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US 2017/0050919 A1Published application
Cyclic hydrocarbon compound
AssigneeToa Eiyo Ltd.
InventorsHidekazu MASAKI, Masayuki KAGEYAMA
Life of this patent
Estimating the term…
Abstract
Provided is a novel compound having an excellent suppression effect against arrhythmia including atrial fibrillation and being useful as a pharmaceutical product without antiviral effect. Disclosed is a compound represented by the following General Formula (I), a pharmaceutically acceptable salt thereof, or a solvate thereof (in the formula, the dotted line portion represents a single bond or a double bond; R1 represents an optionally substituted C1-6 alkyl group; Q represents an oxygen atom, a sulfur atom, or NR5; R2 represents —(C═O)—R6, —CHR6R7, or —CH2OR8; and R3 and R4, which may be identical or different, each represent an amino group, an azide group, or —X—R9, with the proviso that any one of R3 and R4 is an amino group).
Claims12
1:
- A compound represented by Formula (I), a pharmaceutically acceptable salt thereof, or a solvate thereof:
- wherein the dotted line portion represents a single bond or a double bond;
- R1 represents an optionally substituted C1-6 alkyl group;
- Q represents an oxygen atom, a sulfur atom, or NR5;
- R5 represents a hydrogen atom, an optionally substituted C1-6 alkyl group, or an optionally substituted non-aromatic heterocyclic ring formed by combining with R1 and an adjacent nitrogen atom;
- R2 represents —(C═O)—R6, —CHR6R7, or —CH2OR8;
- R6 represents an optionally substituted C1-6 alkyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group;
- R7 represents a hydroxyl group or an optionally substituted C1-6 alkoxy group;
- R8 represents an optionally substituted C1-6 alkyl group;
- R3 and R4, which may be identical or different, each represent an amino group, an azide group, or —X—R9;
- R9 represents a hydrogen atom, an optionally substituted C1-6 alkyl group, —(C═O)—R10, or —(C═O)—NR11R12;
- R10 represents an optionally substituted C1-6 alkyl group, an optionally substituted C1-6 alkoxy group, an optionally substituted aryl group, or an optionally substituted heteroaryl group;
- R11 and R12, which may be identical or different, each represent a hydrogen atom or an optionally substituted C1-6 alkyl group;
- X represents an oxygen atom or NR13;
- and
- R13 represents a hydrogen atom, an optionally substituted C1-6 alkyl group, or an optionally substituted non-aromatic heterocyclic ring formed by combining with R9 and an adjacent nitrogen atom,
- with the proviso that any one of R3 and R4 is an amino group.
14 more elements
2:
- The compound according to claim 1, a pharmaceutically acceptable salt thereof, or a solvate thereof, wherein the dotted line portion in Formula (I) represents a double bond.
3:
- A compound represented by Formula (II), a pharmaceutically acceptable salt thereof, or a solvate thereof:
- wherein
- R1 represents an optionally substituted C1-6 alkyl group;
- Q represents an oxygen atom, a sulfur atom, or NR5;
- R5 represents a hydrogen atom, an optionally substituted C1-6 alkyl group, or an optionally substituted non-aromatic heterocyclic ring formed by combining with R1 and an adjacent nitrogen atom;
- R2 represents —(C═O)—R6, —CHR6R7, or —CH2OR8;
- R6 represents an optionally substituted C1-6 alkyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group;
- R7 represents a hydroxyl group or an optionally substituted C1-6 alkoxy group;
- R8 represents an optionally substituted C1-6 alkyl group;
- R3 and R4, which may be identical or different, each represent an amino group, an azide group, or —X—R9;
- R9 represents a hydrogen atom, an optionally substituted C1-6 alkyl group, —(C═O)—R10, or —(C═O)—NR11R12;
- R10 represents an optionally substituted C1-6 alkyl group, an optionally substituted C1-6 alkoxy group, an optionally substituted aryl group, or an optionally substituted heteroaryl group;
- R11 and R12, which may be identical or different, each represent a hydrogen atom or an optionally substituted C1-6 alkyl group;
- X represents an oxygen atom or NR13;
- and
- R13 represents a hydrogen atom, an optionally substituted C1-6 alkyl group, or an optionally substituted non-aromatic heterocyclic ring formed by combining with R9 and an adjacent nitrogen atom,
- with the proviso that any one of R3 and R4 is an amino group.
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4:
- The compound according to claim 1, a pharmaceutically acceptable salt thereof, or a solvate thereof, wherein the substituent which the C1-6 alkyl group, the aryl group, the heteroaryl group, the C1-6 alkoxy group, or the non-aromatic heterocyclic ring has is one to five substituents selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-6 alkyl group, a C2-6 alkenyl group, a C1-6 alkoxy group, an acyl group, a carboxyl group, a C1-6 alkylcarbonylamino group, a C1-6 alkoxycarbonyl group, a carbamoyl group, a sulfamoyl group, a C1-6 alkylsulfanyl group, a C1-6 alkylsulfenyl group, a C1-6 alkylsulfonyl group, an amino group, a C1-6 alkylamino group, a C1-6 dialkylamino group, an aryl group, a heteroaryl group, and a non-aromatic heterocyclic ring group.
