BENZOYL-PIPERAZINE DERIVATIVES
0 Assignments
0 Petitions
Accused Products
Abstract
The invention relates to compounds of formula
wherein the substituents are described herein. The compounds may be used in the treatment of illnesses based on the glycine uptake inhibitor, such as psychoses, pain, neurodegenerative disfunction in memory and learning, schizophrenia, dementia and other diseases in which cognitive processes are impaired, such as attention deficit disorders or Alzheimer'"'"'s disease.
-
Citations
20 Claims
-
1. A compound of formula
- View Dependent Claims (3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18)
-
3. A compound of formula I according to claim 1, wherein Ar is substituted phenyl, R2 is (C1-C6)-alkyl and R5 is S(O)2CH3 or S(O)2CH2CH3.
-
4. A compound of formula I according to claim 3, wherein the compound is selected from the group consisting of
1-{3-fluoro-4-[4-(2-isopropoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-phenyl}-ethanone, 3-fluoro-4-[4-(2-isopropoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-benzonitrile, 2-Fluoro-4-[4-(2-isopropoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-benzonitrile, [4-(2-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone, 1-{3-fluoro-4-[4-(2-isobutoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-phenyl}-ethanone, 4-[4-(2-isobutoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-benzonitrile, 3-fluoro-4-[4-(2-isobutoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-benzonitrile, 2-fluoro-4-[4-(2-isobutoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-benzonitrile, (2-isobutoxy-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, [4-(2-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-(2-isobutoxy-5-methanesulfonyl-phenyl)-methanone, [4-(3-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-(2-isobutoxy-5-methanesulfonyl-phenyl)-methanone; -
[4-(2-fluoro-4-methanesulfonyl-phenyl)-piperazin-1-yl]-(2-isobutoxy-5-methanesulfonyl-phenyl)-methanone, [4-(2-fluoro-4-methanesulfonyl-phenyl)-piperazin-1-yl]-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone, 2,3-difluoro-4-[4-(2-isopropoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-benzonitrile, 2,3-difluoro-4-[4-(2-isobutoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-benzonitrile, 2,5-difluoro-4-[4-(2-isobutoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-benzonitrile, 2,6-difluoro-4-[4-(2-isobutoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-benzonitrile, and 3,5-difluoro-4-[4-(2-isobutoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-benzonitrile.
-
-
5. A compound of formula I according to claim 3, wherein the compound is selected from the group consisting of
4-[4-(2-tert-butoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-2,3-difluoro-benzonitrile, 5-chloro-2-[4-(2-isopropoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-benzonitrile, 4-[4-(2-tert-butoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-2,5-difluoro-benzonitrile, 4-[4-(2-tert-butoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-3-fluoro-benzonitrile; -
(2-tert-butoxy-5-methanesulfonyl-phenyl)-[4-(2-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, (2-tert-butoxy-5-methanesulfonyl-phenyl)-[4-(2,5-difluoro-4-methanesulfonyl-phenyl)-piperazin-1-yl]-methanone, 1-(4-{4-[2-(2,2-dimethyl-propoxy)-5-methanesulfonyl-benzoyl]-piperazin-1-yl}-3-fluoro-phenyl)-ethanone, 4-{4-[2-(2,2-dimethyl-propoxy)-5-methanesulfonyl-benzoyl]-piperazin-1-yl}-benzonitrile, 4-{4-[2-(2,2-dimethyl-propoxy)-5-methanesulfonyl-benzoyl]-piperazin-1-yl}-3-fluoro-benzonitrile, 4-{4-[2-(2,2-dimethyl-propoxy)-5-methanesulfonyl-benzoyl]-piperazin-1-yl}-2-fluoro-benzonitrile, [2-(2,2-dimethyl-propoxy)-5-methanesulfonyl-phenyl]-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone; [2-(2,2-dimethyl-propoxy)-5-methanesulfonyl-phenyl]-[4-(2-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, [2-(2,2-dimethyl-propoxy)-5-methanesulfonyl-phenyl]-[4-(3-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, [2-(2,2-dimethyl-propoxy)-5-methanesulfonyl-phenyl]-[4-(2-fluoro-4-ethanesulfonyl-phenyl)-piperazin-1-yl]-methanone, rac-1-{4-[4-(2-sec-butoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone; rac-4-[4-(2-sec-butoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-3-fluoro-benzonitrile, rac-4-[4-(2-sec-butoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-2-fluoro-benzonitrile, rac-(2-sec-butoxy-5-methanesulfonyl-phenyl)-[4-(2-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone,
