KR102682408B1 - Novel benzothiazole derivatives, preparation method thereof, and use thereof in preventing or treating liver diseases - Google Patents

Abstract

The present invention relates to novel benzothiazole derivatives, methods for their preparation, and their use for preventing or treating liver disease.

Description

Novel benzothiazole derivatives, preparation method thereof, and use thereof in preventing or treating liver diseases}

The present invention relates to novel benzothiazole derivatives, methods for their preparation, and their use for preventing or treating liver disease.

Fatty liver is defined as a case where the weight due to fat deposition in the liver is more than 5% of the weight of the liver. Non-alcoholic fatty liver disease (NAFLD) refers to a case where the cause of fatty liver is not caused by viruses, drugs, genetics, or alcohol, and is closely related to metabolic syndrome such as insulin resistance, obesity, high blood pressure, and dyslipidemia. It is a chronic liver disease known to be closely related and includes a series of processes ranging from simple steatosis in the liver to non-alcoholic steatohepatitis (NASH) and cirrhosis. Worldwide, the prevalence of non-alcoholic fatty liver disease is reported to vary depending on the population group. In the West, it is known that non-alcoholic fatty liver disease occurs in approximately 20 to 30% of normal adults without any specific cause of liver disease, and in Korea, The prevalence of nonalcoholic fatty liver disease in adults is reported to be approximately 16 to 50%. In general, the prevalence of non-alcoholic fatty liver disease is known to increase in those who are obese, because insulin resistance caused by obesity is known to be an important cause of fat deposition in the liver. In the case of mild fatty liver, such as simple fat deposition, where there is only fat and no damage to liver cells, the prognosis is relatively good, but if left untreated, it can progress to cirrhosis, a serious liver disease, and 4-27% of patients with cirrhosis develop liver cancer. It is known that 30 to 40% of patients with cirrhosis die from complications of liver disease and cardiovascular disease after 10 years, so active management from the beginning is important.

To treat this non-alcoholic fatty liver disease, pioglitazone, vitamin E, and ursodeoxycholic acid (UDCA) are used, but they lack efficacy or may cause side effects during long-term administration. , To date, there is no approved drug for the treatment of non-alcoholic fatty liver disease.

The non-alcoholic fatty liver disease, especially non-alcoholic steatohepatitis (NASH), is expected to become the largest market among liver diseases in the future, and for this reason, many pharmaceutical companies are conducting research on NASH treatments targeting various targets to develop treatments. However, because the mechanism of disease onset is still unclear and there is no non-invasive diagnostic method to diagnose the disease, pharmaceutical companies have not yet succeeded in clinical trials. In consideration of this development situation, in which the exact mechanism of action is unclear, various pathogenic factors exist, and enormous research costs are required, the US FDA considers that at least one item among NAS (NAFLD activity score) and fibrosis score is different from the other items when diagnosing NASH. The criteria were relaxed to allow approval if there is improvement without worsening, but as of February 2021, not all drugs that have entered phase 3 have been approved.

Meanwhile, in March 2018, the New England Journal of Medicine analyzed the genes of approximately 46,000 people and revealed a new predicted target protein for NASH disease, 17β-HSD13. Since then, many companies are developing HSD17b13 inhibitors in the form of siRNA or 17β-HSD13 inhibitors as small molecule compounds.

N. Engl. J. Med., 2018, 378: 1096-1106.

One object of the present invention is to provide novel benzothiazole derivatives.

Another object of the present invention is to provide a method for producing the benzothiazole derivative.

Another object of the present invention is to provide a pharmaceutical composition for preventing or treating liver disease containing the benzothiazole derivative as an active ingredient.

Another object of the present invention is to provide a method for preventing or treating liver disease, comprising administering the pharmaceutical composition to an individual in need thereof.

Another object of the present invention is to provide a food composition for preventing or improving liver disease containing the benzothiazole derivative as an active ingredient.

Another object of the present invention is to provide a feed composition for preventing or improving liver disease containing the benzothiazole derivative as an active ingredient.

Each description and embodiment disclosed in the present invention can also be applied to each other description and embodiment. That is, all combinations of the various elements disclosed in the present invention fall within the scope of the present invention. Additionally, it cannot be said that the scope of the present invention is limited by the specific description described below.

Additionally, those skilled in the art will recognize, or be able to ascertain using no more than routine experimentation, many equivalents to the specific embodiments of the invention described herein. Additionally, such equivalents are intended to be encompassed by this invention.

In addition, throughout the specification of the present invention, when a part is said to "include" a certain component, this does not mean excluding other components, but may further include other components, unless specifically stated to the contrary. it means.

Hereinafter, the present invention will be described in more detail.

To achieve the above object, a first aspect of the present invention provides a compound represented by the following formula (1) or a pharmaceutically acceptable salt thereof:

[Formula 1]

In Formula 1,

X is a simple binding, -nhco- (ch ₂ ) _m- , -N (ch ₃ ) co- (ch ₂ ) _n- , -NHCO- (ch ₂ ) _p -NHCO-, or -NHCO- (CH ₂ ) _q -O-,

m and n are each independently integers from 0 to 5,

R ₁ is carboxyl, or C _1-4 alkoxycarbonyl,

R ₂ is hydrogen, C _1-4 alkyl, C _1-4 alkoxy, halogen, or hydroxy,

R ₃ is C _6-10 aryl, C _3-10 cycloalkyl, 5 to 10 membered heteroaryl, or 5 to 10 membered heterocyclyl,

The C _6-10 aryl, C _3-10 cycloalkyl, 5 to 10 membered heteroaryl, and 5 to 10 membered heterocyclyl are unsubstituted or cyano, halogen, nitro, oxo, hydroxy, carboxyl, amino, C _1-4 alkyl, C _1-4 alkenyl, C _1-4 alkoxy, C _1-4 haloalkyl, C _1-4 haloalkoxy, C _1-4 alkoxycarbonyl, C _1-4 alkylcarbonyl, C _1-4 alkylthio, C _1-4 alkylamino, C _1-4 alkoxy-C _1-4 alkoxy, C _3-10 cycloalkyl, C _3-10 cycloalkyl-C _1-4 alkoxy. C _3-10 cycloalkenyl, C _6-10 aryloxy, C _3-10 cycloalkyl-C _1-4 alkylcarbonyl, C _6-10 aryl-C _1-4 alkylcarbonyl, C _6-10 aryl sulfur Ponyl, C _6-10 aryl-C _1-4 alkylsulfonyl, C _3-10 cycloalkylcarbamoyl, hydroxy-C _1-4 alkylcarbamoyl, carboxy-C _1-4 alkylcarbamoyl, 5 to 10 members Heterocyclyl, 5 to 10 membered heterocyclyloxy, 5 to 10 membered heteroaryl, 5 to 10 membered heteroaryloxy, 5 to 10 membered heteroarylamino, 5 to 10 membered heteroarylsulfonyl, 5 to 10 membered hetero Aryl-C _1-4 alkyl, 5 to 10 membered heteroaryloxy-C _1-4 alkyl, 5 to 10 membered heteroaryl-C _1-4 alkylamino, and 5 to 10 membered heteroaryl-C _1-4 alkylcarba Substituted with one or more selected from the group consisting of moyl.

_{For example ,} in _the above _{formula ,} It may be -, -NHCO-(CH ₂ ) ₂ -NHCO-, or -NHCO-(CH ₂ )-O-, but is not limited thereto.

For example, in the above formula, R ₁ may be carboxyl or ethoxycarbonyl, but is not limited thereto.

For example, in the above formula, R ₂ may be hydrogen, methyl, methoxy, fluoro, chloro, or hydroxy, but is not limited thereto.

For example, in the above formula, R ₃ is phenyl, pyridinyl, furanyl, thiophenyl, indolyl, benzotriazolyl, benzothiazolyl, benzoimidazolyl, pyrrolopyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl. , pyrazolyl, pyrrolyl, spiroheptanyl, cyclobutyl, cyclohexyl, dihydropyridinyl, quinolinyl, imidazolyl, piperazinyl, or piperidinyl, but is not limited to these ring structures. Substituents are unsubstituted or cyano, fluoro, chloro, bromo, iodo, nitro, oxo, hydroxy, carboxyl, amino, methyl, tert-butyl, ethenyl, propenyl, isopropenyl, butenyl, Isobutenyl, methoxy, ethoxy, propoxy, isopropoxy, isobutoxy, trifluoromethyl, difluoromethoxy, 1,1,1-trifluoroethoxy, methoxycarbonyl, methylcarbonyl, Methylthio, methylamino, methoxyethoxy, cyclopropyl, cyclopropylmethoxy, cyclopentenyl, phenoxy, cyclopentylethylcarbonyl, phenylmethylcarbonyl, phenylethylcarbonyl, phenylsulfonyl, benzylsulfonyl, Cyclopropylcarbamoyl, hydroxypropylcarbamoyl, carboxymethylcarbamoyl, pyrrolidinyl, morpholinyl, dihydrobenzofuran, dihydropyrrolotriazole, tetrahydropyranyloxy, furanyl, pyridinyl, pyrrolyl , oxazolyl, pyrazolyl, benzoimidazolyl, benzothiazolyl, indolinyl, benzotriazolyloxy, pyridinyloxy, pyrazolyloxy, pyrimidinylamino, thiophenylsulfonyl, pyridinylmethyl, pyrazolylmethyl, Triazolylmethyl, thiazolylmethyl, pyridinyloxymethyl, benzothiazolyloxymethyl, pyridinylmethylamino, thiazolylmethylcarbamoyl, imidazolylethylcarbamoyl, pyrrolylmethylcarbamoyl, pyrrolylethylcarbamoyl, and It may be substituted with one or more selected from the group consisting of pyridinylmethylcarbamoyl, but is not limited thereto.

For example, in the above formula, _when degree, nitro, oxo, hydroxy, carboxyl, amino, methyl, tert-butyl, ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, methoxy, ethoxy, propoxy, isopropoxy, isobu. Toxy, trifluoromethyl, difluoromethoxy, 1,1,1-trifluoroethoxy, methoxycarbonyl, methylcarbonyl, methylthio, methylamino, methoxyethoxy, cyclopropyl, cyclopropylme Toxy, cyclopentenyl, phenoxy, cyclopentylethylcarbonyl, phenylmethylcarbonyl, phenylethylcarbonyl, phenylsulfonyl, benzylsulfonyl, cyclopropylcarbamoyl, hydroxypropylcarbamoyl, carboxymethylcarbamoyl, p. Rolidinyl, morpholinyl, dihydrobenzofuran, dihydropyrrolotriazole, tetrahydropyranyloxy, furanyl, pyridinyl, pyrrolyl, oxazolyl, pyrazolyl, benzoimidazolyl, benzothiazolyl, indole. Linyl, benzotriazolyloxy, pyridinyloxy, pyrazolyloxy, pyrimidinylamino, thiophenylsulfonyl, pyridinylmethyl, pyrazolylmethyl, triazolylmethyl, thiazolylmethyl, pyridinyloxymethyl, benzothiazolyloxy May be substituted with one or more selected from the group consisting of methyl, pyridinylmethylamino, thiazolylmethylcarbamoyl, imidazolylethylcarbamoyl, pyrrolylmethylcarbamoyl, pyrrolylethylcarbamoyl, and pyridinylmethylcarbamoyl. However, it is not limited to this. At this time, the substitution may include not only substitution through a normal single bond, but also a spiro form in which two ring structures are bonded by sharing one element.

Specifically, the compound is

(1) 2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid),

(2) 2-(3-phenylbutanamido)benzo[d]thiazole-6-carboxylic acid,

(3) 2-(furan-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(furan-2-carboxamido)benzo[d]thiazole-6-carboxylic acid),

(4) 2-(2-methoxyisonicotinamido)benzo[d]thiazole-7-carboxylic acid (2-(2-methoxyisonicotinamido)benzo[d]thiazole-7-carboxylic acid),

(5) 2-(2-cyanoisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-cyanoisonicotinamido)benzo[d]thiazole-6-carboxylic acid),

(6) 2-(6-fluoronicotinamido)benzo[d]thiazole-6-carboxylic acid,

(7) 2-(2-methyl-5-nitrobenzamido)benzo[d]thiazole-6-carboxylic acid (2-(2-methyl-5-nitrobenzamido)benzo[d]thiazole-6-carboxylic acid),

(8) 2-(4-methylthiophene-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(4-methylthiophene-2-carboxamido)benzo[d]thiazole-6- carboxylic acid),

(9) 2-(3-nitrobenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-nitrobenzamido)benzo[d]thiazole-6-carboxylic acid),

(10) 2-(2-nitroisonicotinamido)benzo[d]thiazole-6-carboxylic acid,

(11) 2-(3-fluorobenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-fluorobenzamido)benzo[d]thiazole-6-carboxylic acid),

(12) 2-(3,5-difluorobenzamido)benzo[d]thiazole-6-carboxylic acid ,

(13) 2-(2-fluoroisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-fluoroisonicotinamido)benzo[d]thiazole-6-carboxylic acid),

(14) 2-(3,7-difluoro-1H-indole-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(3,7-difluoro-1H-indole- 2-carboxamido)benzo[d]thiazole-6-carboxylic acid),

(15) 2-(4-chloro-3-fluorobenzamido)benzo[d]thiazole-7-carboxylic acid (2-(4-chloro-3-fluorobenzamido)benzo[d]thiazole-7- carboxylic acid),

(16) 2-(benzo[d]thiazole-4-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(benzo[d]thiazole-4-carboxamido)benzo[d]thiazole -6-carboxylic acid),

(17) 2-(4-chloro-2-methoxybenzamido)benzo[d]thiazole-7-carboxylic acid (2-(4-chloro-2-methoxybenzamido)benzo[d]thiazole-7- carboxylic acid),

(18) 2-(1H-benzo[d][1,2,3]triazole-6-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(1H-benzo[d] [1,2,3]triazole-6-carboxamido)benzo[d]thiazole-6-carboxylic acid),

(19) 2-(1H-pyrrolo[2,3-b]pyridine-4-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(1H-pyrrolo[2,3-b ]pyridine-4-carboxamido)benzo[d]thiazole-6-carboxylic acid),

(20) 2-(1H-benzo[d]imidazole-5-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(1H-benzo[d]imidazole-5-carboxamido)benzo [d]thiazole-6-carboxylic acid),

(21) 2-(3-fluoro-4-methylbenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-fluoro-4-methylbenzamido)benzo[d]thiazole-6- carboxylic acid),

(22) 2-(2,6-dichloroisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2,6-dichloroisonicotinamido)benzo[d]thiazole-6-carboxylic acid),

(23) 2-(5-chloronicotinamido)benzo[d]thiazole-6-carboxylic acid,

(24) 2-(5-fluoronicotinamido)benzo[d]thiazole-6-carboxylic acid,

(25) 2-(2-chloroisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-chloroisonicotinamido)benzo[d]thiazole-6-carboxylic acid),

(26) 2-(3-chloro-4-methylbenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-chloro-4-methylbenzamido)benzo[d]thiazole-6-carboxylic acid),

(27) 2-(3,4-dichlorobenzamido)benzo[d]thiazole-6-carboxylic acid,

(28) 2-(6-ethoxynicotinamido)benzo[d]thiazole-6-carboxylic acid,

(29) 2-(6-cyanonicotinamido)benzo[d]thiazole-6-carboxylic acid,

(30) 2-(2-oxo-1,2-dihydropyridine-4-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(2-oxo-1,2-dihydropyridine- 4-carboxamido)benzo[d]thiazole-6-carboxylic acid),

(31) 2-(2-methoxypyrimidine-4-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(2-methoxypyrimidine-4-carboxamido)benzo[d]thiazole-6 -carboxylic acid),

(32) 2-(4-cyano-3-fluorobenzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-cyano-3-fluorobenzamido)benzo[d]thiazole-6 -carboxylic acid),

(33) 2-(3-cyano-4-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-cyano-4-methoxybenzamido)benzo[d]thiazole-6 -carboxylic acid),

(34) 2-(4-chloro-3-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-chloro-3-methoxybenzamido)benzo[d]thiazole-6- carboxylic acid),

(35) 2-(pyrimidine-5-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(pyrimidine-5-carboxamido)benzo[d]thiazole-6-carboxylic acid),

(36) 2-(5-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid),

(37) 2-(2-methylpyrimidine-5-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(2-methylpyrimidine-5-carboxamido)benzo[d]thiazole-6- carboxylic acid),

(38) 2-(3-chloro-2,4,5-trifluorobenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-chloro-2,4,5-trifluorobenzamido )benzo[d]thiazole-6-carboxylic acid),

(39) 2-(6-cyanonicotinamido)benzo[d]thiazole-6-carboxylic acid,

(40) 2-(pyridazine-4-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(pyridazine-4-carboxamido)benzo[d]thiazole-6-carboxylic acid),

(41) 2-(5-cyanonicotinamido)benzo[d]thiazole-6-carboxylic acid,

(42) 2-(2-(pyrrolidin-1-yl)isonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(pyrrolidin-1-yl)isonicotinamido)benzo [d]thiazole-6-carboxylic acid),

(43) 2-(2,6-difluoroisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2,6-difluoroisonicotinamido)benzo[d]thiazole-6-carboxylic acid ),

(44) 2-(3,5-difluoro-4-hydroxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3,5-difluoro-4-hydroxybenzamido)benzo[ d]thiazole-6-carboxylic acid),

(45) 2-(2-(trifluoromethyl)pyrimidine-5-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(trifluoromethyl)pyrimidine-5-carboxamido) benzo[d]thiazole-6-carboxylic acid),

(46) 2-(5-(trifluoromethyl)pyrazine-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(5-(trifluoromethyl)pyrazine-2-carboxamido)benzo [d]thiazole-6-carboxylic acid),

(47) 2-(5-methoxypyrazine-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(5-methoxypyrazine-2-carboxamido)benzo[d]thiazole-6- carboxylic acid),

(48) 2-(6-methylpyridazine-3-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(6-methylpyridazine-3-carboxamido)benzo[d]thiazole-6- carboxylic acid),

(49) 2-(2-fluoro-3-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(2-fluoro-3-(trifluoromethyl)benzamido) benzo[d]thiazole-6-carboxylic acid),

