IP Library › Granted Patent US 9,834,535
Granted Patent B2
US 9,834,535 · App. 15/103,699 · Granted Dec 5, 2017

Sulfamate derivative compounds for use in treating or alleviating pain

Inventor: Yong Moon Choi (Seoul, KR)
Assignee: Bio-Pharm Solutions Co., Ltd.
C07D317/24A61K31/18A61K31/357A61K31/381A61K31/427A61K31/443A61K31/506C07D317/36C07D317/72C07D405/04C07D409/04C07D417/04
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Quick Facts
Patent No.
US 9,834,535
App. No.
15/103,699
Granted
Dec 5, 2017
Kind
B2
Abstract

The present invention relates to sulfamate derivative compounds and a composition for treating and/or alleviating pain containing the sulfamate derivative compounds or a pharmaceutically acceptable salt thereof as an active ingredient. More specifically, the present invention relates to a pharmaceutical composition for treating or alleviating pain containing a sulfamate derivative compound and/or a pharmaceutically acceptable salt thereof as an active ingredient. Furthermore, the present invention relates to a method for treatment or alleviation of pain comprising administering a sulfamate derivative compound in a pharmaceutically effective amount to a subject in need of treatment or alleviation of pain; and a use of the sulfamate derivative compound or the pharmaceutically acceptable salt thereof in treating and/or alleviating pain, are provided.

Claims (251)

1. A method of treating or alleviating pain in a subject in need thereof comprising administering a pharmaceutically effective amount of a pharmaceutical composition comprising a sulfamate derivative compound represented by the following Chemical Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient:

wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, C 1 -C 5 alkyl group, C 2 -C 5 alkenyl and C 6 -C 10 aryl group, R 1 and R 2 together with the carbon atom to which they attach form a C 3 -C 12 cycloalkyl group, or R 1 and R 2 are bond and they together with the oxygen atom to which they attach form a carbonyl group; R 3 , R 4 , R 5 , R 6 and R 7 are each independently selected from the group consisting of hydrogen, hydroxyl, C 1 -C 5 alkoxy, C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 6 -C 10 aryl, C 1 -C 5 alkoxycarbonyl, carboxyl, C 2 -C 5 acyl, C 1 -C 5 alkylthio, cyano, nitro, amine, C 1 -C 5 alkylamine and halogen; R 8 and R 9 are each independently hydrogen or C 1 -C 3 alkyl group; n and m are each independently an integer of 0-4.

2. The method according to claim 1 , R 8 and R 9 are each independently hydrogen or methyl.

3. The method according to claim 1 , m and n are each independently an integer of 0-2.

4. The method according to claim 1 , wherein the compound is selected from the group consisting of:

(1) (5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methylsulfamate;

(2) (5-(2-chlorophenyl)-2-methyl-1,3-dioxolan-4-yl) methyl sulfamate;

(3) (5-(2-chlorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

(4) (3-(2-chlorophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

(5) (3-(2-chlorophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

(6) (5-(2-chlorophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

(7) (5-(2-fluorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

(8) (5-(2-fluorophenyl)-2-methyl-1,3-dioxolan-4-yl) methyl sulfamate;

(9) (5-(2-fluorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

(10) (3-(2-fluorophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

(11) (3-(2-fluorophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

(12) (5-(2-fluorophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

(13) (5-(2-iodophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

(14) (5-(2-iodophenyl)-2-methyl-1,3-dioxolan-4-yl) methyl sulfamate;

(15) (5-(2-iodophenyl)-2,2-diethyl-1,3-dioxolan-4-yl) methyl sulfamate;

(16) (3-(2-iodophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl) methyl sulfamate;

(17) (3-(2-iodophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

(18) (5-(2-iodophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

(19) (5-(2,4-dichlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

(20) (5-(2,4-dichlorophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl sulfamate;

(21) (5-(2,4-dichlorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

(22) (3-(2,4-dichlorophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

(23) (3-(2,4-dichlorophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

(24) (5-(2,4-dichlorophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

(25) (5-(2,6-dichlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methylsulfamate;

(26) (5-(2,6-dichlorophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl sulfamate;

(27) (5-(2,6-dichlorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

(28) (3-(2,6-dichlorophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

(29) (3-(2,6-dichlorophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

(30) (5-(2,6-dichlorophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

(31) (5-(2-aminophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

(32) (5-(2-aminophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl sulfamate;