-
-
6. A compound of formula I according to claim 3, wherein the compound is selected from the group consisting of
rac-(2-sec-butoxy-5-methanesulfonyl-phenyl)-[4-(3-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, (2-isopropoxy-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethanesulfonyl-phenyl)-piperazin-1-yl]-methanone, (2-isobutoxy-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethanesulfonyl-phenyl)-piperazin-1-yl]-methanone, 2-[4-(2-isopropoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-5-trifluoromethyl-benzonitrile, 1-{2-fluoro-4-[4-(2-isopropoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-phenyl}-ethanone, [4-(3-fluoro-4-methanesulfonyl-phenyl)-piperazin-1-yl]-(2-isobutoxy-5-methanesulfonyl-phenyl)-methanone, 1-{2-fluoro-4-[4-(2-isobutoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-phenyl}-ethanone, 2-[4-(2-isobutoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-5-trifluoromethyl-benzonitrile; -
(5-ethanesulfonyl-2-isopropoxy-phenyl)-[4-(2-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, [4-(4-difluoromethyl-2-fluoro-phenyl)-piperazin-1-yl]-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone, [4-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone, 3-fluoro-4-[4-(2-isopropoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-benzaldehyde, [4-(4-ethanesulfonyl-2-fluoro-phenyl)-piperazin-1-yl]-(2-isobutoxy-5-methanesulfonyl-phenyl)-methanone, rac-(2-sec-butoxy-5-methanesulfonyl-phenyl)-[4-(4-ethanesulfonyl-2-fluoro-phenyl)-piperazin-1-yl]-methanone, [4-(4-cyclobutanesulfonyl-2-fluoro-phenyl)-piperazin-1-yl]-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone, [4-(4-cyclopentanesulfonyl-2-fluoro-phenyl)-piperazin-1-yl]-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone, [4-(4-cyclopropanesulfonyl-2-fluoro-phenyl)-piperazin-1-yl]-(2-isobutoxy-5-methanesulfonyl-phenyl)-methanone, and [4-(4-cyclopropanesulfonyl-2,5-difluoro-phenyl)-piperazin-1-yl]-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone.
-
-
7. A compound of formula I according to claim 1, wherein Ar is substituted phenyl, R2 is (CH2)n—
- (C3-C7)-cycloalkyl and R5 is S(O)2CH3.
-
8. A compound of formula I according to claim 7, wherein the compound is selected from the group consisting of
1-{4-[4-(2-cyclopropylmethoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone, 4-[4-(2-cyclopropylmethoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-benzonitrile, 4-[4-(2-cyclopropylmethoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-3-fluoro-benzonitrile, 4-[4-(2-cyclopropylmethoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-2-fluoro-benzonitrile, (2-cyclopropylmethoxy-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, (2-cyclopropylmethoxy-5-methanesulfonyl-phenyl)-[4-(2-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, (2-cyclopropylmethoxy-5-methanesulfonyl-phenyl)-[4-(3-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, 1-{4-[4-(2-cyclopentyloxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone, 4-[4-(2-cyclopentyloxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-benzonitrile, 4-[4-(2-cyclopentyloxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-3-fluoro-benzonitrile; -
4-[4-(2-cyclopentyloxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-2-fluoro-benzonitrile, (2-cyclopentyloxy-5-methanesulfonyl-phenyl)-[4-(2-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, (2-cyclopentyloxy-5-methanesulfonyl-phenyl)-[4-(3-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, (2-cyclopentyloxy-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, Rac-[2-(1-cyclopropyl-ethoxy)-5-methanesulfonyl-phenyl]-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, 4-[4-(2-cyclopentyloxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-2,3-difluoro-benzonitrile, and 4-[4-(2-cyclopentyloxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-2,5-difluoro-benzonitrile.
