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US 6,586,441 B2Granted
Adenosine receptor ligands and their use in the treatment of disease
AssigneeHoffman-La Roche Inc.
InventorsEdilio Maurizio Borroni, Gerda Huber-Trottmann, Gavin John Kilpatrick, Roger David Norcross
Life of this patent
Estimating the term…
Abstract
The invention relates to cyclic heteroaromatic compounds, containing at least one nitrogen atom, and to their use in the manufacture of medicaments for the treatment of diseases, related to adenosine receptor modulators, such as Alzheimer's disease, Parkinson's disease, neuroprotection, schizophrenia, anxiety, pain, respiration deficits, depression, asthma, allergic responses, hypoxia, ischaemia, seizure, substance abuse, sedation and they may be active as muscle relaxants, antipsychotics, anti epileptics, anticonvulsants and cardiaprotective agents.
Claims23
A method of treatment of a disease state caused by malfunction of the adenosine receptor system comprising administering to a patient in need of such treatment, an effective amount of a composition for treating said disease state, said composition containing a compound that binds to an adenosine receptor and a pharmaceutically acceptable carrier, said compound having the formula:
- wherein
- A is selected from the group consisting of a bond, —S—, —N(R)—, —(CH2)2—, —CH═CH—, —C≡C— or —O—;
- X and Y each are independently selected from the group consisting of —N═ and ═N—;
- R1 is selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower alkynyl, halogen, cyano, cycloalkyl,
- —(CH2)n—C(O)O-lower alkyl,
- —(CH2)n—C(O)O-lower alkyl-phenyl,
- —(CH2)n—NH—C(O)O-lower alkyl-phenyl,
- —(CH2)n—O-lower alkyl,
- —(CH2)n—O-phenyl,
- —(CH2)n—NH-phenyl,
- —(CH2)n-phenyl,
- —(CH2)n-phenyl substituted by 1 or 2 substituents selected from the group consisting of hydroxy, lower alkoxy, lower alkyl, CF3-lower alkenyl, halogen, CF3, OCF3, amino, —(CH2)n—N-di-lower alkyl, —C(O)NH-lower alkyl, and —S(O)2-lower alkyl,
- —(CH2)n-morpholinyl,
- —(CH2)n-amino,
- —(CH2)n-amino substituted by lower alkyl or benzyl,
- —(CH2)n-piperidin-1-yl or —(CH2)n-piperidin-3-yl,
- —(CH2)n-piperidin-1-yl or —(CH2)n-piperidin-3-yl, said —(CH2)-piperidin 1-yl or -3-yl being substituted by lower alkyl,
- —(CH2)n-pyridin-2-yl, —(CH2)n-pyridin-3-yl, —(CH2)n-pyridin-4-yl,
- —(CH2)n-pyridin-2-yl, —(CH2)n-pyridin-3-yl or —(CH2)n-pyridin-4-yl, said —(CH2)-pyridin-2-yl, -3-yl or -4-yl, being substituted by 1 or 2 substituents selected from the group consisting of lower alkyl, hydroxy, nitro, cyano, halogen and CF3,
- —OC(O)N(R)2,
- —(CH2)n—NH—pyridin-2-yl,
- —(CH2)n—NH—pyridin-2-yl, substituted by lower alkyl or halogen,
- —(CH2)n-piperazin-4-yl,
- —(CH2)n-piperazin-4-yl, substituted by lower alkyl, phenyl or carbonyl-phenyl,
- —(CH2)n-phenyl—OC(O)-phenyl,
