DIAMINOPYRIMIDINE DERIVATIVES AND PROCESSES FOR THE PREPARATION THEREOF
First Claim
1. A compound of Formula 1 or its pharmaceutically acceptable salt:
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Abstract
The present invention provides a diaminopyrimidine derivative or its pharmaceutically acceptable salt, a process for the preparation thereof, a pharmaceutical composition comprising the same, and a use thereof. The diaminopyrimidine derivative or its pharmaceutically acceptable salt functions as a 5-HT4 receptor agonist, and therefore can be usefully applied for preventing or treating dysfunction in gastrointestinal motility, one of the gastrointestinal diseases, such as gastroesophageal reflux disease (GERD), constipation, irritable bowel syndrome (IBS), dyspepsia, post-operative ileus, delayed gastric emptying, gastroparesis, intestinal pseudo-obstruction, drug-induced delayed transit, or diabetic gastric atony.
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Citations
5 Claims
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1. A compound of Formula 1 or its pharmaceutically acceptable salt:
- View Dependent Claims (2, 3)
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2. The compound or its pharmaceutically acceptable salt of claim 1, wherein
R1 is a phenyl group substituted with one or more substituents selected from the group consisting of hydroxy, amino, halogen, cyano, nitro, hydroxycarbonyl, C1-3 alkyl (where the C1-3 alkyl is optionally substituted with halogen or amino), C2-6 alkenyl, C2-6 alkynyl, C1-5 alkoxy (where the C1-5 alkoxy is optionally substituted with halogen), C1-5 alkylthio, mono- or di-C1-5 alkylamino, C1-5 alkylsulfonylamino, C1-5 alkylcarbonylamino, C1-5 alkoxycarbonyl, aminosulfonyl, aminocarbonyl, C1-5 alkylaminocarbonyl, and benzyloxycarbonylamino; - or
a heteroaryl group selected from the group consisting of pyridinyl, pyrimidinyl, pyrazinyl, imidazolyl, pyrazolyl, triazolyl, oxazolyl, thiazolyl, furanyl, pyrrolyl, thiophenyl, naphthyl, indanyl, quinolinyl, quinolinonyl, chromenonyl, dihydroindolonyl, isoindoline-1,3-dionyl, dihydrobenzimidazolonyl, benzoxazolonyl, benzofuranyl, benzothiophenyl, benzo[d][1,3]dioxolyl, dihydrobenzo[1,4]dioxinyl, indolyl, indolinyl, benzimidazol-4-yl, benzimidazol-5-yl, benzimidazol-6-yl, benzimidazol-7-yl, benzoxazolyl, benzothiazolyl, and indazolyl, wherein the heteroaryl group may be optionally substituted with one or more substituents selected from the group consisting of amino, di-C1-5 alkylamino, cyano, nitro, halogen, C1-5 alkyl (where the C1-5 alkyl is optionally substituted with halogen), C1-5 alkoxy (where the C1-5 alkoxy is optionally substituted with halogen), acetyl, and C1-5alkylsulfonyl, R2 is the nitrogen-containing cyclic group of Formula B, R3 is a C2-5 alkyl group, R4 is hydrogen;
a C1-5 alkyl group optionally substituted with a substituent selected from the group consisting of hydroxy, C1-5 alkoxy, benzylamino (where the benzylamino is optionally substituted with halogen), phenylamino, C1-5 alkylamino, C3-6 cycloalkylamino, pyrrolidinyl, and hydroxy-C1-5 alkylamino;
a C1-5 alkoxycarbonyl group;
or an aminocarbonyl group,R5 is hydrogen;
a hydroxyl group;
a C1-5 alkoxy group;
a phenoxy group;
a benzyloxy group;
a C1-5 alkyl group optionally substituted with a substituent selected from the group consisting of amino, C1-5 alkoxycarbonylamino, and mono- or di-C1-5 alkylamino;
or a group selected from the group consisting of the Formulas E to I,R6, R7, and R10 are hydrogen, X is —
CH(R7)—
;
—
N(R8)—
;
or —
O—
,R4 and R5 are optionally joined to each other to form a pentagonal or hexagonal ring, R8 is hydrogen;
or a C1-5 alkyl group,R9 is a C1-10 alkyl group optionally substituted with a substituent selected from the group consisting of hydroxy, halogen, C1-5 alkoxy, amino, C1-5 alkoxycarbonylamino, benzyloxycarbonylamino, mono- or di-C1-5 alkylamino, C1-5 alkoxy-C1-5 alkyloxy, phenoxy, benzyloxy, phenyl (where the phenyl is optionally substituted with one or more substituents selected from the group consisting of halogen, amino, C1-5 alkoxy, and hydroxy), thiophenyl, pyridinyl, indolyl, pyrimidinyl, pyrazinyl, imidazolyl, pyrazolyl, triazolyl, oxazolyl, thiazolyl, furanyl, pyrrolyl, piperidinyl, piperazinyl (where the piperazinyl is optionally substituted with benzyl), C3-6 cycloalkyl, acetyl, and benzoyl;
a C3-6 cycloalkyl group;
a piperidinyl group optionally substituted with C1-5 alkoxycarbonyl;
a C1-10 alkenyl group optionally substituted with phenyl;
a trifluoromethyl group;
a trifluoroethyl group;
or a phenyl group optionally substituted with halogen,R11 and R12 are, independently each other, hydrogen;
a C1-10 alkyl group optionally substituted with a substituent selected from the group consisting of amino, C1-5 alkoxycarbonylamino, hydroxy, C1-5 alkylthio, C3-10 cycloalkyl, phenyl (where the phenyl is optionally substituted with one or more substituents selected from the group consisting of hydroxy, C1-5 alkyl, mono- or di-C1-5 alkylamino, trifluoromethyl, halogen, C1-5 alkoxy, and C1-5 alkylcarbonyloxy), thiophenyl, pyrrolyl, furanyl (where the furanyl is optionally substituted with mono- or di-C1-5 alkyl), pyridinyl, pyrimidinyl, pyrazinyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, thiazolyl, and benzyloxy;
a piperidinyl group optionally substituted with benzyl, benzoyl, C1-5 alkyl, or C1-5 alkylcarbonyl;
an azetidinyl group optionally substituted with C1-5 alkoxycarbonyl;
a C1-5 alkylsulfonyl group;
a phenylsulfonyl group (where the phenyl moiety is optionally substituted with halogen);
or a C3-10 cycloalkyl group.