(50) 2-(4-methyl-3-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-methyl-3-(trifluoromethyl)benzamido)benzo [d]thiazole-6-carboxylic acid),

(51) 2-(4-methoxy-3-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-methoxy-3-(trifluoromethyl)benzamido) benzo[d]thiazole-6-carboxylic acid),

(52) 2-(3,5-bis(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3,5-bis(trifluoromethyl)benzamido)benzo[d ]thiazole-6-carboxylic acid),

(53) 2-(3-nitro-5-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-nitro-5-(trifluoromethyl)benzamido)benzo [d]thiazole-6-carboxylic acid),

(54) 2-(2-chloro-4-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(2-chloro-4-(trifluoromethyl)benzamido)benzo [d]thiazole-6-carboxylic acid),

(55) 2-(2-fluoro-4-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(2-fluoro-4-(trifluoromethyl)benzamido) benzo[d]thiazole-6-carboxylic acid),

(56) 2-(3-methoxy-4-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-methoxy-4-(trifluoromethyl)benzamido) benzo[d]thiazole-6-carboxylic acid),

(57) 2-(3-chloro-4-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-chloro-4-(trifluoromethyl)benzamido)benzo [d]thiazole-6-carboxylic acid),

(58) 2-(3,5-difluoro-4-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3,5-difluoro-4- (trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid),

(59) 2-(3-chloro-5-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-chloro-5-(trifluoromethyl)benzamido)benzo [d]thiazole-6-carboxylic acid),

(60) 2-(3-methoxy-5-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-methoxy-5-(trifluoromethyl)benzamido) benzo[d]thiazole-6-carboxylic acid),

(61) 2-(4-chloro-3-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-chloro-3-(trifluoromethyl)benzamido)benzo [d]thiazole-6-carboxylic acid),

(62) 2-(2,4-bis(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(2,4-bis(trifluoromethyl)benzamido)benzo[d ]thiazole-6-carboxylic acid),

(63) 2-(3-cyano-5-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-cyano-5-(trifluoromethyl)benzamido) benzo[d]thiazole-6-carboxylic acid),

(64) 2-(2-chloro-3-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(2-chloro-3-(trifluoromethyl)benzamido)benzo [d]thiazole-6-carboxylic acid),

(65) 2-(2-chloro-5-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(2-chloro-5-(trifluoromethyl)benzamido)benzo [d]thiazole-6-carboxylic acid),

(66) 2-(1-methyl-1H-pyrazole-5-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(1-methyl-1H-pyrazole-5-carboxamido)benzo [d]thiazole-6-carboxylic acid),

(67) 2-(4-chloro-3-fluoro-N-methylbenzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-chloro-3-fluoro-N-methylbenzamido) benzo[d]thiazole-6-carboxylic acid),

(68) 2-(5-(methoxycarbonyl)picolinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-(methoxycarbonyl)picolinamido)benzo[d]thiazole-6- carboxylic acid),

(69) 2-(6-chloro-5-fluoropicolinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-chloro-5-fluoropicolinamido)benzo[d]thiazole-6 -carboxylic acid),

(70) 2-(2-chloro-6-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-chloro-6-methoxyisonicotinamido)benzo[d]thiazole-6 -carboxylic acid),

(71) 2-(2-(thiophen-2-yl)acetamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(thiophen-2-yl)acetamido)benzo[d ]thiazole-6-carboxylic acid),

(72) 2-(2-(3,4-dichlorophenyl)acetamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(3,4-dichlorophenyl)acetamido)benzo[d ]thiazole-6-carboxylic acid),

(73) 2-(2-(3,5-difluorophenyl)acetamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(3,5-difluorophenyl)acetamido)benzo [d]thiazole-6-carboxylic acid),

(74) 2-(3-phenylpropanamido)benzo[d]thiazole-6-carboxylic acid,

(75) 2-(2-(2-fluorophenyl)acetamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(2-fluorophenyl)acetamido)benzo[d]thiazole- 6-carboxylic acid),

(76) 2-(3-(5-fluoronicotinamido)propanamido)benzo[d]thiazole-6-carboxylic acid (2-(3-(5-fluoronicotinamido)propanamido)benzo[d] thiazole-6-carboxylic acid),

(77) 2-(3-(5-chloronicotinamido)propanamido)benzo[d]thiazole-6-carboxylic acid (2-(3-(5-chloronicotinamido)propanamido)benzo[d]thiazole -6-carboxylic acid),

(78) 2-(3-(5-(trifluoromethyl)nicotinamido)propanamido)benzo[d]thiazole-6-carboxylic acid (2-(3-(5-(trifluoromethyl)nicotinamido) )propanamido)benzo[d]thiazole-6-carboxylic acid),

(79) 2-(3-(6-(trifluoromethyl)nicotinamido)propanamido)benzo[d]thiazole-6-carboxylic acid (2-(3-(6-(trifluoromethyl)nicotinamido) )propanamido)benzo[d]thiazole-6-carboxylic acid),

(80) 2-(3-(4-chloro-3-fluorophenyl)propanamido)benzo[d]thiazole-6-carboxylic acid (2-(3-(4-chloro-3-fluorophenyl) propanamido)benzo[d]thiazole-6-carboxylic acid),

(81) 2-(2-(4-chloro-3-fluorophenyl)acetamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(4-chloro-3-fluorophenyl) acetamido)benzo[d]thiazole-6-carboxylic acid),

(82) 2-(2-(4-fluorophenoxy)acetamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(4-fluorophenoxy)acetamido)benzo[d]thiazole -6-carboxylic acid),

(83) 2-(5-carboxy-1H-pyrrole-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(5-carboxy-1H-pyrrole-2-carboxamido)benzo[ d]thiazole-6-carboxylic acid),

(84) 2-(5-(trifluoromethyl)-1H-pyrrole-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(5-(trifluoromethyl)-1H-pyrrole -2-carboxamido)benzo[d]thiazole-6-carboxylic acid),

(85) 2-(2-(methylthio)isonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(methylthio)isonicotinamido)benzo[d]thiazole-6-carboxylic acid ),

(86) 2-(5-(methylthio)nicotinamido)benzo[d]thiazole-6-carboxylic acid ,

(87) 2-(2-(methylamino)isonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(methylamino)isonicotinamido)benzo[d]thiazole-6-carboxylic acid ),

(88) 2-(6-chloronicotinamido)benzo[d]thiazole-6-carboxylic acid,

(89) 2-(5-bromo-6-methoxynicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-bromo-6-methoxynicotinamido)benzo[d]thiazole-6 -carboxylic acid),

(90) 2-(6-(pyrrolidin-1-yl)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-(pyrrolidin-1-yl)nicotinamido)benzo[ d]thiazole-6-carboxylic acid),

(91) 2-(6-(2-methylprop-1-enyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-(2-methylprop-1-enyl) nicotinamido)benzo[d]thiazole-6-carboxylic acid),

(92) 2-(5-chloro-6-hydroxynicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-chloro-6-hydroxynicotinamido)benzo[d]thiazole-6- carboxylic acid),

(93) 2-(5-bromo-6-methylnicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-bromo-6-methylnicotinamido)benzo[d]thiazole-6- carboxylic acid),

(94) 2-(6-chloro-5-fluoronicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-chloro-5-fluoronicotinamido)benzo[d]thiazole-6- carboxylic acid),

(95) 2-(6-bromonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-bromonicotinamido)benzo[d]thiazole-6-carboxylic acid),

(96) 2-(6-carboxyspiro[3.3]heptane-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(6-carboxyspiro[3.3]heptane-2-carboxamido)benzo [d]thiazole-6-carboxylic acid),

(97) 2-(5-(trifluoromethyl)furan-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(5-(trifluoromethyl)furan-2-carboxamido)benzo [d]thiazole-6-carboxylic acid),

(98) 2-(5-bromonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-bromonicotinamido)benzo[d]thiazole-6-carboxylic acid),

(99) 2-(3-hydroxy-3-(trifluoromethyl)cyclobutanecarboxamido)benzo[d]thiazole-6-carboxylic acid (2-(3-hydroxy-3-(trifluoromethyl) cyclobutanecarboxamido)benzo[d]thiazole-6-carboxylic acid),

(100) 2-(3,3-difluoro-1-methylcyclobutanecarboxamido)benzo[d]thiazole-6-carboxylic acid (2-(3,3-difluoro-1-methylcyclobutanecarboxamido)benzo [d]thiazole-6-carboxylic acid),

(101) 2-(4-(2-carboxycyclopropyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-(2-carboxycyclopropyl)benzamido)benzo[d]thiazole- 6-carboxylic acid),

(102) 2-(2-(trifluoromethyl)furan-3-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(trifluoromethyl)furan-3-carboxamido)benzo [d]thiazole-6-carboxylic acid),

(103) 2-(5-carboxythiophene-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(5-carboxythiophene-2-carboxamido)benzo[d]thiazole-6- carboxylic acid),

(104) 2-(2-bromoisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-bromoisonicotinamido)benzo[d]thiazole-6-carboxylic acid),

(105) 2-(4-chloropicolinamido)benzo[d]thiazole-6-carboxylic acid,

(106) 2-(4-fluoropicolinamido)benzo[d]thiazole-6-carboxylic acid,

(107) 2-(6-chloro-5-methylpicolinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-chloro-5-methylpicolinamido)benzo[d]thiazole-6- carboxylic acid),

(108) 2-(5-chloro-3-propoxypicolinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-chloro-3-propoxypicolinamido)benzo[d]thiazole-6 -carboxylic acid),

(109) 2-(5-chloro-3-methylpicolinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-chloro-3-methylpicolinamido)benzo[d]thiazole-6- carboxylic acid),

(110) 2-(5-fluoro-6-methoxynicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-fluoro-6-methoxynicotinamido)benzo[d]thiazole-6 -carboxylic acid),

(111) 2-(4-methoxypicolinamido)benzo[d]thiazole-6-carboxylic acid,

(112) 2-(6-(trifluoromethyl)picolinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-(trifluoromethyl)picolinamido)benzo[d]thiazole-6- carboxylic acid),

(113) 2-(3-fluoropicolinamido)benzo[d]thiazole-6-carboxylic acid,

(114) 2-(4-(trifluoromethyl)picolinamido)benzo[d]thiazole-6-carboxylic acid (2-(4-(trifluoromethyl)picolinamido)benzo[d]thiazole-6- carboxylic acid),

(115) 2-(5-(trifluoromethyl)picolinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-(trifluoromethyl)picolinamido)benzo[d]thiazole-6- carboxylic acid),

(116) 2-(6-carboxynicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-carboxynicotinamido)benzo[d]thiazole-6-carboxylic acid),

(117) 2-(6-methoxypicolinamido)benzo[d]thiazole-6-carboxylic acid,

(118) 2-(6-(2-methoxyethoxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-(2-methoxyethoxy)nicotinamido)benzo[d]thiazole -6-carboxylic acid),

(119) 2-(2-methoxy-6-(trifluoromethyl)isonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-methoxy-6-(trifluoromethyl)isonicotinamido )benzo[d]thiazole-6-carboxylic acid),

(120) 2-(2-isopropoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-isopropoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid),

(121) 2-(6-ethoxy-4-fluoronicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-ethoxy-4-fluoronicotinamido)benzo[d]thiazole-6 -carboxylic acid),

(122) 2-(6-(cyclopropylmethoxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-(cyclopropylmethoxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid),

(123) 2-(6-isobutoxynicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-isobutoxynicotinamido)benzo[d]thiazole-6-carboxylic acid),

(124) 2-(2-(difluoromethoxy)isonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(difluoromethoxy)isonicotinamido)benzo[d]thiazole-6- carboxylic acid),

(125) 2-(6-(difluoromethoxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid acid),

(126) 2-(3-fluoro-4-methoxybenzamido)-4-methylbenzo[d]thiazole-6-carboxylic acid (2-(3-fluoro-4-methoxybenzamido)-4- methylbenzo[d]thiazole-6-carboxylic acid),

(127) 2-(6-methoxynicotinamido)-4-methylbenzo[d]thiazole-6-carboxylic acid (2-(6-methoxynicotinamido)-4-methylbenzo[d]thiazole-6-carboxylic acid),

(128) 2-(2-methoxyisonicotinamido)-4-methylbenzo[d]thiazole-6-carboxylic acid (2-(2-methoxyisonicotinamido)-4-methylbenzo[d]thiazole-6- carboxylic acid),

(129) 4-methyl-2-(2-(trifluoromethyl)isonicotinamido)benzo[d]thiazole-6-carboxylic acid (4-methyl-2-(2-(trifluoromethyl)isonicotinamido) benzo[d]thiazole-6-carboxylic acid),

(130) 4-methyl-2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid (4-methyl-2-(6-(trifluoromethyl)nicotinamido)benzo [d]thiazole-6-carboxylic acid),

(131) 2-(5-fluoro-2-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-fluoro-2-methoxyisonicotinamido)benzo[d]thiazole- 6-carboxylic acid),

(132) 2-(5-chloro-2-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-chloro-2-methoxyisonicotinamido)benzo[d]thiazole-6 -carboxylic acid),

(133) 2-(3-chloro-2-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(3-chloro-2-methoxyisonicotinamido)benzo[d]thiazole-6 -carboxylic acid),

(134) 2-(6-(tetrahydro-2H-pyran-4-yloxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-(tetrahydro-2H-pyran- 4-yloxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid),

(135) 2-(6-phenoxynicotinamido)benzo[d]thiazole-6-carboxylic acid,

(136) 2-(2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-6-methoxynicotinamido)benzo[d]thiazole-6-carboxyl Acid (2-(2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-6-methoxynicotinamido)benzo[d]thiazole-6-carboxylic acid),

(137) 2-(6-(2,2,2-trifluoroethoxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-(2,2,2- trifluoroethoxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid),

(138) 2-(6-isopropoxynicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-isopropoxynicotinamido)benzo[d]thiazole-6-carboxylic acid),

(139) 2-(4-chloro-3-fluorobenzamido)-4-methoxybenzo[d]thiazole-6-carboxylic acid (2-(4-chloro-3-fluorobenzamido)-4- methoxybenzo[d]thiazole-6-carboxylic acid),

(140) 2-(3-fluoro-4-methoxybenzamido)-4-methoxybenzo[d]thiazole-6-carboxylic acid (2-(3-fluoro-4-methoxybenzamido)-4 -methoxybenzo[d]thiazole-6-carboxylic acid),

(141) 4-methoxy-2-(2-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid (4-methoxy-2-(2-methoxyisonicotinamido)benzo[d]thiazole- 6-carboxylic acid),

(142) 2-(2-morpholinoisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-morpholinoisonicotinamido)benzo[d]thiazole-6-carboxylic acid),

(143) 2-(2-ethoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-ethoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid),

(144) 2-(6-methoxynicotinamido)benzo[d]thiazole-6-carboxylic acid,

(145) 2-(3-fluoro-4-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-fluoro-4-(trifluoromethyl)benzamido) benzo[d]thiazole-6-carboxylic acid),

(146) 2-(nicotinamido)benzo[d]thiazole-6-carboxylic acid,

(147) 2-(isonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(isonicotinamido)benzo[d]thiazole-6-carboxylic acid),

(148) 2-(3,4,5-trifluorobenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3,4,5-trifluorobenzamido)benzo[d]thiazole-6 -carboxylic acid),

(149) 2-(2-(trifluoromethyl)isonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(trifluoromethyl)isonicotinamido)benzo[d]thiazole-6- carboxylic acid),

(150) 2-(3-chloro-4-fluorobenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-chloro-4-fluorobenzamido)benzo[d]thiazole-6- carboxylic acid),

(151) 2-(3,4-difluorobenzamido)benzo[d]thiazole-6-carboxylic acid ,

(152) 2-(3-chloro-4-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-chloro-4-methoxybenzamido)benzo[d]thiazole-6- carboxylic acid),

(153) 2-(3-fluoro-5-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-fluoro-5-(trifluoromethyl)benzamido) benzo[d]thiazole-6-carboxylic acid),

(154) 2-(4-chloro-3-fluorobenzamido)-4-fluorobenzo[d]thiazole-6-carboxylic acid (2-(4-chloro-3-fluorobenzamido)-4- fluorobenzo[d]thiazole-6-carboxylic acid),

(155) 2-(4-chloro-2-methoxybenzamido)-4-fluorobenzo[d]thiazole-6-carboxylic acid (2-(4-chloro-2-methoxybenzamido)-4- fluorobenzo[d]thiazole-6-carboxylic acid),

(156) 4-fluoro-2-(3-fluoro-4-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid (4-fluoro-2-(3-fluoro-4- methoxybenzamido)benzo[d]thiazole-6-carboxylic acid),

(157) 4-fluoro-2-(2-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid (4-fluoro-2-(2-methoxyisonicotinamido)benzo[d]thiazole- 6-carboxylic acid),

(158) 2-(2-methyl-5-(4-(trifluoromethyl)pyrimidin-2-ylamino)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(2 -methyl-5-(4-(trifluoromethyl)pyrimidin-2-ylamino)benzamido)benzo[d]thiazole-6-carboxylic acid),

(159) 2-(6-oxo-1,6-dihydropyridine-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(6-oxo-1,6-dihydropyridine- 2-carboxamido)benzo[d]thiazole-6-carboxylic acid),

(160) 2-(3-(1H-imidazol-1-yl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-(1H-imidazol-1-yl)benzamido )benzo[d]thiazole-6-carboxylic acid),

(161) 2-(2-chloro-5-(4-methylpyrimidin-2-ylamino)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(2-chloro-5- (4-methylpyrimidin-2-ylamino)benzamido)benzo[d]thiazole-6-carboxylic acid),

(162) 2-(4-carboxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-carboxybenzamido)benzo[d]thiazole-6-carboxylic acid),

(163) 2-(8-hydroxyquinoline-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(8-hydroxyquinoline-2-carboxamido)benzo[d]thiazole-6- carboxylic acid),

(164) 2-(4-chloro-2-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-chloro-2-methoxybenzamido)benzo[d]thiazole-6- carboxylic acid),

(165) 2-(3,4-dimethoxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3,4-dimethoxybenzamido)benzo[d]thiazole-6-carboxylic acid),

