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US 2010/0168105 A1Published application
Spirocyclopropyl Piperidine Derivatives
AssigneeAstrazeneca AB
InventorsPeter Bernstein, Dean Brown, Joseph Cacciola, Phil Edwards, James Folmer, Thierry Groblewski, Mark Sylvester, Steven Wesolowski
Life of this patent
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Abstract
Disclosed herein is at least one piperidine derivative, at least one pharmaceutical composition comprising at least one piperidine derivative disclosed herein for treating at least one histamine H3 receptor associated condition therewith
Claims20
A compound of formula I, enantiomers thereof, pharmaceutically acceptable salts thereof, or mixtures thereof:
- wherein:
- R1 is aryl, heteroaryl, arylalkyl, heteroarylalkyl, cycloalkyl, heterocycloalkylalkyl, alkyl, alkoxyalkyl, hydroxyalkyl, aminoalkyl, aminocarbonylalkyl, heterocycle, arylalkenyl, or heterocycloalkyl;
- wherein R1 is optionally substituted with at least one substituent selected independently from alkyl, cyano, sulfinyl, haloalkyl, amide, alkoxy, halogen, arylalkoxy, alkylcarbonyl, carboxy (—C(═O)OH), hydroxy (—OH), amino, alkoxycarbonyl, and alkylsulfonyl;
- and
- R2 is aryl, heteroaryl, cycloalkyl, alkyl, heterocycloalkyl, or cycloalkylalkyl;
- wherein R2 is optionally substituted with at least one substituent selected independently from C1-C6alkyl, alkoxy, and cycloalkyl;
- with the provisos that:
- 1) when R2 is a cyclohexyl, R1 is not a substituted or unsubstituted phenyl;
- 2) when R2 is aryl, R2 is not unsubstituted phenyl;
- and
- 3) when R1 is tetrahydropyran-4-yl and R2 is a substituted phenyl, the substituted phenyl is not ortho- or meta-substituted with methyl or meta-substituted with methoxy.
8 more elements
A compound selected from:
- (4-Cyclohexyl-piperazin-1-yl)-[6-(tetrahydro-pyran-4-yl)-6-aza-spiro[2.5]oct-1-yl]-methanone;
- (4-Cyclohexylmethyl-piperazin-1-yl)-[6-(tetrahydro-pyran-4-yl)-6-aza-spiro[2.5]oct-1-yl]-methanone;
- [6-(2-Ethyl-butyl)-6-aza-spiro[2.5]oct-1-yl]-(4-methyl-piperazin-1-yl)-methanone;
- (4-Methyl-piperazin-1-yl)-[6-((E)-3-phenyl-allyl)-6-aza-spiro[2.5]oct-1-yl]-methanone;
- (4-Methyl-piperazin-1-yl)-(6-phenethyl-6-aza-spiro[2.5]oct-1-yl)-methanone;
- (4-Methyl-piperazin-1-yl)-[6-(1-methyl-piperidin-4-yl)-6-aza-spiro[2.5]oct-1-yl]-methanone;
- (4-Methyl-piperazin-1-yl)-[6-(tetrahydro-pyran-4-yl)-6-aza-spiro[2.5]oct-1-yl]-methanone;
- (4-Cyclobutylpiperazin-1-yl)(6-(tetrahydro-2H-pyran-4-yl)-6-azaspiro[2.5]octan-1-yl)methanone;
- (4-Cyclopropylpiperazin-1-yl)(6-(tetrahydro-2H-pyran-4-yl)-6-azaspiro[2.5]octan-1-yl)methanone;
- (4-Isopropylpiperazin-1-yl)(6-(tetrahydro-2H-pyran-4-yl)-6-azaspiro[2.5]octan-1-yl)methanone;
- (4-Cycloheptylpiperazin-1-yl)(6-(tetrahydro-2H-pyran-4-yl)-6-azaspiro[2.5]octan-1-yl)methanone;
- (4-cyclopentylpiperazin-1-yl)(6-(tetrahydro-2H-pyran-4-yl)-6-azaspiro[2.5]octan-1-yl)methanone;
- 4-Pyridin-2-yl-piperazin-1-yl)-[6-(tetrahydro-pyran-4-yl)-6-aza-spiro[2.5]oct-1-yl]-methanone;