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3. The compound or its pharmaceutically acceptable salt of claim 1, which is selected from the group consisting of:
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N-(4-fluorophenyl)-4-(piperidin-1-yl)-6-propylpyrimidin-2-amine; N-(4-fluorophenyl)-4-morpholino-6-propylpyrimidin-2-amine; 4-(azepan-1-yl)-N-(4-fluorophenyl)-6-propylpyrimidin-2-amine; N-(4-fluorophenyl)-4-(2-methylpiperidin-1-yl)-6-propylpyrimidin-2-amine; N-(4-fluorophenyl)-4-(3-methylpiperidin-1-yl)-6-propylpyrimidin-2-amine; N-(4-fluorophenyl)-4-propyl-6-thiomorpholinopyrimidin-2-amine; 4-(2,5-dimethylpiperazin-1-yl)-N-(4-fluorophenyl)-6-propylpyrimidin-2-amine; 4-(5,6-dihydropyridin-1(2H)-yl)-N-(4-fluorophenyl)-6-propylpyrimidin-2-amine; N-(4-fluorophenyl)-4-(decahydroquinolin-1(2H)-yl)-6-propylpyrimidin-2-amine; N-(4-fluorophenyl)-4-[decahydroisoquinolin-1(2H)-yl]-6-propylpyrimidin-2-amine; N-(4-fluorophenyl)-4-(4-phenylpiperidin-1-yl)-6-propylpyrimidin-2-amine; N-(4-fluorophenyl)-4-(piperazin-1-yl)-6-propylpyrimidin-2-amine; 4-(2-ethylpiperidin-1-yl)-N-(4-fluorophenyl)-6-propylpyrimidin-2-amine; 2-{1-[2-(4-fluorophenylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; ethyl 1-[2-(4-fluorophenylamino)-6-propylpyrimidin-4-yl]piperidin-2-carboxylate; 1-[2-(4-fluorophenylamino)-6-propylpyrimidin-4-yl]piperidin-4-carboxamide; {1-[2-(4-fluorophenylamino)-6-propylpyrimidin-4-yl]piperidin-4-yl}methanol; 1-[2-(4-fluorophenylamino)-6-propylpyrimidin-4-yl]piperidin-4-one; 4-butyl-N-(4-fluorophenyl)-6-(piperidin-1-yl)pyrimidin-2-amine; 4-butyl-6-(2-ethylpiperidin-1-yl)-N-(4-fluorophenyl)pyrimidin-2-amine; 2-{1-[6-butyl-2-(4-fluorophenylamino)pyrimidin-4-yl]piperidin-2-yl}ethanol; 4-butyl-N-(4-fluorophenyl)-6-morpholinopyrimidin-2-amine; 2-{1-[2-(4-chloro-3-nitrophenylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; 2-(1-{2-[3-(methylthio)phenylamino]-6-propylpyrimidin-4-yl}piperidin-2-yl)ethanol; 4-(2,6-dimethylmorpholino)-N-(4-fluorophenyl)-6-propylpyrimidin-2-amine; 8-[2-(4-fluorophenylamino)-6-propylpyrimidin-4-yl]-8-azabicyclo[3.2.1]octan-3-ol; N-{1-[2-(4-fluorophenylamino)-6-propylpyrimidin-4-yl]piperidin-3-yl}acetamide; N-(4-fluorophenyl)-4-{4-[3-(piperidin-4-yl)propyl]piperidin-1-yl}-6-propylpyrimidin-2-amine; 4-[3-(benzyloxy)piperidin-1-yl]-N-(4-fluorophenyl)-6-propylpyrimidin-2-amine; 4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-N-(4-fluorophenyl)-6-propylpyrimidin-2-amine; N-[4-(piperidin-1-yl)-6-propylpyrimidin-2-yl]-1-H-indol-5-amine; N-(3-chloro-4-methylphenyl)-4-(piperidin-1-yl)-6-propylpyrimidin-2-amine; N-[4-(piperidin-1-yl)-6-propylpyrimidin-2-yl]quinolin-6-amine; 4-(piperidin-1-yl)-6-propyl-N-[3-(trifluoromethyl)phenyl]pyrimidin-2-amine; N-[4-(piperidin-1-yl)-6-propylpyrimidin-2-yl]-2-(trifluoromethyl)-1H-benzo[d]imidazol-5-amine; N-[3-(methylthio)phenyl]-4-(piperidin-1-yl)-6-propylpyrimidin-2-amine; N-(5-methoxy-2-methylphenyl)-4-(piperidin-1-yl)-6-propylpyrimidin-2-amine; N-(5-chloro-2-methylphenyl)-4-(piperidin-1-yl)-6-propylpyrimidin-2-amine; N-(4-fluoro-3-nitrophenyl)-4-(piperidin-1-yl)-6-propylpyrimidin-2-amine; N-(4-methoxyphenyl)-4-(piperidin-1-yl)-6-propylpyrimidin-2-amine; N-(3-methoxyphenyl)-4-(piperidin-1-yl)-6-propylpyrimidin-2-amine; N-(3-chlorophenyl)-4-(piperidin-1-yl)-6-propylpyrimidin-2-amine; N-(3-nitrophenyl)-4-(piperidin-1-yl)-6-propylpyrimidin-2-amine; N-(4-chloro-3-nitrophenyl)-4-(piperidin-1-yl)-6-propylpyrimidin-2-amine; 3-[4-(piperidin-1-yl)-6-propylpyrimidin-2-ylamino]benzonitrile; N-(4-methyl-3-nitrophenyl)-4-(piperidin-1-yl)-6-propylpyrimidin-2-amine; 4-(4-ethylpiperazin-1-yl)-N-(4-fluorophenyl)-6-methylpyrimidin-2-amine; N-(4-fluorophenyl)-4-[4-(4-methoxyphenyl)piperazin-1-yl]-6-methylpyrimidin-2-amine; N-(4-fluorophenyl)-4-[4-(4-fluorophenyl)piperazin-1-yl]-6-methylpyrimidin-2-amine; N-(4-fluorophenyl)-4-methyl-6-(morpholin-4-yl)pyrimidin-2-amine; 1-[2-(4-fluorophenylamino)-6-methylpyrimidin-4-yl]piperidin-4-one; N-(4-fluorophenyl)-4-methyl-6-(piperidin-1-yl)pyrimidin-2-amine; 4-(azetidin-1-yl)-N-(4-fluorophenyl)-6-methylpyrimidin-2-amine; 1-[2-(4-fluorophenylamino)-6-methylpyrimidin-4-yl]piperidin-3-ol; 1-[2-(4-fluorophenylamino)-6-methylpyrimidin-4-yl]piperidin-4-ol; N-(4-fluorophenyl)-4-methyl-6-(2-methylpiperidin-1-yl)pyrimidin-2-amine; N-(4-fluorophenyl)-4-methyl-6-(3-methylpiperidin-1-yl)pyrimidin-2-amine; 4-(3,5-cis-dimethylpiperidin-1-yl)-N-(4-fluorophenyl)-6-methylpyrimidin-2-amine; 4-(azepan-1-yl)-N-(4-fluorophenyl)-6-methylpyrimidin-2-amine; 4-(2-ethylpiperidin-1-yl)-N-(4-fluorophenyl)-6-methylpyrimidin-2-amine; 4-((2R,6S)-2,6-dimethylpiperidin-1-yl)-N-(4-fluorophenyl)-6-methylpyrimidin-2-amine; N-(4-fluorophenyl)-4-methyl-6-(4-phenylpiperidin-1-yl)pyrimidin-2-amine; N-(4-fluorophenyl)-4-methyl-6-(piperazin-1-yl)pyrimidin-2-amine; N-(4-fluorophenyl)-4-methyl-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine; 