(166) 2-(2-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid),

(167) 2-(4-chloro-3-fluorobenzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-chloro-3-fluorobenzamido)benzo[d]thiazole-6- carboxylic acid),

(168) 2-(4-fluoro-3-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-fluoro-3-methoxybenzamido)benzo[d]thiazole-6 -carboxylic acid),

(169) 2-(3-fluoro-4-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-fluoro-4-methoxybenzamido)benzo[d]thiazole-6 -carboxylic acid),

(170) 2-(4-cyanobenzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-cyanobenzamido)benzo[d]thiazole-6-carboxylic acid),

(171) 2-(3-cyanobenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-cyanobenzamido)benzo[d]thiazole-6-carboxylic acid),

(172) 2-(3-hydroxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-hydroxybenzamido)benzo[d]thiazole-6-carboxylic acid),

(173) 2-(3-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid),

(174) 2-(4-methylcyclohexanecarboxamido)benzo[d]thiazole-6-carboxylic acid,

(175) 2-(5-bromo-2-methoxynicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-bromo-2-methoxynicotinamido)benzo[d]thiazole-6 -carboxylic acid),

(176) 2-(2-tert-butylisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-tert-butylisonicotinamido)benzo[d]thiazole-6-carboxylic acid),

(177) 5-chloro-2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid (5-chloro-2-(6-(trifluoromethyl)nicotinamido)benzo [d]thiazole-6-carboxylic acid),

(178) 5-methoxy-2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid (5-methoxy-2-(6-(trifluoromethyl)nicotinamido) benzo[d]thiazole-6-carboxylic acid),

(179) 5-hydroxy-2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid (5-hydroxy-2-(6-(trifluoromethyl)nicotinamido) benzo[d]thiazole-6-carboxylic acid),

(180) 2-(5-fluoro-2-methoxynicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-fluoro-2-methoxynicotinamido)benzo[d]thiazole-6 -carboxylic acid),

(181) 2-(5-bromo-2-methylnicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-bromo-2-methylnicotinamido)benzo[d]thiazole-6- carboxylic acid),

(182) 2-(6-bromonicotinamido)-5-methoxybenzo[d]thiazole-6-carboxylic acid (2-(6-bromonicotinamido)-5-methoxybenzo[d]thiazole-6- carboxylic acid),

(183) 2-(2-aminoisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-aminoisonicotinamido)benzo[d]thiazole-6-carboxylic acid),

(184) 2-(2-bromo-6-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-bromo-6-methoxyisonicotinamido)benzo[d]thiazole- 6-carboxylic acid),

(185) 2-(6-bromo-2-chloronicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-bromo-2-chloronicotinamido)benzo[d]thiazole-6- carboxylic acid),

(186) 2-(6-tert-butylnicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-tert-butylnicotinamido)benzo[d]thiazole-6-carboxylic acid),

(187) 2-(5,6-dichloronicotinamido)benzo[d]thiazole-6-carboxylic acid,

(188) 2-(5-vinylnicotinamido)benzo[d]thiazole-6-carboxylic acid,

(189) 2-(5-(furan-3-yl)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-(furan-3-yl)nicotinamido)benzo[d] thiazole-6-carboxylic acid),

(190) 2-(5-cyclopentenylnicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-cyclopentenylnicotinamido)benzo[d]thiazole-6-carboxylic acid),

(191) 2-(5-(2-methylprop-1-enyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-(2-methylprop-1-enyl) nicotinamido)benzo[d]thiazole-6-carboxylic acid),

(192) 2-(2,6-dibromonicotinamido)benzo[d]thiazole-6-carboxylic acid ,

(193) 2-(6-amino-5-bromonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-amino-5-bromonicotinamido)benzo[d]thiazole-6- carboxylic acid),

(194) 2-(2-iodoisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-iodoisonicotinamido)benzo[d]thiazole-6-carboxylic acid),

(195) 2-(2-methylisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-methylisonicotinamido)benzo[d]thiazole-6-carboxylic acid),

(196) 2-(5-fluoronicotinamido)benzo[d]thiazole-5-carboxylic acid,

(197) 2-(5-chloronicotinamido)benzo[d]thiazole-5-carboxylic acid,

(198) 2-(isonicotinamido)benzo[d]thiazole-5-carboxylic acid (2-(isonicotinamido)benzo[d]thiazole-5-carboxylic acid),

(199) 2-(3-fluoro-4-(trifluoromethyl)benzamido)benzo[d]thiazole-5-carboxylic acid (2-(3-fluoro-4-(trifluoromethyl)benzamido) benzo[d]thiazole-5-carboxylic acid),

(200) 2-(2-chloroisonicotinamido)benzo[d]thiazole-5-carboxylic acid (2-(2-chloroisonicotinamido)benzo[d]thiazole-5-carboxylic acid),

(201) 2-(nicotinamido)benzo[d]thiazole-5-carboxylic acid,

(202) 2-(6-oxo-1,6-dihydropyridine-2-carboxamido)benzo[d]thiazole-5-carboxylic acid (2-(6-oxo-1,6-dihydropyridine- 2-carboxamido)benzo[d]thiazole-5-carboxylic acid),

(203) 2-(3,4,5-trifluorobenzamido)benzo[d]thiazole-5-carboxylic acid (2-(3,4,5-trifluorobenzamido)benzo[d]thiazole-5 -carboxylic acid),

(204) 2-(3-fluoro-4-methylbenzamido)benzo[d]thiazole-5-carboxylic acid (2-(3-fluoro-4-methylbenzamido)benzo[d]thiazole-5- carboxylic acid),

(205) 2-(2-ethoxyisonicotinamido)benzo[d]thiazole-5-carboxylic acid (2-(2-ethoxyisonicotinamido)benzo[d]thiazole-5-carboxylic acid),

(206) 2-(2-morpholinoisonicotinamido)benzo[d]thiazole-5-carboxylic acid (2-(2-morpholinoisonicotinamido)benzo[d]thiazole-5-carboxylic acid),

(207) 2-(6-chloro-5-fluoropicolinamido)benzo[d]thiazole-5-carboxylic acid (2-(6-chloro-5-fluoropicolinamido)benzo[d]thiazole-5 -carboxylic acid),

(208) 2-(5-carboxypicolinamido)benzo[d]thiazole-5-carboxylic acid,

(209) 2-(2-chloro-6-methoxyisonicotinamido)benzo[d]thiazole-5-carboxylic acid (2-(2-chloro-6-methoxyisonicotinamido)benzo[d]thiazole-5 -carboxylic acid),

(210) 2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-5-carboxylic acid (2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-5-carboxylic acid),

(211) 2-(2-(trifluoromethyl)isonicotinamido)benzo[d]thiazole-5-carboxylic acid (2-(2-(trifluoromethyl)isonicotinamido)benzo[d]thiazole-5- carboxylic acid),

(212) 2-(2-methoxyisonicotinamido)benzo[d]thiazole-5-carboxylic acid (2-(2-methoxyisonicotinamido)benzo[d]thiazole-5-carboxylic acid),

(213) 2-(3-fluoro-4-methoxybenzamido)benzo[d]thiazole-5-carboxylic acid (2-(3-fluoro-4-methoxybenzamido)benzo[d]thiazole-5 -carboxylic acid),

(214) 2-(4-(4-methoxyphenyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(4-methoxyphenyl)piperazin-1-yl )benzo[d]thiazole-6-carboxylic acid),

(215) 2-(4-(4-acetylphenyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(4-acetylphenyl)piperazin-1-yl) benzo[d]thiazole-6-carboxylic acid),

(216) 2-(4-(2,3-dichlorophenyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(2,3-dichlorophenyl)piperazin- 1-yl)benzo[d]thiazole-6-carboxylic acid),

(217) 2-(4-(4-cyanophenyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(4-cyanophenyl)piperazin-1-yl )benzo[d]thiazole-6-carboxylic acid),

(218) 2-(4-(pyridin-4-yl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(pyridin-4-yl)piperazin-1 -yl)benzo[d]thiazole-6-carboxylic acid),

(219) 2-(4-(pyridin-3-yl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(pyridin-3-yl)piperazin-1 -yl)benzo[d]thiazole-6-carboxylic acid),

(220) 2-(4-(2,4-difluorophenyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(2,4-difluorophenyl) piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(221) 2-(4-(3-methoxyphenyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(3-methoxyphenyl)piperazin-1-yl )benzo[d]thiazole-6-carboxylic acid),

(222) 2-(4-(3-phenylpropanoyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(3-phenylpropanoyl)piperazin-1- yl)benzo[d]thiazole-6-carboxylic acid),

(223) 2-(4-(2-phenylacetyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(2-phenylacetyl)piperazin-1-yl) benzo[d]thiazole-6-carboxylic acid),

(224) 2-(4-(3-chloro-4-fluorophenylsulfonyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(3-chloro -4-fluorophenylsulfonyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(225) 2-(4-(thiophen-2-ylsulfonyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(thiophen-2-ylsulfonyl)piperazin -1-yl)benzo[d]thiazole-6-carboxylic acid),

(226) 2-(4-(2-(4-fluorophenyl)acetyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(2-(4) -fluorophenyl)acetyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(227) 2-(4-(3-cyclopentylpropanoyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(3-cyclopentylpropanoyl)piperazin-1 -yl)benzo[d]thiazole-6-carboxylic acid),

(228) 2-(4-(benzylsulfonyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(benzylsulfonyl)piperazin-1-yl)benzo[d ]thiazole-6-carboxylic acid),

(229) 2-(4-(3,4-difluorophenylsulfonyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(3,4- difluorophenylsulfonyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(230) 2-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(4-chlorophenyl) -4-hydroxypiperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(231) 2-(3H-spiro[benzofuran-2,4'-piperidin]-1'-yl)benzo[d]thiazole-6-carboxylic acid (2-(3H-spiro[benzofuran- 2,4'-piperidine]-1'-yl)benzo[d]thiazole-6-carboxylic acid),

(232) 2-(4-(4-fluorophenyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(4-fluorophenyl)piperidin-1- yl)benzo[d]thiazole-6-carboxylic acid),

(233) 2-(4-hydroxy-4-phenylpiperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-hydroxy-4-phenylpiperidin-1-yl) benzo[d]thiazole-6-carboxylic acid),

(234) 2-(4-(2-methoxypyridin-4-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(2-methoxypyridin- 4-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(235) 2-(4-hydroxy-4-(pyridin-4-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-hydroxy-4- (pyridin-4-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(236) 2-(4-(pyridin-4-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(pyridin-4-yl)piperidin- 1-yl)benzo[d]thiazole-6-carboxylic acid),

(237) 2-(4-(3-(trifluoromethyl)phenyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(3-(trifluoromethyl) )phenyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(238) 2-(4-hydroxy-4-(pyridin-3-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-hydroxy-4- (pyridin-3-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(239) 2-(4-(pyridin-3-yloxy)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(pyridin-3-yloxy)piperidin -1-yl)benzo[d]thiazole-6-carboxylic acid),

(240) 2-(4-((pyridin-3-yloxy)methyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-((pyridin-3 -yloxy)methyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(241) 2-(4-(pyridin-3-ylmethyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(pyridin-3-ylmethyl)piperidin -1-yl)benzo[d]thiazole-6-carboxylic acid),

(242) 2-(4-(thiazol-2-ylmethyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(thiazol-2-ylmethyl) piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(243) 2-(4-((4-methyl-1H-pyrazol-1-yl)methyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4 -((4-methyl-1H-pyrazol-1-yl)methyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(244) 2-(4-((4H-1,2,4-triazol-4-yl)methyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2- (4-((4H-1,2,4-triazol-4-yl)methyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(245) 2-(4-(oxazol-5-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(oxazol-5-yl)piperidin -1-yl)benzo[d]thiazole-6-carboxylic acid),

(246) 2-(4-(1H-pyrrol-1-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(1H-pyrrol-1- yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(247) 2-(4-(4-methyl-1H-pyrazol-1-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(4 -methyl-1H-pyrazol-1-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(248) 2-(4-(1H-benzo[d]imidazol-2-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(1H -benzo[d]imidazol-2-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(249) 2-(4-(6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl)piperidin-1-yl)benzo [d]thiazole-6-carboxylic acid (2-(4-(6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl)piperidin-1 -yl)benzo[d]thiazole-6-carboxylic acid),

(250) 2-(4-((benzo[d]thiazol-2-yloxy)methyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4- ((benzo[d]thiazol-2-yloxy)methyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(251) 2-(2-oxospiro[indoline-3,4'-piperidine]-1'-yl)benzo[d]thiazole-6-carboxylic acid (2-(2-oxospiro[indoline -3,4'-piperidine]-1'-yl)benzo[d]thiazole-6-carboxylic acid),

(252) 2-(4-(pyridin-3-ylmethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(pyridin-3- ylmethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(253) 2-(4-(pyridin-4-ylmethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(pyridin-4- ylmethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(254) 2-(4-((5-fluoropyridin-3-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4 -((5-fluoropyridin-3-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(255) 2-(4-((6-(trifluoromethyl)pyridin-3-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid ( 2-(4-((6-(trifluoromethyl)pyridin-3-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(256) 2-(4-((5-chloropyridin-3-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4- ((5-chloropyridin-3-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(257) 2-(4-((2-methoxypyridin-4-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4 -((2-methoxypyridin-4-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(258) 2-(4-carboxypiperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-carboxypiperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(259) 2-(4-((6-methoxypyridin-3-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4 -((6-methoxypyridin-3-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(260) 2-(4-(cyclopropylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(cyclopropylcarbamoyl)piperidin-1-yl) benzo[d]thiazole-6-carboxylic acid),

(261) 2-(4-(3-hydroxypropylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(3-hydroxypropylcarbamoyl)piperidin -1-yl)benzo[d]thiazole-6-carboxylic acid),

(262) 2-(4-(carboxymethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(carboxymethylcarbamoyl)piperidin-1-yl) benzo[d]thiazole-6-carboxylic acid),

(263) 2-(4-((1H-pyrrol-2-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-( (1H-pyrrol-2-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(264) 2-(4-(thiazol-2-ylmethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(thiazol-2 -ylmethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),

(265) 2-(4-(2-(1H-pyrrol-1-yl)ethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4 -(2-(1H-pyrrol-1-yl)ethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid), or

(266) 2-(4-(2-(1H-imidazol-1-yl)ethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-( It may be 4-(2-(1H-imidazol-1-yl)ethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid), but is not limited thereto.

The compounds of the present invention may exist in the form of pharmaceutically acceptable salts. As a salt, an acid salt formed by a pharmaceutically acceptable free acid is useful. The term "pharmaceutically acceptable salt" of the present invention refers to any of the compounds at a concentration that is relatively non-toxic and harmless to patients and has an effective effect, and side effects due to the salt do not reduce the beneficial efficacy of the compound represented by Formula 1. refers to all organic or inorganic addition salts of

Acid addition salts are prepared by conventional methods, for example, by dissolving the compound in an excess of aqueous acid solution and precipitating the salt using a water-miscible organic solvent, such as methanol, ethanol, acetone or acetonitrile. Equimolar amounts of the compound and an acid or alcohol (e.g., glycol monomethyl ether) in water can be heated, and the mixture can then be evaporated to dryness, or the precipitated salt can be suction filtered.

At this time, organic acids and inorganic acids can be used as free acids. Hydrochloric acid, phosphoric acid, sulfuric acid, nitric acid, tartaric acid, etc. can be used as inorganic acids, and methanesulfonic acid, p-toluenesulfonic acid, acetic acid, trifluoroacetic acid, and maleic acid can be used as organic acids. (maleic acid), succinic acid, oxalic acid, benzoic acid, tartaric acid, fumaric acid, manderic acid, propionic acid, citric acid, lactic acid, glycolic acid, gluconic acid. (gluconic acid), galacturonic acid, glutamic acid, glutaric acid, glucuronic acid, aspartic acid, ascorbic acid, carbonic acid, vanillic acid, hydroiodic acid, etc. can be used. , but is not limited to these.

Additionally, a pharmaceutically acceptable metal salt can be prepared using a base. The alkali metal salt or alkaline earth metal salt is obtained, for example, by dissolving the compound in an excess of alkali metal hydroxide or alkaline earth metal hydroxide solution, filtering the insoluble compound salt, and then evaporating and drying the filtrate. At this time, it is pharmaceutically suitable to prepare metal salts, especially sodium, potassium, or calcium salts, but is not limited to these. Additionally, the corresponding silver salt can be obtained by reacting an alkali metal or alkaline earth metal salt with an appropriate silver salt (e.g., silver nitrate).

Pharmaceutically acceptable salts of the compounds of the present invention include salts of acidic or basic groups that may be present in the compound of formula (1), unless otherwise indicated. For example, pharmaceutically acceptable salts may include sodium, calcium, and potassium salts of hydroxy groups, and other pharmaceutically acceptable salts of amino groups include hydrobromide, sulfate, hydrogen sulfate, phosphate, and hydrogen phosphate. , dihydrogen phosphate, acetate, succinate, citrate, tartrate, lactate, mandelate, methanesulfonate (mesylate) and p-toluenesulfonate (tosylate) salts, etc., and the preparation of salts known in the art. It can be manufactured through a method.

The salt of the benzothiazole derivative compound of the present invention is a pharmaceutically acceptable salt, and any salt of a benzothiazole derivative that exhibits pharmacological activity equivalent to that of the benzothiazole derivative compound can be used without limitation.

In addition, the compound represented by Formula 1 according to the present invention includes, without limitation, not only its pharmaceutically acceptable salts, but also solvates such as possible hydrates that can be prepared therefrom, and all possible stereoisomers. Solvates and stereoisomers of the compound represented by Formula 1 can be prepared from the compound represented by Formula 1 using methods known in the art.

Furthermore, the compound represented by Formula 1 according to the present invention can be prepared in crystalline form or amorphous form, and when prepared in crystalline form, it can be arbitrarily hydrated or solvated. In the present invention, not only the stoichiometric hydrate of the compound represented by Formula 1, but also compounds containing various amounts of water may be included. Solvates of the compound represented by Formula 1 according to the present invention include both stoichiometric solvates and non-stoichiometric solvates.