-
-
9. A compound of formula I according to claim 7, wherein the compound is selected from the group consisting of
4-[4-(2-cyclobutylmethoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-benzonitrile, 4-[4-(2-cyclobutylmethoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-2-fluoro-benzonitrile, 4-[4-(2-cyclobutylmethoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-3-fluoro-benzonitrile; -
(2-cyclobutylmethoxy-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, 1-{4-[4-(2-cyclobutylmethoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone, 2-[4-(2-cyclobutylmethoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-5-trifluoromethyl-benzonitrile, 4-[4-(2-cyclobutylmethoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-2,3-difluoro-benzonitrile, 4-[4-(2-cyclobutylmethoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-2,5-difluoro-benzonitrile; 4-[4-(2-cyclobutylmethoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-3,5-difluoro-benzonitrile, 4-[4-(2-cyclobutylmethoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-2,6-difluoro-benzonitrile, 4-[4-(2-cyclopropylmethoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-3,5-difluoro-benzonitrile, 4-[4-(2-cyclopentyloxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-3,5-difluoro-benzonitrile, 4-[4-(2-cyclopropylmethoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-2,6-difluoro-benzonitrile; 4-[4-(2-cyclopentyloxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-2,6-difluoro-benzonitrile, 5-chloro-2-[4-(2-cyclopropylmethoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-benzonitrile, and 4-[4-(2-cyclohexyloxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-benzonitrile.
-
-
10. A compound of formula I according to claim 7, wherein the compound is selected from the group consisting of
4-[4-(2-cyclohexyloxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-3-fluoro-benzonitrile, 4-[4-(2-cyclohexyloxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-2-fluoro-benzonitrile, (2-cyclohexyloxy-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, (2-cyclohexyloxy-5-methanesulfonyl-phenyl)-[4-(3-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, (2-cyclohexyloxy-5-methanesulfonyl-phenyl)-[4-(2-fluoro-4-methanesulfonyl-phenyl)-piperazin-1-yl]-methanone, 1-{4-[4-(2-cyclobutoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone, 4-[4-(2-cyclobutoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-3-fluoro-benzonitrile; -
(2-cyclobutoxy-5-methanesulfonyl-phenyl)-[4-(3-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, (2-cyclopentyloxy-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethanesulfonyl-phenyl)-piperazin-1-yl]-methanone, 1-{4-[4-(2-cyclopropylmethoxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-2-fluoro-phenyl}-ethanone, 2-[4-(2-cyclopentyloxy-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-5-trifluoromethyl-benzonitrile, (2-cyclopropylmethoxy-5-methanesulfonyl-phenyl)-[4-(4-ethanesulfonyl-2-fluoro-phenyl)-piperazin-1-yl]-methanone, (2-cyclopentyloxy-5-methanesulfonyl-phenyl)-[4-(4-ethanesulfonyl-2-fluoro-phenyl)-piperazin-1-yl]-methanone, (2-cyclohexyloxy-5-methanesulfonyl-phenyl)-[4-(4-ethanesulfonyl-2-fluoro-phenyl)-piperazin-1-yl]-methanone, (2-cyclopentyloxy-5-methanesulfonyl-phenyl)-[4-(4-cyclopropanesulfonyl-2-fluoro-phenyl)-piperazin-1-yl]-methanone, (2-cyclohexyloxy-5-methanesulfonyl-phenyl)-[4-(4-cyclopropanesulfonyl-2-fluoro-phenyl)-piperazin-1-yl]-methanone, and (2-cyclobutoxy-5-methanesulfonyl-phenyl)-[4-(4-cyclopropanesulfonyl-2-fluoro-phenyl)-piperazin-1-yl]-methanone.
