US 7,071,215 B2Granted

Anthelmintic and insecticidal compositions

AssigneePharmacia & Upjohn Company

InventorByung Hyun Lee

Life of this patent

Estimating the term…

Abstract

Novel anthelmintic compositions containing thiophene derivatives as active ingredients are disclosed.

Claims14

Dependent claims

A compound of Formula I comprising:

wherein:
R1 and R2 are selected from the group consisting of H, alkyl, phenyl, substituted phenyl, benzyl, substituted benzyl, heteroaryl, substituted heteroaryl, hetroarylmethylene, and substituted hetroarylmethylene;
or
R1 and R2, along with the carbons to which they are attached, may form a 5- to 10-membered substituted or unsubstituted carbocyclic or heterocycloalkyl ring;
R3 is alkyl, heteroalkyl, cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R4 and R5 are independently H, alkyl, heteroalkyl, cycloalkyl, aryl, aralkyl, heteroaryl or heteroaralkyl;
R4 and R5 taken together with the nitrogen to which they are attached, may form a 3- to 8-membered substituted or unsubstituted nitrogen containing ring;
R6 and R7 are independently alkyl, heteroalkyl, aryl, aralkyl, heteroaryl or heteroaralkyl;
M1 is hydrogen and M2 is —OH;
or
M1 and M2 taken together may form a carbonyl (C═O).

8 more elements

A composition comprising 1 to 3 compounds selected from the group consisting of:

