IP Library › Granted Patent US 7,834,034
Granted Patent B2
US 7,834,034 · App. 11/918,913 · Granted Nov 16, 2010

Benzothiophene derivatives

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Quick Facts
Patent No.
US 7,834,034
App. No.
11/918,913
Granted
Nov 16, 2010
Kind
B2
Abstract

The present invention relates to a novel class of benzothiophene amide derivatives. The hydroxamic acid compounds can be used to treat cancer. The benzothiophene amide compounds can also inhibit histone deacetylase and are suitable for use in selectively inducing terminal differentiation, and arresting cell growth and/or apoptosis of neoplastic cells, thereby inhibiting proliferation of such cells. Thus, the compounds of the present invention are useful in treating a patient having a tumor characterized by proliferation of neoplastic cells. The compounds of the invention may also be useful in the prevention and treatment of TRX-mediated diseases, such as autoimmune, allergic and inflammatory diseases, and in the prevention and/or treatment of diseases of the central nervous system (CNS), such as neurodegenerative diseases. The present invention further provides pharmaceutical compositions comprising the hydroxamic acid derivatives and safe dosing regimens of these pharmaceutical compositions, which are easy to follow, and which result in a therapeutically effective amount of the hydroxamic acid derivatives in vivo.

Claims (125)

1. A compound represented by the following structural Formula:

wherein A is

wherein R 11 and R 12 are independently of each other, a hydrogen or an unsubstituted or substituted C 1 -C 10 alkyl, unsubstituted or substituted C 2 -C 10 alkenyl, unsubstituted or substituted aryl, unsubstituted or substituted C 3 -C 8 cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C 1 -C 10 alkylaryl, unsubstituted or substituted C 1 -C 10 alkylcycloalkyl or unsubstituted or substituted C 1 -C 10 alkylheterocyclyl; or R 11 and R 12 together with the nitrogen atom to which they are attached, form a nitrogen-containing heterocyclic ring, wherein said nitrogen-containing heterocyclic ring may be optionally substituted;

R 17 is independently selected from hydrogen, unsubstituted or substituted C 1 -C 10 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted C 3 -C 8 cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C 1 -C 10 alkylaryl, unsubstituted or substituted C 1 -C 10 alkyl-C 3 -C 8 cycloalkyl, unsubstituted or substituted C 1 -C 10 alkylheterocyclyl, —OH and —NR 18 R 19 ;

R 18 and R 19 are independently selected from hydrogen, unsubstituted or substituted C 1 -C 10 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted C 3 -C 8 cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C 1 -C 10 alkylaryl, unsubstituted or substituted C 1 -C 10 alkylcycloalkyl, unsubstituted or substituted C 1 -C 10 alkylheterocyclyl, —C(═O)R 25 , —C(═O)OR 25 , —C(═O)N{R 26 } 2 and —S(═O) 2 R 25 , or R 18 and R 19 , together with the nitrogen atom to which they are attached, form a nitrogen-containing heterocyclic ring, wherein said nitrogen-containing heterocyclic ring may be optionally substituted;

R 20 and R 26 are independently selected from hydrogen, unsubstituted or substituted C 1 -C 10 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted C 3 -C 8 cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C 1 -C 10 alkylaryl, unsubstituted or substituted C 1 -C 10 alkyl-C 3 -C 8 cycloalkyl and unsubstituted or substituted C 1 -C 10 alkylheterocyclyl;

When m is 1 or 2, R 21 is selected from: unsubstituted or substituted aryl, unsubstituted or substituted C 3 -C 8 cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C 1 -C 10 alkylaryl, unsubstituted or substituted C 1 -C 10 alkylcycloalkyl or unsubstituted or substituted C 1 -C 10 alkylheterocyclyl;

When m is 0, R 21 is unsubstituted or substituted aryl or

wherein ring D is selected from unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl,

ring E is selected from unsubstituted or substituted aryl, and unsubstituted or substituted heterocyclyl;

R 25 is independently selected from unsubstituted or substituted C 1 -C 10 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted C 3 -C 8 cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C 1 -C 10 alkylaryl, unsubstituted or substituted C 1 -C 10 alkyl-C 3 -C 8 cycloalkyl and unsubstituted or substituted C 1 -C 10 alkylheterocyclyl;

or a stereoisomer or pharmaceutically acceptable salt thereof.