-
-
11. A compound of formula I according to claim 1, wherein Ar is substituted phenyl, R2 is (C1-C6)-alkyl substituted by halogen and R5 is S(O)2CH3.
-
12. A compound of formula I according to claim 11, wherein the compound is selected from the group consisting of
1-(3-fluoro-4-{4-[5-methanesulfonyl-2-(2,2,2-trifluoro-ethoxy)-benzoyl]-piperazin-1-yl}-phenyl)-ethanone, 3-fluoro-4-{4-[5-methanesulfonyl-2-(2,2,2-trifluoro-ethoxy)-benzoyl]-piperazin-1-yl}-benzonitrile, [4-(2-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-[5-methanesulfonyl-2-(2,2,2-tri-fluoro-ethoxy)-phenyl]-methanone, [4-(3-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-[5-methanesulfonyl-2-(2,2,2-tri-fluoro-ethoxy)-phenyl]-methanone, [4-(2-fluoro-4-methanesulfonyl-phenyl)-piperazin-1-yl]-[5-methanesulfonyl-2-(2,2,2-trifluoro-ethoxy)-phenyl]-methanone, 3-fluoro-4-{4-[5-methanesulfonyl-2-(3,3,3-trifluoro-propoxy)-benzoyl]-piperazin-1-yl}-benzonitrile, [4-(3-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-[5-methanesulfonyl-2-(3,3,3-trifluoro-propoxy)-phenyl]-methanone, [4-(2-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-[5-methanesulfonyl-2-(3,3,3-trifluoro-propoxy)-phenyl]-methanone, 1-(3-fluoro-4-{4-[5-methanesulfonyl-2-(3,3,3-trifluoro-propoxy)-benzoyl]-piperazin-1-yl}-phenyl)-ethanone, 2,5-difluoro-4-[4-(5-methanesulfonyl-2-trifluoromethoxy-benzoyl)-piperazin-1-yl]-benzonitrile; -
2,3-difluoro-4-{4-[2-(2-fluoro-1-fluoromethyl-ethoxy)-5-methanesulfonyl-benzoyl]-piperazin-1-yl}-benzonitrile, 2-fluoro-4-{4-[5-methanesulfonyl-2-(2,2,3,3,3-pentafluoro-propoxy)-benzoyl]-piperazin-1-yl}-benzonitrile, [5-methanesulfonyl-2-(2,2,3,3,3-pentafluoro-propoxy)-phenyl]-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, 2,3-difluoro-4-{4-[5-methanesulfonyl-2-(2,2,3,3,3-pentafluoro-propoxy)-benzoyl]-piperazin-1-yl}-benzonitrile, 3,5-difluoro-4-{4-[5-methanesulfonyl-2-(2,2,3,3,3-pentafluoro-propoxy)-benzoyl]-piperazin-1-yl}-benzonitrile, 2-{4-[2-(2-fluoro-1-fluoromethyl-ethoxy)-5-methanesulfonyl-benzoyl]-piperazin-1-yl}-5-trifluoromethyl-benzonitrile, rac-2,3-difluoro-4-{4-[5-methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-benzoyl]-piperazin-1-yl}-benzonitrile, 2-Fluoro-4-{4-[5-methanesulfonyl-2-(2,2,3,3-tetrafluoro-propoxy)-benzoyl]-piperazin-1-yl}-benzonitrile, and 3-fluoro-4-{4-[5-methanesulfonyl-2-(2,2,3,3-tetrafluoro-propoxy)-benzoyl]-piperazin-1-yl}-benzonitrile.