(33) (5-(2-aminophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

(34) (3-(2-aminophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

(35) (3-(2-aminophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

(36) (5-(2-aminophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

(37) (5-(2-nitrophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

(38) (5-(2-nitrophenyl)-2-methyl-1,3-dioxolan-4-yl) methyl sulfamate;

(39) (5-(2-nitrophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

(40) (3-(2-nitrophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

(41) (3-(2-nitrophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

(42) (5-(2-nitrophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

(43) (5-(2-nitrophenyl)-2-oxo-1,3-dioxolan-4-yl)methyl sulfamate;

(44) (5-(2-methylphenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

(45) (5-(2-methylphenyl)-2-methyl-1,3-dioxolan-4-yl)methyl sulfamate;

(46) (5-(2-methylphenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

(47) (3-(2-methylphenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

(48) (3-(2-methylphenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

(49) (5-(2-methylphenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

(50) (5-(2-methylaminophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl methyl sulfamate;

(51) (5-phenyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

(52) (5-phenyl-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

(53) (3-phenyl-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

(54) (3-phenyl-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

(55) 2-(5-benzyl-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

(56) 2-(5-benzyl-2,2-diethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

(57) 2-(3-benzyl-1,4-dioxaspiro[4,4]nonan-2-yl)ethyl sulfamate;

(58) 2-(3-benzyl-1,4-dioxaspiro[4,5]decane-2-yl)ethyl sulfamate;

(59) (5-benzyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

(60) (5-benzyl-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

(61) (3-benzyl-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

(62) (3-benzyl-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

(63) 2-(5-phenyl-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

(64) 2-(5-phenyl-2,2-diethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

(65) 2-(3-phenyl-1,4-dioxaspiro[4,4]nonan-2-yl)ethyl sulfamate;

(66) 3-(3-phenyl-1,4-dioxaspiro[4,5]decan-2-yl)ethyl sulfamate;

(67) 2-(5-(2-chlorobenzyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

(68) 2-(5-(2-chlorobenzyl)-2,2-diethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

(69) 2-(3-(2-chlorobenzyl)-1,4-dioxaspiro[4,4]nonan-2-yl)ethyl sulfamate;

(70) 2-(3-(2-chlorobenzyl)-1,4-dioxaspiro[4,5]decan-2-yl)ethyl sulfamate;

(71) (5-(2-chlorobenzyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

(72) (5-(2-chlorobenzyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

(73) (3-(2-chlorobenzyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

(74) (3-(2-chlorobenzyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

(75) 2-(5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

(76) 2-(5-(2-chlorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

(77) 2-(3-(2-chlorophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)ethyl sulfamate; and

(78) 2-(3-(2-chlorophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)ethyl sulfamate.

5. The method according to claim 1 , wherein the compound is selected from the group consisting of:

((4R,5R)-5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S,5S)-5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

(5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate (SS & RR mixture);

(5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate (SR & RS mixture);

((4R,5R)-5-(2-chlorophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2-chlorophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R, 5R)-5-(2-chlorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2-chlorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((2R, 3R)-3-(2-chlorophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

((2S, 3S)-3-(2-chlorophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

((2R, 3R)-3-(2-chlorophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

((2S, 3S)-3-(2-chlorophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

((4R,5R)-5-(2-chlorophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S,5S)-5-(2-chlorophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R,5R)-5-(2-fluorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S,5S)-5-(2-fluorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R,5R)-5-(2-fluorophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2-fluorophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R,5R)-5-(2-fluorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S,5S)-5-(2-fluorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((2R, 3R)-3-(2-fluorophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

((2S, 3S)-3-(2-fluorophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

((2R, 3R)-3-(2-fluorophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

((2S, 3S)-3-(2-fluorophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

((4R,5R)-5-(2-fluorophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S,5S)-5-(2-fluorophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R,5R)-5-(2-iodophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S,5S)-5-(2-iodophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R,5R)-5-(2-iodophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2-iodophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R,5R)-5-(2-iodophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S,5S)-5-(2-iodophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((2R, 3R)-3-(2-iodophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