2. The compound of claim 1 , wherein A is

R 17 is independently selected from hydrogen, unsubstituted or substituted C 1 -C 10 alkyl, unsubstituted or substituted C 1 -C 10 alkylaryl, unsubstituted or substituted C 1 -C 10 alkylheterocyclyl and —NR 18 R 19 ;

R 18 and R 19 are independently selected from hydrogen, unsubstituted or substituted C 1 -C 10 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted C 3 -C 8 cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C 1 -C 10 alkylaryl, unsubstituted or substituted C 1 -C 10 alkylcycloalkyl, unsubstituted or substituted C 1 -C 10 alkylheterocyclyl, unsubstituted or substituted —C(═O)aryl and unsubstituted or substituted —C(═O)C 1 -C 10 alkyl, or R 18 and R 19 , together with the nitrogen atom to which they are attached, form a nitrogen-containing heterocyclic ring, wherein said nitrogen-containing heterocyclic ring may be optionally substituted;

R 20 is independently selected from hydrogen, unsubstituted or substituted C 1 -C 10 alkyl, unsubstituted or substituted C 1 -C 10 alkylaryl and unsubstituted or substituted C 1 -C 10 alkylheterocyclyl;

When m is 1 or 2, R 21 is selected from: unsubstituted or substituted aryl, unsubstituted or substituted C 3 -C 8 cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C 1 -C 10 alkylaryl, C 1 -C 10 alkylcycloalkyl or unsubstituted or substituted C 1 -C 10 alkylheterocyclyl;

When m is 0, R 21 is unsubstituted or substituted aryl or

wherein ring D is selected from unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl,

ring E is selected from unsubstituted or substituted aryl, and unsubstituted or substituted heterocyclyl;

or a stereoisomer or pharmaceutically acceptable salt, thereof.

3. The compound of claim 1 , wherein A is

R 11 and R 12 are independently a unsubstituted or substituted group selected from: phenyl, naphthyl, biphenyl, benzyl, —CH 2 CH 2 Ph, —CH═CHPh, cyclohexyl, quinolinyl, isoquinolinyl, —CH 2 -cyclohexyl, —CH 2 -quinolinyl, —CH 2 -isoquinolinyl, pyridyl, —CH(Ph) 2 , methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl; and R 17 is selected from: hydrogen, C 1 -C 6 alkyl and —NR 18 R 19 ;

or a stereoisomer or pharmaceutically acceptable salt thereof.

4. The compound of claim 1 represented by the following structural Formula II:

R 17 is independently selected from hydrogen, unsubstituted or substituted C 1 -C 10 alkyl, unsubstituted or substituted C 1 -C 10 alkylaryl, unsubstituted or substituted C 1 -C 10 alkylheterocyclyl and —NR 18 R 19 ;

R 18 and R 19 are independently selected from hydrogen, unsubstituted or substituted C 1 -C 10 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted C 3 -C 8 cycloalkyl, unsubstituted or substituted C 1 -C 10 alkylaryl, unsubstituted or substituted C 1 -C 10 alkylcycloalkyl, unsubstituted or substituted C 1 -C 10 alkylheterocyclyl, unsubstituted or substituted —C(═O)aryl and unsubstituted or substituted —C(═O)C 1 -C 10 alkyl, or R 18 and R 19 , together with the nitrogen atom to which they are attached, form a nitrogen-containing heterocyclic ring, wherein said nitrogen-containing heterocyclic ring may be optionally substituted

R 20 is independently selected from hydrogen, unsubstituted or substituted C 1 -C 10 alkyl, unsubstituted or substituted C 1 -C 10 alkylaryl and unsubstituted or substituted C 1 -C 10 alkylheterocyclyl;

m is 0, 1 or 2;

or a stereoisomer or pharmaceutically acceptable salt thereof.

5. The compound of claim 1 or 3 , wherein R 21 is

R 27 is selected from hydrogen, C 1 -C 7 alkyl, or L 2 -R 35 , wherein R 35 is substituted or unsubstituted heteroaryl, substituted or unsubstituted aryl, L 2 is selected from a bond or C 1 -C 4 alkylene;

R 28 is OH, SH or NH 2 ; and

R 29 is H or halo.

6. The compound of claim 5 , wherein R 27 is

R 30 and R 34 are independently selected from hydrogen or fluoro;

R 31 , R 32 or R 33 are independently selected from hydrogen, halo, methyl, methoxy or halomethyl.