-
-
13. A compound of formula I according to claim 11, wherein the compound is selected from the group consisting of
[5-methanesulfonyl-2-(2,2,3,3-tetrafluoro-propoxy)-phenyl]-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, [4-(2-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-[5-methanesulfonyl-2-(2,2,3,3-tetrafluoro-propoxy)-phenyl]-methanone, 2,3-difluoro-4-{4-[5-methanesulfonyl-2-(2,2,3,3-tetrafluoro-propoxy)-benzoyl]-piperazin-1-yl}-benzonitrile, 3,5-Difluoro-4-{4-[5-methanesulfonyl-2-(2,2,3,3-tetrafluoro-propoxy)-benzoyl]-piperazin-1-yl}-benzonitrile, [4-(3,4-dichloro-phenyl)-piperazin-1-yl]-[5-methanesulfonyl-2-(2,2,2-trifluoro-ethoxy)-phenyl]-methanone, rac-5-chloro-2-{4-[5-methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-benzoyl]-piperazin-1-yl}-benzonitrile, rac-3,5-difluoro-4-{4-[5-methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-benzoyl]-piperazin-1-yl}-benzonitrile, rac-2,5-difluoro-4-{4-[5-methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-benzoyl]-piperazin-1-yl}-benzonitrile, rac-2,6-difluoro-4-{4-[5-methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-benzoyl]-piperazin-1-yl}-benzonitrile; -
rac-4-{4-[5-methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-benzoyl]-piperazin-1-yl}-benzonitrile, rac-3-fluoro-4-{4-[5-methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-benzoyl]-piperazin-1-yl}-benzonitrile, rac-2-fluoro-4-{4-[5-methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-benzoyl]-piperazin-1-yl}-benzonitrile, rac-5-methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, rac-[4-(2-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-[5-methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-methanone, rac-[4-(3-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-[5-methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-methanone, [4-(2-fluoro-4-trifluoromethyl-phenyl)-piperazin-1-yl]-[5-methanesulfonyl-2-((S or R)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-methanone, [5-methanesulfonyl-2-((S or R)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, and [5-methanesulfonyl-2-((R or S)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone.
-
-
14. A compound of formula I according to claim 1, wherein Ar is substituted phenyl, R2 is (C1-C6)-alkyl, (C1-C6)-alkyl substituted by halogen, CH2)n—
- (C3-C7)-cycloalkyl, bicycle[2.2.1]heptyl, (CH2)n—
O—
(C1-C6)-alkyl or (CH2)n-heterocycloalkyl and R5 is NO2.
- (C3-C7)-cycloalkyl, bicycle[2.2.1]heptyl, (CH2)n—
-
15. A compound of formula I according to claim 14, wherein the compound is selected from the group consisting of
1-(3-fluoro-4-{4-[2-(2-methoxy-ethoxy)-5-nitro-benzoyl]-piperazin-1-yl}-phenyl)-ethanone, (2-isopropoxy-5-nitro-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, (2-cyclopropylmethoxy-5-nitro-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, (2-cyclobutylmethoxy-5-nitro-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, (2-butoxy-5-nitro-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, [2-(2,2-dimethyl-propoxy)-5-nitro-phenyl]-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, (2-isobutoxy-5-nitro-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, (2-cyclopentyloxy-5-nitro-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone; -
(5-nitro-2-propoxy-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, (2-cyclobutoxy-5-nitro-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, Rac-(2-sec-butoxy-5-nitro-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, [5-nitro-2-(2,2,3,3-tetrafluoro-propoxy)-phenyl]-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, [5-nitro-2-(2,2,2-trifluoro-ethoxy)-phenyl]-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, [2-(bicyclo[2.2.1]hept-2-yloxy)-5-nitro-phenyl]-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, [2-(2-chloro-ethoxy)-5-nitro-phenyl]-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, and [5-nitro-2-(2,2,3,3,3-pentafluoro-propoxy)-phenyl]-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone.
-
-
16. A compound of formula I according to claim 1, wherein Ar is substituted phenyl, R2 is (C1-C6)-alkyl, (C1-C6)-alkyl substituted by halogen or (CH2)n—
- (C3-C7)-cycloalkyl and R5 is S(O)2NHCH3.