- —(CH2)n-phenyl—OC(O)-phenyl substituted by halogen or the group
- —(CH2)n-S-phenyl or —(CH2)n—S(O)2-phenyl,
- —(CH2)n—S-lower alkyl,
- (CH2)n(CH═CH)m-phenyl,
- (CH2)n(CH≡CH)m-phenyl,
- —(CH2)n—NH-cycloalkyl,
- —(CH2)n—NH-phenyl,
- —(CH2)n—NH-phenyl, substituted by amino or nitro,
- —(CH2)n-tetrahydro-pyran-4-yl,
- —(CH2)n-quinolin-2-yl,
- —(CH2)n-naphthyl or —(CH2)n—NH-naphthyl,
- —(CH2)n-3,4-dihydro-1H-isoquinolin-2-yl,
- —(CH2)n-benzo[1,3]dioxolyl,
- —(CH2)n—NH—S(O)2-phenyl,
- —(CH2)n—NH—S(O)2-phenyl substituted by halogen,
- —(CH2)n-1,2,3,4-tetrahydro-quinolin-2-yl,
- —(CH2)n-1,2,3,4-tetrahydro-quinolin-2-yl, substituted by lower alkyl, and
- —(CH2)n-furanyl;
- R2 is selected from the group consisting of hydrogen, halogen, cyano, nitro, lower alkyl, lower alkenyl, —C(O)—lower alkyl, —C(O)O-lower alkyl, —C(O)O-lower alkyl-phenyl, lower alkynyl-phenyl, lower alkenyl—C(O)O-lower alkyl, lower alkenyl-cyano or phenyl, C(O)O-lower alkyl, —C(O)O-lower alkyl-phenyl, lower alkynyl-phenyl, lower alkenyl-C(O)O-lower alkyl, lower alkenyl-cyano or phenyl, substituted by halogen;
- R3 is selected from the group consisting of lower alkyl, phenyl, phenyl substituted by lower alkyl, lower alkoxy, or halogen,
- thien-2yl or fur-2yl,
- thien-2yl or fur-2yl, substituted by a substituent selected from the group consisting of lower alkyl, S-lower alkyl, halogen, lower alkoxy, —C(O)O-lower alkyl, —C(═CH2)—O-lower alkyl, —(CH2)n-halogen, —(CH2)n—OH, —(CH2)n-lower alkoxy, cyano, CHF2 and CH2F,
- 2,3-dihydro-benzo[1.4]dioxin-6-yl,
- benzo[1.3]dioxol-5-yl,
- isoxazol-5-yl, pyridin-2-yl, pyridin-3-yl,
- —C(═CH2)O-lower alkyl,
- 4,5-dihydrofuran-2-yl,
- 5,6-dihydro-4H-pyran-2-yl,
- oxazol-2-yl,
- benzofuranyl,
- pyrazin-2-yl,
- —O—(CH2)n-phenyl,
- —O—(CH2)n-pyridyl,
- —O—(CH2)n-pyridyl substituted by lower alkyl,
- —S—(CH2)n-pyridyl,
- pyrazol-1-yl, and
- pyrazol-1-yl substituted by lower alkyl or halogen;
- R4 and R5 are independently from each other selected from the group consisting of hydrogen, —CO—(CH2)n-phenyl, optionally substituted by halogen or —CH2N(R)(CH2)n-lower alkyl,
- phenyl, phenyl substituted by lower alkoxy and
- —C(O)-phenyl;
- R is selected from the group consisting of hydrogen or lower alkyl;
- and
- A and R2 may be together with the two carbon atoms
- and wherein
- n is 0,1,2,3 or 4;
- m is 1 or 2;
- or a pharmaceutically acceptable salt thereof.
69 more elements
A method of treatment of diseases responsive to Adenosine A2A receptor antagonists comprising administering a therapeutically effective amount of
- wherein A is selected from the group consisting of a bond, —S—, —N(R)—, —(CH2)2—, —CH═CH—, —C≡C— or —O—;
- R1 is selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower alkynyl, halogen, cyano, cycloalkyl,
- —(CH2)n—C(O)O-lower alkyl,
- —(CH2)n—C(O)O-lower alkyl-phenyl,
- —(CH2)n—NH—C(O)O-lower alkyl-phenyl,