4-(2,5-dimethylpiperazin-1-yl)-N-(4-fluorophenyl)-6-methylpyrimidin-2-amine; 4-(3,5-dimethylpiperazin-1-yl)-N-(4-fluorophenyl)-6-methylpyrimidin-2-amine; N-(4-fluorophenyl)-4-methyl-6-(octahydroquinolin-1(2H)-yl)pyrimidin-2-amine; N-(4-fluorophenyl)-4-methyl-6-(octahydroisoquinolin-2(1H)-yl)pyrimidin-2-amine; 4-(5,6-dihydropyridin-1(2H)-yl)-N-(4-fluorophenyl)-6-methylpyrimidin-2-amine; 2-{1-[2-(4-fluorophenylamino)-6-methylpyrimidin-4-yl]piperidin-2-yl}ethanol; 2-{1-[2-(4-fluorophenylamino)-6-methylpyrimidin-4-yl]piperidin-2-yl}methanol; N-[4-(octahydroquinolin-1(2H)-yl)-6-propylpyrimidin-2-yl]-1H-indol-6-amine; 2-{1-[2-(1H-indol-6-ylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; N-[4-(piperidin-1-yl)-6-propylpyrimidin-2-yl]-1H-indol-6-amine; N-(4-morpholino-6-propylpyrimidin-2-yl)-1H-indol-6-amine; N-[4-(2-ethylpiperidin-1-yl)-6-propylpyrimidin-2-yl]-1H-indol-6-amine; (R)-3-[4-(3-ethylmorpholino)-6-propylpyrimidin-2-ylamino]benzonitrile; (R)-tert-butyl 4-[2-(3-cyanophenylamino)-6-propylpyrimidin-4-yl]-3-methylpiperazin-1-carboxylate; (R)-3-[4-(2-methylpiperazin-1-yl)-6-propylpyrimidin-2-ylamino]benzonitrile; 4-morpholino-N-(3-nitrophenyl)-6-propylpyrimidin-2-amine; N-(4-fluoro-3-nitrophenyl)-4-morpholino-6-propylpyrimidin-2-amine; N-(4-chloro-3-nitrophenyl)-4-morpholino-6-propylpyrimidin-2-amine; N-(3-methoxyphenyl)-4-morpholino-6-propylpyrimidin-2-amine; N-(4-methoxyphenyl)-4-morpholino-6-propylpyrimidin-2-amine; N-[3-(methylthio)phenyl]-4-morpholino-6-propylpyrimidin-2-amine; N-(3-chlorophenyl)-4-morpholino-6-propylpyrimidin-2-amine; N-(3-chloro-4-methylphenyl)-4-morpholino-6-propylpyrimidin-2-amine; 4-morpholino-6-propyl-N-[3-(trifluoromethyl)phenyl]pyrimidin-2-amine; N-(4-morpholino-6-propylpyrimidin-2-yl)-1H-indol-5-amine; N-(4-morpholino-6-propylpyrimidin-2-yl)-2-(trifluoromethyl)-1H-benzo[d]imidazol-6-amine; N-(4-morpholino-6-propylpyrimidin-2-yl)quinolin-6-amine; 3-(4-morpholino-6-propylpyrimidin-2-ylamino)benzonitrile; N-(5-methoxy-2-methylphenyl)-4-morpholino-6-propylpyrimidin-2-amine; N-(5-chloro-2-methylphenyl)-4-morpholino-6-propylpyrimidin-2-amine; N-(4-morpholino-6-propylpyrimidin-2-yl)quinolin-3-amine; 4-(2-ethylpiperidin-1-yl)-N-(3-nitrophenyl)-6-propylpyrimidin-2-amine; 4-(2-ethylpiperidin-1-yl)-N-(4-fluoro-3-nitrophenyl)-6-propylpyrimidin-2-amine; N-(4-chloro-3-nitrophenyl)-4-(2-ethylpiperidin-1-yl)-6-propylpyrimidin-2-amine; 4-(2-ethylpiperidin-1-yl)-N-(3-methoxyphenyl)-6-propylpyrimidin-2-amine; 4-(2-ethylpiperidin-1-yl)-N-(4-methoxyphenyl)-6-propylpyrimidin-2-amine; 4-(2-ethylpiperidin-1-yl)-N-[3-(methylthio)phenyl]-6-propylpyrimidin-2-amine; N-(3-chlorophenyl)-4-(2-ethylpiperidin-1-yl)-6-propylpyrimidin-2-amine; N-(3-chloro-4-methylphenyl)-4-(2-ethylpiperidin-1-yl)-6-propylpyrimidin-2-amine; 4-(2-ethylpiperidin-1-yl)-6-propyl-N-[3-(trifluoromethyl)phenyl]pyrimidin-2-amine; N-[4-(2-ethylpiperidin-1-yl)-6-propylpyrimidin-2-yl]-1H-indol-5-amine; N-[4-(2-ethylpiperidin-1-yl)-6-propylpyrimidin-2-yl]-2-(trifluoromethyl)-1H-benzo[d]imidazol-6-amine; N-[4-(2-ethylpiperidin-1-yl)-6-propylpyrimidin-2-yl]quinolin-6-amine; 3-[4-(2-ethylpiperidin-1-yl)-6-propylpyrimidin-2-ylamino]benzonitrile; 4-(2-ethylpiperidin-1-yl)-N-(5-methoxy-2-methylphenyl)-6-propylpyrimidin-2-amine; N-(5-chloro-2-methylphenyl)-4-(2-ethylpiperidin-1-yl)-6-propylpyrimidin-2-amine; N-[4-(2-ethylpiperidin-1-yl)-6-propylpyrimidin-2-yl]quinolin-3-amine; (R)—
N-(4-chloro-3-nitrophenyl)-4-(2-methylpiperazin-1-yl)-6-propylpyrimidin-2-amine;(R)—
N-[4-(2-methylpiperazin-1-yl)-6-propylpyrimidin-2-yl]-1-H-indol-6-amine;(R)—
N-(2-methylpiperazin-1-yl)-6-propyl-N-[3-(trifluoromethyl)phenyl]pyrimidin-2-amine;(R)—
N-(2-methylpiperazin-1-yl)-N-(3-nitrophenyl)-6-propylpyrimidin-2-amine;(R)—
N-(4-fluoro-3-nitrophenyl)-4-(2-methylpiperazin-1-yl)-6-propylpyrimidin-2-amine;(R)—
N-(4-methyl-3-nitrophenyl)-4-(2-methylpiperazin-1-yl)-6-propylpyrimidin-2-amine;(R)-4-fluoro-N1-[4-(2-methylpiperazin-1-yl)-6-propylpyrimidin-2-yl]benzene-1,3-diamine; (R)—
N1-[4-(2-methylpiperazin-1-yl)-6-propylpyrimidin-2-yl]-3-(trifluoromethyl)benzene-1,4-diamine;(R)-2-fluoro-5-[4-(2-methylpiperazin-1-yl)-6-propylpyrimidin-2-ylamino]benzonitrile; (R)-2-methyl-5-[4-(2-methylpiperazin-1-yl)-6-propylpyrimidin-2-ylamino]benzonitrile; (R)-2-amino-5-[4-(2-methylpiperazin-1-yl)-6-propylpyrimidin-2-ylamino]benzonitrile; (R)—
