US 9,527,807 B2Granted

Sulfonamide derivative and use thereof

AssigneeTakeda Pharmaceutical Company Limited

InventorsShoji Fukumoto, Osamu Ujikawa, Shinji Morimoto, Yasutomi Asano, Satoshi Mikami, Norihito Tokunaga, Masakuni Kori, Toshihiro Imaeda, Koichiro Fukuda, Shinji Nakamura, Kouichi Iwanaga

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Abstract

Provided is a compound having an AMPA receptor function enhancing action, and useful as a prophylactic or therapeutic drug for depression, Alzheimer's disease, schizophrenia, attention deficit hyperactivity disorder (ADHD) and the like. A compound represented by the formula (I): wherein each symbol is as defined in the present specification, or a salt thereof.

Claims11

Dependent claims

A compound represented by the formula (I)

wherein
R1 is
a C1-6 alkyl group optionally substituted by 1 to 3 substituent(s) selected from a halogen atom and a C1-3 alkoxy group;
a C3-6 cycloalkyl group;
or
an amino group substituted by a C1-6 alkyl group,
R2 and R3 are hydrogen atoms,
X is —O—,
ring A is selected from
C3-6 cycloalkane;
a tetrahydrofuran ring;
a tetrahydropyran ring;
a piperidine ring;
a tetrahydrothiopyran ring;
and
a 8-oxabicyclo[3.2.1]octane ring, each optionally substituted by 1 to 3 substituents selected from
(1) 1 to 3 halogen atoms;
(2) a C1-6 alkyl group optionally substituted by one phenyl group;
(3) a carbamoyl group substituted by a C1-6 alkyl group;
(4) a C1-6 alkyl-carbonyl group;
(5) a C1-6 alkoxy-carbonyl group;
(6) an oxo group;
(7) a hydroxyl group;
and
(8) a C1-6 alkylsulfonyl group, and
ring B is selected from
a benzene ring;
C3-6 cycloalkane;
a dihydroindene ring;
a naphthalene ring;
a pyridine ring;
a chromene ring;
an indole ring;
and
a benzothiazole ring, each optionally having 1 to 3 substituent(s) selected from
(1) a halogen atom;
(2) a cyano group;
(3) a C1-6 alkyl group optionally substituted by 1 to 3 substituents selected from a halogen atom and a cyano group;
(4) a hydroxyl group optionally substituted by a C1-6 alkyl group optionally substituted by 1 to 3 halogen atoms or a phenyl group;
(5) an amino group optionally substituted by 1 or 2 substituents selected from a C1-6 alkyl group, a C1-6 alkyl-carbonyl and a phenyl group;
(6) a C3-6 cycloalkyl group;
(7) a tricyclo[3.3.1.1.3.7]decyl group;
(8) phenyl optionally substituted by 1 to 3 substituents selected from a halogen atom and a cyano group;
(9) pyridyl optionally substituted by 1 to 3 substituents selected from a halogen atom, a cyano group and a C1-6 alkyl group optionally substituted by 1 to 3 halogen atoms;
(10) pyrazolyl optionally substituted by 1 to 3 substituents selected from a halogen atom, a cyano group, a C1-6 alkyl group optionally substituted by 1 to 3 halogen atoms and a C1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms;
(11) imidazolyl optionally substituted by a C1-6 alkyl group;
(12) thienyl optionally substituted by a cyano group;
(13) pyrimidinyl optionally substituted by 1 to 3 substituents selected from a halogen atom and a cyano group;
(14) isoxazolyl substituted by a C1-6 alkyl group;
(15) oxazolyl optionally substituted by a C1-6 alkyl group optionally substituted by 1 to 3 halogen atoms;
(16) thiazolyl optionally substituted by 1 to 3 substituents selected from a halogen atom and a C1-6alkyl group optionally substituted by 1 to 3 halogen atoms;
(17) piperidyl optionally substituted by 1 to 3 substituents selected from a C1-6 alkyl group optionally substituted by 1 to 3 halogen atoms and an oxo group;
(18) pyrrolidyl optionally substituted by 1 to 3 substituents selected from a halogen atom and an oxo group;
(19) dihydropyridyl optionally substituted by 1 to 3 substituents selected from a C1-6 alkyl group and an oxo group;
(20) tetrahydropyridazinyl optionally substituted by 1 to 3 substituents selected from a C1-6 alkyl group and an oxo group;
(21) oxetanyl;
(22) morpholinyl;
(23) tetrahydropyranyl;
(24) a sulfanyl group optionally substituted by a C1-6 alkyl group substituted by 1 to 3 halogen atoms;
(25) a C1-6 alkyl-carbonyl group;
(26) a C1-6 alkoxy-carbonyl group;
and
(27) an oxo group,
or a salt thereof.

61 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/009,456Filed 5 Apr 2012
Priority: JP 2011-0841005 Apr 2011
Published: US 2014/0024650 A123 Jan 2014
Granted: 27 Dec 2016
Term ends: Not estimatedThe source records don’t support an estimate.

