Thiazolyl(pyridyl)ethyne compounds

Details Thiazolyl(pyridyl)ethyne compounds Thiazolyl(pyridyl)ethyne compounds

2002-08-13

2004-08-10

Rao, Deepak (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S342000, C514S365000, C546S209000, C546S269700, C548S202000

Reexamination Certificate

active

06774138

ABSTRACT:

FIELD OF INVENTION
The present invention relates to novel heterocyclic compounds which contain a heterocylic ring bearing at least one substituent, linked together by a linker containing an acetylenic group, a vinylic group or an azo group. In addition, the present invention relates to pharmaceutical compositions containing novel invention compounds.
BACKGROUND OF THE INVENTION
Unsaturated heterocylic compounds find a wide variety of uses. For example, compounds of this class find uses as modulators of physiological processes that are mediated by ligand-activated receptors Receptors that are activated by ligands are located throughout the nervous, cardiac, renal, digestive and bronchial systems, among others. Therefore, in the nervous system, for example, heterocyclic compounds are capable of functioning as agonists or antagonists of receptors for neurotransmitters, neurohormones and neuromodulators. Ligand-activated receptors have been identified in a wide variety of species, including humans, other mammals and vertebrates as well as in invertebrate species. Therefore, compounds of this class are also able to modulate receptor-mediated processes throughout phylogeny and find uses in a wide variety of applications, e.g., as insecticides and fungicides.
Accordingly, there is a continuing need in the art for new members of this compound class.
BRIEF DESCRIPTION OF THE INVENTION
In accordance with the present invention, there is provided a novel class of heterocyclic compounds. Compounds of the invention contain a substituted, unsaturated five, six or seven membered heterocyclic ring that includes at least one nitrogen atom and at least one carbon atom. The ring additionally includes three, four or five atoms independently selected from carbon, nitrogen, sulfur and oxygen atoms. The heterocyclic ring has at least one substituent located at a ring position adjacent to a ring nitrogen atom. This mandatory substituent of the ring includes a moiety (B), linked to the heterocyclic ring via a carbon-carbon double bond, a carbon-carbon triple bond or an azo group. The mandatory substituent is positioned adjacent to the ring nitrogen atom.
Invention compounds are useful for a wide variety of applications. For example heterocyclic compounds can act to modulate physiological processes by functioning as agonists and antagonists of receptors in the nervous system. Invention compounds may also act as insecticides, and as fungicides. Pharmaceutical compositions containing invention compounds also have wide utility.
DETAILED DESCRIPTION OF THE INVENTION
In accordance with the present invention, there are provided compounds having the structure:
A—L—B
or enantiomers, diastereomeric isomers or mixtures of any two or more thereof, or pharmaceutically acceptable salts thereof, wherein:
A is a 5-, 6- or 7-membered ring having the structure:
 wherein at least one of W, X, Y and Z is (CR)
p
, wherein p is 0, 1 or 2;
the remainder of W, X, Y and Z are each independently O, N or S; and
each R is independently halogen, substituted or unsubstituted hydrocarbyl, substituted or unsubstituted aryl, heterocycle, mercapto, nitro, carboxyl, carbamate, carboxamide, hydroxy, ester, cyano, amine, amide, amidine, amido, sulfonyl or sulfonamide, wherein q is 0, 1, 2 or 3;
L is substituted or unsubstituted alkenylene, alkynylene, or azo; and
B is substituted or unsubstituted hydrocarbyl, substituted or unsubstituted cyclohydrocarbyl, substituted or unsubstituted heterocycle, optionally containing one or more double bonds, or substituted or unsubstituted aryl;
provided, that the following compounds are excluded:
the compounds wherein
A is a 6-membered ring wherein:
W, X, Y and Z are (CR)
p
wherein p is 1; and