((2S, 3S)-3-(2-iodophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

((2R, 3R)-3-(2-iodophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

((2S, 3S)-3-(2-iodophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

((4R,5R)-5-(2-iodophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S,5S)-5-(2-iodophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R,5R)-5-(2,4-dichlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S,5S)-5-(2,4-dichlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R,5R)-5-(2,4-dichlorophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2,4-dichlorophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R,5R)-5-(2,4-dichlorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S,5S)-5-(2,4-dichlorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((2R, 3R)-3-(2,4-dichlorophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

((2S, 3S)-3-(2,4-dichlorophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

((2R, 3R)-3-(2,4-dichlorophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

((2S, 3S)-3-(2,4-dichlorophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

((4R, 5R)-5-(2,4-dichlorophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S,5S)-5-(2,4-dichlorophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R, 5R)-5-(2,6-dichlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2,6-dichlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R, 5R)-5-(2,6-dichlorophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2,6-dichlorophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R, 5R)-5-(2,6-dichlorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2,6-dichlorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((2R, 3R)-3-(2,6-dichlorophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

((2S, 3S)-3-(2,6-dichlorophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

((2R, 3R)-3-(2,6-dichlorophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

((2S, 3S)-3-(2,6-dichlorophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

((4R, 5R)-5-(2,6-dichlorophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S,5 S)-5-(2,6-dichlorophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R, 5R)-5-(2-aminophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2-aminophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R, 5R)-5-(2-aminophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2-aminophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R, 5R)-5-(2-aminophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2-aminophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((2R, 3R)-3-(2-aminophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

((2S, 3S)-3-(2-aminophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

((2R, 3R)-3-(2-aminophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

((2S, 3S)-3-(2-aminophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

((4R, 5R)-5-(2-aminophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2-aminophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R, 5R)-5-(2-nitrophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2-nitrophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R, 5R)-5-(2-nitrophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2-nitrophenyl)-2-methyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R,5R)-5-(2-nitrophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S,5S)-5-(2-nitrophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((2R, 3R)-3-(2-nitrophenyl)-1,4-dioxaspiro[4,4]nonane-2-yl)methyl sulfamate;

((2S, 3S)-3-(2-nitrophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

((2R, 3R)-3-(2-nitrophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

((2S, 3S)-3-(2-nitrophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

((4R, 5R)-5-(2-nitrophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2-nitrophenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R, 5R)-5-(2-nitrophenyl)-2-oxo-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2-nitrophenyl)-2-oxo-1,3-dioxolan-4-yl)methyl sulfamate;

((4R, 5R)-5-(2-methylphenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2-methylphenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R, 5R)-5-(2-methylphenyl)-2-methyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2-methylphenyl)-2-methyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R, 5R)-5-(2-methylphenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2-methylphenyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((2R, 3R)-3-(2-methylphenyl)-1,4-dioxaspiro[4,4]nonane-2-yl)methyl sulfamate;

((2S, 3S)-3-(2-methylphenyl)-1,4-dioxaspiro[4,4]nonane-2-yl)methyl sulfamate;

((2R, 3R)-3-(2-methylphenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

((2S, 3S)-3-(2-methylphenyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

((4R, 5R)-5-(2-methylphenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2-methylphenyl)-2-phenyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R, 5R)-5-(2-methylaminophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl methylsulfamate;

((4S, 5S)-5-(2-methylaminophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl methylsulfamate;

((4R, 5R)-5-phenyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-phenyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R, 5R)-5-phenyl-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-phenyl-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((2R 3R)-3-phenyl-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

((2S, 3S)-3-phenyl-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

((2R, 3R)-3-phenyl-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

((2S, 3S)-3-phenyl-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

2-((4S, 5S)-5-benzyl-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

2-((4R, 5R)-5-benzyl-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

2-((4S, 5S)-5-benzyl-2,2-diethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

2-((4R, 5R)-5-benzyl-2,2-diethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

2-((2S, 3S)-3-benzyl-1,4-dioxaspiro[4,4]nonan-2-yl)ethyl sulfamate;

2-((2R, 3R)-3-benzyl-1,4-dioxaspiro[4,4]nonan-2-yl)ethyl sulfamate;

2-((2S, 3S)-3-benzyl-1,4-dioxaspiro[4,5]decane-2-yl)ethyl sulfamate;

2-((2R, 3R)-3-benzyl-1,4-dioxaspiro[4,5]decan-2-yl)ethyl sulfamate;

((4S, 5S)-5-benzyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R, 5R)-5-benzyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-benzyl-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R, 5R)-5-benzyl-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((2S, 3S)-3-benzyl-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