A second aspect of the present invention provides a method for producing the compound of the first aspect, or a pharmaceutically acceptable salt thereof, comprising the first step of reacting the compounds represented by the following formulas (2) and (3):

[Formula 2]

[Formula 3]

In Formula 2 or 3,

R' is -NHR" or halogen,

R" is H or CH ₃ ,

X' is H, -(CH ₂ ) _m -COOH, -CONH-(CH ₂ ) _p -COOH, or -O-(CH ₂ ) _q -COOH,

m is an integer from 0 to 5,

R ₁ is carboxyl, or C _1-4 alkoxycarbonyl,

R ₂ is hydrogen, C _1-4 alkyl, C _1-4 alkoxy, halogen, or hydroxy,

R ₃ is C _6-10 aryl, C _3-10 cycloalkyl, 5 to 10 membered heteroaryl, or 5 to 10 membered heterocyclyl,

The C _6-10 aryl, C _3-10 cycloalkyl, 5 to 10 membered heteroaryl, and 5 to 10 membered heterocyclyl are unsubstituted or cyano, halogen, nitro, oxo, hydroxy, carboxyl, amino, C _1-4 alkyl, C _1-4 alkenyl, C _1-4 alkoxy, C _1-4 haloalkyl, C _1-4 haloalkoxy, C _1-4 alkoxycarbonyl, C _1-4 alkylcarbonyl, C _1-4 alkylthio, C _1-4 alkylamino, C _1-4 alkoxy-C _1-4 alkoxy, C _3-10 cycloalkyl, C _3-10 cycloalkyl-C _1-4 alkoxy. C _3-10 cycloalkenyl, C _6-10 aryloxy, C _3-10 cycloalkyl-C _1-4 alkylcarbonyl, C _6-10 aryl-C _1-4 alkylcarbonyl, C _6-10 aryl sulfur Ponyl, C _6-10 aryl-C _1-4 alkylsulfonyl, C _3-10 cycloalkylcarbamoyl, hydroxy-C _1-4 alkylcarbamoyl, carboxy-C _1-4 alkylcarbamoyl, 5 to 10 members Heterocyclyl, 5 to 10 membered heterocyclyloxy, 5 to 10 membered heteroaryl, 5 to 10 membered heteroaryloxy, 5 to 10 membered heteroarylamino, 5 to 10 membered heteroarylsulfonyl, 5 to 10 membered hetero Aryl-C _1-4 alkyl, 5 to 10 membered heteroaryloxy-C _1-4 alkyl, 5 to 10 membered heteroaryl-C _1-4 alkylamino, and 5 to 10 membered heteroaryl-C _1-4 alkylcarba Substituted with one or more selected from the group consisting of moyl.

For example, the first step is i) EDCI (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide), HATU (1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5- b] pyridinium 3-oxide hexafluorophosphate, or Hexafluorophosphate Azabenzotriazole Tetramethyl Uronium), PyBroP (bromo-tris-pyrrolidino-phosphonium hexafluorophosphate), and PyBOP (benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate) at least one catalyst selected from the group consisting of; HOBt (1-hydroxybenzotriazole), or DMAP (4-dimethylaminopyridine); and one or more Hunig's bases selected from the group consisting of N,N-diisopropylethylamine (DIPEA), triethylamine (TEA), and pyridine. ; It may be performed in the presence of, or ii) basic conditions, but is not limited thereto. Specifically, method ii) may be performed in the presence of a basic substance such as K ₂ CO ₃ , KOH, Cs ₂ CO ₃ , but is not limited thereto.

For example, except in the case where The reaction may be carried out using any method, but is not limited thereto.

For example, the first step may be achieved by stirring at room temperature when using method i) or method ii), but is not limited thereto. Furthermore, the reaction in the first step can be performed for 3 to 48 hours, but is not limited thereto. In addition, the reaction in the first step is carried out in a polar organic solvent, such as N,N-dimethylformamide (DMF), dichloromethane (DCM), or acetonitrile (ACN). It can be performed in a solution state in which an aprotic solvent (polar aprotic solvent) is dissolved alone or in a mixture of two or more solvents, but is not limited thereto.

Furthermore, the production method of the present invention is a second step of reacting the product of the first step with a base and then adding an acid to carboxylate it when R ₁ is C _1-4 alkoxycarbonyl, and then precipitating it. It may additionally include, but is not limited to this.

A third aspect of the present invention provides a pharmaceutical composition for preventing or treating liver disease, comprising the compound of the first aspect, or a pharmaceutically acceptable salt thereof, as an active ingredient.

The terms of the present invention, “compound of the first embodiment”, and “pharmaceutically acceptable salt” are as described above.

In the terms of the present invention, “prevention” refers to all actions that suppress or delay the occurrence, spread, and recurrence of liver disease by administering the composition of the present invention, and “treatment” refers to the treatment of the disease by administering the composition of the present invention. It refers to any action that improves or changes symptoms to a benefit.

The pharmaceutical composition of the present invention can exert pharmacological activity by inhibiting 17β-HSD13 (17β-Hydroxysteroid dehydrogenase type 13 or 17β-HSD type 13).

The term "17β-HSD13" of the present invention is an enzyme encoded by the HSD17B13 gene, which is significantly overexpressed in the liver of patients with liver disease, such as non-alcoholic fatty liver disease, and is known to enhance lipogenesis.

For example, the liver diseases include non-alcoholic steatohepatitis (NASH), nonalcoholic fatty liver disease (NAFLD), alcoholic fatty liver disease, alcoholic hepatitis, alcoholic cirrhosis, Cirrhosis, liver cancer, liver failure and acute liver failure, biliary tract cancer, cholangiocarcinoma, primary biliary cholangitis, primary biliary cholangitis, jaundice, portal hypertension, cholelithiasis, acute or chronic cholecystitis, gallbladder polyps, gallbladder wall thickening, intrahepatic bile duct cancer It may be one or more types selected from the group consisting of hilar bile duct cancer, distal bile duct cancer, and biliary obstruction. Specifically, it may be non-alcoholic steatohepatitis or non-alcoholic fatty liver disease, but is not limited thereto.

Preferably, the pharmaceutical composition according to the present invention contains the compound represented by Formula 1, or a pharmaceutically acceptable salt thereof, as an active ingredient in an amount of 0.1 to 75% by weight, more preferably 1 to 75% by weight, based on the total weight of the composition. It can be contained at 50% by weight.

The composition of the present invention may further include a pharmaceutically acceptable carrier, diluent or excipient, and may be formulated into powders, granules, tablets, capsules, suspensions, emulsions, syrups, etc. according to conventional methods to suit each purpose of use. It can be formulated and used in a variety of forms, such as oral formulations such as aerosols and injections of sterile injectable solutions, and can be administered orally or through various routes including intravenous, intraperitoneal, subcutaneous, rectal, and topical administration. Examples of suitable carriers, excipients or diluents that may be included in such compositions include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, gum acacia, alginates, gelatin, calcium phosphate, calcium silicate, Examples include cellulose, methylcellulose, microcrystalline cellulose, polyvinylpyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate, and mineral oil. In addition, the composition of the present invention may further include fillers, anti-coagulants, lubricants, wetting agents, fragrances, emulsifiers, preservatives, etc.

Solid preparations for oral administration include tablets, pills, powders, granules, capsules, etc., and these solid preparations contain at least one excipient, such as starch, calcium carbonate, sucrose, lactose, gelatin, etc. Formulated by mixing. Additionally, in addition to simple excipients, lubricants such as magnesium stearate and talc may be used.

Liquid preparations for oral use include suspensions, oral solutions, emulsions, and syrups. In addition to the commonly used simple diluents such as water and liquid paraffin, various excipients such as wetting agents, sweeteners, fragrances, and preservatives may be included. You can.

Preparations for parenteral administration include sterilized aqueous solutions, non-aqueous solutions, suspensions, emulsions, lyophilized preparations, and suppositories. Non-aqueous solvents and suspensions include propylene glycol, polyethylene glycol, vegetable oil such as olive oil, and injectable esters such as ethyl oleate. The basis of suppositories is Wethepsol, Macrogol, and Twin 61. Cacao, laurel, glycerogeratin, etc. can be used. Meanwhile, injectables may contain conventional additives such as solubilizers, isotonic agents, suspending agents, emulsifiers, stabilizers, preservatives, etc.

At this time, the composition of the present invention is administered in a pharmaceutically effective amount. The term "pharmaceutically effective amount" of the present invention refers to an amount that is sufficient to treat a disease with a reasonable benefit/risk ratio applicable to medical treatment and does not cause side effects, and the effective dose level refers to the patient's health condition, Factors including the type of disease, severity, activity of the drug, sensitivity to the drug, method of administration, time of administration, route of administration and excretion rate, duration of treatment, drugs combined or used simultaneously, and other factors well known in the field of medicine. You can. The composition of the present invention may be administered as an individual therapeutic agent or in combination with other therapeutic agents, may be administered sequentially or simultaneously with conventional therapeutic agents, and may be administered singly or multiple times. Considering all of the above factors, it is important to administer an amount that can achieve maximum effect with the minimum amount without side effects, and this can be easily determined by a person skilled in the art.

For example, the dosage may increase or decrease depending on the route of administration, severity of disease, gender, weight, age, etc., so the above dosage does not limit the scope of the present invention in any way.

Specifically, the effective amount of the compound in the composition of the present invention may vary depending on the patient's age, gender, and body weight, and is generally administered at 1 to 100 mg per kg of body weight, preferably 5 to 60 mg per kg of body weight every day or every other day, or 1 It can be administered in divided doses 1 to 3 times a day. However, since it may increase or decrease depending on the route of administration, severity of disease, gender, weight, age, etc., the above dosage does not limit the scope of the present invention in any way.

A fourth aspect of the present invention provides a method for preventing or treating liver disease, comprising administering the pharmaceutical composition of the third aspect to an individual in need thereof.

The terms of the present invention, “pharmaceutical composition of the third aspect,” “liver disease,” “prevention,” and “treatment” are as described above.

The term "individual" of the present invention refers to monkeys, cows, horses, sheep, pigs, chickens, turkeys, quail, cats, dogs, mice, rats, rabbits, or guinea pigs, including humans in which the liver disease has developed or can be developed. refers to all animals, including, and the disease can be effectively prevented or treated by administering the pharmaceutical composition of the present invention to an individual. The pharmaceutical composition of the present invention can be administered in combination with existing therapeutic agents.

The term "improvement" in the present invention refers to any action in which the symptoms of an individual suspected of or suffering from the disease are improved or beneficially changed by using the food composition of the present invention.

The term "administration" of the present invention means providing a predetermined substance to a patient by any suitable method, and the administration route of the composition of the present invention can be administered through any general route as long as it can reach the target tissue. there is. It may be administered intraperitoneally, intravenously, intramuscularly, subcutaneously, intradermally, orally, topically, intranasally, intrapulmonaryly, or rectally, but is not limited thereto. Additionally, the pharmaceutical composition of the present invention may be administered by any device that allows the active agent to move to target cells. Preferred administration methods and formulations include intravenous injection, subcutaneous injection, intradermal injection, intramuscular injection, and drip injection. Injections include aqueous solvents such as physiological saline solution and Ringer's solution, non-aqueous solvents such as vegetable oil, higher fatty acid esters (e.g., ethyl oleate, etc.), and alcohols (e.g., ethanol, benzyl alcohol, propylene glycol, glycerin, etc.). It can be manufactured using stabilizers to prevent deterioration (e.g., ascorbic acid, sodium bisulfite, sodium pyrosulphite, BHA, tocopherol, EDTA, etc.), emulsifiers, buffers for pH adjustment, and agents to prevent microbial growth. It may contain pharmaceutical carriers such as preservatives (e.g., phenylmercuric nitrate, thimerosal, benzalkonium chloride, phenol, cresol, benzyl alcohol, etc.).

The term "therapeutically effective amount" used in combination with an active ingredient in the present invention refers to a benzothiazole derivative compound, a stereoisomer thereof, a mixture of stereoisomers thereof, or a pharmaceutically acceptable compound thereof that is effective in preventing or treating the target disease. It refers to the amount of salt available.

The pharmaceutical composition of the present invention contains benzothiazole as an active ingredient, depending on the type of disease to be prevented or treated. It may further include known drugs used for the prevention or treatment of known diseases other than derivative compounds or pharmaceutically acceptable salts thereof.

A fifth aspect of the present invention provides a food composition for preventing or improving liver disease, comprising the compound of the first aspect, or a foodologically acceptable salt thereof, as an active ingredient.

The terms of the present invention, “compound of the first aspect,” “liver disease,” “prevention,” and “improvement” are as described above. Additionally, the term “foodologically acceptable salt” of the present invention may be defined in the same way as the above-mentioned pharmaceutically acceptable salt.

The food composition according to the present invention includes the form of pills, powders, granules, precipitates, tablets, capsules, or liquids. Foods to which the composition of the present invention can be added include, for example, various foods, such as , beverages, gum, tea, vitamin complexes, health supplements, etc.

The essential ingredients that can be included in the food composition of the present invention are not limited to other ingredients other than the compound of Formula 1 or a foodologically acceptable salt thereof, and include various herbal extracts, food supplements, natural carbohydrates, etc. like regular foods. It may contain as an additional ingredient.

In addition, the food auxiliary additives include food auxiliary additives common in the art, such as flavoring agents, flavors, colorants, fillers, stabilizers, etc.

Examples of such natural carbohydrates include monosaccharides such as glucose, fructose, etc.; Disaccharides such as maltose, sucrose, etc.; and polysaccharides, such as common sugars such as dextrin and cyclodextrin, and sugar alcohols such as xylitol, sorbitol, and erythritol. In addition to the above-mentioned flavoring agents, natural flavoring agents (e.g., rebaudioside A, glycyrrhizin, etc.) and synthetic flavoring agents (saccharin, aspartame, etc.) can be advantageously used.

In addition to the above, the food composition of the present invention contains various nutrients, vitamins, minerals (electrolytes), flavoring agents such as synthetic and natural flavors, colorants and fillers (cheese, chocolate, etc.), pectic acid and its salts, alginic acid and its It may contain salts, organic acids, protective colloidal thickeners, pH adjusters, stabilizers, preservatives, glycerin, alcohol, carbonating agents used in carbonated beverages, etc. In addition, it may contain pulp for the production of natural fruit juice, fruit juice drinks, and vegetable drinks. These ingredients can be used independently or in combination.

In the present invention, the food composition includes health functional foods and health supplements.

The above-mentioned health functional food (functional food) is the same term as food for special health use (FoSHU), and is a food manufactured and/or processed using raw materials or ingredients with functional properties useful to the human body. In other words, it refers to foods with high medical effects that have been processed to efficiently perform bioregulatory functions in addition to supplying nutrients. Here, “function” means adjusting nutrients to the structure and function of the human body or obtaining useful effects for health purposes, such as physiological effects. As mentioned above, foods that contain ingredients useful to the human body and whose function and safety have been recognized by the Ministry of Food and Drug Safety are called health functional foods. Other foods that have not been approved by the Ministry of Food and Drug Safety but are considered to have beneficial effects on the human body are called health functional foods. It is classified as a (supplementary) food. The food of the present invention can be manufactured by methods commonly used in the industry, and can be manufactured by adding raw materials and ingredients commonly added in the industry. Additionally, the food formulation can be manufactured without limitation as long as it is a formulation recognized as a food. The food composition of the present invention can be manufactured in various forms, and unlike general drugs, it is made from food as a raw material, so it has the advantage of not having side effects that may occur when taking the drug for a long time, and is highly portable.

A sixth aspect of the present invention provides a feed composition for preventing or improving liver disease, comprising the compound of the first aspect, or a feedologically acceptable salt thereof, as an active ingredient.

The terms of the present invention, “compound of the first aspect,” “liver disease,” “prevention,” and “improvement” are as described above. In addition, the term "foodologically acceptable salt" in the present invention is defined as a foodologically acceptable salt.

As used herein, the term "feed" means any natural or artificial diet, meal, etc., or a component of the meal, for or suitable for eating, ingestion, and digestion by animals.

The type of feed is not particularly limited, and feed commonly used in the art can be used. Non-limiting examples of the feed include plant feeds such as grains, roots and fruits, food processing by-products, algae, fiber, pharmaceutical by-products, oils and fats, starches, cucurbits or grain by-products; Examples include animal feeds such as proteins, inorganic substances, fats and oils, minerals, fats and oils, single-cell proteins, zooplanktons or foods. These may be used alone or in combination of two or more types.

The feed of the present invention may be powder feed, solid feed, moist pellet feed, dry pellet feed, EP (Extruder Pellet) feed, raw feed, etc., but is not limited thereto.

The feed composition of the present invention may include binders, emulsifiers, preservatives, etc. added to prevent quality deterioration, and the feed composition may include feed additives. To increase utility, there may be amino acids, vitamins, enzymes, flavors, non-protein nitrogen compounds, silicate agents, buffers, extractants, oligosaccharides, etc. added to feed. In addition, feed mixtures, etc. may be additionally included, but are not limited thereto.

The benzothiazole derivative of the present invention can inhibit 17β-HSD13 activity and further inhibit lipogenesis, so it can be usefully used in the prevention or treatment of liver diseases, including non-alcoholic fatty liver disease or non-alcoholic steatohepatitis.

Hereinafter, the present invention will be described in more detail through examples. However, these examples are for illustrative purposes only and the scope of the present invention is not limited to these examples.

Example 1: Preparation of 2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid

(a) EDCI, HOBt, DIPEA, rt, 24 h;

(b) 1N NaOH, THF, MeOH, rt, 24 h.

Step 1-1: Preparation of ethyl 2-(6-(trifluoromethyl)ticotinamido)benzo[d]thiazole-6-carboxylate

6-(trifluoromethyl)nicotinic acid (258 mg, 1.35 mmol) dissolved in N,N-dimethylformamide (DMF, 2 mL), EDCI hydrochloride ( 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 345 mg, 1.80 mmol), HOBt (1-hydroxybenzotriazole, 243 mg, 1.80 mmol) solution, N,N-diisopropylethylamine , 0.78 mL, 4.50 mmol) and ethyl 2-aminobenzo[d]thiazole-6-carboxylate (200 mg, 0.90 mmol) were added at room temperature. The mixture was stirred at room temperature for one day. The reaction was terminated by adding distilled water, and the precipitated solid was filtered. The filtered solid was dried to obtain the title compound (157 mg, 0.40 mmol) (yield 44%).

