012000, C560S014000, C560S021000, C560S023000, C560S034000, C560S055000, C560S056000, C558S013000, C558S414000, C514S532000, C514S543000, C514S570000, C562S470000
Reexamination Certificate
active
06566547
ABSTRACT:
The invention provides a compound having the general formula (I):
and stereoisomers thereof, wherein X, Y and Z, which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted alkynyl, haloalkyl, alkoxy, haloalkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, optionally substituted arylazo, acylamino, nitro, nitrile, —CO
2
R
3
, —CONR
4
R
5
, —COR
6
, —CR
7
═NR
8
, or —N═CR
9
R
10
groups or the groups X and Y, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, R
9
, and R
10
, which may be the same or different, are hydrogen atoms or alkyl, cycloalkyl, alkenyl, alkynyl, optionally substituted aryl, optionally substituted aralkyl, or cycloalaylalkyl groups; and metal complexes thereof.
The compounds of the invention contain at least one carbon-carbon double bond, and are sometimes obtained in the form of mixtures of geometric isomers. However, these mixtures can be separated into individual isomers, and this invention embraces such isomers.
Alkyl groups can be in the form of straight or branched chains, and preferably contain 1 to 6 carbon atoms; examples are methyl, ethyl, propyl, (n- or iso-propyl) and butyl (n-, sec-, iso- or t-butyl). The methyl group is the preferred alkyl group for both R
1
and R
2
.
In a further aspect the invention provides compounds having the general formula (I):
and stereoisomers thereof, wherein X, Y and Z, which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted alkynyl, haloalkyl, alkoxy, haloalkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, amino, acylamino, nitro, nitrile, —CO
2
R
3
, —CONR
4
R
5
, or —COR
6
groups; and R
1
, R
2
, R
3
, R
4
, R
5
and R
6
, which may be the same or different, are hydrogen atoms or alkyl, cycloalkyl, alkenyl, alkynyl, optionally substituted aryl, optionally substituted aralkyl, or cycloalkylalkyl groups; and metal complexes thereof.
In another aspect the invention provides compounds having the general formula (I):
and stereoisomers thereof, wherein X, Y and Z, which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted alkynyl, haloalkyl, alkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted amino, —CO
2
R
3
, —COR
6
groups, or the groups X and Y, when they are in adjacent positions on the phenyl ring, may join to form a fused aromatic ring; and R
1
, R
2
, R
3
and R
6
, which may be the same or different, are alkyl, optionally substituted phenyl, or optionally substituted aralkyl groups.
In a still further aspect the invention provides compounds having the general formula (I):
and stereoisomners thereof, wherein X, Y and Z, which may be the same or different, are hydrogen, fluorine, chlorine or bromine atoms, or C
1-4
alkyl, C
2-5
alkenyl, C
2-5
alkynyl, phenyl, C
1-4
haloalkyl, C
1-4
alkoxy, phenoxy, benzyloxy or mono- or dialkylamino groups, or the groups X and Y, when they are in adjacent positions on the phenyl ring, join to form a fused aromatic ring, the aliphatic moieties of any of the foregoing being optionally substituted with one or more C
1-4
alkoxy groups, fluorine, chlorine or bromine atoms, phenyl rings which themselves are optionally substituted, heterocyclic rings which are either aromatic or non-aromatic and are themselves optionally substituted, nitro, amino, nitrile, hydroxyl or carboxyl groups; and wherein the phenyl moieties of any of the foregoing are optionally substituted with one or more fluorine, chlorine or bromine atoms, phenyl rings, C
1-4
alkyl, C
1-4
alkoxy, nitro, amino, nitrile, hydroxyl or carboxyl groups; and R
1
and R
2
, which may be the same or different, are C
1-4
alkyl, phenyl or benzyl groups, each optionally substituted with halogen atoms.
In yet another aspect the invention provides compounds having the general formula (XI):
wherein R is an optionally substituted phenyl or an optionally substituted benzyl group, and Y is a hydrogen of a halogen (fluorine, chlorine or bromine) atom or a methyl, methoxyl, nitro, nitrile, carboxyl or methoxycarbonyl group.
In another aspect the invention provides compounds having the general formula (XII):
and stereoisomers thereof, wherein X is an alkyl, alkenyl, alkynyl, aryloxy or arylalkoxy group, each of which is optionally substituted.
In a further aspect the invention provides compounds having the general formula (XIII):
and stereoisomers thereof, wherein X is an optionally substituted alkyl, optionally substituted alkenyl, or optionally substituted alkynyl group.
In particular the invention, in a still further aspect, provides compounds wherein the optional substituents in the foregoing paragraph are phenyl, itself optionally substituted with one or more of the following: fluorine, chlorine, bromine, C
1-4
alkyl (especially methyl), C
1-4
alkoxy (especially methoxy), or nitro.