((2R, 3R)-3-benzyl-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

((2S, 3S)-3-benzyl-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

((2R, 3R)-3-benzyl-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

2-((4R, 5R)-5-phenyl-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

2-((4S, 5S)-5-phenyl-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

2-((4R, 5R)-5-phenyl-2,2-diethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

2-((4S, 5S)-5-phenyl-2,2-diethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

2-((2R, 3R)-3-phenyl-1,4-dioxaspiro[4,4]nonan-2-yl)ethyl sulfamate;

2-((2S, 3S)-3-phenyl-1,4-dioxaspiro[4,4]nonan-2-yl)ethyl sulfamate;

2-(2R, 3R)-3-phenyl-1,4-dioxaspiro[4,5]decan-2-yl)ethyl sulfamate;

2-((2S, 3S)-3-phenyl-1,4-dioxaspiro[4,5]decan-2-yl)ethyl sulfamate;

2-((4S, 5S)-5-(2-chlorobenzyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

2-((4R, 5R)-5-(2-chlorobenzyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

2-((4S, 5S)-5-(2-chlorobenzyl)-2,2-diethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

2-((4R, 5R)-5-(2-chlorobenzyl)-2,2-diethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

2-((2S, 3S)-3-(2-chlorobenzyl)-1,4-dioxaspiro[4,4]nonan-2-yl)ethyl sulfamate;

2-((2R, 3R)-3-(2-chlorobenzyl)-1,4-dioxaspiro[4,4]nonan-2-yl)ethyl sulfamate;

2-((2S, 3S)-3-(2-chlorobenzyl)-1,4-dioxaspiro[4,5]decan-2-yl)ethyl sulfamate;

2-((2R, 3R)-3-(2-chlorobenzyl)-1,4-dioxaspiro[4,5]decan-2-yl)ethyl sulfamate;

((4S, 5S)-5-(2-chlorobenzyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R, 5R)-5-(2-chlorobenzyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4S, 5S)-5-(2-chlorobenzyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R, 5R)-5-(2-chlorobenzyl)-2,2-diethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((2S, 3S)-3-(2-chlorobenzyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

((2R, 3R)-3-(2-chlorobenzyl)-1,4-dioxaspiro[4,4]nonan-2-yl)methyl sulfamate;

((2S, 3S)-3-(2-chlorobenzyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

((2R, 3R)-3-(2-chlorobenzyl)-1,4-dioxaspiro[4,5]decan-2-yl)methyl sulfamate;

2-((4R, 5R)-5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

2-((4S, 5S)-5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

2-((4R, 5R)-5-(2-chlorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

2-((4S, 5S)-5-(2-chlorophenyl)-2,2-diethyl-1,3-dioxolan-4-yl)ethyl sulfamate;

2-((2R, 3R)-3-(2-chlorophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)ethyl sulfamate;

2-((2S, 3S)-3-(2-chlorophenyl)-1,4-dioxaspiro[4,4]nonan-2-yl)ethyl sulfamate;

2-((2R, 3R)-3-(2-chlorophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)ethyl sulfamate;

2-((2S, 3S)-3-(2-chlorophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)ethyl sulfamate;

((4S, 5R)-5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

((4R, 5S)-5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;

Sodium ((((4R, 5R)-5-(2-aminophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfonyl)amide;

Sodium ((((4S, 5S)-5-(2-aminophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfonyl)amide; and

sodium ((((4S,5S)-5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)sulfonyl)amide.

6. The method according to claim 1 , wherein the pain is one or more selected from the group consisting of nociceptive pain, psychogenic pain, inflammatory pain, and pathological pain.

7. The method according to claim 1 , wherein the pain is one or more selected from the group consisting of neuropathic pain, cancer pain, postoperative pain, trigeminal neuralgia pain, idiopathic pain, diabetic neuropathic pain, and migraine.

8. The method according to claim 1 , wherein the compound is in the form of a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers.

9. The method according to claim 4 , wherein the compound is in the form of a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 8, 2017
From: CHOI, YONG MOON
To: BIO-PHARM SOLUTIONS CO., LTD.
Reel/Frame 043234/0128 →
Continuity (3)
Provisional Application 61915046 · Dec 12, 2013
Provisional Application 61915047 · Dec 12, 2013
Related Publication 20160318894A1 · Nov 3, 2016