- —(CH2)n—O-lower alkyl,
- —(CH2)n—O-phenyl,
- —(CH2)n—NH-phenyl,
- —(CH2)n-phenyl,
- —(CH2)n-phenyl substituted by 1 or 2 substituents selected from the group consisting of hydroxy, lower alkoxy, lower alkyl, CF3—lower alkenyl, halogen, CF3, OCF3, amino, —(CH2)n—N-di-lower alkyl, —C(O)NH-lower alkyl and —S(O)2—lower alkyl,
- —(CH2)n-morpholinyl,
- —(CH2)n-amino,
- —(CH2)n-amino substituted by lower alkyl or benzyl,
- —(CH2)n-piperidin-1-yl or —(CH2)n-piperidin-3-yl,
- —(CH2)n-piperidin-1-yl or —(CH2)n-piperidin-3-yl, said —(CH2)n-piperidin-1-yl or -3-yl being substituted by lower alkyl,
- —(CH2)n-pyridin-2-yl, —(CH2)n-pyridin-3-yl, —(CH2)n-pyridin-4-yl,
- —(CH2)n-pyridin-2-yl, —(CH2)n-pyridin-3-yl or —(CH2)n-pyridin-4-yl, said pyridin-2-yl, -3-yl or -4-yl being substituted by 1 or 2 substituents, selected from the group consisting of lower alkyl, hydroxy, nitro, cyano, halogen, CF3 and —OC(O)N(R)2,
- —(CH2)n—NH-pyridin-2-yl,
- —(CH2)n—NH-pyridin-2-yl, substituted by a substitutuent selected from lower alkyl and halogen,
- —(CH2)n-piperazin-4-yl,
- —(CH2)n-piperazin-4-yl, substituted by a substitutuent selected from lower alkyl, phenyl and carbonyl-phenyl,
- —(CH2)n-phenyl—OC(O)-phenyl,
- —(CH2)n-phenyl—OC(O)-phenyl substituted by halogen,
- the group
- —(CH2)n—S-phenyl or —(CH2)n—S(O)2-phenyl,
- —(CH2)n—S-lower alkyl,
- —(CH2)n(CH═CH)m-phenyl,
- —(CH2)n(CH≡CH)m-phenyl,
- —(CH2)n—NH-cycloalkyl,
- —(CH2)n—NH-phenyl,
- —(CH2)n—NH-phenyl, substituted by amino or nitro,
- —(CH2)n-tetrahydro-pyran-4-yl,
- —(CH2)n-quinolin-2-yl,
- —(CH2)n-naphthyl or —(CH2)n—NH-naphthyl,
- —(CH2)n-3,4-dihydro-1H-isoquinolin-2-yl,
- —(CH2)n-benzo[1,3]dioxolyl,
- —(CH2)n—NH—S(O)2-phenyl,
- —(CH2)n—NH—S(O)2-phenyl substituted by halogen,
- —(CH2)n-1,2,3,4-tetrahydro-quinolin-2-yl,
- —(CH2)n-1,2,3,4-tetrahydro-quinolin-2-yl, substituted by lower alkyl and
- —(CH2)n-furanyl;
- and
- R3 is selected from the group consisting of lower alkyl, phenyl, phenyl substituted by a substitutent selected from the group consisting of lower alkyl, lower alkoxy and halogen,
- thien-2yl or fur-2yl,
- thien-2yl or fur-2yl, substituted by lower alkyl, S-lower alkyl, halogen, lower alkoxy, —C(O)O-lower alkyl, —C(═CH2)—O-lower alkyl, —(CH2)n-halogen, —(CH2)n—OH, —(CH2)n-lower alkoxy, cyano, CHF2 and CH2F,
- 2,3-dihydro-benzo[1.4]dioxin-6-yl,
- benzo[1.3]dioxol-5-yl,
- isoxazol-5-yl, pyridin-2-yl, pyridin-3-yl,
- —C(═CH2)O-lower alkyl,
- 4,5-dihydrofuran-2-yl,
- 5,6-dihydro-4H-pyran-2-yl,
- oxazol-2-yl,
- benzofuranyl,
- pyrazin-2-yl,
- —O—(CH2)n-phenyl,
- —O—(CH2)n-pyridyl,
- —O—(CH2)n-pyridyl substituted by lower alkyl,
- —S—(CH2)n-pyridyl,
- pyrazol-1-yl, and
- pyrazol-1-yl substituted by lower alkyl or halogen;
- and
- R is selected from the group consisting of hydrogen and lower alkyl;
- or a pharmaceutically acceptable salt thereof.