N1-[4-(2-methylpiperazin-1-yl)-6-propylpyrimidin-2-yl]-3-nitrobenzene-1,4-diamine;(R)-3-amino-5-[4-(2-methylpiperazin-1-yl)-6-propylpyrimidin-2-ylamino]benzonitrile; (R)-3-[4-(2-methylpiperazin-1-yl)-6-propylpyrimidin-2-ylamino]benzamide; 3-{4-[2-(2-hydroxyethyl)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}benzonitrile; 2-{1-[2-(1-ethyl-1H-indol-6-ylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; 2-{1-[2-(1H-indol-5-ylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; 2-(1-{6-propyl-2-[2-(trifluoromethyl)-1H-benzo[d]imidazol-6-ylamino]pyrimidin-4-yl}piperidin-2-yl)ethanol; 2-{1-[2-(4-methoxyphenylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; 2-{1-[2-(3-methoxyphenylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; 2-{1-[2-(5-methoxy-2-methylphenylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; 2-{1-[2-(3-chloro-4-methylphenylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; 2-{1-[2-(3-nitrophenylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; 2-{1-[2-(4-fluoro-3-nitrophenylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; 2-{1-[2-(2,3-dimethylbenzofuran-5-ylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; 2-{1-[6-propyl-2-(quinolin-6-ylamino)pyrimidin-4-yl]piperidin-2-yl}ethanol; 2-{1-[2-(3-chlorophenylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; 7-{4-[2-(2-hydroxyethyl)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}-4-methyl-2H-chromen-2-one; 2-{1-[6-propyl-2-(3-trifluoromethylphenylamino)pyrimidin-4-yl]piperidin-2-yl}ethanol; 2-{1-[6-propyl-2-(quinolin-3-ylamino)pyrimidin-4-yl]piperidin-2-yl}ethanol; (S)-5-[4-(3-aminopiperidin-1-yl)-6-propylpyrimidin-2-ylamino]-2-methylbenzonitrile; (S)-4-(3-aminopiperidin-1-yl)-N-(3-nitrophenyl)-6-propylpyrimidin-2-amine; (S)-3-[4-(3-aminopiperidin-1-yl)-6-propylpyrimidin-2-ylamino]benzonitrile; (R)-5-[4-(3-aminopiperidin-1-yl)-6-propylpyrimidin-2-ylamino]-2-methylbenzonitrile; (S)-5-{4-[3-(butylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}-2-methylbenzonitrile; (S)-5-{4-[3-(pentylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}-2-methylbenzonitrile; (S)-5-{4-[3-(isobutylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}-2-methylbenzonitrile; (S)-5-{4-[3-(isopentylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}-2-methylbenzonitrile; (S)-2-methyl-5-{4-[3-(neopentylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}benzonitrile; (S)-5-(4-{3-[(1H-pyrrol-2-yl)methylamino]piperidin-1-yl}-6-propylpyrimidin-2-ylamino)-2-methylbenzonitrile; (S)-2-methyl-5-(4-propyl-6-{3-[(thiophen-2-ylmethyl)amino]piperidin-1-yl}pyrimidin-2-ylamino)benzonitrile; (S)-5-(4-{3-[(4,5-dimethylfuran-2-ylmethyl)amino]piperidin-1-yl}-6-propylpyrimidin-2-ylamino)-2-methylbenzonitrile; (S)-2-methyl-5-{4-[3-(3-methylthiopropylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}benzonitrile; (S)-5-{4-[3-(cyclopropylmethylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}-2-methylbenzonitrile; (S)-5-{4-[3-(4-hydroxybenzylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}-2-methylbenzonitrile; (S)-5-[4-(3-diethylaminopiperidin-1-yl)-6-propylpyrimidin-2-ylamino]-2-methylbenzonitrile; (S)-5-(4-{3-[bis(cyclopropylmethyl)amino]piperidin-1-yl}-6-propylpyrimidin-2-ylamino)-2-methylbenzonitrile; (R)-5-(4-{3-[bis(cyclopropylmethyl)amino]piperidin-1-yl}-6-propylpyrimidin-2-ylamino)-2-methylbenzonitrile; 4-ethyl-N-(4-fluorophenyl)-6-(piperidin-1-yl)pyrimidin-2-amine; 4-ethyl-N-(4-fluorophenyl)-6-(octahydroquinolin-1(2H)-yl)pyrimidin-2-amine; 4-ethyl-6-(2-ethylpiperidin-1-yl)-N-(4-fluorophenyl)pyrimidin-2-amine; 2-{1-[6-ethyl-2-(4-fluorophenylamino)pyrimidin-4-yl]piperidin-2-yl}ethanol; 4-ethyl-N-(4-fluorophenyl)-6-morpholinopyrimidin-2-amine; 2-{1-[2-(4-methyl-3-nitrophenylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; 2-{1-[2-(4-amino-3-trifluoromethylphenylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; 2-{1-[2-(4-amino-3-nitrophenylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; 5-{4-[2-(2-hydroxyethyl)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}-2-methylbenzonitrile; 2-fluoro-5-{4-[2-(2-hydroxyethyl)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}benzonitrile; 2-amino-5-{4-[2-(2-hydroxyethyl)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}benzonitrile; 2-{1-[2-(3-amino-4-methylphenylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; 2-{1-[2-(3-amino-4-fluorophenylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; 2-{1-[2-(3-amino-4-chlorophenylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; 2-{1-[2-(indolin-6-ylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; (S)-2-{1-[2-(4-chloro-3-nitrophenylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; (S)-2-{1-[2-(4-amino-3-nitrophenylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; (R)-2-{1-[2-(4-amino-3-nitrophenylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl}ethanol; 3-[4-(octahydroquinolin-1(2H)-yl)-6-propylpyrimidin-2-ylamino]benzonitrile; N-(3-nitrophenyl)-4-(octahydroquinolin-1(2H)-yl)-6-propylpyrimidin-2-amine; N-(4-fluoro-3-nitrophenyl)-4-(octahydroquinolin-1(2H)-yl)-6-propylpyrimidin-2-amine; N-(4-chloro-3-nitrophenyl)-4-(octahydroquinolin-1(2H)-yl)-6-propylpyrimidin-2-amine; N-(3-methoxyphenyl)-4-(octahydroquinolin-1(2H)-yl)-6-propylpyrimidin-2-amine; N-(5-methoxy-2-methylphenyl)-4-(octahydroquinolin-1(2H)-yl)-6-propylpyrimidin-2-amine; N-(4-methoxyphenyl)-4-(octahydroquinolin-1(2H)-yl)-6-propylpyrimidin-2-amine; 