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 1.36 (t, J = 7.13 Hz, 3 H) 4.26 - 4.40 (m, 2 H) 7.84 - 7.92 (m, 1 H) 8.06 (dd, J = 8.51, 1.75 Hz, 1 H) 8.15 (d, J = 8.25 Hz, 1H) 8.70 - 8.74 (m, 2 H) 9.40 (d, J = 1.88 Hz, 1 H) 13.58 (br s, 1 H);

[M+1]: 395.36.

Step 1-2: Preparation of 2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid

Ethyl 2-(6-(trifluoromethyl)ticotinamido)benzo[d] obtained from step 1-1 above, dissolved in tetrahydrofuran (THF, 2 mL) and MeOH (2 mL) To a solution of thiazole-6-carboxylate (157 mg, 0.40 mmol), NaOH (79 mg, 2.00 mmol) dissolved in distilled water (2 mL) was added and stirred at room temperature for one day. 1N HCl was added to the mixture to adjust the pH to 3 to 4, the precipitated solid was filtered, and the residue was washed with distilled water. The washed solid was dried to obtain the title compound (96 mg, 0.3 mmol).

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 13.49 (br s, 1H), 9.40 (d, J = 1.88 Hz, 1H), 8.67 - 8.75 (m, 2H), 8.15 (d, J = 8.25 Hz) , 1H), 8.06 (dd, J = 1.75, 8.50 Hz, 1H), 7.83 - 7.91 (m, 1H);

[M+1]: 368.3.

The compounds of Examples 2 to 213 below were synthesized in a similar manner to Example 1, but using appropriate reactants considering the structure of the title compound.

Example 2: 2-(3-phenylbutanamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.50 - 8.63 (m, 1H), 7.96 - 8.03 (m, 1H), 7.70 - 7.78 (m, 1H), 7.28 - 7.33 (m, 4H), 7.14 -7.21 (m, 1H), 3.33 - 3.35 (m, 1H), 2.75 - 2.87 (m, 2H), 1.26 (d, J = 6.88 Hz, 3H);

[M+1]: 341.4.

Example 3: 2-(furan-2-carboxamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.40 (s, 2H), 7.94 (dd, J = 1.38, 8.38 Hz, 1H), 7.79 (s, 1H), 7.47 - 7.68 (m, 1H), 6.97 - 7.19 (m, 1H);

[M+1]: 289.28.

Example 4: 2-(2-methoxyisonicotinamido)benzo[d]thiazole-7-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 8.38 - 8.43 (m, 1 H) 8.03 - 8.09 (m, 1 H) 7.97 - 8.01 (m, 1 H) 7.59 - 7.66 (m, 2 H) 7.48 - 7.52 (m, 1 H) 3.94 (s, 3 H);

[M+1]: 330.33.

Example 5: 2-(2-cyanoisonicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.93 - 9.00 (m, 1H), 8.66 - 8.73 (m, 2H), 8.23 - 8.29 (m, 1H), 8.02 - 8.13 (m, 1H), 7.82 - 7.95 (m, 1H);

[M+1]: 325.31.

Example 6: 2-(6-fluoronicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.89 (d, J = 1.88 Hz, 1H), 8.28 - 8.39 (m, 1H), 8.08 - 8.24 (m, 1H), 7.73 - 7.85 (m, 1H) ), 7.21 - 7.36 (m, 1H), 6.77 - 6.86 (m, 1H);

[M+1]: 318.3.

Example 7: 2-(2-methyl-5-nitrobenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.65 - 8.72 (m, 1H), 8.48 - 8.59 (m, 1H), 8.28 - 8.37 (m, 1H), 8.01 - 8.07 (m, 1H), 7.81 - 7.89 (m, 1H), 7.60 - 7.73 (m, 1H), 2.56 - 2.58 (m, 3H);

[M+1]: 358.34.

Example 8: 2-(4-methylthiophene-2-carboxamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.58 - 8.66 (m, 1H), 8.11 - 8.22 (m, 1H), 8.01 (br d, J = 1.75 Hz, 1H), 7.77 - 7.92 (m, 1H), 7.54 - 7.73 (m, 1H), 2.26 - 2.29 (m, 3H);

[M+1]: 319.37.

Example 9: 2-(3-nitrobenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.99 (t, J = 1.88 Hz, 1H), 8.66 (s, 1H), 8.55 - 8.62 (m, 1H), 8.47 - 8.53 (m, 1H), 8.05 (dd, J = 1.75, 8.50 Hz, 1H), 7.88 (d, J = 8.13 Hz, 1H);

[M+1]: 344.31.

Example 10: 2-(2-nitroisonicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.90 - 8.96 (m, 1H), 8.60 - 8.71 (m, 1H), 8.48 - 8.54 (m, 1H), 8.37 - 8.55 (m, 1H), 8.02 - 8.10 (m, 1H), 7.82 - 7.91 (m, 1H), 7.46 - 7.65 (m, 1H);

[M+1]: 345.3.

Example 11: 2-(3-fluorobenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.17 (d, J = 1.25 Hz, 1H), 7.94 - 8.04 (m, 1H), 7.85 - 7.93 (m, 1H), 7.79 (dd, J = 1.56) , 8.32 Hz, 1H), 7.39 - 7.46 (m, 1H), 7.38 - 7.46 (m, 1H), 7.34 - 7.38 (m, 1H), 7.18 - 7.25 (m, 1H)

[M+1]: 317.31

Example 12: 2-(3,5-difluorobenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.39 - 8.44 (m, 1H), 8.09 - 8.25 (m, 1H), 7.69 - 7.88 (m, 2H), 7.34 - 7.45 (m, 1H), 7.22 (s, 1H);

[M+1]: 353.3.

Example 13: 2-(2-fluoroisonicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.76 (m, 1H), 8.51 (m, 1H), 8.07 (s, 1H), 7.86 - 7.68 (m, 2H), 7.77 (m, 1H);

[M+1]: 318.3.

Example 14: 2-(3,7-difluoro-1H-indole-2-carboxamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.23 - 8.27 (m, 1H), 7.83 - 7.87 (m, 2H), 7.76 - 7.81 (m, 2H), 7.32 - 7.39 (m, 1H);

[M+1]: 374.33.

Example 15: 2-(4-chloro-3-fluorobenzamido)benzo[d]thiazole-7-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 8.15 (br d, J = 10.01 Hz, 1 H) 8.01 (br d, J = 7.75 Hz, 1 H) 7.68 - 7.89 (m, 3 H) 7.45 (br d, J = 7.13 Hz, 1 H);

[M+1]: 351.75.

Example 16: 2-(benzo[d]thiazole-4-carboxamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 9.85 (s, 1H), 8.52 - 8.58 (m, 1H), 8.43 - 8.51 (m, 1H), 8.38 (br d, J = 7.00 Hz, 1H) , 7.97 - 8.06 (m, 1H), 7.76 (s, 1H), 7.68 (br d, J = 8.25 Hz, 1H);

[M+1]: 356.39.

Example 17: 2-(4-chloro-2-methoxybenzamido)benzo[d]thiazole-7-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 12.15 (br s, 1 H) 7.95 - 8.06 (m, 2 H) 7.76 (d, J = 8.25 Hz, 1H) 7.60 (t, J J = . 75 Hz, 1 H) 7.35 (d, J = 1.88 Hz, 1 H) 7.20 (dd, J = 8.25, 1.88 Hz, 1 H) 3.97 (s, 3 H);

[M+1]: 363.79.

Example 18: 2-(1H-benzo[d][1,2,3]triazole-6-carboxamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.53 - 8.68 (m, 1H), 7.99 - 8.06 (m, 1H), 7.74 - 7.89 (m, 2H), 7.63 - 7.71 (m, 1H), 7.06 - 7.17 (m, 1H);

[M+1]: 340.33.

Example 19: 2-(1H-pyrrolo[2,3-b]pyridine-4-carboxamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 11.91 - 12.03 (m, 1H), 8.53 - 8.68 (m, 1H), 8.30 - 8.47 (m, 1H), 7.98 - 8.09 (m, 1H), 7.79 - 7.85 (m, 2H), 7.66 - 7.72 (m, 1H), 6.91 - 7.00 (m, 1H);

[M+1]: 339.34.

Example 20: 2-(1H-benzo[d]imidazole-5-carboxamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 9.43 (s, 1H), 8.63 (dd, J = 1.13, 9.63 Hz, 2H), 8.24 (br d, J = 1.63 Hz, 1H), 8.03 (d) , J = 1.75 Hz, 1H), 7.97 (d, J = 9.13 Hz, 1H), 7.85 (d, J = 8.50 Hz, 1H);

[M+1]: 339.34.

Example 21: 2-(3-fluoro-4-methylbenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 7.23 - 7.24 (m, 1 H) 7.24 - 7.33 (m, 2 H) 7.73 - 7.82 (m, 2 H) 7.88 (dd, J = 7.69, 1.31 Hz, 1 H) 8.14 (d, J = 1.25 Hz, 1 H);

[M+1]: 331.33.

Example 22: 2-(2,6-dichloroisonicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 7.82 - 7.87 (m, 1 H) 8.05 (dd, J = 8.51, 1.75 Hz, 1 H) 8.13 - 8.16 (m, 2 H) 8.67 (s, 1H);

[M+1]: 369.19.

Example 23: 2-(5-chloronicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 7.84 (br d, J = 8.38 Hz, 1 H) 8.00 - 8.07 (m, 1 H) 8.54 - 8.61 (m, 1 H) 8.66 (s, 1 H) 8.89 (br d, J = 2.25 Hz, 1 H) 9.18 (d, J = 1.75 Hz, 1 H);

[M+1]: 334.75.

Example 24: 2-(5-fluoronicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 7.86 (d, J = 8.50 Hz, 1 H) 8.05 (dd, J = 8.51, 1.75 Hz, 1 H) 8.36 - 8.44 (m, 1 H) 8.69 (d, J = 1.50 Hz, 1 H) 8.88 (d, J = 2.75 Hz, 1 H) 9.14 (t, J = 1.56 Hz, 1 H);

[M+1]: 318.3.

Example 25: 2-(2-chloroisonicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 7.36 (d, J = 8.25 Hz, 1 H) 7.82 (br dd, J = 8.19, 1.56 Hz, 1 H) 7.95 - 8.05 (m, 2 H) 8.21 (s, 1 H) 8.46 (d, J = 5.00 Hz, 1 H);

[M+1]: 334.75.

Example 26: 2-(3-chloro-4-methylbenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 2.43 (s, 3 H) 7.57 (d, J = 8.38 Hz, 1 H) 7.85 (d, J = 8.50 Hz, 1 H) 8.00 - 8.07 (m , 2 H) 8.22 (d, J = 1.75 Hz, 1 H) 8.66 (d, J = 1.50 Hz, 1 H);

[M+1]: 347.79.

Example 27: 2-(3,4-dichlorobenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 7.77 - 7.91 (m, 2 H) 8.01 - 8.14 (m, 2 H) 8.41 (d, J = 2.13 Hz, 1 H) 8.66 (d, J = 1.50 Hz, 1 H);

[M+1]: 368.21.

Example 28: 2-(6-ethoxynicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 1.35 (t, J = 7.07 Hz, 3 H) 4.41 (q, J = 7.09 Hz, 2 H) 6.96 (d, J = 8.63 Hz, 1 H) 7.84 (d, J = 8.50 Hz, 1 H) 8.03 (dd, J = 8.44, 1.69 Hz, 1 H) 8.38 (dd, J = 8.82, 2.56 Hz, 1 H) 8.65 (d, J = 1.38 Hz, 1 H) 8.96 (d, J = 2.13 Hz, 1 H);

[M+1]: 344.36.

Example 29: 2-(6-cyanonicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 7.89 (d, J = 8.50 Hz, 2 H) 8.04 (dd, J = 8.51, 1.75 Hz, 1 H) 8.31 (br d, J = 0.63 Hz, 1 H) 8.33 (dd, J = 8.07, 0.81 Hz, 1 H) 8.41 - 8.58 (m, 2 H) 8.69 (d, J = 1.63 Hz, 1 H) 9.20 - 9.25 (m, 1 H);

[M+1]: 325.31.

Example 30: 2-(2-oxo-1,2-dihydropyridine-4-carboxamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 2.53 - 2.57 (m, 1 H) 3.13 - 3.29 (m, 1 H) 6.67 (br d, J = 6.63 Hz, 1 H) 7.06 (s, 1 H) 7.56 (d, J = 6.88 Hz, 1 H) 7.85 (d, J = 8.63 Hz, 1 H) 8.04 (dd, J = 8.63, 1.63 Hz, 1 H) 8.65 - 8.69 (m, 1 H);

[M+1]: 316.3.

Example 31: 2-(2-methoxypyrimidine-4-carboxamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 2.53 - 2.59 (m, 2 H) 4.14 (s, 3 H) 7.79 (d, J = 4.88 Hz, 1 H) 7.90 (d, J = 8.50 Hz , 1 H) 8.05 (br d, J = 1.63 Hz, 1 H) 8.72 (d, J = 1.38 Hz, 1 H) 8.96 (d, J = 4.75 Hz, 1 H);

[M+1]: 331.32.

Example 32: 2-(4-cyano-3-fluorobenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 7.76 - 7.91 (m, 2 H) 7.95 (s, 1 H) 8.01 - 8.26 (m, 4 H) 8.68 (s, 1 H);

[M+1]: 342.32.

Example 33: 2-(3-cyano-4-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 2.53 - 2.57 (m, 1 H) 4.04 (s, 3 H) 7.46 (d, J = 9.13 Hz, 1 H) 7.85 (d, J = 8.63 Hz) , 1 H) 8.04 (dd, J = 8.63, 1.63 Hz, 1 H) 8.44 (dd, J = 9.07, 2.31 Hz, 1 H) 8.56 (d, J = 2.25 Hz, 1 H) 8.65 (d, J = 1.38 Hz, 1 H);

[M+1]: 354.35.

Example 34: 2-(4-chloro-3-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 3.88 (s, 3 H) 7.41 (m, 1 H) 7.55 (d, J = 8.93 Hz, 1 H) 7.85 (d, J = 7.93 Hz, 1 H) 7.59 (dd, J = 8.71, 1.57 Hz, 1 H) 7.68 (dd, J = 9.27, 2.51 Hz, 1 H) 8.06 (d, J = 1.98 Hz, 1 H) 8.59 (d, J = 1.54 Hz) , 1 H);

[M+1]: 363.79.

Example 35: 2-(pyrimidine-5-carboxamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 2.21 - 2.33 (m, 1 H) 2.34 - 2.39 (m, 1 H) 2.43 (br s, 1 H) 2.53 - 2.57 (m, 2 H) 7.38 (d, J = 8.38 Hz, 1 H) 7.80 - 7.94 (m, 1 H) 8.06 (dd, J = 8.51, 1.75 Hz, 1 H) 8.27 (d, J = 1.63 Hz, 1 H) 8.69 (s, 1 H) 9.40 - 9.43 (m, 2 H);

[M+1]: 301.29.

Example 36: 2-(5-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 2.53 - 2.57 (m, 1 H) 7.86 (br d, J = 8.50 Hz, 1 H) 8.05 (dd, J = 8.50, 1.75 Hz, 1 H) 8.68 (s, 1 H) 8.89 (s, 1 H) 9.23 - 9.27 (m, 1 H) 9.50 (d, J = 1.88 Hz, 1 H);

[M+1]: 368.3.

Example 37: 2-(2-methylpyrimidine-5-carboxamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 2.74 (s, 3 H) 7.86 (d, J = 8.50 Hz, 1 H) 8.05 (dd, J = 8.44, 1.69 Hz, 1 H) 8.68 (d , J = 1.50 Hz, 1 H) 9.31 (s, 2 H);

[M+1]: 315.32.

Example 38: 2-(3-chloro-2,4,5-trifluorobenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 2.53 - 2.57 (m, 1 H) 4.09 (d, J = 2.75 Hz, 2 H) 7.79 - 7.93 (m, 2 H) 8.02 - 8.13 (m, 2 H) 8.68 (dd, J = 3.56, 1.56 Hz, 1 H);

[M+1]: 387.73.

Example 39: 2-(6-cyanonicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 9.30 (dd, J = 0.75, 2.25 Hz, 1H), 8.65 (d, J = 1.38 Hz, 1H), 8.57 - 8.61 (m, 1H), 8.18 - 8.21 (m, 1H), 8.04 (dd, J = 1.69, 8.44 Hz, 1H), 7.86 (d, J = 8.50 Hz, 1H), 3.32 - 3.55 (m, 16H), 3.16 (s, 3H), 2.88 (s, 1H), 2.72 (d, J = 0.63 Hz, 1H), 2.53 - 2.56 (m, 1H);

[M+1]: 325.31.

Example 40: 2-(pyridazine-4-carboxamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 9.76 (dd, J = 1.19, 2.31 Hz, 1H), 9.55 (dd, J = 1.19, 5.32 Hz, 1H), 8.66 - 8.72 (m, 1H), 8.27 (dd, J = 2.31, 5.32 Hz, 1H), 8.06 (dd, J = 1.75, 8.50 Hz, 1H), 2.53 - 2.58 (m, 1H);

[M+1]: 301.29.

Example 41: 2-(5-cyanonicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 9.40 (d, J = 2.25 Hz, 1H), 9.25 (d, J = 2.00 Hz, 1H), 8.92 (t, J = 2.13 Hz, 1H), 8.64 (d, J = 1.50 Hz, 1H), 8.04 (dd, J = 1.75, 8.51 Hz, 1H), 7.85 (d, J = 8.50 Hz, 1H), 3.28 - 3.55 (m, 19H), 3.16 (s, 1H), 2.88 (s, 1H), 2.53 - 2.55 (m, 1H);

[M+1]: 325.31.