60 more elements
A method of treatment of diseases responsive to Adenosine A2A receptor antagonists
- wherein A is —N(R);
- R1 is selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower alkynyl, halogen, cyano, cycloalkyl,
- —(CH2)n—C(O)O-lower alkyl,
- —(CH2)n—C(O)O-lower alkyl-phenyl,
- —(CH2)n—NH—C(O)O-lower alkyl-phenyl,
- —(CH2)n—O-lower alkyl,
- —(CH2)n—O-phenyl,
- —(CH2)n—NH-phenyl,
- —(CH2)n-phenyl,
- —(CH2)n-phenyl substituted by 1 or 2 substituents selected from the group consisting of hydroxy, lower alkoxy, lower alkyl, CF3-lower alkenyl, halogen, CF3, OCF3, amino, —(CH2)n—N-di-lower alkyl, —C(O)NH-lower alkyl and —S(O)2-lower alkyl,
- —(CH2)n-morpholinyl,
- —(CH2)n-amino,
- —(CH2)n-amino substituted by lower alkyl or benzyl,
- —(CH2)n-piperidin-1-yl or —(CH2)n-piperidin-3-yl,
- —(CH2)n-piperidin-1-yl or —(CH2)n-piperidin-3-yl, said —(CH2)n-piperidin-1-yl or -3-yl being substituted by lower alkyl,
- —(CH2)n-pyridin-2-yl, —(CH2)n-pyridin-3-yl, —(CH2)n-pyridin-4-yl,
- —(CH2)n-pyridin-2-yl, —(CH2)n-pyridin-3-yl or —(CH2)n-pyridin-4-yl, said pyridin-2-yl, -3-yl or -4-yl being substituted by 1 or 2 substituents, selected from the group consisting of lower alkyl, hydroxy, nitro, cyano, halogen, CF3 and —OC(O)N(R)2,
- —(CH2)n—NH-pyridin-2-yl,
- —(CH2)n—NH-pyridin-2-yl, substituted by a substitutuent selected from lower alkyl and halogen,
- —(CH2)n-piperazin-4-yl,
- —(CH2)n-piperazin-4-yl, substituted by a substitutuent selected from lower alkyl, phenyl and carbonyl-phenyl,
- —(CH2)n-phenyl—OC(O)-phenyl,
- —(CH2)n-phenyl—OC(O)-phenyl substituted by halogen,
- the group
- —(CH2)n—S-phenyl or —(CH2)n—S(O)2-phenyl,
- —(CH2)n—S-lower alkyl,
- —(CH2)n(CH═CH)m-phenyl,
- (CH2)n(CH≡CH)m-phenyl,
- —(CH2)n—NH-cycloalkyl,
- —(CH2)n—NH-phenyl,
- —(CH2)n—NH-phenyl, substituted by amino or nitro,
- —(CH2)n-tetrahydro-pyran-4-yl,
- —(CH2)n-naphthyl or —(CH2)n—NH-naphthyl,
- —(CH2)n-3,4-dihydro-1H-isoquinolin-2-yl,
- —(CH2)n-benzo[1,3]dioxolyl,
- —(CH2)n—NH—S(O)2-phenyl,
- —(CH2)n—NH—S(O)2-phenyl substituted by halogen,
- —(CH2)n-1,2,3,4-tetrahydro-quinolin-2-yl,
- —(CH2)n-1,2,3,4-tetrahydro-quinolin-2-yl, substituted by lower alkyl and
- —(CH2)n-furanyl;
- and
- R3 is selected from the group consisting of lower alkyl, phenyl, phenyl substituted by a substitutent selected from the group consisting of lower alkyl, lower alkoxy and halogen,
- thien-2yl or fur-2yl,
- thien-2yl or fur-2yl, substituted by lower alkyl, S-lower alkyl, halogen, lower alkoxy, —C(O)O-lower alkyl, —C(═CH2)—O-lower alkyl, —(CH2)n-halogen, —(CH2)n—OH, —(CH2)n-lower alkoxy, cyano, CHF2 and CH2F,
- 2,3-dihydro-benzo[1.4]dioxin-6-yl,
- benzo[1.3]dioxol-5-yl,
- isoxazol-5-yl, pyridin-2-yl, pyridin-3-yl,
- —C(═CH2)O-lower alkyl,
- 4,5-dihydrofuran-2-yl,
- 5,6-dihydro-4H-pyran-2-yl,
- oxazol-2-yl,
- benzofuranyl,
- pyrazin-2-yl,
- —O—(CH2)n-phenyl,
- —O—(CH2)n-pyridyl,
- —O—(CH2)n-pyridyl substituted by lower alkyl,
- —S—(CH2)n-pyridyl,
- pyrazol-1-yl, and
- pyrazol-1-yl substituted by lower alkyl or halogen;
- and
- R is selected from the group consisting of hydrogen and lower alkyl;
- or a pharmaceutically acceptable salt thereof.