4-(octahydroquinolin-1(2H)-yl)-6-propyl-N-(3-trifluoromethylphenyl)pyrimidin-2-amine; N-(3-chlorophenyl)-4-(octahydroquinolin-1(2H)-yl)-6-propylpyrimidin-2-amine; N-(5-chloro-2-methylphenyl)-4-(octahydroquinolin-1(2H)-yl)-6-propylpyrimidin-2-amine; N-(3-chloro-4-methylphenyl)-4-(octahydroquinolin-1(2H)-yl)-6-propylpyrimidin-2-amine; N-(3-methylthiophenyl)-4-(octahydroquinolin-1(2H)-yl)-6-propylpyrimidin-2-amine; N-[4-(octahydroquinolin-1(2H)-yl)-6-propylpyrimidin-2-yl]-1H-indol-5-amine; N-[4-(octahydroquinolin-1(2H)-yl)-6-propylpyrimidin-2-yl]-2-(trifluoromethyl)-1H-benzo[d]imidazol-5-amine; N-[4-(octahydroquinolin-1(2H)-yl)-6-propylpyrimidin-2-yl]quinolin-6-amine; 4-methyl-7-[4-(octahydroquinolin-1(2H)-yl)-6-propylpyrimidin-2-amino]-2H-chromen-2-one; N-[4-(octahydroquinolin-1(2H)-yl)-6-propylpyrimidin-2-yl]quinolin-3-amine; (R)-5-{4-[3-(ethylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}-2-methylbenzonitrile; (R)-5-{4-[3-(propylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}-2-methylbenzonitrile; (R)-5-{4-[3-(butylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}-2-methylbenzonitrile; (R)-2-methyl-5-{4-[3-(pentylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}benzonitrile; (R)-5-{4-[3-(isobutylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}-2-methylbenzonitrile; (R)-5-{4-[3-(isopentylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}-2-methylbenzonitrile; (R)-2-methyl-5-{4-[3-(neopentylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}benzonitrile; (R)-5-{4-[3-(isopropylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}-2-methylbenzonitrile; (R)-5-(4-{3-[(1H-pyrrol-2-yl)methylamino]piperidin-1-yl}-6-propylpyrimidin-2-ylamino)-2-methylbenzonitrile; (R)-2-methyl-5-(4-propyl-6-{3-[(thiophen-2-ylmethyl)amino]piperidin-1-yl}pyrimidin-2-ylamino)benzonitrile; (R)-5-(4-{3-[(4,5-dimethylfuran-2-ylmethyl)amino]piperidin-1-yl}-6-propylpyrimidin-2-ylamino)-2-methylbenzonitrile; (R)-2-methyl-5-{4-[3-(3-methylthiopropylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}benzonitrile; (R)-5-{4-[3-(cyclopropylmethylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}-2-methylbenzonitrile; (R)-5-{4-[3-(cyclopentylmethylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}-2-methylbenzonitrile; (R)-5-{4-[3-(4-hydroxybenzylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}-2-methylbenzonitrile; (R)—
N-{1-[2-(3-cyano-4-methylphenylamino)-6-propylpyrimidin-4-yl]piperidin-3-yl}acetamide;(R)-3-[4-(3-aminopiperidin-1-yl)-6-propylpyrimidin-2-ylamino]benzonitrile; (R)-5-[4-(3-aminopiperidin-1-yl)-6-propylpyrimidin-2-ylamino]-2-fluorobenzonitrile; (R)-3-{4-[3-(propylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}benzonitrile; (R)-3-{4-[3-(cyclopropylmethylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}benzonitrile; (R)-2-fluoro-5-{4-[3-(propylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}benzonitrile; (R)-5-{4-[3-(cyclopropylmethylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}-2-fluorobenzonitrile; (R)—
N1-{4-[3-(cyclopropylmethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl}-4-fluorobenzene-1,3-diamine;(R)—
N1-{4-[3-(cyclopropylmethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl}-3-nitrobenzene-1,4-diamine;(R)-3-amino-5-{4-[3-(cyclopropylmethylamino)piperidin-1-yl]-6-propylpyrimidin-2-ylamino}benzonitrile; (R)—
N1-{4-[3-(cyclopropylmethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl}-3-(trifluoromethyl)benzene-1,4-diamine;(R)—
N1-{4-[3-(cyclopropylmethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl}-5-(trifluoromethyl)benzene-1,3-diamine;(R)—
N-{1-[2-(4-amino-3-nitrophenylamino)-6-butylpyrimidin-4-yl]piperidin-3-yl}acetamide;(R)—
N-{1-[6-butyl-2-(4-methyl-3-nitrophenylamino)pyrimidin-4-yl]piperidin-3-yl}acetamide;(R)—
N-{1-[6-butyl-2-(4-fluoro-3-nitrophenylamino)pyrimidin-4-yl]piperidin-3-yl}acetamide;(R)—
N-{1-[6-butyl-2-(4-chloro-3-nitrophenylamino)pyrimidin-4-yl]piperidin-3-yl}acetamide;(R)—
N-{1-[2-(3-amino-5-cyanophenylamino)-6-butylpyrimidin-4-yl]piperidin-3-yl}acetamide;(R)—
N-{1-[2-(3-amino-5-trifluoromethylphenylamino)-6-butylpyrimidin-4-yl]piperidin-3-yl}acetamide;(R)—
N-{1-[2-(4-amino-3-trifluoromethylphenylamino)-6-butylpyrimidin-4-yl]piperidin-3-yl}acetamide;(R)—
N-{1-[6-butyl-2-(4-fluoro-3-trifluoromethylphenylamino)pyrimidin-4-yl]piperidin-3-yl}acetamide;(R)—
N-{1-[6-butyl-2-(3-cyano-4-fluorophenylamino)pyrimidin-4-yl]piperidin-3-yl}acetamide;(R)—
N-{1-[2-(3-amino-4-fluorophenylamino)-6-butylpyrimidin-4-yl]piperidin-3-yl}acetamide;(R)—
N-{1-[2-(3-amino-4-chlorophenylamino)-6-butylpyrimidin-4-yl]piperidin-3-yl}acetamide;(R)—
N-{1-[2-(4-amino-3-cyanophenylamino)-6-butylpyrimidin-4-yl]piperidin-3-yl}acetamide;(R)—
N-{1-[2-(3-cyano-4-methylphenylamino)-6-propylpyrimidin-4-yl]piperidin-3-yl}-2-hydroxyacetamide;(R)—
N-{1-[2-(3-cyanophenylamino)-6-propylpyrimidin-4-yl]piperidin-3-yl}-2-hydroxyacetamide;(R)—
N-{1-[2-(3-cyano-4-fluorophenylamino)-6-propylpyrimidin-4-yl]piperidin-3-yl}-2-hydroxyacetamide;(R)—