-
17. A compound of formula I according to claim 16, wherein the compound is selected from the group consisting of
3-[4-(4-Cyano-3-fluoro-phenyl)-piperazine-1-carbonyl]-N-methyl-4-trifluoromethoxy-benzenesulfonamide, 3-[4-(4-cyano-3-fluoro-phenyl)-piperazine-1-carbonyl]-4-isobutoxy-N-methyl-benzenesulfonamide, 3-[4-(4-cyano-3-fluoro-phenyl)-piperazine-1-carbonyl]-4-cyclopentyloxy-N-methyl-benzenesulfonamide, 3-[4-(4-cyano-3-fluoro-phenyl)-piperazine-1-carbonyl]-4-cyclobutoxy-N-methyl-benzenesulfonamide, 3-[4-(4-cyano-3-fluoro-phenyl)-piperazine-1-carbonyl]-4-cyclobutylmethoxy-N-methyl-benzenesulfonamide, 3-[4-(4-cyano-phenyl)-piperazine-1-carbonyl]-4-isobutoxy-N-methyl-benzenesulfonamide, 3-[4-(4-cyano-phenyl)-piperazine-1-carbonyl]-4-cyclopentyloxy-N-methyl-benzenesulfonamide, 3-[4-(4-cyano-phenyl)-piperazine-1-carbonyl]-4-cyclobutylmethoxy-N-methyl-benzenesulfonamide, 3-[4-(4-cyano-2-fluoro-phenyl)-piperazine-1-carbonyl]-4-isobutoxy-N-methyl-benzenesulfonamide, 3-[4-(4-cyano-2-fluoro-phenyl)-piperazine-1-carbonyl]-4-(2,2-dimethyl-propoxy)-N-methyl-benzenesulfonamide, 3-[4-(4-cyano-2-fluoro-phenyl)-piperazine-1-carbonyl]-4-isopropoxy-N-methyl-benzenesulfonamide; -
3-[4-(4-cyano-2-fluoro-phenyl)-piperazine-1-carbonyl]-4-cyclopentyloxy-N-methyl-benzenesulfonamide, 3-[4-(4-cyano-2-fluoro-phenyl)-piperazine-1-carbonyl]-4-cyclobutoxy-N-methyl-benzenesulfonamide, 3-[4-(4-cyano-2-fluoro-phenyl)-piperazine-1-carbonyl]-4-cyclopropylmethoxy-N-methyl-benzenesulfonamide, 3-[4-(4-cyano-2-fluoro-phenyl)-piperazine-1-carbonyl]-4-cyclobutylmethoxy-N-methyl-benzenesulfonamide, 3-[4-(4-acetyl-2-fluoro-phenyl)-piperazine-1-carbonyl]-4-isobutoxy-N-methyl-benzenesulfonamide, and 3-[4-(4-acetyl-2-fluoro-phenyl)-piperazine-1-carbonyl]-4-(2,2-dimethyl-propoxy)-N-methyl-benzenesulfonamide.