Example 42: 2-(2-(pyrrolidin-1-yl)isonicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.65 (d, J = 1.63 Hz, 1H), 8.11 (d, J = 6.13 Hz, 1H), 7.51 (s, 1H), 7.22 (d, J = 6.00 Hz, 1H), 3.77 - 4.06 (m, 56H), 3.31 - 3.58 (m, 35H), 3.16 (s, 1H), 2.53 - 2.53 (m, 1H), 2.01 - 2.05 (m, 4H);

[M+1]: 369.41.

Example 43: 2-(2,6-difluoroisonicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.72 (d, J = 1.38 Hz, 1H), 8.27 (d, J = 8.63 Hz, 1H), 8.06 (dd, J = 1.75, 8.50 Hz, 1H) , 7.91 (br d, J = 8.50 Hz, 1H), 7.88 (br d, J = 8.63 Hz, 1H), 4.36 (d, J = 7.13 Hz, 2H), 3.48 - 3.61 (m, 8H), 3.13 - 3.36 (m, 5H), 2.78 (s, 3H), 2.53 - 2.62 (m, 1H), 1.36 (t, J = 7.13 Hz, 3H);

[M+1]: 336.29.

Example 44: 2-(3,5-difluoro-4-hydroxybenzamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 12.85 - 13.10 (m, 1H), 10.71 (br s, 1H), 8.67 (d, J = 1.38 Hz, 1H), 8.03 (dd, J = 1.75, 8.51 Hz, 1H), 7.85 (d, J = 8.38 Hz, 1H), 7.13 - 7.35 (m, 2H), 3.44 - 3.62 (m, 3H), 2.53 - 2.60 (m, 1H);

[M+1]: 351.3.

Example 45: 2-(2-(trifluoromethyl)pyrimidine-5-carboxamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 9.63 (s, 2H), 8.69 (s, 1H), 8.06 (dd, J = 1.69, 8.44 Hz, 1H), 3.57 (s, 3H), 3.04 - 3.30 (m, 7H), 2.53 - 2.61 (m, 4H);

[M+1]: 369.29.

Example 46: 2-(5-(trifluoromethyl)pyrazine-2-carboxamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 9.52 (d, J = 1.00 Hz, 1H), 9.40 (s, 1H), 8.71 (d, J = 1.50 Hz, 1H), 8.05 (dd, J = 1.75, 8.50 Hz, 1H), 7.89 (d, J = 8.50 Hz, 1H), 3.57 (s, 2H), 3.48 (br s, 2H), 2.53 - 2.58 (m, 3H);

[M+1]: 369.29.

Example 47: 2-(5-methoxypyrazine-2-carboxamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.99 (d, J = 1.25 Hz, 1H), 8.67 (d, J = 1.38 Hz, 1H), 8.47 (d, J = 1.38 Hz, 1H), 8.02 (d, J = 8.59 Hz, 1H), 7.86 (d, J = 8.38 Hz, 1H), 4.04 (s, 3H);

[M+1]: 331.32.

Example 48: 2-(6-methylpyridazine-3-carboxamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.69 (s, 1H), 8.27 (d, J = 8.63 Hz, 1H), 8.02 - 8.11 (m, 1H), 7.89 (dd, J = 5.25, 8.51 Hz, 2H), 3.90 - 3.95 (m, 2H), 2.78 (s, 4H);

[M+1]: 315.32.

Example 49: 2-(2-fluoro-3-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.68 (d, J = 1.25 Hz, 1H), 8.01 - 8.16 (m, 3H), 7.86 (d, J = 8.50 Hz, 1H), 7.59 (t, J = 7.78 Hz, 1H), 3.56 - 3.84 (m, 9H), 2.53 - 2.75 (m, 4H);

[M+1]: 385.3.

Example 50: 2-(4-methyl-3-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.65 (d, J = 1.50 Hz, 1H), 8.44 - 8.51 (m, 1H), 8.31 (dd, J = 1.50, 8.00 Hz, 1H), 8.04 ( dd, J = 1.69, 8.44 Hz, 1H), 7.85 (d, J = 8.51 Hz, 1H), 7.67 (d, J = 8.13 Hz, 1H), 7.61 (d, J = 7.70 Hz, 1H), 3.56 - 3.84 (m, 6H), 2.53 - 2.57 (m, 4H), 2.09 (s, 1H);

[M+1]: 381.34.

Example 51: 2-(4-methoxy-3-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.65 (d, J = 1.50 Hz, 1H), 8.49 (d, J = 2.00 Hz, 1H), 8.46 (dd, J = 2.19, 8.82 Hz, 1H) , 8.03 (dd, J = 1.75, 8.50 Hz, 1H), 7.84 (d, J = 8.38 Hz, 1H), 7.47 (d, J = 8.88 Hz, 1H), 4.01 (s, 3H), 3.56 - 3.78 ( m, 4H), 2.53 - 2.65 (m, 1H), 2.09 (s, 1H);

[M+1]: 397.34.

Example 52: 2-(3,5-bis(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.78 (s, 2H), 8.65 - 8.68 (m, 1H), 8.44 (s, 1H), 8.05 (dd, J = 1.75, 8.51 Hz, 1H), 7.86 (s, 1H), 3.56 - 3.75 (m, 8H), 3.26 (br s, 4H), 2.53 - 2.59 (m, 2H), 2.08 (s, 1H);

[M+1]: 435.31.

Example 53: 2-(3-nitro-5-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 9.17 (t, J = 1.63 Hz, 1H), 8.91 (s, 1H), 8.70 - 8.83 (m, 1H), 8.66 (d, J = 1.38 Hz, 1H), 8.05 (dd, J = 1.69, 8.44 Hz, 1H), 7.84 (brd, J = 8.50 Hz, 1H), 3.57 - 3.85 (m, 20H), 3.00 - 3.21 (m, 3H), 2.60 - 2.80 (m, 3H), 2.53 - 2.59 (m, 5H);

[M+1]: 412.31.

Example 54: 2-(2-chloro-4-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.69 (d, J = 1.75 Hz, 1H), 7.85 - 8.10 (m, 6H), 3.55 - 3.68 (m, 10H), 2.53 - 2.75 (m, 4H) );

[M+1]: 401.76.

Example 55: 2-(2-fluoro-4-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.68 (d, J = 1.50 Hz, 1H), 8.04 (dd, J = 1.75, 8.51 Hz, 2H), 7.93 (d, J = 9.79 Hz, 1H) , 7.86 (d, J = 8.50 Hz, 1H), 7.78 (d, J = 8.13 Hz, 1H), 3.56 - 3.72 (m, 6H);

[M+1]: 385.3.

Example 56: 2-(3-methoxy-4-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.67 (d, J = 1.25 Hz, 1H), 8.05 (dd, J = 1.75, 8.51 Hz, 1H), 8.00 (s, 1H), 7.79 - 7.88 ( m, 3H), 4.03 (s, 4H), 3.95 (s, 3H), 3.56 - 3.77 (m, 7H);

[M+1]: 397.34.

Example 57: 2-(3-chloro-4-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.67 (d, J = 1.50 Hz, 1H), 8.44 (s, 1H), 8.24 (d, J = 9.01 Hz, 1H), 7.99 - 8.13 (m, 2H), 7.85 (br d, J = 8.50 Hz, 1H), 3.56 - 3.84 (m, 5H), 2.53 - 2.66 (m, 1H), 2.07 - 2.32 (m, 1H);

[M+1]: 401.76.

Example 58: 2-(3,5-difluoro-4-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.64 - 8.68 (m, 1H), 8.02 - 8.10 (m, 3H), 7.80 - 7.88 (m, 1H), 4.05 (s, 2H), 3.56 - 3.81 (m, 6H), 2.53 - 2.59 (m, 1H), 2.09 (s, 1H);

[M+1]: 403.3.

Example 59: 2-(3-chloro-5-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.65 (d, J = 1.50 Hz, 1H), 8.46 (s, 2H), 8.19 (s, 1H), 8.04 (dd, J = 1.69, 8.44 Hz, 1H), 7.84 (d, J = 8.38 Hz, 1H), 3.56 - 3.84 (m, 15H);

[M+1]: 401.76.

Example 60: 2-(3-methoxy-5-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.65 (d, J = 1.50 Hz, 1H), 7.98 - 8.08 (m, 3H), 7.84 (d, J = 8.38 Hz, 1H), 7.54 (s, 1H), 3.95 (s, 5H), 3.90 (s, 1H), 2.53 - 2.80 (m, 8H);

[M+1]: 397.34.

Example 61: 2-(4-chloro-3-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.65 (d, J = 1.50 Hz, 1H), 8.62 (d, J = 2.00 Hz, 1H), 8.40 (dd, J = 2.06, 8.44 Hz, 1H) , 8.04 (dd, J = 1.75, 8.51 Hz, 1H), 7.96 (d, J = 8.50 Hz, 1H), 7.84 (d, J = 8.38 Hz, 1H), 3.56 - 3.84 (m, 5H), 2.53 - 2.66 (m, 1H);

[M+1]: 401.76.

Example 62: 2-(2,4-bis(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.69 (d, J = 1.25 Hz, 1H), 8.27 (d, J = 8.59 Hz, 2H), 8.26 (s, 1H), 8.14 (d, J = 7.50 Hz, 1H), 8.04 (dd, J = 1.69, 8.44 Hz, 1H), 7.86 (d, J = 8.50 Hz, 1H);

[M+1]: 435.31.

Example 63: 2-(3-cyano-5-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.93 (s, 1H), 8.76 (s, 1H), 8.63 - 8.70 (m, 1H), 8.41 (s, 1H), 8.05 (dd, J = 1.69 , 8.44 Hz, 1H), 7.77 - 7.91 (m, 1H);

[M+1]: 392.32.

Example 64: 2-(2-chloro-3-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.68 (d, J = 1.38 Hz, 1H), 8.00 - 8.07 (m, 3H), 7.86 (d, J = 8.50 Hz, 1H), 7.72 (t, J = 7.82 Hz, 1H), 2.96 - 3.24 (m, 4H), 2.53 - 2.66 (m, 1H);

[M+1]: 401.76.

Example 65: 2-(2-chloro-5-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.93 (s, 1H), 8.76 (s, 1H), 8.63 - 8.70 (m, 1H), 8.41 (s, 1H), 8.05 (dd, J = 1.69 , 8.44 Hz, 1H), 7.77 - 7.91 (m, 1H);

[M+1]: 401.76.

Example 66: 2-(1-methyl-1H-pyrazole-5-carboxamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.66 (s, 1H), 8.03 (dd, J = 1.75, 8.50 Hz, 1H), 7.84 (br d, J = 8.50 Hz, 1H), 7.61 (d) , J = 2.13 Hz, 1H), 7.45 (br s, 1H), 4.17 (s, 3H), 3.57 (s, 1H), 3.41 - 3.49 (m, 1H), 3.16 - 3.32 (m, 2H), 2.53 - 2.57 (m, 1H), 2.36 - 2.46 (m, 1H);

[M+1]: 303.31.

Example 67: 2-(4-chloro-3-fluoro-N-methylbenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.27 - 8.38 (m, 1H), 8.01 - 8.18 (m, 1H), 7.69 - 7.78 (m, 1H), 7.57 - 7.65 (m, 1H), 5.56 - 5.74 (m, 1H);

[M+1]: 365.78.

Example 68: 2-(5-(methoxycarbonyl)picolinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.67 (d, J = 1.75 Hz, 1H), 8.37 (s, 1H), 8.26 (d, J = 1.75 Hz, 1H), 8.24 - 8.24 (m, 1H), 8.03 (d, J = 1.63 Hz, 1H), 7.81 - 7.86 (m, 3H), 7.77 (d, J = 8.63 Hz, 2H), 7.54 - 7.60 (m, 1H), 7.45 - 7.50 (m) , 4H), 7.38 - 7.42 (m, 2H), 7.37 - 7.42 (m, 1H), 3.92 - 3.94 (m, 3H), 3.89 - 3.93 (m, 5H), 1.73 - 1.85 (m, 4H), 1.51 - 1.59 (m, 4H);

[M+1]: 358.34.

Example 69: 2-(6-chloro-5-fluoropicolinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 9.14 (t, J = 1.50 Hz, 1H), 8.84 (d, J = 2.75 Hz, 1H), 8.63 (d, J = 1.50 Hz, 1H), 8.37 (d, J = 9.44 Hz, 1H), 8.02 (dd, J = 1.69, 8.44 Hz, 1H), 7.82 (d, J = 8.38 Hz, 1H), 3.52 - 3.79 (m, 3H), 2.53 - 2.58 ( m, 1H);

[M+1]: 352.74.

Example 70: 2-(2-chloro-6-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 9.19 (d, J = 1.63 Hz, 1H), 8.90 (s, 1H), 8.67 (s, 1H), 8.60 (s, 1H), 8.05 (d, J = 8.50 Hz, 1H), 7.86 (br d, J = 8.25 Hz, 1H), 3.10 - 3.26 (m, 2H), 2.53 - 2.59 (m, 1H);

[M+1]: 364.78.

Example 71: 2-(2-(thiophen-2-yl)acetamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.60 (d, J = 1.63 Hz, 1H), 8.00 (dd, J = 1.75, 8.50 Hz, 1H), 7.81 (d, J = 8.50 Hz, 1H) , 7.43 (dd, J = 1.25, 5.13 Hz, 1H), 6.99 - 7.19 (m, 2H), 4.10 (s, 3H), 3.66 - 3.90 (m, 7H), 3.17 (s, 6H), 2.53 - 2.61 (m, 3H), 2.06 - 2.32 (m, 1H);

[M+1]: 319.37.

Example 72: 2-(2-(3,4-dichlorophenyl)acetamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 12.82 (s, 2H), 8.61 (d, J = 1.38 Hz, 1H), 8.00 (dd, J = 1.75, 8.50 Hz, 1H), 7.81 (d, J = 8.38 Hz, 1H), 7.66 (d, J = 2.00 Hz, 1H), 7.62 (d, J = 8.25 Hz, 1H), 7.36 (dd, J = 2.00, 8.25 Hz, 1H), 3.93 (s, 2H), 3.39 - 3.65 (m, 3H), 2.53 - 2.58 (m, 1H);

[M+1]: 382.23.

Example 73: 2-(2-(3,5-difluorophenyl)acetamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.61 (d, J = 1.25 Hz, 1H), 7.98 - 8.04 (m, 1H), 7.81 (d, J = 8.50 Hz, 1H), 7.08 - 7.22 ( m, 4H), 3.95 (s, 3H);

[M+1]: 349.32.

Example 74: 2-(3-phenylpropanamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.61 (d, J = 1.25 Hz, 1H), 7.98 - 8.04 (m, 1H), 7.81 (d, J = 8.50 Hz, 1H), 7.08 - 7.22 ( m, 4H), 3.95 (s, 3H);

[M+1]: 327.37.

Example 75: 2-(2-(2-fluorophenyl)acetamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.61 (d, J = 1.75 Hz, 1H), 8.01 (dd, J = 1.69, 8.44 Hz, 1H), 7.82 (d, J = 8.50 Hz, 1H) , 7.31 - 7.48 (m, 2H), 7.13 - 7.28 (m, 2H), 3.96 (s, 2H), 3.88 (s, 1H), 3.12 - 3.30 (m, 2H), 2.53 - 2.69 (m, 5H) ;

[M+1]: 331.33.

Example 76: 2-(3-(5-fluoronicotinamido)propanamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 12.63 (s, 1H), 8.96 (t, J = 5.38 Hz, 1H), 8.88 (t, J = 1.56 Hz, 1H), 8.74 (d, J = 2.75 Hz, 1H), 8.61 (d, J = 1.75 Hz, 1H), 8.05 - 8.10 (m, 1H), 8.00 (dd, J = 1.75, 8.51 Hz, 1H), 7.79 (d, J = 8.88 Hz, 1H), 3.88 (s, 1H), 3.55 - 3.72 (m, 3H), 3.39 - 3.51 (m, 1H), 3.28 - 3.30 (m, 1H), 2.85 (t, J = 6.75 Hz, 2H), 2.53 - 2.58 (m, 1H);

[M+1]: 389.37.

Example 77: 2-(3-(5-chloronicotinamido)propanamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 9.16 (br t, J = 5.07 Hz, 1H), 8.96 (d, J = 1.88 Hz, 1H), 8.77 (d, J = 2.38 Hz, 1H), 8.39 (d, J = 1.25 Hz, 1H), 8.33 (s, 1H), 7.96 (dd, J = 1.56, 8.32 Hz, 1H), 7.58 (d, J = 8.25 Hz, 1H), 3.49 - 3.75 (m , 4H), 2.81 (br t, J = 6.69 Hz, 3H), 2.53 - 2.67 (m, 2H);

[M+1]: 405.83.

Example 78: 2-(3-(5-(trifluoromethyl)nicotinamido)propanamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 9.19 (t, J = 5.65 Hz, 1H), 8.93 (d, J = 5.00 Hz, 1H), 8.60 (d, J = 1.63 Hz, 1H), 8.24 (s, 1H), 8.08 (dd, J = 1.06, 4.94 Hz, 1H), 8.00 (dd, J = 1.75, 8.38 Hz, 1H), 7.79 (d, J = 8.50 Hz, 1H), 3.41 - 3.69 ( m, 4H), 2.86 (t, J = 6.69 Hz, 2H), 2.53 - 2.58 (m, 2H);

[M+1]: 439.38.

Example 79: 2-(3-(6-(trifluoromethyl)nicotinamido)propanamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 9.07 - 9.15 (m, 2H), 8.59 (d, J = 1.25 Hz, 1H), 8.44 (d, J = 8.35 Hz, 1H), 8.05 (d, J = 8.31 Hz, 1H), 7.99 (dd, J = 1.75, 8.50 Hz, 1H), 7.78 (d, J = 8.76 Hz, 1H), 3.45 - 3.71 (m, 5H), 2.86 (t, J = 6.63 Hz, 2H), 2.53 - 2.58 (m, 1H);

[M+1]: 439.38.