R at the W position is hydrogen, lower alkyl, hydroxy, hydroxy-lower alkyl, amino-lower alkyl, lower alkylamino-lower alkyl, di-lower alkylamino-lower alkyl, unsubstituted or hydroxy-substituted lower alkyleneamino-lower alkyl, lower alkoxy, lower alkanoyloxy, amino-lower alkoxy, lower alkylamino-lower alkoxy, di-lower alkylamino-lower alkoxy, phthalimido-lower alkoxy, unsubstituted or hydroxy- or 2-oxo-imidazolidin-1-yl-substitued lower alkyleneamino-lower alkoxy, carboxy, esterified or amidated carboxy, carboxy-lower alkoxy or esterified carboxy-lower-alkoxy; R at the X position is hydrogen; R at the Y position is hydrogen, lower alkyl, carboxy, esterified carboxy, amidated carboxy, hydroxy-lower alkyl, hydroxy, lower alkoxy or lower alkanoyloxy; and R at the Z position is hydrogen, lower alkyl, hydroxy-lower alkyl, carboxy, esterified carboxy, amidated carboxy, unsubstituted or lower alkyl-, lower alkoxy-, halo- and/or trifluoromethyl-substituted N-lower alkyl-N-phenylcarbamoyl, lower alkoxy, halo-lower alkyl or halo-lower alkoxy;
L is substituted or unsubstituted alkenylene, alkynylene or azo,
B is substituted or unsubstituted aryl or heterocycle having two or more double bonds, wherein substituents are independently lower alkyl, lower alkenyl, lower alkynyl, phenyl, phenyl-lower alkynyl, hydroxy, hydroxy-lower alkyl, lower alkoxy, lower alkenyloxy, lower alkylenedioxy, lower alkanoyloxy, phenoxy, phenyl-lower alkoxy, acyl, carboxy, esterified carboxy, amidated carboxy, cyano, nitro, amino, acylamino, N-acyl-N-lower alkylamino, halo and halo-lower alkyl, wherein phenyl, phenyl-lower alkynyl, phenoxy, and phenyl-lower alkoxy may bear further substituents; and
the compounds wherein
A is a 6-membered ring wherein:
W, X, Y and Z are (CR)
p
wherein p is 1; R at the X position is not hydrogen; and R at the W, Y and Z positions are hydrogen;
L is alkenylene or alkynylene; and
B is a substituted or unsubstituted aryl or heterocycle containing two or more double bonds; and
the compounds wherein
A is a 5-membered ring wherein:
one of W, X, Y and Z is (CR)
p
, and p is 0, two of W, X, Y and Z are (CR)
p
and p is 1, and the remaining variable ring member is O or S; or
one of W, X, Y and Z is N, one of W, X, Y and Z is (CR)
p
and p is 1, one of W, X, Y and Z is (CR)
p
and p is 0, and the remaining variable ring member is O, S or (CR)
p
, and p is 1; or
two of W, X, Y and Z are N, one of W, X, Y and Z is (CR)
p
, and p is 0, and the remaining variable ring member is, O or S or (CR)
p
, and p is 1;
each R is independently hydrogen, nitro, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, C
3
-C
6
-alkenyl or C
3
-C
8
-cycloalkyl;
L is alkynylene; and
B is substituted or unsubstituted aryl, wherein substituents are independently nitro, cyano, C
1
-C
6
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, C
1
-C
4
-alkoxycarbonyl, C
3
-C
6
-alkenyl, phenyl or phenoxy, wherein phenyl and phenoxy may bear further substituents; and
the compounds wherein
A is a 6-membered ring wherein:
W, X, Y and Z are (CR)p, wherein p is 1 and R is hydrogen,
L is alkynylene; and
B is unsubstituted 1-cyclopenten-1-yl or unsubstituted 1-cyclohexen-1-yl; and
the compounds wherein
A is a 5-membered ring wherein:
W is (CR)p, and p is 0, Y and Z are (CR)p, and p is 1, X is N or S; and R is phenyl; or
W is (CR)p, and p is 0, X and Z are (CR)p, and p is 1, Y is O, N or S; and R is phenyl;
L is unsubstituted alkenylene and
B is unsubstituted phenyl; and
the compounds wherein A is a 5-membered ring containing two double bonds, wherein one of W, X, Y and Z is (CR)
p
, and p is 0, and the remaining ring members are (CR)
p
and p is 1; and
the compounds wherein A is unsubstituted heterocycle containing two or more double bonds; L is alkenylene or alkynylene, and B is unsubstituted phenyl.
In one aspect, this invention is directed to a compound having the structure:
A—L—B
or enantiomers, diastereomeric isomers or mixtures of any two or more thereof, or pharmaceutically acceptable salts thereof, wherein B is substituted or unsubstituted pyridyl, thiazolyl, furyl, dihydropyranyl, dihydrothiopyranyl, or piperidinyl; wherein said substitution is by hydroxy, alkoxy, mercapto, aryl, halogen, trifluoromethyl, pe

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