# US 11,896,593 B2 · Sulfamate derivative compounds for use in treating or alleviating a psychiatric disorder

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- Number: US 11,896,593 B2
- Document ID: US11896593B2
- Status: Granted
- Kind: B2
- Application number: 16/980,822
- Filed: 2020-09-10
- Published: 2022-07-14
- Granted: 2024-02-13
- Earliest claimed: 2020-09-10
- Assignees: Bio-Pharm Solutions Co., Ltd.
- Applicants: Bio-Pharm Solutions Co., Ltd.
- Inventors: Yong Moon Choi
- Web page: https://patentgrep.com/patent/US11896593B2

## CPC

- A61K 31/506: not condensed and containing further heterocyclic rings
- A61K 31/357: having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
- A61K 31/381: having five-membered rings
- A61K 31/427: not condensed and containing further heterocyclic rings
- A61K 31/443: containing a five-membered ring with oxygen as a ring hetero atom
- A61P 25/24: Antidepressants
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to a pharmaceutical composition for treating and/or alleviating a psychiatric disorder comprising a sulfamate derivative compound and/or a pharmaceutically acceptable salt thereof as an active ingredient. Furthermore, the present invention relates to a pharmaceutical composition for inducing anti-stress, anti-anxiety and/or anti-depressant activities comprising a sulfamate derivative compound and/or a pharmaceutically acceptable salt thereof as an active ingredient.

## Claims

### Claim 1

A method for treating a psychiatric disorder in a subject, comprising:
selecting a subject having a psychiatric disorder; and
administering to the subject a pharmaceutical composition comprising a sulfamate derivative compound of Chemical Formula I or a pharmaceutically acceptable salt thereof:
wherein
R1 and R2 are each independently selected from the group consisting of hydrogen, C1-C5 alkyl, C2-C5 alkenyl and C6-C10 aryl, R1 and R2 together with the carbon atom to which they attach form a C3-C12 cycloalkyl group, or R1 and R2 are bond and they together with the oxygen atom to which they attach form a carbonyl group;
A is an aryl moiety or a heterocyclic moiety optionally substituted by one or more substituents selected from the group consisting of hydrogen, hydroxyl, C1-C5 alkoxy, C1-C5 alkyl, C2-C5 alkenyl, C6-C10 aryl, C1-C5 alkoxycarbonyl, carboxyl, C2-C5 acyl, C1-C5 alkylthio, cyano, nitro, amine, C1-C5 alkylamine and halogen;
R3 and R4 are each independently hydrogen or C1-C3 alkyl;
l and m are each independently an integer of 0˜4; and
the psychiatric disorder is selected from the group consisting of anxiety disorder, mood disorder, somatoform disorder, dissociative disorder, psychotic disorder, personality disorder, sexual disorder, sexual identity disorder, substance-related disorder, eating disorder, sleep disorder, impulse control disorder and adjustment disorder.

### Claim 2 (depends on 1)

The method according to claim 1, wherein A is the aryl moiety representing a C6-C10 aryl group.

### Claim 3 (depends on 1)

The method according to claim 1, wherein A is the heterocyclic moiety representing a C3-C10 heterocyclic group.

### Claim 4 (depends on 1)

The method according to claim 1, wherein A is phenyl optionally substituted by one or more substituents selected from the group consisting of hydrogen, halogen, C1-C5 alkyl, nitro, amine and C1-C5 alkyl amine or C3-C10 heterocyclic group optionally substituted by one or more substituents selected from the group consisting of hydrogen, halogen, C1-C5 alkyl and C6-C10 aryl.

### Claim 5 (depends on 4)

The method according to claim 4, wherein A is selected from the group consisting of:
wherein each X is independently selected from the group consisting of halogen, nitro, amine and C1-C5 alkyl;
n is an integer of 0˜5; and
Z is selected from the group consisting of S, O and NH.

### Claim 6 (depends on 5)

The method according to claim 5, wherein n is an integer of 0˜2.

### Claim 7 (depends on 1)

The method according to claim 1, wherein R3 and R4 are each independently hydrogen or methyl.

### Claim 8 (depends on 1)

The method according to claim 1, wherein 1 and m are each independently an integer of 0˜2.

### Claim 9 (depends on 1)

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) 2-(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;
(78) 2-(3-(2-chlorophenyl)-1,4-dioxaspiro[4,5]decan-2-yl)ethyl sulfamate;
(79) (5-(2,4-dichlorothiazol-5-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl sulfamate;
(80) (5-(2-chlorothiazol-5-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)methylsulfamate;
(81) (2,2-di methyl-5-(4-methylthiazol-5-yl)-1,3-dioxolan-4-yl)methyl sulfamate;
(82) (2,2-dimethyl-5-(2-chloro-4-methylthiazol-5-yl)-1,3-dioxolan-4-yl)methylsulfamate;
(83) (2,2-dimethyl-5-(thiophen-3-yl)-1,3-dioxolan-4-yl)methyl sulfamate;
(84) (2,2-dimethyl-5-(5-chlorothiophen-2-yl)-1,3-dioxolan-4-yl)methylsulfamate;
(85) (5-(3-chloropyridin-4-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)methylsulfamate;
(86) (5-(4-chloropyridin-3-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)methylsulfamate;
(87) (2,2-dimethyl-5-(pyrimidin-5-yl)-1,3-dioxolan-4-yl)methylsulfamate; and
(88) (2,2-dimethyl-5-(2-chloropyrimidin-5-yl)-1,3-dioxolan-4-yl)methylsulfamate.

### Claim 10 (depends on 1)

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.

### Claim 11 (depends on 1)

The method according to claim 1, wherein the pharmaceutically acceptable salt is produced by reacting the compound with an inorganic acid, an organic acid, an amino acid, sulfonic acid, an alkali metal or ammonium ion.

### Claim 12 (depends on 1)

The method according to claim 1, wherein:
the anxiety disorder is generalized anxiety disorder, phobia, panic disorder, obsessive compulsive disorder or post traumatic stress disorder (PTSD);
the mood disorder is depressive disorder or bipolar disorder;
the somatoform disorder is somatization disorder, conversion disorder, pain disorder, hypochondria or body dysmorphic disorder;
the dissociative disorder is dissociative amnesia or dissociative identity disorder;
the psychotic disorder is schizophrenia, schizoaffective disorder or delusional disorder;
the personality disorder is schizoid personality disorder, borderline personality disorder or obsessive-compulsive personality disorder;
the substance-related disorder is disorder of being addicted to addictive substances including alcohol, tobacco or drugs;
the eating disorder is anorexia nervosa or bulimia nervosa;
the sleep disorder is sleep disturbance or dyssomnia; and
the impulse-control disorder is intermittent explosive disorder, gambling disorder, arsonism or trichotillomania.

### Claim 13 (depends on 12)

The method according to claim 12, wherein the depressive disorder is major depressive disorder, dysthymic disorder, persistent depressive disorder, premenstrual dysphoric disorder or postpartum depression.