-
-
18. A compound of formula I according to claim 16, wherein the compound is selected from the group consisting of 3-[4-(4-acetyl-2-fluoro-phenyl)-piperazine-1-carbonyl]-4-cyclopentyloxy-N-methyl-benzenesulfonamide,
3-[4-(4-acetyl-2-fluoro-phenyl)-piperazine-1-carbonyl]-4-cyclobutoxy-N-methyl-benzenesulfonamide, 3-[4-(4-acetyl-2-fluoro-phenyl)-piperazine-1-carbonyl]-4-cyclopropylmethoxy-N-methyl-benzenesulfonamide, 4-isobutoxy-N-methyl-3-[4-(4-trifluoromethyl-phenyl)-piperazine-1-carbonyl]-benzenesulfonamide, 4-(2,2-dimethyl-propoxy)-N-methyl-3-[4-(4-trifluoromethyl-phenyl)-piperazine-1-carbonyl]-benzenesulfonamide; -
4-isopropoxy-N-methyl-3-[4-(4-trifluoromethyl-phenyl)-piperazine-1-carbonyl]-benzenesulfonamide, 4-cyclopentyloxy-N-methyl-3-[4-(4-trifluoromethyl-phenyl)-piperazine-1-carbonyl]-benzenesulfonamide, 4-cyclobutoxy-N-methyl-3-[4-(4-trifluoromethyl-phenyl)-piperazine-1-carbonyl]-benzenesulfonamide, 4-cyclopropylmethoxy-N-methyl-3-[4-(4-trifluoromethyl-phenyl)-piperazine-1-carbonyl]-benzenesulfonamide, 4-cyclobutylmethoxy-N-methyl-3-[4-(4-trifluoromethyl-phenyl)-piperazine-1-carbonyl]-benzenesulfonamide, N-methyl-3-[4-(4-trifluoromethyl-phenyl)-piperazine-1-carbonyl]-4-(3,3,3-trifluoro-propoxy)-benzenesulfonamide, 3-[4-(4-cyano-2-fluoro-phenyl)-piperazine-1-carbonyl]-N-methyl-4-(2,2,2-trifluoro-ethoxy)-benzenesulfonamide, N-methyl-4-(2,2,2-trifluoro-ethoxy)-3-[4-(4-trifluoromethyl-phenyl)-piperazine-1-carbonyl]-benzenesulfonamide rac-N-methyl-4-(2,2,2-trifluoro-1-methyl-ethoxy)-3-[4-(4-trifluoromethyl-phenyl)-piperazine-1-carbonyl]-benzenesulfonamide, rac-3-[4-(4-cyano-2,5-difluoro-phenyl)-piperazine-1-carbonyl]-N-methyl-4-(2,2,2-trifluoro-1-methyl-ethoxy)-benzenesulfonamide, and rac-3-[4-(4-cyano-2,3-difluoro-phenyl)-piperazine-1-carbonyl]-N-methyl-4-(2,2,2-trifluoro-1-methyl-ethoxy)-benzenesulfonamide.
-
-
3. A compound of formula I according to claim 1, wherein Ar is substituted phenyl, R2 is (C1-C6)-alkyl and R5 is S(O)2CH3 or S(O)2CH2CH3.
-
2. A compound of formula
-
19. A composition comprising one or more compounds of formula
-
20. A method of treating an illness selected from the group consisting of psychoses, pain, disfunction in memory and learning, schizophrenia, dementia, attention deficit disorders, and Alzheimer'"'"'s disease, which method comprises administering to an individual an effective amount of one or more compounds of formula
Specification
- Resources
Thank you for your request. You will receive a custom alert email when the Litigation Campaign Assessment is available.
×
-
Current AssigneeEmmanuel Pinard, Henri Stalder, Matthias Heinrich Nettekoven, Robert Narquizian, Roger David Norcross, Synese Jolidon
-
Original AssigneeEmmanuel Pinard, Henri Stalder, Matthias Heinrich Nettekoven, Robert Narquizian, Roger David Norcross, Synese Jolidon
-
InventorsStalder, Henri, Jolidon, Synese, Pinard, Emmanuel, Narquizian, Robert, Nettekoven, Matthias Heinrich, Norcross, Roger David
-
Granted Patent
-
Time in Patent OfficeDays
-
Field of Search
-
US Class Current514/255.01
-
CPC Class CodesA61P 25/00 Drugs for disorders of the ...A61P 25/04 Centrally acting analgesics...A61P 25/18 Antipsychotics, i.e. neurol...A61P 25/24 AntidepressantsA61P 25/28 for treating neurodegenerat...A61P 43/00 Drugs for specific purposes...C07D 213/85 in position 3C07D 239/42 One nitrogen atom nitro rad...C07D 241/20 Nitrogen atoms nitro radica...C07D 251/42 One nitrogen atomC07D 257/04 Five-membered ringsC07D 263/32 with only hydrogen atoms, h...C07D 271/06 1,2,4-Oxadiazoles; Hydrogen...C07D 295/192 from aromatic carboxylic acidsC07D 309/12 only hydrogen atoms and one...