7. The compound of claim 1 represented by the following structural Formula:

wherein A is

R 17 is independently selected from hydrogen, fluoro, unsubstituted or substituted C 1 -C 10 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted C 3 -C 8 cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C 1 -C 10 alkylaryl, unsubstituted or substituted C 1 -C 10 alkyl-C 3 -C 8 cycloalkyl, unsubstituted or substituted C 1 -C 10 alkylheterocyclyl, —OH and —NR 18 R 19 ;

R 18 and R 19 are independently selected from hydrogen, unsubstituted or substituted C 1 -C 10 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted C 3 -C 8 cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C 1 -C 10 alkylaryl, unsubstituted or substituted C 1 -C 10 alkylcycloalkyl, unsubstituted or substituted C 1 -C 10 alkylheterocyclyl, —C(═O)R 25 , —C(═O)OR 25 , —C(═O)N{R 26 } 2 and —S(═O) 2 R 25 , or R 18 and R 19 , together with the nitrogen atom to which they are attached, form a nitrogen-containing heterocyclic ring, wherein said nitrogen-containing heterocyclic ring may be optionally substituted;

R 20 is independently selected from hydrogen, fluoro, unsubstituted or substituted C 1 -C 10 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted C 3 -C 8 cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C 1 -C 10 alkylaryl, unsubstituted or substituted C 1 -C 10 alkyl-C 3 -C 8 cycloalkyl and unsubstituted or substituted C 1 -C 10 alkylheterocyclyl;

provided that at least one of R 17 and R 20 is fluoro;

R 26 is independently selected from hydrogen, unsubstituted or substituted C 1 -C 10 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted C 3 -C 8 cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C 1 -C 10 alkylaryl, unsubstituted or substituted C 1 -C 10 alkyl-C 3 -C 8 cycloalkyl and unsubstituted or substituted C 1 -C 10 alkylheterocyclyl;

R 21 is selected from: unsubstituted or substituted aryl, unsubstituted or substituted C 3 -C 8 cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C 1 -C 10 alkylaryl, unsubstituted or substituted C 1 -C 10 alkylcycloalkyl or unsubstituted or substituted C 1 -C 10 alkylheterocyclyl;

R 25 is independently selected from unsubstituted or substituted C 1 -C 10 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted C 3 -C 8 cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted C 1 -C 10 alkylaryl, unsubstituted or substituted C 1 -C 10 alkyl-C 3 -C 8 cycloalkyl and unsubstituted or substituted C 1 -C 10 alkylheterocyclyl;

m is 1 or 2;

or a stereoisomer or pharmaceutically acceptable salt thereof.

8. The compound according to claim 7 , wherein :

R 21 is :

wherein ring E are independently selected from unsubstituted or substituted aryl, and unsubstituted or substituted heterocyclyl,

or a stereoisomer or pharmaceutically acceptable salt thereof.

9. The compound of claim 1 selected from:

6-(Benzylcarbamoyl-methyl)-benzo[b]thiophene-2-carboxylic acid (4-amino-1-phenyl-1H-pyrazol-3-yl)-amide;

6-Carbamoylmethyl-benzo[b]thiophene-2-carboxylic acid (4-amino-1-phenyl-1H-pyrazol-3-yl)-amide;

6-(Benzylcarbamoyl-fluoro-methyl)-benzo[b]thiophene-2-carboxylic acid (4-amino-biphenyl-3-yl)amide;

6-(Fluoro-phenylcarbamoyl-methyl)-benzo[b]thiophene-2-carboxylic acid (4-amino-biphenyl-3-yl)amide;

6-[(4-Chloro-phenylcarbamoyl)-fluoro-methyl]-benzo[b]thiophene-2-carboxylic acid (4-amino-biphenyl-3-yl)amide;

6-[(4-Chloro-benzylcarbamoyl)-fluoro-methyl]-benzo[b]thiophene-2-carboxylic acid (4-amino-biphenyl-3-yl)amide;

6-{[1-(S)-(4-Chloro-phenyl)-ethylcarbamoyl]-fluoro-methyl}-benzo[b]thiophene-2-carboxylic acid (4-amino-biphenyl-3-yl)amide;

6-[(2,4-Dichloro-benzylcarbamoyl)-fluoro-methyl]-benzo[b]thiophene-2-carboxylic acid (4-amino-biphenyl-3-yl)amide;