Classification53 codes

C07C 311/07
Of an acyclic saturated carbon skeleton: having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other…
A61P 25/14
Drugs for disorders of the nervous system: for treating abnormal movements, e.g. chorea, dyskinesia
A61P 25/18
Drugs for disorders of the nervous system: antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
A61P 25/22
Drugs for disorders of the nervous system: anxiolytics

Family

US 2014/0024650 A1Pre-grant publication · published 23 Jan 2014
US 9,527,807 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound represented by the formula (I)

wherein
R1 is
a C1-6 alkyl group optionally substituted by 1 to 3 substituent(s) selected from a halogen atom and a C1-3 alkoxy group;
a C3-6 cycloalkyl group;
or
an amino group substituted by a C1-6 alkyl group,
R2 and R3 are hydrogen atoms,
X is —O—,
ring A is selected from
C3-6 cycloalkane;
a tetrahydrofuran ring;
a tetrahydropyran ring;
a piperidine ring;
a tetrahydrothiopyran ring;
and
a 8-oxabicyclo[3.2.1]octane ring, each optionally substituted by 1 to 3 substituents selected from
(1) 1 to 3 halogen atoms;
(2) a C1-6 alkyl group optionally substituted by one phenyl group;
(3) a carbamoyl group substituted by a C1-6 alkyl group;
(4) a C1-6 alkyl-carbonyl group;
(5) a C1-6 alkoxy-carbonyl group;
(6) an oxo group;
(7) a hydroxyl group;
and
(8) a C1-6 alkylsulfonyl group, and
ring B is selected from
a benzene ring;
C3-6 cycloalkane;
a dihydroindene ring;
a naphthalene ring;
a pyridine ring;
a chromene ring;
an indole ring;
and
a benzothiazole ring, each optionally having 1 to 3 substituent(s) selected from
(1) a halogen atom;
(2) a cyano group;
(3) a C1-6 alkyl group optionally substituted by 1 to 3 substituents selected from a halogen atom and a cyano group;
(4) a hydroxyl group optionally substituted by a C1-6 alkyl group optionally substituted by 1 to 3 halogen atoms or a phenyl group;
(5) an amino group optionally substituted by 1 or 2 substituents selected from a C1-6 alkyl group, a C1-6 alkyl-carbonyl and a phenyl group;
(6) a C3-6 cycloalkyl group;
(7) a tricyclo[3.3.1.1.3.7]decyl group;
(8) phenyl optionally substituted by 1 to 3 substituents selected from a halogen atom and a cyano group;
(9) pyridyl optionally substituted by 1 to 3 substituents selected from a halogen atom, a cyano group and a C1-6 alkyl group optionally substituted by 1 to 3 halogen atoms;
(10) pyrazolyl optionally substituted by 1 to 3 substituents selected from a halogen atom, a cyano group, a C1-6 alkyl group optionally substituted by 1 to 3 halogen atoms and a C1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms;
(11) imidazolyl optionally substituted by a C1-6 alkyl group;
(12) thienyl optionally substituted by a cyano group;
(13) pyrimidinyl optionally substituted by 1 to 3 substituents selected from a halogen atom and a cyano group;
(14) isoxazolyl substituted by a C1-6 alkyl group;
(15) oxazolyl optionally substituted by a C1-6 alkyl group optionally substituted by 1 to 3 halogen atoms;
(16) thiazolyl optionally substituted by 1 to 3 substituents selected from a halogen atom and a C1-6alkyl group optionally substituted by 1 to 3 halogen atoms;
(17) piperidyl optionally substituted by 1 to 3 substituents selected from a C1-6 alkyl group optionally substituted by 1 to 3 halogen atoms and an oxo group;
(18) pyrrolidyl optionally substituted by 1 to 3 substituents selected from a halogen atom and an oxo group;
(19) dihydropyridyl optionally substituted by 1 to 3 substituents selected from a C1-6 alkyl group and an oxo group;
(20) tetrahydropyridazinyl optionally substituted by 1 to 3 substituents selected from a C1-6 alkyl group and an oxo group;
(21) oxetanyl;
(22) morpholinyl;
(23) tetrahydropyranyl;
(24) a sulfanyl group optionally substituted by a C1-6 alkyl group substituted by 1 to 3 halogen atoms;
(25) a C1-6 alkyl-carbonyl group;
(26) a C1-6 alkoxy-carbonyl group;
and
(27) an oxo group,
or a salt thereof.

61 more elements

Facts

Application

14/009,456Filed 5 Apr 2012

Priority

JP 2011-0841005 Apr 2011

Published

US 2014/0024650 A123 Jan 2014

Granted

27 Dec 2016

Term ends

Not estimatedThe source records don’t support an estimate.

Classification53 codes

C07C 311/07
Of an acyclic saturated carbon skeleton: having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other…
A61P 25/14
Drugs for disorders of the nervous system: for treating abnormal movements, e.g. chorea, dyskinesia
A61P 25/18
Drugs for disorders of the nervous system: antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
A61P 25/22
Drugs for disorders of the nervous system: anxiolytics