Example 80: 2-(3-(4-chloro-3-fluorophenyl)propanamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 12.58 (s, 1H), 8.60 (d, J = 1.75 Hz, 1H), 8.00 (dd, J = 1.75, 8.50 Hz, 1H), 7.79 (d, J = 8.50 Hz, 1H), 7.51 (t, J = 8.07 Hz, 1H), 7.36 (dd, J = 1.94, 10.69 Hz, 1H), 7.15 (dd, J = 1.75, 8.25 Hz, 1H), 2.97 ( br d, J = 7.50 Hz, 2H), 2.87 (br d, J = 7.63 Hz, 2H), 2.53 - 2.59 (m, 1H);

[M+1]: 379.81.

Example 81: 2-(2-(4-chloro-3-fluorophenyl)acetamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.54 - 8.66 (m, 1H), 7.98 - 8.03 (m, 1H), 7.81 - 7.86 (m, 1H), 7.55 - 7.61 (m, 1H), 7.41 - 7.46 (m, 1H), 7.21 - 7.25 (m, 1H), 3.93 - 3.94 (m, 2H);

[M+1]: 365.78.

Example 82: 2-(2-(4-fluorophenoxy)acetamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.63 (d, J = 1.63 Hz, 1H), 8.02 (dd, J = 1.75, 8.50 Hz, 1H), 7.83 (d, J = 8.50 Hz, 1H) , 7.10 - 7.19 (m, 2H), 6.91 - 7.09 (m, 3H), 4.94 (s, 2H), 4.66 (s, 1H);

[M+1]: 347.33.

Example 83: 2-(5-carboxy-1H-pyrrole-2-carboxamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.75 - 12.96 (m, 1H), 12.41 - 12.69 (m, 1H), 8.55 - 8.67 (m, 1H), 7.97 - 8.06 (m, 1H), 7.78 - 7.90 (m, 1H), 7.14 - 7.29 (m, 1H), 6.79 - 6.88 (m, 1H);

[M+1]: 332.3.

Example 84: 2-(5-(trifluoromethyl)-1H-pyrrole-2-carboxamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.81 - 12.94 (m, 1H), 12.72 - 12.78 (m, 1H), 8.59 - 8.68 (m, 1H), 8.00 - 8.05 (m, 1H), 7.82 - 7.86 (m, 1H), 7.39 - 7.45 (m, 1H), 7.10 - 7.18 (m, 1H);

[M+1]: 356.29.

Example 85: 2-(2-(methylthio)isonicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.60 (d, J = 1.35 Hz, 1H), 8.52 (m, 2H), 7. 96 (m, 1H), 7.66 (m, 1H), 7.37 ( m, 1H), 2.54 (s, 3H);

[M+1]: 346.4.

Example 86: 2-(5-(methylthio)nicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.97 (d, J = 1.25 Hz, 1H), 8.63 - 8.75 (m, 2H), 8.30 - 8.39 (m, 1H), 7.99 - 8.10 (m, 1H) ), 7.79 - 7.91 (m, 1H), 2.64 (s, 3H);

[M+1]: 346.4.

Example 87: 2-(2-(methylamino)isonicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 8.66 (d, J = 1.50 Hz, 1H), 7.99 - 8.12 (m, 2H), 7.81 - 7.86 (m, 1H), 7.61 - 7.71 (m, 1H) ), 7.30 - 7.37 (m, 1H), 3.04 (s, 3H);

[M+1]: 329.35.

Example 88: 2-(6-chloronicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.19 (br s, 2H), 9.10 (d, J = 2.50 Hz, 1H), 8.67 (d, J = 1.50 Hz, 1H), 8.50 (dd, J = 2.50, 8.38 Hz, 1H), 8.04 (dd, J = 1.69, 8.44 Hz, 1H), 7.85 (d, J = 8.50 Hz, 1H), 7.76 (d, J = 8.38 Hz, 1H);

[M+1]: 334.75.

Example 89: 2-(5-bromo-6-methoxynicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.08 (br s, 2H), 8.93 (d, J = 2.13 Hz, 1H), 8.71 (d, J = 2.13 Hz, 1H), 8.65 (d, J = 1.38 Hz, 1H), 8.03 (dd, J = 1.75, 8.50 Hz, 1H), 7.84 (d, J = 8.50 Hz, 1H), 4.04 (s, 3H);

[M+1]: 409.23.

Example 90: 2-(6-(pyrrolidin-1-yl)nicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 11.72 - 13.90 (m, 1H), 8.90 (d, J = 2.38 Hz, 1H), 8.60 (d, J = 1.38 Hz, 1H), 8.19 (dd, J = 2.38, 9.01 Hz, 1H), 8.01 (dd, J = 1.69, 8.44 Hz, 1H), 7.79 (d, J = 8.50 Hz, 1H), 6.54 (d, J = 9.13 Hz, 1H), 3.18 - 3.43 (m, 4H), 1.97 (br s, 4H);

[M+1]: 369.41.

Example 91: 2-(6-(2-methylprop-1-enyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.74 - 13.37 (m, 2H), 9.23 (s, 1H), 8.64 - 8.69 (m, 1H), 8.41 (dd, J = 2.44, 8.32 Hz, 1H ), 8.04 (dd, J = 1.75, 8.50 Hz, 1H), 7.85 (d, J = 8.50 Hz, 1H), 7.43 (d, J = 8.38 Hz, 1H), 6.42 (s, 1H), 2.19 - 2.23 (m, 3H), 1.98 (s, 3H);

[M+1]: 354.39.

Example 92: 2-(5-chloro-6-hydroxynicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.87 (br s, 2H), 8.62 (d, J = 1.25 Hz, 1H), 8.45 (d, J = 2.38 Hz, 1H), 8.34 (d, J = 2.50 Hz, 1H), 8.02 (dd, J = 1.75, 8.51 Hz, 1H), 7.80 (d, J = 7.97 Hz, 1H);

[M+1]: 350.75.

Example 93: 2-(5-bromo-6-methylnicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.16 (br s, 2H), 9.11 (d, J = 2.00 Hz, 1H), 8.66 (dd, J = 1.63, 12.13 Hz, 1H), 8.03 (dd , J = 1.75, 8.51 Hz, 1H), 7.83 (d, J = 8.50 Hz, 1H), 2.68 (s, 3H);

[M+1]: 392.23.

Example 94: 2-(6-chloro-5-fluoronicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.28 (br s, 2H), 8.98 (d, J = 1.75 Hz, 1H), 8.67 (d, J = 1.38 Hz, 1H), 8.56 (dd, J = 1.81, 9.07 Hz, 1H), 8.03 - 8.08 (m, 1H), 7.85 (br d, J = 8.50 Hz, 1H);

[M+1]: 352.74.

Example 95: 2-(6-bromonicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.18 (br s, 2H), 9.07 (dd, J = 0.63, 2.50 Hz, 1H), 8.67 (d, J = 1.50 Hz, 1H), 8.38 (dd , J = 2.50, 8.38 Hz, 1H), 8.04 (dd, J = 1.75, 8.50 Hz, 1H), 7.89 (d, J = 8.52 Hz, 1H), 7.84 (d, J = 8.50 Hz, 1H);

[M+1]: 379.2.

Example 96: 2-(6-carboxyspiro[3.3]heptane-2-carboxamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.41 (br s, 1H), 8.58 (d, J = 1.38 Hz, 1H), 7.99 (dd, J = 1.69, 8.44 Hz, 1H), 7.76 (d , J = 8.50 Hz, 1H), 3.59 - 3.62 (m, 1H), 2.93 (quin, J = 8.38 Hz, 1H), 2.09 - 2.33 (m, 8H);

[M+1]: 361.38.

Example 97: 2-(5-(trifluoromethyl)furan-2-carboxamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 13.30 - 13.54 (m, 1H), 8.64 - 8.69 (m, 1H), 8.04 (dd, J = 1.75, 8.51 Hz, 1H), 7.77 - 7.88 (m , 2H), 7.49 - 7.55 (m, 1H);

[M+1]: 357.28.

Example 98: 2-(5-bromonicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.17 (br s, 2H), 9.21 (d, J = 1.88 Hz, 1H), 8.97 (d, J = 2.25 Hz, 1H), 8.71 (t, J = 2.06 Hz, 1H), 8.66 (d, J = 1.25 Hz, 1H), 8.04 (dd, J = 1.69, 8.44 Hz, 1H), 7.84 (d, J = 8.50 Hz, 1H);

[M+1]: 379.2.

Example 99: 2-(3-hydroxy-3-(trifluoromethyl)cyclobutanecarboxamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.55 (br s, 1H), 8.62 (d, J = 1.63 Hz, 1H), 8.00 (dd, J = 1.69, 8.44 Hz, 1H), 7.80 (d , J = 8.50 Hz, 1H), 6.77 (br s, 1H), 3.12 - 3.22 (m, 1H), 2.61 - 2.69 (m, 2H), 2.43 - 2.49 (m, 2H);

[M+1]: 361.31.

Example 100: 2-(3,3-difluoro-1-methylcyclobutanecarboxamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 11.63 - 13.28 (m, 2H), 8.62 (d, J = 1.38 Hz, 1H), 8.01 (dd, J = 1.69, 8.44 Hz, 1H), 7.80 ( d, J = 8.38 Hz, 1H), 3.08 - 3.21 (m, 2H), 2.58 - 2.69 (m, 2H), 1.58 (s, 3H);

[M+1]: 327.32.

Example 101: 2-(4-(2-carboxycyclopropyl)benzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.57 (d, J = 1.50 Hz, 1H), 8.05 - 8.09 (m, J = 8.38 Hz, 2H), 8.00 (dd, J = 1.69, 8.44 Hz, 1H), 7.77 (d, J = 8.50 Hz, 1H), 7.32 - 7.36 (m, J = 8.50 Hz, 2H), 2.45 - 2.49 (m, 1H), 1.92 - 1.98 (m, 1H), 1.40 - 1.54 (m, 3H);

[M+1]: 383.39.

Example 102: 2-(2-(trifluoromethyl)furan-3-carboxamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.21 (br s, 2H), 8.67 (d, J = 1.50 Hz, 1H), 8.16 (d, J = 1.50 Hz, 1H), 8.05 (dd, J = 1.75, 8.50 Hz, 1H), 7.86 (d, J = 8.38 Hz, 1H), 7.43 (s, 1H);

[M+1]: 357.28.

Example 103: 2-(5-carboxthiophene-2-carboxamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.58 (d, J = 1.38 Hz, 1H), 8.10 (d, J = 3.75 Hz, 1H), 8.00 (dd, J = 1.69, 8.44 Hz, 1H) , 7.76 (d, J = 8.38 Hz, 1H), 7.61 (d, J = 4.00 Hz, 1H);

[M+1]: 349.35.

Example 104: 2-(2-bromoisonicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.28 (br s, 2H), 8.68 (d, J = 1.38 Hz, 1H), 8.65 (d, J = 5.23 Hz, 1H), 8.29 (d, J = 1.00 Hz, 1H), 8.01 - 8.08 (m, 2H), 7.86 (br d, J = 8.50 Hz, 1H);

[M+1]: 379.2.

Example 105: 2-(4-chloropicolinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.68 (br s, 2H), 8.84 (d, J = 1.38 Hz, 1H), 8.68 (d, J = 1.38 Hz, 1H), 8.17 - 8.30 (m , 2H), 8.04 (dd, J = 1.63, 8.51 Hz, 1H), 7.87 (d, J = 8.50 Hz, 1H);

[M+1]: 334.75.

Example 106: 2-(4-fluoropicolinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.95 (br s, 1H), 12.59 (br s, 1H), 8.81 (d, J = 2.88 Hz, 1H), 8.69 (d, J = 1.25 Hz, 1H), 8.32 (dd, J = 4.56, 8.69 Hz, 1H), 8.01 - 8.08 (m, 2H), 7.88 (d, J = 8.50 Hz, 1H);

[M+1]: 318.3.

Example 107: 2-(6-chloro-5-methylpicolinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.28 - 12.70 (m, 1H), 8.68 (d, J = 1.25 Hz, 1H), 8.08 - 8.13 (m, 2H), 8.04 (dd, J = 1.75) , 8.51 Hz, 1H), 7.87 (d, J = 8.38 Hz, 1H), 2.46 (s, 3H);

[M+1]: 348.78.

Example 108: 2-(5-chloro-3-propoxypicolinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.68 (br s, 1H), 8.66 (d, J = 1.75 Hz, 1H), 8.27 (dd, J = 1.25, 4.50 Hz, 1H), 8.03 (dd , J = 1.75, 8.50 Hz, 1H), 7.83 - 7.86 (m, J = 8.88 Hz, 1H), 7.71 (dd, J = 1.19, 8.69 Hz, 1H), 7.58 - 7.63 (m, 1H), 4.10 ( t, J = 6.44 Hz, 2H), 1.70 - 1.78 (m, 2H), 0.97 (t, J = 7.38 Hz, 3H);

[M+1]: 392.83.

Example 109: 2-(5-chloro-3-methylpicolinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.65 (br s, 1H), 8.67 (d, J = 1.75 Hz, 1H), 8.64 (d, J = 2.25 Hz, 1H), 8.10 (dd, J = 0.69, 2.31 Hz, 1H), 8.03 (dd, J = 1.69, 8.44 Hz, 1H), 7.86 (d, J = 8.88 Hz, 1H), 2.61 (s, 3H);

[M+1]: 348.78.

Example 110: 2-(5-fluoro-6-methoxynicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.84 - 13.65 (m, 1H), 8.81 (d, J = 2.00 Hz, 1H), 8.65 (d, J = 1.50 Hz, 1H), 8.33 (d, J = 10.98 Hz, 1H), 8.04 (dd, J = 1.75, 8.38 Hz, 1H), 7.84 (d, J = 8.50 Hz, 1H), 4.06 (s, 3H);

[M+1]: 348.32.

Example 111: 2-(4-methoxypicolinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.96 (br s, 1H), 12.39 (br s, 1H), 8.69 (d, J = 1.63 Hz, 1H), 8.61 (d, J = 5.75 Hz, 1H), 8.04 (dd, J = 1.75, 8.51 Hz, 1H), 7.87 (d, J = 8.51 Hz, 1H), 7.74 (d, J = 2.63 Hz, 1H), 7.32 (dd, J = 2.63, 5.63 Hz, 1H), 3.97 (s, 3H);

[M+1]: 330.33.

Example 112: 2-(6-(trifluoromethyl)picolinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.90 (br s, 2H), 8.71 (d, J = 1.50 Hz, 1H), 8.44 - 8.49 (m, 1H), 8.38 - 8.44 (m, 1H) , 8.25 (dd, J = 1.00, 7.63 Hz, 1H), 8.06 (dd, J = 1.75, 8.51 Hz, 1H), 7.89 (d, J = 8.50 Hz, 1H);

[M+1]: 368.3.

Example 113: 2-(3-fluoropicolinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.87 (br s, 2H), 8.70 (d, J = 1.75 Hz, 1H), 8.63 (td, J = 1.38, 4.50 Hz, 1H), 7.99 - 8.07 (m, 2H), 7.88 (d, J = 8.88 Hz, 1H), 7.82 (td, J = 4.22, 8.57 Hz, 1H);

[M+1]: 318.3.

Example 114: 2-(4-(trifluoromethyl)picolinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.91 (br s, 2H), 9.09 (d, J = 5.00 Hz, 1H), 8.70 (d, J = 1.75 Hz, 1H), 8.43 - 8.46 (m , 1H), 8.16 (d, J = 5.26 Hz, 1H), 8.05 (dd, J = 1.75, 8.38 Hz, 1H), 7.89 (d, J = 8.50 Hz, 1H);

[M+1]: 368.3.

Example 115: 2-(5-(trifluoromethyl)picolinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.89 (br s, 2H), 9.17 - 9.21 (m, 1H), 8.70 (d, J = 1.75 Hz, 1H), 8.55 (dd, J = 1.81, 8.32 Hz, 1H), 8.40 (d, J = 8.25 Hz, 1H), 8.05 (dd, J = 1.75, 8.51 Hz, 1H), 7.89 (d, J = 8.50 Hz, 1H);

[M+1]: 368.3.

Example 116: 2-(6-carboxynicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.74 (br s, 3H), 9.22 (dd, J = 0.81, 2.06 Hz, 1H), 8.70 (d, J = 1.50 Hz, 1H), 8.56 (dd , J = 2.00, 8.13 Hz, 1H), 8.33 (d, J = 7.87 Hz, 1H), 8.05 (dd, J = 1.75, 8.50 Hz, 1H), 7.89 (d, J = 8.38 Hz, 1H);

[M+1]: 344.31.

Example 117: 2-(6-methoxypicolinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.97 (br s, 1H), 12.47 (br s, 1H), 8.70 (d, J = 1.25 Hz, 1H), 8.05 (dd, J = 1.75, 8.50 Hz, 1H), 7.99 (dd, J = 7.32, 8.32 Hz, 1H), 7.87 - 7.90 (m, 1H), 7.83 (dd, J = 0.75, 7.25 Hz, 1H), 7.17 (dd, J = 0.75, 8.25 Hz, 1H), 4.12 (s, 3H);

[M+1]: 330.33.

Example 118: 2-(6-(2-methoxyethoxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.04 (br s, 2H), 8.97 (t, J = 1.00 Hz, 1H), 8.66 (d, J = 1.38 Hz, 1H), 8.39 (dd, J = 2.50, 8.75 Hz, 1H), 8.04 (dd, J = 1.75, 8.51 Hz, 1H), 7.84 (d, J = 8.38 Hz, 1H), 7.01 (t, J = 8.63 Hz, 1H), 4.47 - 4.52 (m, 2H), 3.66 - 3.73 (m, 2H), 3.31 (s, 3H);

[M+1]: 374.38.

Example 119: 2-(2-methoxy-6-(trifluoromethyl)isonicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.44 (br s, 1H), 13.11 (br s, 1H), 8.68 (d, J = 1.38 Hz, 1H), 8.09 (d, J = 1.00 Hz, 1H), 8.06 (dd, J = 1.75, 8.50 Hz, 1H), 7.86 (br d, J = 8.38 Hz, 1H), 7.80 (s, 1H), 4.00 (s, 3H);

[M+1]: 398.33.