N-[3-(4-chlorobenzoyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl]-2-piperidin-1-ylacetamide;
N-{3-[(4-chlorophenyl)(hydroxy)methyl]-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl}-2-piperidin-1-ylacetamide;
N-[3-(4-chlorobenzoyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl]-2-(3-hydroxypiperidin-1-yl)acetamide;
N-{3-[(4-chlorophenyl)(hydroxy)methyl]-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl}-2-(3-hydroxypiperidin-1-yl)acetamide;
N-[5-ethyl-3-(4-methoxybenzoyl)thien-2-yl]-2-piperidin-1-ylacetamide;
N-[5-ethyl-3-(4-methoxybenzoyl)thien-2-yl]-2-pyrrolidin-1-ylacetamide;
N-[4-methyl-3-(benzoyl)thien-2-yl]-2-piperidin-1-ylacetamide;
N-[4,5-dimethyl-3-(4-chlorobenzoyl)thien-2-yl]-2-piperidin-1-ylacetamide;
N-[3-(4-chlorobenzoyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]-2-piperidin-1-ylacetamide;
N-[3-(4-chlorobenzoyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]-2-(3-hydroxypiperidin-1-yl) acetamide;
N-[3-(2-furoyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]-2-piperidin-1-ylacetamide;
N-[3-(2-furoyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]-2-(3-hydroxypiperidin-1-yl)acetamide;
methyl 4-({2-[(piperidin-1-ylacetyl)amino]-4,7-dihydro-5H-thieno[2,3-c]pyran-3-yl} carbonyl)benzoate;
N-[3-(3-chlorobenzoyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl]-2-piperidin-1-ylacetamide;
N-[3-(2-furoyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl]-2-piperidin-1-ylacetamide;
N-[3-(2-furoyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl]-2-(3-hydroxypiperidin-1-yl)acetamide;
N-{3-[(4-chlorophenyl)sulfonyl]thien-2-yl}-2-piperidin-1-ylacetamide;
N-[(2Z,3Z)-3-(4-chlorobenzylidene)-3,4,5,7-tetrahydro-2H-thieno[2,3-c]pyran-2-ylidene]-2-piperidin-1-ylacetamide;
N-{3-[(4-chlorophenyl)(diethylamino)methyl]-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl}-2-piperidin-1-ylacetamide, dihydrochloride;
N-{3-[(4-chlorophenyl)(hydroxy)methyl]-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl}-2-piperidin-1-ylacetamide;
N-{3-[(4-chlorophenyl)(hydroxy)methyl]-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl}-2-(3-hydroxypiperidin-1-yl)acetamide;
N-{3-[(4-chlorophenyl)(hydroxy)methyl]-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl}-2-(3-hydroxypiperidin-1-yl)acetamide;
N-[3-(4-chlorobenzoyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl]-2-[3-(hydroxymethyl)piperidin-1-yl]acetamide;
N-[3-(4-chlorobenzoyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]-2-[3-(hydroxymethyl)piperidin-1-yl]acetamide;
2-azepan-1-yl-N-[3-(4-chlorobenzoyl)-4,7-dihydro-H-thieno[2,3-c]thiopyran-2-yl]acetamide;
2-azepan-1-yl-N-{3-[(4-chlorophenyl)(hydroxy)methyl]-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl}acetamide;
N-[3-(4-chlorobenzoyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]-N-methyl-2-piperidin-1-ylacetamide;
2-(3-hydroxypiperidin-1-yl)-N-[3-(4-methylbenzoyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl]acetamide;
N-[3-(4-methylbenzoyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl]-2-piperidin-1-ylacetamide;
N-[3-(4-methylbenzoyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]-2-piperidin-1-ylacetamide;
2-(3-hydroxypiperidin-1-yl)-N-[3-(4-methylbenzoyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]acetamide;
N-[3-(3-chlorobenzoyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]-2-piperidin-1-ylacetamide;
N-{3-[(3-chlorophenyl)(hydroxy)methyl]-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl}-2-(3-hydroxypiperidin-1-yl)acetamide;
N-{3-[(3-chlorophenyl)(hydroxy)methyl]-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl}-2-(3-hydroxypiperidin-1-yl)acetamide;
N-[3-(3-chlorobenzoyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]-2-(3-hydroxypiperidin-1-yl)acetamide;
2-(3-hydroxypiperidin-1-yl)-N-{3-[3-(trifluoromethyl)benzoyl]-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl}acetamide;
2-piperidin-1-yl-N-{3-[3-(trifluoromethyl)benzoyl]-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl}acetamide;
2-(3-hydroxypiperidin-1-yl)-N-(3-{hydroxy[3-(trifluoromethyl)phenyl]methyl}-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl)acetamide;
N-[3-(3,4-dichlorobenzoyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]-2-piperidin-1-ylacetamide;
N-[3-(2,2-dimethylpropanoyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]-2-(3-hydroxypiperidin-1-yl)acetamide;
2-piperidin-1-yl-N-[3-(thien-2-ylcarbonyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]acetamide;
2-(3-hydroxypiperidin-1-yl)-N-[3-(thien-2-ylcarbonyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]acetamide;
N-[3-(3,4-dichlorobenzoyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]-2-(3-hydroxypiperidin-1-yl)acetamide;
N-{3-[hydroxy(4-methylphenyl)methyl]-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl}-2-(3-hydroxypiperidin-1-yl)acetamide;
N-{3-[hydroxy(4-methylphenyl)methyl]-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl}-2-(3-hydroxypiperidin-1-yl)acetamide;