6-(Carbamoyl-fluoro-methyl)-benzo[b]thiophene-2-carboxylic acid (4-amino-biphenyl-3-yl)amide;

6-(Fluoro-methylcarbamoyl-methyl)-benzo[b]thiophene-2-carboxylic acid (4-amino-biphenyl-3-yl)amide;

6-[(4-Amino-biphenyl-3-ylcarbamoyl)-fluoro-methyl]-benzo[b]thiophene-2-carboxylic acid (4-amino-biphenyl-3-yl)amide;

6-[(2,2-Difluoro-1-phenyl-ethylcarbamoyl)-fluoro-methyl]-benzo[b]thiophene-2-carboxylic acid

(4-amino-biphenyl-3-yl)amide;

6-{[1-(R)-(4-Chloro-phenyl)-ethylcarbamoyl]-fluoro-methyl}-benzo[b]thiophene-2-carboxylic acid (4-amino-biphenyl-3-yl)amide;

6-[Fluoro-(indan-1-(S)-ylcarbamoyl)-methyl]-benzo[b]thiophene-2-carboxylic acid (4-amino-biphenyl-3-yl)amide;

6-{[1-(S)-Phenyl-ethylcarbamoyl]-fluoro-methyl}-benzo[b]thiophene-2-carboxylic acid (4-amino-biphenyl-3-yl)amide;

6-(Benzylcarbamoyl-fluoro-methyl)-benzo[b]thiophene-2-carboxylic acid (2-amino-5-thiophen-2-yl-phenyl)amide;

6-(Carbamoyl-fluoro-methyl)-benzo[b]thiophene-2-carboxylic acid (2-amino-5-thiophen-2-yl-phenyl)amide;

6-(Fluoro-methylcarbamoyl-methyl)-benzo[b]thiophene-2-carboxylic acid (2-amino-5-thiophen-2-yl-phenyl)amide;

6-[Fluoro-(1-(S)-phenyl-ethylcarbamoyl)-methyl]-benzo[b]thiophene-2-carboxylic acid (2-amino-5-thiophen-2-yl-phenyl)amide;

6-[(2-Amino-5-thiophen-2-yl-phenylcarbamoyl)-fluoro-methyl]-benzo[b]thiophene-2-carboxylic acid (2-amino-5-thiophen-2-yl-phenyl)amide;

6-(Benzylcarbamoyl-fluoro-methyl)-benzo[b]thiophene-2-carboxylic acid (2-amino-5-thiophen-3-yl-phenyl)amide;

6-(Benzylcarbamoyl-fluoro-methyl)-benzo[b]thiophene-2-carboxylic acid [4-amino-1-(3-chloro-phenyl)-1H-pyrazol-3-yl]-amide;

6-(Benzylcarbamoyl-fluoro-methyl)-benzo[b]thiophene-2-carboxylic acid [4-amino-1-(3-chloro-phenyl)-1H-pyrazol-3-yl]-amide;

6-(Carbamoyl-fluoro-methyl)-benzo[b]thiophene-2-carboxylic acid (4-amino-1-phenyl-1H-pyrazol-3-yl)amide;

6-{Fluoro-[(pyridin-3-ylmethyl)-carbamoyl]-methyl}-benzo[b]thiophene-2-carboxylic acid (4-amino-1-phenyl-1H-pyrazol-3-yl)amide;

N-(4-amino-1-phenyl-1H-pyrazol-3-yl)-6-[2-(benzylamino)-1-fluoro-2-oxoethyl]-1-benzothiophene-2-carboxamide;

6-(Diethylcarbamoyl-difluoro-methyl)-benzo[b]thiophene-2-carboxylic acid (2-amino-5-thiophen-2-yl-phenyl)amide;

6-(Carbamoyl-difluoro-methyl)-benzo[b]thiophene-2-carboxylic acid (2-amino-5-thiophen-2-yl-phenyl)amide;

6-(Diethylcarbamoyl-difluoro-methyl)-benzo[b]thiophene-2-carboxylic acid (2-amino-5-thiophen-3-yl-phenyl)amide;