59 more elements
A method of treatment of Parkinson's Disease, hypertension and ischemia comprising administering to a patient in need of such treatment, a therapeutically effective amount of a compound of formula
- wherein A is —NH—;
- R1 is selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower alkynyl, halogen, cyano, cycloalkyl,
- —(CH2)n—C(O)O-lower alkyl,
- —(CH2)n—C(O)O-lower alkyl-phenyl,
- —(CH2)n—NH—C(O)O-lower alkyl-phenyl,
- —(CH2)n—O-lower alkyl,
- —(CH2)n—O-phenyl,
- —(CH2)n—NH-phenyl,
- —(CH2)n-phenyl,
- —(CH2)n-phenyl substituted by 1 or 2 substituents selected from the group consisting of hydroxy, lower alkoxy, lower alkyl, CF3-lower alkenyl, halogen, CF3, OCF3, amino, —(CH2)n—N-di-lower alkyl, —C(O)NH-lower alkyl and —S(O)2-lower alkyl,
- —(CH2)n-morpholinyl,
- —(CH2)n-amino,
- —(CH2)n-amino substituted by lower alkyl or benzyl,
- —(CH2)n-piperidin-1-yl or —(CH2)n-piperidin-3-yl,
- —(CH2)n-piperidin-1-yl or —(CH2)n-piperidin-3-yl, said —(CH2)n-piperidin-1-yl or -3-yl being substituted lower alkyl,
- —(CH2)n-pyridin-2-yl, —(CH2)n-pyridin-3-yl, —(CH2)n-pyridin-4-yl,
- —(CH2)n-pyridin-2-yl, —(CH2)n-pyridin-3-yl or —(CH2)n-pyridin-4-yl, said pyridin-2-yl, -3-yl-or -4-yl being substituted by 1 or 2 substituents, selected from the group consisting of lower alkyl, hydroxy, nitro, cyano, halogen, CF3 and —OC(O)N(R)2,
- —(CH2)—NH—pyridin-2-yl,
- —(CH2)n—NH—pyridin-2-yl, substituted by a substitutuent selected from lower alkyl and halogen,
- —(CH2)n-piperazin-4-yl,
- —(CH2)n-piperazin-4-yl, substituted by a substitutuent selected from lower alkyl, phenyl and carbonyl-phenyl,
- —(CH2)n-phenyl—OC(O)-phenyl,
- —(CH2)n-phenyl—OC(O)-phenyl substituted by a substituent selected from the group consisting of halogen and the group
- —(CH2)n—S-phenyl or —(CH2)n—S(O)2-phenyl,
- —(CH2)n—S-lower alkyl,
- —(CH2)n(CH═CH)m-phenyl,
- —(CH2)n(CH≡CH)m-phenyl,
- —(CH2)n—NH-cycloalkyl,
- —(CH2)n—NH-phenyl,
- —(CH2)n—NH-phenyl, substituted by amino or nitro,
- —(CH2)n-tetrahydro-pyran-4-yl,
- —(CH2)n-quinolin-2-yl,
- —(CH2)n-naphthyl or —(CH2)n—NH-naphthyl,
- —(CH2)n-3,4-dihydro-1H-isoquinolin-2-yl,
- —(CH2)n-benzo[1,3]dioxolyl,
- —(CH2)n—NH—S(O)2-phenyl,
- —(CH2)n—NH—S(O)2-phenyl substituted by halogen,
- —(CH2)n-1,2,3,4-tetrahydro-quinolin-2-yl,
- —(CH2)n-1,2,3,4-tetrahydro-quinolin-2-yl, substituted by lower alkyl and
- —(CH2)n-furanyl;
- and
- R3 is selected from the group consisting of lower alkyl, phenyl, phenyl substituted by a substitutent selected from the group consisting of lower alkyl, lower alkoxy and halogen,
- thien-2yl or fur-2yl,
- thien-2yl or fur-2yl, substituted by a substituent selected from the group consisting of lower alkyl, S-lower alkyl, halogen, lower alkoxy, —C(O)O-lower alkyl, —C(═CH2)—O-lower alkyl, —(CH2)n-halogen, —(CH2)n—OH, —(CH2)n-lower alkoxy, cyano, CHF2 and CH2F,
- 2,3-dihydro-benzo[1.4]dioxin-6-yl,
- benzo[1.3]dioxol-5-yl,
- isoxazol-5-yl, pyridin-2-yl, pyridin-3-yl,
- —C(═CH2)O-lower alkyl,
- 4,5-dihydrofuran-2-yl,
- 5,6-dihydro-4H-pyran-2-yl,
- oxazol-2-yl,
- benzofuranyl,
- pyrazin-2-yl,
- —O—(CH2)n-phenyl,
- —O—(CH2)n-pyridyl,
- —O—(CH2)n-pyridyl substituted by lower alkyl,
- —S—(CH2)n-pyridyl,
- pyrazol-1-yl, and
- pyrazol-1-yl substituted by lower alkyl or halogen;
- or a pharmaceutically acceptable salt thereof.