N-(1-{2-[3-amino-5-(trifluoromethyl)phenylamino]-6-propylpyrimidin-4-yl}piperidin-3-yl)-2-hydroxyacetamide;(R)—
N-(1-{2-[4-amino-3-(trifluoromethyl)phenylamino]-6-propylpyrimidin-4-yl}piperidin-3-yl)-2-hydroxyacetamide;(R)—
N-(1-{2-[4-fluoro-3-(trifluoromethyl)phenylamino]-6-propylpyrimidin-4-yl}piperidin-3-yl)-2-hydroxyacetamide;(R)—
N-{1-[2-(3-amino-4-fluorophenylamino)-6-propylpyrimidin-4-yl]piperidin-3-yl}-2-hydroxyacetamide;(R)—
N-{1-[2-(3-amino-4-chlorophenylamino)-6-propylpyrimidin-4-yl]piperidin-3-yl}-2-hydroxyacetamide;(R)—
N-{1-[2-(3-amino-4-methylphenylamino)-6-propylpyrimidin-4-yl]piperidin-3-yl}-2-hydroxyacetamide;(R)—
N-{1-[2-(3-chloro-4-methylphenylamino)-6-propylpyrimidin-4-yl]piperidin-3-yl}-2-hydroxyacetamide;(R)-2-hydroxy-N-(1-{2-[4-methyl-3-(trifluoromethyl)phenylamino]-6-propylpyrimidin-4-yl}piperidin-3-yl)acetamide; (R)—
N-{1-[2-(3-amino-5-cyanophenylamino)-6-propylpyrimidin-4-yl]piperidin-3-yl}-2-hydroxyacetamide;(R)—
N1-[4-(3-aminopiperidin-1-yl)-6-propylpyrimidin-2-yl]-5-(trifluoromethyl)benzene-1,3-diamine;(R)—
N1-[4-(3-aminopiperidin-1-yl)-6-propylpyrimidin-2-yl]-3-(trifluoromethyl)benzene-1,4-diamine;(R)-4-(3-aminopiperidin-1-yl)-N-(3-fluoro-4-methylphenyl)-6-propylpyrimidin-2-amine; (R)—
N1-[4-(3-aminopiperidin-1-yl)-6-propylpyrimidin-2-yl]-4-fluorobenzene-1,3-diamine;(R)-3-amino-5-{[4-(3-aminopiperidin-1-yl)-6-propylpyrimidin-2-yl]amino}benzonitrile; (R)-2-amino-5-{[4-(3-aminopiperidin-1-yl)-6-propylpyrimidin-2-yl]amino}benzonitrile; (R)—
N1-[4-(3-aminopiperidin-1-yl)-6-propylpyrimidin-2-yl]-4-chlorobenzene-1,3-diamine;(R)-4-(3-aminopiperidin-1-yl)-N-[4-methyl-3-(trifluoromethyl)phenyl]-6-propylpyrimidin-2-amine; (R)—
N-[4-(3-aminopiperidin-1-yl)-6-propylpyrimidin-2-yl]-1-H-indol-6-amine;(R)-4-(3-aminopiperidin-1-yl)-N-(4-methyl-3-nitrophenyl)-6-propylpyrimidin-2-amine; (R)—
N1-[4-(3-aminopiperidin-1-yl)-6-propylpyrimidin-2-yl]-3-nitrobenzene-1,4-diamine;(R)—
N-{1-[2-(3-cyano-4-fluorophenylamino)-6-propylpyrimidin-4-yl]piperidin-3-yl}acetamide;(R)-5-[4-(3-diethylaminopiperidin-1-yl)-6-propylpyrimidin-2-ylamino]-2-methylbenzonitrile; (R)-5-[4-(3-diethylaminopiperidin-1-yl)-6-propylpyrimidin-2-ylamino]-2-fluorobenzonitrile; (R)-5-[4-(3-ethylaminopiperidin-1-yl)-6-propylpyrimidin-2-ylamino]-2-fluorobenzonitrile; (R)—
N-{1-[6-butyl-2-(3-cyanophenylamino)pyrimidin-4-yl]piperidin-3-yl}acetamide;(R)—
N-{1-[2-(3-cyanophenylamino)-6-propylpyrimidin-4-yl]piperidin-3-yl}acetamide;(R)—
N-{1-[2-(3-amino-5-cyanophenylamino)-6-propylpyrimidin-4-yl]piperidin-3-yl}acetamide;N-{1-[2-(4-amino-3-nitrophenylamino)-6-propylpyrimidin-4-yl]piperidin-3-yl}acetamide; N-{1-[2-(3-amino-4-fluorophenylamino)-6-propylpyrimidin-4-yl]piperidin-3-yl}acetamide; (R)—
N-{1-[2-(4-fluoro-3-trifluoromethylphenylamino)-6-propylpyrimidin-4-yl]piperidin-3-yl}acetamide;(R)—
N-(1-{2-[3-amino-5-(trifluoromethyl)phenylamino]-6-propylpyrimidin-4-yl}piperidin-3-yl)acetamide;(R)—
N-(1-{2-[4-amino-3-(trifluoromethyl)phenylamino]-6-propylpyrimidin-4-yl}piperidin-3-yl)acetamide;(R)-5-[4-(3-ethylaminopiperidin-1-yl)-6-propylpyrimidin-2-ylamino]-2-methylbenzonitrile; (R)-2-fluoro-5-[4-(3-methylaminopiperidin-1-yl)-6-propylpyrimidin-2-ylamino]benzonitrile; (R)-2-methyl-5-[4-(3-methylaminopiperidin-1-yl)-6-propylpyrimidin-2-ylamino]benzonitrile; (R)—
N1-[4-(3-methylaminopiperidin-1-yl)-6-propylpyrimidin-2-yl]-5-(trifluoromethyl)benzene-1,3-diamine;(R)—
N1-[4-(3-methylaminopiperidin-1-yl)-6-propylpyrimidin-2-yl]-3-(trifluoromethyl)benzene-1,4-diamine;(R)-3-amino-5-[4-(3-methylaminopiperidin-1-yl)-6-propylpyrimidin-2-ylamino]benzonitrile; (R)-(4-fluoro-3-trifluoromethylphenyl)-[4-(3-methylaminopiperidin-1-yl)-6-propylpyrimidin-2-yl]amine; (R)—
N1-[4-(3-ethylaminopiperidin-1-yl)-6-propylpyrimidin-2-yl]-3-nitrobenzene-1,4-diamine;(R)—
N1-[4-(3-ethylaminopiperidin-1-yl)-6-propylpyrimidin-2-yl]-4-fluorobenzene-1,3-diamine;(R)—
N1-[4-(3-ethylaminopiperidin-1-yl)-6-propylpyrimidin-2-yl]-5-(trifluoromethyl)benzene-1,3-diamine;(R)—
N1-[4-(3-ethylaminopiperidin-1-yl)-6-propylpyrimidin-2-yl]-3-(trifluoromethyl)benzene-1,4-diamine;(R)-3-amino-5-[4-(3-ethylaminopiperidin-1-yl)-6-propylpyrimidin-2-ylamino]benzonitrile; (R)-5-[4-(3-aminopiperidin-1-yl)-6-butylpyrimidin-2-ylamino]-2-methylbenzonitrile; (R)-5-[4-(3-aminopiperidin-1-yl)-6-butylpyrimidin-2-ylamino]-2-fluorobenzonitrile; (R)—