N-(2-aminophenyl)-6-[2-(benzylamino)-1-methyl-2-oxoethyl]-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-(2-anilino-1-methyl-2-oxoethyl)-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-{2-[benzyl(methyl)amino]-1-methyl-2-oxoethyl}-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-5-(2-anilino-2-oxoethyl)-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-5-[2-(benzylamino)-2-oxoethyl]-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-5-{2-oxo-2-[(2-phenylethyl)amino]ethyl}-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-(2-anilino-2-oxoethyl)-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-[2-oxo-2-(quinolin-8-ylamino)ethyl]-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-{2-oxo-2-[(2-phenylethyl)amino]ethyl}-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-(2-oxo-2-pyrrolidin-1-ylethyl]-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-[2-(benzylamino)-2-oxoethyl]-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-[2-oxo-2-(quinolin-6-ylamino)ethyl]-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-{2-[benzyl(methyl)amino]-2-oxoethyl}-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-{2-[(4-bromobenzyl)amino]-2-oxoethyl}-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-{1-[(4-methoxybenzyl)amino]-2-[(4-methoxyphenyl)-amino]-2-oxoethyl}-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-{1-[(4-methoxybenzyl)(trifluoroacetyl)amino]-2-[(4-methoxyphenyl)amino]-2-oxoethyl}-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-{1-(cyclohexylamino)-2-[(4-methoxyphenyl)amino]-2-oxoethyl}-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-{2-[(4-methoxyphenyl)amino]-2-oxo-1-[(2-phenylethyl)amino]ethyl}-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-{1-(benzylamino)-2-[(4-methoxyphenyl)amino]-2-oxoethyl}-1-benzothiophene-2-carboxamide;

6-{1-amino-2-[(4-methoxyphenyl)amino]-2-oxoethyl}-N-(2-aminophenyl)-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-{1-(benzoylamino)-2-[(4-methoxyphenyl)amino]-2-oxoethyl}-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-{2-[(4-methoxyphenyl)amino]-2-oxo-1-[(pyridin-4-ylmethyl)amino]ethyl}-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-{2-[(2-morpholin-4-ylethyl)amino]-2-oxo-1-[(2-phenylethyl)amino]ethyl}-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-{2-(benzylamino)-2-oxo-1-[(2-phenylethyl)amino]ethyl}-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-{2-(benzylamino)-1-[(2-methoxyethyl)amino]-2-oxoethyl}-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-{2-(benzylamino)-1-[(2-hydroxyethyl)amino]-2-oxoethyl}-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-{2-(benzylamino)-1-[(2-morpholin-4-ylethyl)amino]-2-oxoethyl}-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-(2-(benzylamino)-1-{[3-(dimethylamino)propyl]amino}-2-oxoethyl)-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-[2-(benzylamino)-2-oxo-1-pyrrolidin-1-ylethyl]-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-(2-(benzylamino)-1-{[2-(1H-imidazol-5-yl)ethyl]amino}-2-oxoethyl)-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-{2-(benzylamino)-2-oxo-1-[(pyridin-3-ylmethyl)amino]ethyl}-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-[2-(benzylamino)-1-(4-methylpiperazin-1-yl)-2-oxoethyl]-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-[2-(benzylamino)-1-morpholin-4-yl-2-oxoethyl]-1-benzothiophene-2-carboxamide;

N-(2-aminophenyl)-6-{2-(benzylamino)-2-oxo-1-[(2-pyridin-4-ylethyl)amino]ethyl}-1-benzothiophene-2-carboxamide; and

N-(2-aminophenyl)-6-{2-(benzylamino)-2-oxo-1-[(2-pyridin-2-ylethyl)amino]ethyl}-1-benzothiophene-2-carboxamide;

or a pharmaceutically acceptable salt or stereoisomer thereof.

10. The compound of claim 1 selected from:

6-(B enzylcarbamoyl-methyl)-benzo[b]thiophene-2-carboxylic acid (4-amino-1-phenyl-1H-pyrazol-3-yl)-amide; and

6-Carbamoylmethyl-benzo[b]thiophene-2-carboxylic acid (4-amino-1-phenyl-1H-pyrazol-3-yl)-amide;

or a pharmaceutically acceptable salt or stereoisomer thereof.

11. A pharmaceutical composition comprising a pharmaceutically effective amount of the compound of claim 1 , and a pharmaceutically acceptable carrier.

Assignments (2)
MERGER Recorded Aug 8, 2022
From: MERCK SHARP & DOHME CORP.
To: MERCK SHARP & DOHME LLC
Reel/Frame 061102/0145 →
CHANGE OF NAME Recorded Jan 26, 2010
From: MERCK & CO., INC.
To: MERCK SHARP & DOHME CORP.
Reel/Frame 023845/0940 →