57 more elements
A compound selected from the group consisting of 2-amino-4-ethoxy-6-furan-2-yl-pyrimidine-5-carbonitrile,
- 2-amino-4-benzyloxy-6-furan-2-yl-pyrimidine-5-carbonitrile,
- 2-amino-4-furan-2-yl-6-phenethyloxy-pyrimidine-5-carbonitrile,
- 2-amino-4-furan-2-yl-6-(3-phenyl-propoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-cyclohexyloxy-6-furan-2-yl-pyrimidine-5-carbonitrile,
- 2-amino-4-furan-2-yl-6-isopropoxy-pyrimidine-5-carbonitrile,
- 2-amino-4-furan-2-yl-6-(pyridin-2-yl-methoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-phenethyloxy-6-phenyl-pyrimidine-5-carbonitrile,
- 2-amino-4-phenyl-6-(pyridin-2-yl-methoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-(pyridin-2-ylmethoxy)-6-thiophen-2-yl-pyrimidine-5-carbonitrile,
- 2-amino-4-furan-2-yl-6-(pyridin-3-yl-methoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-furan-2-yl-6-(6-methyl-pyridin-2-yl-methoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-furan-2-yl-6-(2-pyridin-2-yl-ethoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-(5-methyl-furan-2-yl)-6-(6-methyl-pyridin-2-yl-methoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-(5-methyl-furan-2-yl)-6-(pyridin-2-yl-methoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-furan-2-yl-6-(3-phenyl-allyloxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-furan-2-yl-6-(naphthalen-2-yl-methoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-furan-2-yl-6-(3-methyl-pyridin-2-yl-methoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-furan-2-yl-6-(5-methyl-pyridin-2-yl-methoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-furan-2-yl-6-(isoquinolin-3-yl-methoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-furan-2-yl-6-(4-methyl-pyridin-2-yl-methoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-furan-2-yl-6-(6-methyl-pyridin-3-yl-methoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-(3,5-dimethyl-pyridin-2-yl-methoxy)-6-furan-2-yl-pyrimidine-5-carbonitrile,
- 2-amino-4-(3-fluoro-phenyl)-6-(2-pyridin-2-yl-ethoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-(4-methyl-furan-2-yl)-6-(2-pyridin-2-yl-ethoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-(5-methyl-furan-2-yl)-6-(3-methyl-pyridin-2-yl-methoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-(3,5-dimethyl-pyridin-2-ylmethoxy)-6-(5-methyl-furan-2-yl)-pyrimidine-5-carbonitrile,
- 2-amino-4-(5-bromo-furan-2-yl)-6-(5-methyl-pyridin-2-yl-methoxy)-pyrimidine-5carbonitrile,
- 2-amino-4-(5-bromo-furan-2-yl)-6-(3-methyl-pyridin-2-yl-methoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-(5-bromo-furan-2-yl)-6-(2-pyridin-2-yl-ethoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-(5-chloro-furan-2-yl)-6-(2-pyridin-2-yl-ethoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-(5-chloro-furan-2-yl)-6-(3,5-dimethyl-pyridin-2-yl-methoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-(5-chloro-furan-2-yl)-6-(3-methyl-pyridin-2-yl-methoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-(5-chloro-furan-2-yl)-6-(5-methyl-pyridin-2-yl-methoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-(4-bromo-furan-2-yl)-6-(5-methyl-pyridin-2-yl-methoxy)-pyrimidine-5-carbonitrile,
- 2-amino-4-(4-bromo-furan-2-yl)-6-(3,5-dimethyl-pyridin-2-yl-methoxy)-pyrimidine-5-carbonitrile and 2-amino-4-(4-bromo-furan-2-yl)-6-(3-methyl-pyridin-2-yl-methoxy)-pyrimidine-5-carbonitrile;
- or a pharmaceutically acceptable salt thereof.