In a still further aspect the invention provides compounds having the general formula (XIV):
and stereoisomers thereof, wherein X is an optionally substituted aryloxy group or an optionally substituted arylalkoxy group.
In the foregoing paragraph X can be phenoxy or benzyloxy, either of which can be optionally substituted with one or more halogens (fluorine, chlorine or bromine) or a methyl, methoxyl, ethyl, ethoxyl, nitro, nitrile, carboxyl or methoxycarbonyl group.
In a yet further aspect the invention provides compound having the general formula (XV):
and stereoisomers thereof, wherein X, Y and Z, which may be the same or different, are fluorine, chlorine, bromine, or hydrogen atoms, or methyl, methoxyl or nitro groups.
The invention provides the compounds:
(compound number 9 of Table I below).
(Compound number 13 of Table I below).
(Compound number 19 of Table I below).
(Compound number 1 of Table II below).
(Compound number 1 of Table IV below).
TABLE I
(I)
Compound
Melting
No.
R
1
R
2
X
Y
Z
point (° C.)
olefinic*
isomer
+
1
CH
3
CH
3
H
H
H
37-38
7.55
E
2
CH
3
CH
3
H
H
H
oil
6.65
Z
3
CH
3
CH
2
CH
3
H
H
H
oil
7.53
E
4
CH
3
CH
3
CH
2
H
H
H
oil
7.62
E
5
CH
3
CH
2
CH
3
CH
2
H
H
H
oil
7.62
E
6
C
6
H
5
CH
2
CH
3
H
H
H
oil
7.56
E
7
CH
3
C
6
H
5
CH
2
H
H
H
37-38
7.67
E
8
(CH
3
)
3
C
CH
3
H
H
H
oH
7.44
E
9
CH
3
CH
3
2-(
E
-C
6
H
5
CH:CH)
H
H
107-108
7.63
E
10
CH
3
CH
3
2-(
E
-C
6
H
5
CH:CH)
H
H
oil
6.57
Z
11
CH
3
CH
3
3-(
E
-C
6
H
5
CH:CH)
H
H
104-105
7.58
E
12
CH
3
CH
3
4-(
E
-C
6
H
5
CH:CH)
H
H
75-76
7.56
E
13
CH
3
CH
3
2-(
Z
-C
6
H
5
CH:CH)
H
H
oil
7.50
E
14
CH
3
CH
3
2-(
Z
-C
6
H
5
CH:CH)
H
H
93-94
6.34
15
(CH
3
)
3
C
CH
3
2-(
Z
-C
6
H
5
CH:CH)
H
H
oil
7.37
E
16
CH
3
(CH
3
)
3
C
2-(
Z
-C
6
H
5
CH:CH)
H
H
oil
7.87
E
17
CH
3
CH
3
2-C
6
H
5
CH
2
CH(CH
3
)
H
H
E
18
CH
3
CH
3
2-(C
6
H
5
CH
2
C(CH
3
)
2
H
H
E
19
CH
3
CH
3
2-C
6
H
5
C:C
H
H
86-87
7.58
E
20
CH
3
CH
3
2-CH
2
:CH
H
H
oil
7.57
E
21
CH
3
CH
3
2-Cl
H
H
65-66
7.60
E
22
CH
3
CH
3
4-Cl
H
H
61-62
7.56
E
23
CH
3
CH
3
2-Cl
4-Cl
H
68-69
7.56
E
24
CH
3
CH
3
2-Cl
6-Cl
H
141-142
7.61
E
25
CH
3
CH
3
3-Cl
5-Cl
H
126-127
7.58
E
26
CH
3
CH
3
3-Cl
5-Cl
H
oil
6.70
Z
27
CH
3
CH
3
2-Cl
6-F
H
79-80
7.62
E
28
CH
3
CH
3
2-CH
3
H
H
oil
7.55
E
29
CH
3
CH
3
2-CH
3
H
H
62-63
6.52
Z
30
CH
3
CH
3
2-(CO
2
CH
3
)
H
H
oil
7.52
E
31
CH
3
CH
3
2-CF
3
H
H
65-66
7.56
E
32
CH
3
CH
3
2-C
6
H
5
H
H
106-107
7.34
E
33
CH
3
CH
3
2-C
6
H
5
N(CH
3
)CO
H
H
34
CH
3
CH
3
2-C
6
H
5
CON(CH
3
)
H
H
35
CH
3
CH
3
2-C
6
H
5
CO
H
H
82-85
7.30
E
36
CH
3
CH
3
2-C
6
H
5
CO
2
H
H
E
37
CH
3
CH
3
2-C
6
H
5
O
2
C
H
H
E
38
CH
3
CH
3
2-(CH
3
)
3
CO
2
C
H
H
E
39
CH
3
CH
3
2-(cyclohexyl)
Anthony Vivienne M
Beautement Kevin
Bushell Michael J
Clough John M
deFraine Paul
Killos Paul J.
Morgan & Lewis & Bockius, LLP
Zeneca Limited
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