- (4-Pyridin-4-yl-piperazin-1-yl)-[6-(tetrahydro-pyran-4-yl)-6-aza-spiro[2.5]oct-1-yl]-methanone;
- [4-(4-Methoxy-phenyl)-piperazin-1-yl]-[6-(tetrahydro-pyran-4-yl)-6-aza-spiro[2.5]oct-1-yl]-methanone;
- (4-Cyclohexyl-piperazin-1-yl)-(6-phenethyl-6-aza-spiro[2.5]oct-1-yl)-methanone;
- (6-Cyclohexyl-6-aza-spiro[2.5]oct-1-yl)-(4-cyclohexyl-piperazin-1-yl)-methanone;
- (4-Cyclohexyl-piperazin-1-yl)-[6-(1-methyl-piperidin-4-yl)-6-aza-spiro[2.5]oct-1-yl]-methanone;
- (4-Cyclohexyl-piperazin-1-yl)-(6-isopropyl-6-aza-spiro[2.5]oct-1-yl)-methanone;
- (6-Cyclobutyl-6-aza-spiro[2.5]oct-1-yl)-[4-(tetrahydro-pyran-4-yl)-piperazin-1-yl]-methanone;
- (6-Benzyl-6-aza-spiro[2.5]oct-1-yl)-(4-cyclohexyl-piperazin-1-yl)-methanone;
- [6-(Tetrahydro-pyran-4-yl)-6-aza-spiro[2.5]oct-1-yl]-[4-(tetrahydro-pyran-4-yl)-piperazin-1-yl]-methanone;
- [6-(2-Benzyloxy-ethyl)-6-aza-spiro[2.5]oct-1-yl]-(4-cyclohexyl-piperazin-1-yl)-methanone;
- (4-Cyclobutyl-piperazin-1-yl)-[6-(tetrahydro-thiopyran-3-yl)-6-aza-spiro[2.5]oct-1-yl]-methanone;
- (4-Cyclobutyl-piperazin-1-yl)-(6-cyclohexyl-6-aza-spiro[2.5]oct-1-yl)-methanone;
- (4-Cyclobutyl-piperazin-1-yl)-[6-(tetrahydro-pyran-3-yl)-6-aza-spiro[2.5]oct-1-yl]-methanone;
- (4-Cyclobutyl-piperazin-1-yl)-[6-(tetrahydro-furan-3-yl)-6-aza-spiro[2.5]oct-1-yl]-methanone;
- (4-Cyclobutyl-piperazin-1-yl)-[6-(2-morpholin-4-yl-ethyl)-6-aza-spiro[2.5]oct-1-yl]-methanone;
- (4-Cyclohexyl-piperazin-1-yl)-(6-pyridin-4-yl-6-aza-spiro[2.5]oct-1-yl)-methanone;
- [1-(4-Cyclobutyl-piperazine-1-carbonyl)-6-aza-spiro[2.5]oct-6-yl]-acetic acid tert-butyl ester;
- 2-[1-(4-Cyclobutyl-piperazine-1-carbonyl)-6-aza-spiro[2.5]oct-6-yl]-N-methyl-acetamide;
- (4-Cyclobutyl-piperazin-1-yl)-[6-(4-methanesulfonyl-phenyl)-6-aza-spiro[2.5]oct-1-yl]-methanone;
- (4-Cyclobutyl-piperazin-1-yl)-[6-(4-methoxy-phenyl)-6-aza-spiro[2.5]oct-1-yl]-methanone;
- 4-[1-(4-Cyclobutyl-piperazine-1-carbonyl)-6-aza-spiro[2.5]oct-6-yl]-benzoic acid methyl ester;
- (4-Cyclobutyl-piperazin-1-yl)[6-(6-methoxy-pyridin-2-yl)-6-aza-spiro[2.5]oct-1-yl]-methanone;
- [6-(6-Chloro-pyridin-2-yl)-6-aza-spiro[2.5]oct-1-yl]-(4-cyclobutyl-piperazin-1-yl)-methanone;
- (4-Cyclohexyl-piperazin-1-yl)-[6-(2-methoxy-ethyl)-6-aza-spiro[2.5]oct-1-yl]-methanone;
- (4-Cyclobutyl-piperazin-1-yl)-(6-pyridin-2-yl-6-aza-spiro[2.5]oct-1-yl)-methanone;
- (4-Cyclobutyl-piperazin-1-yl)-(6-p-tolyl-6-aza-spiro[2.5]oct-1-yl)-methanone;
- 4-Cyclohexyl-piperazin-1-yl)-[6-(5-trifluoromethyl-pyridin-2-yl)-6-aza-spiro[2.5]oct-1-yl]-methanone;
- (6-Benzo[1,3]dioxol-5-yl-6-aza-spiro[2.5]oct-1-yl)-(4-cyclohexyl-piperazin-1-yl)-methanone;
- (4-(pyridin-3-yl)piperazin-1-yl)(6-(tetrahydro-2H-pyran-4-yl)-6-azaspiro[2.5]octan-1-yl)methanone;
- (4-(2-methylpyridin-4-yl)piperazin-1-yl)(6-(tetrahydro-2H-pyran-4-yl)-6-azaspiro[2.5]octan-1-yl)methanone;
- and
- (4-(3-methylpyridin-4-yl)piperazin-1-yl)(6-(tetrahydro-2H-pyran-4-yl)-6-azaspiro[2.5]octan-1-yl)methanone;
- and
- enantiomers thereof, pharmaceutically acceptable salts thereof, or mixtures thereof.
44 more elements
11-13. (canceled)
(canceled)
Dependencies are inferred from the claim text.