5:
- The compound according to claim 1, a pharmaceutically acceptable salt thereof, or a solvate thereof, wherein Q is an oxygen atom.
6:
- The compound according to claim 1, a pharmaceutically acceptable salt thereof, or a solvate thereof, wherein R3 is an amino group and R4 is —NH(C═O)—R10 or —NH—(C═O)—NR11R12.
7:
- A pharmaceutical agent comprising the compound according to claim 1, a pharmaceutically acceptable salt thereof, or a solvate thereof.
8:
- The pharmaceutical agent according to claim 7, wherein the agent is a therapeutic agent suitable for treatment of arrhythmia.
9:
- A pharmaceutical composition comprising:
- the compound according to claim 1, a pharmaceutically acceptable salt thereof, or a solvate thereof;
- and
- a pharmaceutically acceptable carrier.
1 more element
10-11. (canceled)
12:
- A method for treating arrhythmia, comprising administering an effective amount of the compound according to claim 1, a pharmaceutically acceptable thereof, or a solvate thereof to a patient in need thereof.
13:
- The compound according to claim 1, a pharmaceutically acceptable salt thereof, or a solvate thereof, which is selected from the group consisting of:
- N-[(1R,2R,6S)-6-amino-2-(1-ethylpropoxy)-4-(thiophene-2-carbonyl)-3-cyclohexen-1-yl]acetamide;
- N-[(1R,2R,6S)-6-amino-2-(1-ethylpropoxy)-4-(thiophene-2-carbonyl)-3-cyclohexen-1-yl]acetamide hydrochloride;
- N-[(1R,2R,6S)-6-amino-2-(1-ethylpropoxy)-4-(5-methylfuran-2-carbonyl)-3-cyclohexen-1-yl]acetamide;
- N-[(1R,2R,6S)-6-amino-2-(1-ethylpropoxy)-4-(5-methylthiophene-2-carbonyl)-3-cyclohexen-1-yl]acetamide;
- N-[(1R,2R,6S)-6-amino-2-(1-ethylpropoxy)-4-(4-fluorobenzoyl)-3-cyclohexen-1-yl]acetamide;
- N-[(1R,2R,6S)-6-amino-4-benzoyl-2-(1-ethylpropoxy)-3-cyclohexen-1-yl]acetamide hydrochloride;
- N-[(1R,2R,6S)-6-amino-2-(1-ethylpropoxy)-4-phenylacetyl-3-cyclohexen-1-yl]acetamide;
- N-[(1R,2R,6S)-6-amino-2-(1-ethylpropoxy)-4-(furan-2-carbonyl)-3-cyclohexen-1-yl]acetamide;
- N-[(1R,2R,6S)-6-amino-2-(1-ethylpropoxy)-4-(1-methyl-1H-pyrrole-2-carbonyl)-3-cyclohexen-1-yl]acetamide;
- N-[(1R,2R,6S)-6-amino-4-(2,2-dimethylpropionyl)-2-(1-ethylpropoxy)-3-cyclohexen-1-yl]acetamide;
- N-[(1R,2R,6S)-6-amino-2-(1-ethylpropoxy)-4-(thiazole-2-carbonyl)-3-cyclohexen-1-yl]acetamide;
- N-[(1R,2R,6S)-6-amino-2-(1-ethylpropoxy)-4-pentanoyl-3-cyclohexen-1-yl]acetamide hydrochloride;
- N-[(1R,2R,6S)-6-amino-4-benzoyl-2-(1-ethylpropoxy)-3-cyclohexen-1-yl]-2,2-dimethylpropionamide;
- N-[(1S,5R,6R)-6-amino-3-benzoyl-5-(1-ethylpropoxy)-3-cyclohexen-1-yl]acetamide;
- N-[(1S,5R,6R)-6-amino-5-(1-ethylpropoxy)-3-(thiophene-2-carbonyl)-3-cyclohexen-1-yl]acetamide;
- N-[(1R,2R,6S)-6-amino-2-(1-ethylpropoxy)-4-(thiophene-2-carbonyl)-3-cyclohexen-1-yl]-3-methylbutylamide;
- [(1R,2R,6S)-6-amino-2-(1-ethylpropoxy)-4-(thiophene-2-carbonyl)cyclohexen-3-yl]-3-ethylurea;
- N-[(1R,2R,6S)-6-amino-2-(1-ethylpropoxy)-4-heptanoyl-3-cyclohexen-1-yl]acetamide;
- N-[(1R,2R,6S)-6-amino-2-(1-ethylpropoxy)-4-(thiophene-3-carbonyl)-3-cyclohexen-1-yl]acetamide;
- N-[(1R,2R,6S)-6-amino-4-cyclohexanecarbonyl-2-(1-ethylpropoxy)-3-cyclohexen-1-yl]acetamide hydrochloride;
- and
- N-[(1R,2R,6S)-6-amino-2-(1-ethylpropoxy)-4-(5-methoxythiophene-2-carbonyl)-3-cyclohexen-1-yl]acetamide hydrochloride.
20 more elements