2-(3-hydroxypiperidin-1-yl)-N-(3-{hydroxy[3-(trifluoromethyl)phenyl]methyl}-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl)acetamide;
2-(3-hydroxypiperidin-1-yl)-N-(3-{[1-methyl-5-(trifluoromethyl)-1H-pyrazol-4-yl]carbonyl}-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl)acetamide;
2-piperidin-1-yl-N-[3-(thien-2-ylcarbonyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl]acetamide;
2-(3-hydroxypiperidin-1-yl)-N-[3-(thien-2-ylcarbonyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl]acetamide;
N-(3-{[1-methyl-5-(trifluoromethyl)-1H-pyrazol-4-yl]carbonyl}-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl)-2-piperidin-1-ylacetamide;
N-(3-{hydroxy[1-methyl-5-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl)-2-piperidin-1-ylacetamide;
N-(3-{hydroxy[1-methyl-5-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl)-2-(3-hydroxypiperidin-1-yl)acetamide;
2-(3-hydroxypiperidin-1-yl)-N-{3-[hydroxy(thien-2-yl)methyl]-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl}acetamide;
N-{3-[hydroxy(thien-2-yl)methyl]-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl}-2-piperidin-1-ylacetamide;
N-[3-(4-fluorobenzoyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]-2-piperidin-1-ylacetamide;
2-piperidin-1-yl-N-[3-(4-piperidin-1-ylbenzoyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]acetamide;
N-[3-(4-fluorobenzoyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]-2-(3-hydroxypiperidin-1-yl)acetamide;
N-{3-[(4-fluorophenyl)(hydroxy)methyl]-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl}-2-(3-hydroxypiperidin-1-yl)acetamide;
N-[3-(3,4-difluorobenzoyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]-2-(3-hydroxypiperidin-1-yl)acetamide;
N-[3-(3-fluorobenzoyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]-2-piperidin-1-ylacetamide,
N-[3-(3-fluorobenzoyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]-2-(3-hydroxypiperidin-1-yl)acetamide;
N-{3-[(3-fluorophenyl)(hydroxy)methyl]-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl}-2-(3-hydroxypiperidin-1-yl)acetamide;
N-[3-(3-chlorobenzoyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl]-2-(3-hydroxypiperidin-1-yl)acetamide;
N-{3-[(3-fluorophenyl)(hydroxy)methyl]-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl}-2-piperidin-1-ylacetamide;
N-{3-[hydroxy(4-methylphenyl)methyl]-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl}-2-piperidin-1-ylacetamide;
N-[3-(3-fluorobenzoyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl]-2-piperidin-1-ylacetamide;
N-{3-[2-(3-fluorophenoxy)benzoyl]-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl}-2-piperidin-1-ylacetamide;
N-[3-(3-fluorobenzoyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl]-2-(3-hydroxypiperidin-1-yl)acetamide;
N-{3-[2-(3-fluorophenoxy)benzoyl]-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl}-2-(3-hydroxypiperidin-1-yl)acetamide;
N-{3-[(3-fluorophenyl)(hydroxy)methyl]-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl}-2-piperidin-1-ylacetamide;
2-piperidin-1-yl-N-{3-[3-(trifluoromethyl)benzoyl]-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl}acetamide;
2-(3-hydroxypiperidin-1-yl)-N-{3-[3-(trifluoromethyl)benzoyl]-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl}acetamide;
N-[3-(1,1′-biphenyl-4-ylcarbonyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]-2-piperidin-1-ylacetamide;
N-(3-{hydroxy[3-(trifluoromethyl)phenyl]methyl}-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl)-2-piperidin-1-ylacetamide;
and
N-[3-(1,1′-biphenyl-4-ylcarbonyl)-4,7-dihydro-5H-thieno[2,3-c]thiopyran-2-yl]-2-(3-hydroxypiperidin-1-yl)acetamide.

73 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/687,496Filed 16 Oct 2003 · us provisional application
Priority: 17 Oct 2002
Published: US 2004/0127548 A11 Jul 2004
Granted: 4 Jul 2006
Term ends: Not estimatedThe source records don’t support an estimate.

Classification11 codes

C07D 495/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 33/00
Antiparasitic agents
A61P 33/02
Antiparasitic agents: antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
A61P 33/06
Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis: antimalarials

Family

Application60/419,133Us provisional application · filed 17 Oct 2002
US 2004/0127548 A1Pre-grant publication · published 1 Jul 2004
US 7,071,215 B2This patent

From the US filing history. Foreign family members aren’t listed.

Timeline

Citations

Open elsewhere

patentgrep

Loading patent…

Facts

Application

10/687,496Filed 16 Oct 2003 · us provisional application

Priority

17 Oct 2002

Published

US 2004/0127548 A11 Jul 2004

Granted

4 Jul 2006

Term ends

Not estimatedThe source records don’t support an estimate.

Classification11 codes

C07D 495/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 33/00
Antiparasitic agents
A61P 33/02
Antiparasitic agents: antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
A61P 33/06
Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis: antimalarials