N-{1-[6-butyl-2-(3-cyano-4-methylphenylamino)pyrimidin-4-yl]piperidin-3-yl}acetamide;(S)-5-[4-(3-ethylaminopiperidin-1-yl)-6-propylpyrimidin-2-ylamino]-2-methylbenzonitrile; 5-[4-(3-ethylaminopiperidin-1-yl)-6-propylpyrimidin-2-ylamino]-2-methylbenzonitrile; N-{1-[6-butyl-2-(3-cyano-4-methylphenylamino)pyrimidin-4-yl]piperidin-3-yl}acetamide; (R)-5-({4-butyl-6-[3-(ethylamino)piperidin-1-yl]pyrimidin-2-yl}amino)-2-methylbenzonitrile; (R)-5-({4-butyl-6-[3-(butylamino)piperidin-1-yl]pyrimidin-2-yl}amino)-2-methylbenzonitrile; (R)-5-({4-butyl-6-[3-(pentylamino)piperidin-1-yl]pyrimidin-2-yl}amino)-2-methylbenzonitrile; (R)-5-({4-butyl-6-[3-(isobutylamino)piperidin-1-yl]pyrimidin-2-yl}amino)-2-methylbenzonitrile; (R)-5-({4-butyl-6-[3-(isopentylamino)piperidin-1-yl]pyrimidin-2-yl}amino)-2-methylbenzonitrile; (R)-5-({4-butyl-6-[3-(neopentylamino)piperidin-1-yl]pyrimidin-2-yl}amino)-2-methylbenzonitrile; (R)-5-{[4-butyl-6-(3-{[3-(methylthio)propyl]amino}piperidin-1-yl)pyrimidin-2-yl]amino}-2-methylbenzonitrile; (R)-4-fluoro-N1-{4-[3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl}benzene-1,3-diamine; (R)-4-chloro-N1-{4-[3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl}benzene-1,3-diamine; (R)-2-amino-5-({4-[3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl}amino)benzonitrile; (R)—
N-(3-methoxy-4-methylphenyl)-4-[3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-amine;(R)-4-methyl-N1-{4-[3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl}benzene-1,3-diamine; (R)-5-({4-butyl-6-[3-(methylamino)piperidin-1-yl]pyrimidin-2-yl}amino)-2-methylbenzonitrile; (R)-5-({4-butyl-6-[3-(methylamino)piperidin-1-yl]pyrimidin-2-yl}amino)-2-fluorobenzonitrile; (R)—
N1-{4-butyl-6-[3-(methylamino)piperidin-1-yl]pyrimidin-2-yl}-5-(trifluoromethyl)benzene-1,3-diamine;(R)—
N1-{4-butyl-6-[3-(methylamino)piperidin-1-yl]pyrimidin-2-yl}-3-(trifluoromethyl)benzene-1,4-diamine;(R)-3-amino-5-({4-butyl-6-[3-(methylamino)piperidin-1-yl]pyrimidin-2-yl}amino)benzonitrile; (R)-2-amino-5-({4-butyl-6-[3-(methylamino)piperidin-1-yl]pyrimidin-2-yl}amino)benzonitrile; (R)—
N1-{4-butyl-6-[3-(methylamino)piperidin-1-yl]pyrimidin-2-yl}-4-fluorobenzene-1,3-diamine;(R)-4-butyl-N-(3-methoxy-4-methylphenyl)-6-[3-(methylamino)piperidin-1-yl]pyrimidin-2-amine; (R)—
N1-{4-butyl-6-[3-(methylamino)piperidin-1-yl]pyrimidin-2-yl}-4-methylbenzene-1,3-diamine;(R)-4-butyl-N-[4-fluoro-3-(trifluoromethyl)phenyl]-6-[3-(methylamino)piperidin-1-yl]pyrimidin-2-amine; (R)—
N1-{4-[3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl}-3-nitrobenzene-1,4-diamine;(R)—
N-(3,4-dimethylphenyl)-4-[3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-amine;(R)—
N-(3-fluoro-4-methylphenyl)-4-[3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-amine;(R)—
N-[4-methyl-3-(trifluoromethyl)phenyl]-4-[3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-amine;(R)-4-methoxy-N1-{4-[3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl}benzene-1,3-diamine; (R)—
N-{4-[3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl}-1-H-indazol-6-amine;(R)—
N4-{4-[3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl}benzene-1,2,4-triamine;(R)—
N1-{4-butyl-6-[3-(methylamino)piperidin-1-yl]pyrimidin-2-yl}-3-nitrobenzene-1,4-diamine;(R)-3-({4-butyl-6-[3-(methylamino)piperidin-1-yl]pyrimidin-2-yl}amino)benzonitrile; (R)-4-butyl-N-(3,4-dimethylphenyl)-6-[3-(methylamino)piperidin-1-yl]pyrimidin-2-amine; (R)-4-butyl-N-(3-fluoro-4-methylphenyl)-6-[3-(methylamino)piperidin-1-yl]pyrimidin-2-amine; (R)-4-butyl-N-[4-methyl-3-(trifluoromethyl)phenyl]-6-[3-(methylamino)piperidin-1-yl]pyrimidin-2-amine; (R)—
N1-{4-butyl-6-[3-(methylamino)piperidin-1-yl]pyrimidin-2-yl}-4-methoxybenzene-1,3-diamine;(R)—
N-{4-butyl-6-[3-(methylamino)piperidin-1-yl]pyrimidin-2-yl}-1H-indazol-6-amine;(R)—
N4-{4-butyl-6-[3-(methylamino)piperidin-1-yl]pyrimidin-2-yl}benzene-1,2,4-triamine;(R)-4-(3-aminopiperidin-1-yl)-6-butyl-N-(3-nitrophenyl)pyrimidin-2-amine; (R)—
N1-[4-(3-aminopiperidin-1-yl)-6-butylpyrimidin-2-yl]-3-nitrobenzene-1,4-diamine;(R)-4-(3-aminopiperidin-1-yl)-6-butyl-N-(4-fluoro-3-nitrophenyl)pyrimidin-2-amine; (R)-4-(3-aminopiperidin-1-yl)-6-butyl-N-(4-methyl-3-nitrophenyl)pyrimidin-2-amine; (R)—
N1-[4-(3-aminopiperidin-1-yl)-6-butylpyrimidin-2-yl]-3-(trifluoromethyl)benzene-1,4-diamine;(R)—
N1-[4-(3-aminopiperidin-1-yl)-6-butylpyrimidin-2-yl]-5-(trifluoromethyl)benzene-1,3-diamine;(R)-3-amino-5-{[4-(3-aminopiperidin-1-yl)-6-butylpyrimidin-2-yl]amino}benzonitrile; (R)-4-(3-aminopiperidin-1-yl)-6-butyl-N-[4-methyl-3-(trifluoromethyl)phenyl]pyrimidin-2-amine; (R)-4-(3-aminopiperidin-1-yl)-6-butyl-N-(3-fluoro-4-methylphenyl)pyrimidin-2-amine; (R)-4-(3-aminopiperidin-1-yl)-6-butyl-N-(3-methoxy-4-methylphenyl)pyrimidin-2-amine; (R)—
N1-[4-(3-aminopiperidin-1-yl)-6-butylpyrimidin-2-yl]-4-methylbenzene-1,3-diamine;(R)-4-(3-aminopiperidin-1-yl)-6-butyl-N-(3,4-dimethylphenyl)pyrimidin-2-amine; (R)-4-(3-aminopiperidin-1-yl)-6-butyl-N-[4-fluoro-3-(trifluoromethyl)phenyl]pyrimidin-2-amine; (R)—
N1-[4-(3-aminopiperidin-1-yl)-6-butylpyrimidin-2-yl]-4-fluorobenzene-1,3-diamine;(R)-2-amino-5-{[4-(3-aminopiperidin-1-yl)-6-butylpyrimidin-2-yl]amino}benzonitrile; (R)-3-{[4-(3-aminopiperidin-1-yl)-6-butylpyrimidin-2-yl]amino}benzonitrile; (R)—
N1-[4-(3-aminopiperidin-1-yl)-6-butylpyrimidin-2-yl]benzene-1,4-diamine;(R)-4-(3-aminopiperidin-1-yl)-6-butyl-N-(4-chloro-3-nitrophenyl)pyrimidin-2-amine; and (R)—
N4-[4-(3-aminopiperidin-1-yl)-6-butylpyrimidin-2-yl]benzene-1,2,4-triamine.