33 more elements
A compound selected from the group consisting of
- 2-Amino-4-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile
- 2-amino-4-benzylsulfanyl-6-furan-2-yl-pyrimidine-5-carbonitrile,
- 2-amino-4-butylsulfanyl-6-furan-2-yl-pyrimidine-5-carbonitrile,
- 2-amino-4-ethylsulfanyl-6-furan-2-yl-pyrimidine-5-carbonitrile,
- 2-amino-4-phenyl-6-(3-phenyl-propylsulfanyl)-pyrimidine-5-carbonitrile,
- 2-amino-4-furan-2-yl-6-phenethylsulfanyl-pyrimidine-5-carbonitrile,
- 2-amino-4-furan-2-yl-6-(3-phenyl-propylsulfanyl)-pyrimidine-5-carbonitrile,
- 2-amino-4-furan-2-yl-6-(pyridin-2-yl-methylsulfanyl)-pyrimidine-5-carbonitrile,
- 2-amino-4-furan-2-yl-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidine-5-carbonitrile,
- 2-amino-4-(2-pyridin-2-yl-ethylsulfanyl)-6-thiophen-2-yl-pyrimidine-5-carbonitrile,
- 2-amino-4-(4-methyl-furan-2-yl)-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidine-5-carbonitrile,
- 2-amino-4-(5-chloro-furan-2-yl)-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidine-5-carbonitrile,
- 2-amino-4-(5-bromo-furan-2-yl)-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidine-5-carbonitrile,
- 2-amino-4-(4-bromo-furan-2-yl)-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidine-5-carbonitrile,
- 2-amino-4-(5-cyanomethyl-furan-2-yl)-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidine-5-carbonitrile,
- 2-amino-4-(4-cyano-furan-2-yl)-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidine-5-carbonitrile and
- 2-amino-4-(5-difluoromethyl-furan-2-yl)-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidine-5-carbonitrile,
- or a pharmaceutically acceptable salt thereof.
15 more elements
A compound selected from the group consisting of
- 2-Amino-4-furan-2-yl-6-piperidin-1-yl-pyrimidine-5-carbonitrile,
- 2-amino-6-furan-2-yl-pyrimidine-4,5-dicarbonitrile,
- 2-amino-4-furan-2-yl-6-phenyl-pyrimidine-5-carbonitrile,
- (E)-2-amino-4-furan-2-yl-6-styryl-pyrimidine-5-carbonitrile and
- 2-amino-4-(3,4-dihydro-1H-isoquinolin-2-yl)-6-furan-2-yl-pyrimidine-5-carbonitrile;
- or a pharmaceutically acceptable salt thereof.
3 more elements
A compound selected from the group consisting of:
- 5-Bromo-4-furan-2-yl-6-(pyridin-2-yl-methoxy)-pyrimidin-2-yl-amine,
- 5-bromo-6-furan-2-yl-N4-(3-phenyl-propyl)-pyrimidine-2,4-diamine,
- 5-bromo-4-furan-2-yl-6-(3-phenyl-propoxy)-pyrimidin-2-yl-amine,
- 4-furan-2-yl-5-iodo-6-(3-phenyl-propoxy)-pyrimidin-2-yl-amine,
- 5-bromo-4-furan-2-yl-6-phenethylsulfanyl-pyrimidin-2-yl-amine,
- 5-bromo-4-furan-2-yl-6-(3-phenyl-allyloxy)-pyrimidin-2-yl-amine,
- 4-benzyloxy-6-furan-2-yl-5-nitro-pyrimidin-2-yl-amine,
- 5-chloro-6-furan-2-yl-N4-(3-phenyl-propyl)-pyrimidine-2,4-diamine,
- 5-chloro-4-furan-2-yl-6-(3-phenyl-propoxy)-pyrimidin-2-yl-amine,
- 5-chloro-4-furan-2-yl-6-phenethyloxy-pyrimidin-2-yl-amine,
- 4-benzylsulfanyl-5-chloro-6-furan-2-yl-pyrimidin-2-yl-amine,
- 4-furan-2-yl-5-iodo-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidin-2-yl-amine,
- 5-bromo-4-furan-2-yl-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidin-2-yl-amine and
- 5-chloro-4-furan-2-yl-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidin-2-yl-amine;
- or a pharmaceutically acceptable salt thereof.
12 more elements
A compound N-[5-Cyano-4-furan-2-yl-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidin-2-yl]-benzamide.
Dependencies are inferred from the claim text.