-
-
2. The compound or its pharmaceutically acceptable salt of claim 1, wherein
-
4. A pharmaceutical composition for agonizing a 5-HT4 receptor, comprising a therapeutically effective amount of a compound of Formula 1 or its pharmaceutically acceptable salt;
- and a pharmaceutically acceptable carrier;
- View Dependent Claims (5)
-
5. The pharmaceutical composition of claim 4, wherein
R1 is a phenyl group substituted with one or more substituents selected from the group consisting of hydroxy, amino, halogen, cyano, nitro, hydroxycarbonyl, C1-5 alkyl (where the C1-5 alkyl is optionally substituted with halogen or amino), C2-6 alkenyl, C2-6 alkynyl, C1-5 alkoxy (where the C1-5 alkoxy is optionally substituted with halogen), C1-5 alkylthio, mono- or di-C1-5 alkylamino, C1-5 alkylsulfonylamino, C1-5 alkylcarbonylamino, C1-5 alkoxycarbonyl, aminosulfonyl, aminocarbonyl, C1-5 alkylaminocarbonyl, and benzyloxycarbonylamino; - or
a heteroaryl group selected from the group consisting of pyridinyl, pyrimidinyl, pyrazinyl, imidazolyl, pyrazolyl, triazolyl, oxazolyl, thiazolyl, furanyl, pyrrolyl, thiophenyl, naphthyl, indanyl, quinolinyl, quinolinonyl, chromenonyl, dihydroindolonyl, isoindoline-1,3-dionyl, dihydrobenzimidazolonyl, benzoxazolonyl, benzofuranyl, benzothiophenyl, benzo[d][1,3]dioxolyl, dihydrobenzo[1,4]dioxinyl, indolyl, indolinyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, and indazolyl, wherein the heteroaryl group may be optionally substituted with one or more substituents selected from the group consisting of amino, di-C1-5 alkylamino, cyano, nitro, halogen, C1-5 alkyl (where the C1-5 alkyl is optionally substituted with halogen), C1-5 alkoxy (where the C1-5 alkoxy is optionally substituted with halogen), acetyl, and C1-5 alkylsulfonyl, R2 is the nitrogen-containing cyclic group of Formula B, R3 is a C1-5 alkyl group, R4 is hydrogen;
a C1-5 alkyl group optionally substituted with a substituent selected from the group consisting of hydroxy, C1-5 alkoxy, benzylamino (where the benzylamino is optionally substituted with halogen), phenylamino, C1-5 alkylamino, C3-6 cycloalkylamino, pyrrolidinyl, and hydroxy-C1-5 alkylamino;
a C1-5 alkoxycarbonyl group;
or an aminocarbonyl group,R5 is hydrogen;
a hydroxyl group;
a C1-5 alkoxy group;
a phenoxy group;
a benzyloxy group;
a C1-5 alkyl group optionally substituted with a substituent selected from the group consisting of amino, C1-5 alkoxycarbonylamino, and mono- or di-C1-5 alkylamino;
or a group selected from the group consisting of the Formulas E to I,R6, R7, and R10 are hydrogen, X is —
CH(R7)—
;
—
N(R8)—
;
or —
O—
,R4 and R5 are optionally joined to each other to form a pentagonal or hexagonal ring, R8 is hydrogen;
or a C1-5 alkyl group,R9 is a C1-10 alkyl group optionally substituted with a substituent selected from the group consisting of hydroxy, halogen, C1-5 alkoxy, amino, C1-5 alkoxycarbonylamino, benzyloxycarbonylamino, mono- or di-C1-5 alkylamino, C1-5 alkoxy-C1-5 alkyloxy, phenoxy, benzyloxy, phenyl (where the phenyl is optionally substituted with one or more substituents selected from the group consisting of halogen, amino, C1-5 alkoxy, and hydroxy), thiophenyl, pyridinyl, indolyl, pyrimidinyl, pyrazinyl, imidazolyl, pyrazolyl, triazolyl, oxazolyl, thiazolyl, furanyl, pyrrolyl, piperidinyl, piperazinyl (where the piperazinyl is optionally substituted with benzyl), C3-6 cycloalkyl, acetyl, and benzoyl;
a C3-6 cycloalkyl group;
a piperidinyl group optionally substituted with C1-5 alkoxycarbonyl;
a C1-10 alkenyl group optionally substituted with phenyl;
a trifluoromethyl group;
a trifluoroethyl group;
or a phenyl group optionally substituted with halogen,R11 and R12 are, independently each other, hydrogen;
a C1-10 alkyl group optionally substituted with a substituent selected from the group consisting of amino, C1-5 alkoxycarbonylamino, hydroxy, C1-5 alkylthio, C3-10 cycloalkyl, phenyl (where the phenyl is optionally substituted with one or more substituents selected from the group consisting of hydroxy, C1-5 alkyl, mono- or di-C1-5 alkylamino, trifluoromethyl, halogen, C1-5 alkoxy, and C1-5 alkylcarbonyloxy), thiophenyl, pyrrolyl, furanyl (where the furanyl is optionally substituted with mono- or di-C1-5 alkyl), pyridinyl, pyrimidinyl, pyrazinyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, thiazolyl, and benzyloxy;
a piperidinyl group optionally substituted with benzyl, benzoyl, C1-5 alkyl, or C1-5 alkylcarbonyl;
an azetidinyl group optionally substituted with C1-5 alkoxycarbonyl;
a C1-5 alkylsulfonyl group;
a phenylsulfonyl group (where the phenyl moiety is optionally substituted with halogen);
or a C3-10 cycloalkyl group.
- or
-
5. The pharmaceutical composition of claim 4, wherein
- and a pharmaceutically acceptable carrier;
Specification
- Resources
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Current AssigneeYuhan Corporation
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Original AssigneeYuhan Corporation
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InventorsLEE, Hyun-Joo, KIM, Dong-Hoon, KIM, Tae-Kyun, YOON, Young-Ae, SIM, Jae-Young, CHA, Myung-Hun, JUNG, Eun-Jung, AHN, Kyoung-Kyu, LEE, Tai-Au
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Granted Patent
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Time in Patent OfficeDays
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Field of Search
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US Class Current
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CPC Class CodesA61P 1/00 Drugs for disorders of the ...A61P 1/04 for ulcers, gastritis or re...A61P 1/10 LaxativesA61P 1/12 AntidiarrhoealsA61P 1/14 Prodigestives, e.g. acids, ...A61P 43/00 Drugs for specific purposes...C07D 401/04 directly linked by a ring-m...C07D 403/04 directly linked by a ring-m...C07D 413/04 directly linked by a ring-m...C07D 413/14 containing three or more he...C07D 417/04 directly linked by a ring-m...