Example 120: 2-(2-isopropoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.20 (br s, 1H), 13.04 (br s, 1H), 8.68 (d, J = 1.50 Hz, 1H), 8.38 (d, J = 5.25 Hz, 1H), 8.05 (dd, J = 1.75, 8.51 Hz, 1H), 7.87 (d, J = 8.38 Hz, 1H), 7.55 (dd, J = 1.50, 5.38 Hz, 1H), 7.39 (s, 1H), 5.25 - 5.34 (m, 1H), 1.34 (d, J = 6.25 Hz, 6H);

[M+1]: 358.38.

Example 121: 2-(6-ethoxy-4-fluoronicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.32 (br s, 1H), 13.02 (br s, 1H), 8.69 (d, J = 1.50 Hz, 1H), 8.35 (d, J = 1.25 Hz, 1H), 8.04 (dd, J = 1.75, 8.50 Hz, 1H), 7.87 (d, J = 8.50 Hz, 1H), 7.22 (d, J = 4.50 Hz, 1H), 4.34 (q, J = 7.09 Hz, 2H), 1.34 (t, J = 7.00 Hz, 3H);

[M+1]: 362.35.

Example 122: 2-(6-(cyclopropylmethoxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.04 (br s, 2H), 8.96 (d, J = 2.13 Hz, 1H), 8.66 (d, J = 1.38 Hz, 1H), 8.38 (dd, J = 2.50, 8.76 Hz, 1H), 8.04 (dd, J = 1.75, 8.51 Hz, 1H), 7.84 (br d, J = 8.38 Hz, 1H), 6.99 (d, J = 8.75 Hz, 1H), 4.21 ( d, J = 7.25 Hz, 2H), 1.23 - 1.33 (m, 1H), 0.54 - 0.62 (m, 2H), 0.34 - 0.41 (m, 2H);

[M+1]: 370.39.

Example 123: 2-(6-isobutoxynicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.05 (br s, 2H), 8.96 (t, J = 2.00 Hz, 1H), 8.66 (d, J = 1.50 Hz, 1H), 8.39 (dd, J = 2.63, 8.75 Hz, 1H), 8.04 (dd, J = 1.75, 8.50 Hz, 1H), 7.84 (d, J = 8.50 Hz, 1H), 6.99 (d, J = 8.76 Hz, 1H), 4.15 (d , J = 6.63 Hz, 2H), 2.07 (quind, J = 6.69, 13.38 Hz, 1H), 0.99 (d, J = 6.75 Hz, 6H);

[M+1]: 372.41.

Example 124: 2-(2-(difluoromethoxy)isonicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.25 (br s, 2H), 8.69 (d, J = 1.50 Hz, 1H), 8.51 (d, J = 5.31 Hz, 1H), 8.06 (dd, J = 1.75, 8.50 Hz, 1H), 7.96 - 7.98 (m, 1H), 7.84 - 7.91 (m, 2H), 7.78 (s, 1H), 7.73 (s, 1H), 7.60 - 7.62 (m, 1H);

[M+1]: 366.31.

Example 125: 2-(6-(difluoromethoxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.13 (br s, 2H), 9.01 (d, J = 2.25 Hz, 1H), 8.67 (d, J = 1.38 Hz, 1H), 8.58 (dd, J = 2.44, 8.69 Hz, 1H), 8.04 (dd, J = 1.69, 8.44 Hz, 1H), 8.02 (s, 1H), 7.86 (s, 1H), 7.84 (s, 1H), 7.66 (s, 1H) , 7.29 (d, J = 8.63 Hz, 1H);

[M+1]: 366.31.

Example 126: 2-(3-fluoro-4-methoxybenzamido)-4-methylbenzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.99 (br s, 2H), 8.46 (d, J = 1.13 Hz, 1H), 8.04 - 8.10 (m, 1H), 7.85 (dd, J = 0.81, 1.56 Hz, 1H), 7.36 (t, J = 8.76 Hz, 1H), 3.96 (s, 3H), 2.66 (s, 3H);

[M+1]: 361.36.

Example 127: 2-(6-methoxynicotinamido)-4-methylbenzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.10 (br s, 2H), 8.99 (d, J = 2.50 Hz, 1H), 8.46 (d, J = 1.13 Hz, 1H), 8.40 (dd, J = 2.63, 8.75 Hz, 1H), 7.85 (dd, J = 0.88, 1.63 Hz, 1H), 6.99 (d, J = 9.26 Hz, 1H), 3.96 (s, 3H), 2.66 (s, 3H);

[M+1]: 344.36.

Example 128: 2-(2-methoxyisonicotinamido)-4-methylbenzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.32 (br s, 1H), 12.92 (br s, 1H), 12.68 - 13.57 (m, 1H), 8.49 (d, J = 1.00 Hz, 1H), 8.40 (dd, J = 0.63, 5.25 Hz, 1H), 7.87 (dd, J = 0.88, 1.63 Hz, 1H), 7.61 (dd, J = 1.44, 5.32 Hz, 1H), 7.52 (dd, J = 0.75, 1.38 Hz, 1H), 3.94 (s, 3H), 2.67 (s, 3H);

[M+1]: 344.36.

Example 129: 4-methyl-2-(2-(trifluoromethyl)isonicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.28 (br s, 1H), 8.49 (d, J = 1.13 Hz, 1H), 8.39 (d, J = 5.25 Hz, 1H), 7.87 (dd, J = 0.81, 1.56 Hz, 1H), 7.61 (dd, J = 1.44, 5.32 Hz, 1H), 7.51 (s, 1H), 3.93 (s, 3H), 2.66 (s, 3H);

[M+1]: 382.33.

Example 130: 4-methyl-2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.45 (br s, 1H), 13.00 (br s, 1H), 9.41 (d, J = 1.88 Hz, 1H), 8.73 (dd, J = 1.88, 8.13 Hz, 1H), 8.50 (d, J = 1.00 Hz, 1H), 8.14 (d, J = 8.25 Hz, 1H), 7.88 (dd, J = 0.81, 1.56 Hz, 1H), 2.67 (s, 3H);

[M+1]: 382.33.

Example 131: 2-(5-fluoro-2-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.25 (br s, 2H), 8.69 (d, J = 1.38 Hz, 1H), 8.37 (d, J = 1.13 Hz, 1H), 8.05 (dd, J = 1.75, 8.51 Hz, 1H), 7.87 (d, J = 8.38 Hz, 1H), 7.26 (d, J = 4.50 Hz, 1H), 3.90 (s, 3H);

[M+1]: 348.32.

Example 132: 2-(5-chloro-2-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.27 (br s, 2H), 8.69 (d, J = 1.38 Hz, 1H), 8.41 (d, J = 0.50 Hz, 1H), 8.04 (dd, J = 1.75, 8.51 Hz, 1H), 7.87 (d, J = 8.50 Hz, 1H), 7.29 (d, J = 0.50 Hz, 1H), 3.92 (s, 3H);

[M+1]: 364.78.

Example 133: 2-(3-chloro-2-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.31 (br s, 2H), 8.69 (d, J = 1.38 Hz, 1H), 8.30 (d, J = 5.00 Hz, 1H), 8.04 (dd, J = 1.75, 8.51 Hz, 1H), 7.86 (d, J = 8.50 Hz, 1H), 7.34 (d, J = 5.00 Hz, 1H), 4.01 (s, 3H);

[M+1]: 364.78.

Example 134: 2-(6-(tetrahydro-2H-pyran-4-yloxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.06 (br s, 2H), 8.95 (s, 1H), 8.65 (d, J = 1.50 Hz, 1H), 8.39 (dd, J = 2.50, 8.75 Hz , 1H), 8.04 (dd, J = 1.75, 8.51 Hz, 1H), 7.84 (d, J = 8.50 Hz, 1H), 6.97 (d, J = 8.76 Hz, 1H), 5.32 (tt, J = 4.28, 8.97 Hz, 1H), 3.88 (td, J = 4.30, 11.79 Hz, 2H), 3.49 - 3.57 (m, 2H), 2.00 - 2.08 (m, 2H), 1.67 (dtd, J = 4.13, 9.29, 13.18 Hz) , 2H);

[M+1]: 400.42.

Example 135: 2-(6-phenoxynicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.12 (br s, 2H), 8.90 (dd, J = 0.63, 2.50 Hz, 1H), 8.66 (d, J = 1.50 Hz, 1H), 8.53 (dd , J = 2.56, 8.69 Hz, 1H), 8.04 (dd, J = 1.69, 8.44 Hz, 1H), 7.84 (d, J = 8.51 Hz, 1H), 7.45 - 7.52 (m, 2H), 7.29 (tt, J = 1.08, 7.43 Hz, 1H), 7.18 - 7.24 (m, 3H);

[M+1]: 392.4.

Example 136: 2-(2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-6-methoxynicotinamido)benzo[d]thiazole-6-car boxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.18 (br s, 2H), 8.69 (d, J = 1.50 Hz, 1H), 8.41 (d, J = 8.38 Hz, 1H), 8.19 (d, J = 8.50 Hz, 1H), 8.05 (dd, J = 1.75, 8.51 Hz, 1H), 7.88 (dd, J = 8.44, 17.82 Hz, 2H), 7.70 (dt, J = 0.75, 7.63 Hz, 1H), 7.55 (ddd, J = 1.00, 7.10, 8.29 Hz, 1H), 6.89 (d, J = 8.25 Hz, 1H), 3.14 (s, 3H);

[M+1]: 463.44.

Example 137: 2-(6-(2,2,2-trifluoroethoxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 13.09 (br s, 2H), 8.97 - 9.02 (m, 1H), 8.66 (d, J = 1.50 Hz, 1H), 8.48 (dd, J = 2.44, 8.69 Hz, 1H), 8.04 (dd, J = 1.69, 8.44 Hz, 1H), 7.85 (d, J = 8.38 Hz, 1H), 7.18 (d, J = 8.76 Hz, 1H), 5.13 (q, J = 9.01 Hz, 2H);

[M+1]: 398.33.

Example 138: 2-(6-isopropoxynicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.05 (br s, 2H), 8.96 (d, J = 2.50 Hz, 1H), 8.65 (d, J = 1.50 Hz, 1H), 8.36 (dd, J = 2.50, 8.76 Hz, 1H), 8.03 (dd, J = 1.75, 8.50 Hz, 1H), 7.84 (d, J = 8.38 Hz, 1H), 6.91 (d, J = 9.26 Hz, 1H), 5.37 (spt) , J = 6.19 Hz, 1H), 1.34 (s, 3H), 1.33 (s, 3H);

[M+1]: 358.38.

Example 139: 2-(4-chloro-3-fluorobenzamido)-4-methoxybenzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.35 (br s, 1H), 13.04 (br s, 1H), 8.26 (d, J = 1.25 Hz, 1H), 8.19 (dd, J = 1.88, 10.13 Hz, 1H), 8.02 (dd, J = 1.56, 8.44 Hz, 1H), 7.83 (t, J = 7.94 Hz, 1H), 7.51 (d, J = 1.25 Hz, 1H), 4.00 (s, 3H);

[M+1]: 381.78.

Example 140: 2-(3-fluoro-4-methoxybenzamido)-4-methoxybenzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.41 (br s, 2H), 8.39 (d, J = 5.25 Hz, 1H), 8.27 (d, J = 1.13 Hz, 1H), 7.61 (dd, J = 1.19, 5.32 Hz, 1H), 7.51 (s, 2H), 3.99 (s, 3H), 3.93 (s, 3H);

[M+1]: 377.36.

Example 141: 4-methoxy-2-(2-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 13.12 (br s, 1H), 8.24 (s, 1H), 8.03 - 8.10 (m, 2H), 7.50 (s, 1H), 7.36 (t, J = 8.76 Hz, 1H), 3.99 (s, 3H), 3.95 (s, 3H);

[M+1]: 360.36.

Example 142: 2-(2-morpholinoisonicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.78 - 14.20 (m, 1H), 8.68 (d, J = 1.38 Hz, 1H), 8.30 (d, J = 5.50 Hz, 1H), 8.05 (dd, J = 1.69, 8.44 Hz, 1H), 7.86 (d, J = 8.50 Hz, 1H), 7.68 (s, 1H), 7.29 (dd, J = 1.13, 5.50 Hz, 1H), 3.73 - 3.79 (m, 5H) ), 3.61 - 3.67 (m, 4H), 3.60 (br d, J = 2.63 Hz, 1H);

[M+1]: 385.41.

Example 143: 2-(2-ethoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.93 - 13.44 (m, 2H), 8.68 (d, J = 1.38 Hz, 1H), 8.38 (d, J = 5.75 Hz, 1H), 8.05 (dd, J = 1.75, 8.50 Hz, 1H), 7.86 (d, J = 8.50 Hz, 1H), 7.58 (dd, J = 1.50, 5.25 Hz, 1H), 7.45 (s, 1H), 4.37 (q, J = 7.00 Hz, 2H), 1.36 (t, J = 7.07 Hz, 3H);

[M+1]: 344.36.

Example 144: 2-(6-methoxynicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.07 (br s, 2H), 8.99 (d, J = 2.50 Hz, 1H), 8.66 (d, J = 1.50 Hz, 1H), 8.39 (dd, J = 2.50, 8.76 Hz, 1H), 8.03 (dd, J = 1.75, 8.50 Hz, 1H), 7.84 (d, J = 8.38 Hz, 1H), 7.00 (d, J = 9.26 Hz, 1H), 3.96 (s) , 3H);

[M+1]: 330.33.

Example 145: 2-(3-fluoro-4-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.37 (br s, 1H), 8.68 (d, J = 1.25 Hz, 1H), 8.23 (d, J = 11.63 Hz, 1H), 8.12 - 8.17 (m , J = 8.38 Hz, 1H), 8.01 - 8.08 (m, 2H), 7.86 (br d, J = 8.25 Hz, 1H);

[M+1]: 385.3.

Example 146: 2-(nicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.26 (br s, 1H), 9.27 (dd, J = 0.69, 2.19 Hz, 1H), 8.84 (dd, J = 1.63, 4.88 Hz, 1H), 8.68 (d, J = 1.50 Hz, 1H), 8.50 (td, J = 1.88, 8.25 Hz, 1H), 8.05 (dd, J = 1.75, 8.51 Hz, 1H), 7.86 (d, J = 8.38 Hz, 1H) , 7.64 (ddd, J = 0.75, 4.88, 8.00 Hz, 1H);

[M+1]: 300.3.

Example 147: 2-(isonicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.42 (br s, 1H), 8.88 (d, J = 5.02 Hz, 2H), 8.69 (d, J = 1.50 Hz, 1H), 8.09 (d, J = 6.13 Hz, 2H), 8.06 (dd, J = 1.69, 8.44 Hz, 1H), 7.87 (d, J = 8.38 Hz, 1H);

[M+1]: 300.3.

Example 148: 2-(3,4,5-trifluorobenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 13.20 (br s, 1H), 8.65 (d, J = 1.38 Hz, 1H), 8.07 - 8.14 (m, 2H), 8.04 (dd, J = 1.69, 8.44 Hz, 1H), 7.78 - 7.87 (m, 1H);

[M+1]: 353.29.

Example 149: 2-(2-(trifluoromethyl)isonicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 13.54 (br s, 1H), 9.04 (d, J = 5.00 Hz, 1H), 8.68 - 8.72 (m, 1H), 8.56 (s, 1H), 8.33 (dd, J = 1.19, 4.94 Hz, 1H), 8.06 (dd, J = 1.69, 8.44 Hz, 1H), 7.87 (br d, J = 8.50 Hz, 1H);

[M+1]: 368.3.

Example 150: 2-(3-chloro-4-fluorobenzamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.17 (br s, 1H), 8.66 (d, J = 1.38 Hz, 1H), 8.41 (dd, J = 2.25, 7.00 Hz, 1H), 8.17 (ddd , J = 2.25, 4.66, 8.72 Hz, 1H), 8.04 (dd, J = 1.75, 8.50 Hz, 1H), 7.85 (d, J = 8.38 Hz, 1H), 7.65 (t, J = 8.94 Hz, 1H) ;

[M+1]: 351.75.

Example 151: 2-(3,4-difluorobenzamido)benzo[d]thiazole-6-carboxylic acid

[M+1]: 335.3

Example 152: 2-(3-chloro-4-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.03 (br s, 1H), 8.65 (d, J = 1.38 Hz, 1H), 8.28 (d, J = 2.25 Hz, 1H), 8.18 (dd, J = 2.19, 8.69 Hz, 1H), 8.03 (dd, J = 1.69, 8.44 Hz, 1H), 7.84 (d, J = 8.38 Hz, 1H), 7.34 (d, J = 8.88 Hz, 1H), 3.89 - 4.00 (m, 3H);

[M+1]: 363.79.

Example 153: 2-(3-fluoro-5-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.36 (br s, 1H), 8.65 - 8.70 (m, 1H), 8.40 (s, 1H), 8.27 (br d, J = 9.76 Hz, 1H), 8.03 - 8.09 (m, 2H), 7.85 (br d, J = 8.25 Hz, 1H);

[M+1]: 385.3.

Example 154: 2-(4-chloro-3-fluorobenzamido)-4-fluorobenzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.48 (br s, 1H), 8.54 (d, J = 1.38 Hz, 1H), 8.19 (dd, J = 2.00, 10.13 Hz, 1H), 8.02 (td) , J = 1.06, 8.38 Hz, 1H), 7.82 - 7.87 (m, 1H), 7.76 (dd, J = 1.50, 11.26 Hz, 1H);

[M+1]: 369.74.

Example 155: 2-(4-chloro-2-methoxybenzamido)-4-fluorobenzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.10 - 12.96 (m, 1H), 8.53 (d, J = 1.38 Hz, 1H), 7.76 (dd, J = 1.38, 11.26 Hz, 1H), 7.71 ( d, J = 8.25 Hz, 1H), 7.34 (d, J = 1.88 Hz, 1H), 7.18 (dd, J = 1.88, 8.25 Hz, 1H), 3.95 (s, 3H);

[M+1]: 381.78.

Example 156: 4-Fluoro-2-(3-fluoro-4-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 13.25 (br s, 1H), 8.52 (d, J = 1.50 Hz, 1H), 8.04 - 8.14 (m, 2H), 7.76 (dd, J = 1.50, 11.26 Hz, 1H), 7.35 - 7.41 (m, 1H), 3.96 (s, 3H);

[M+1]: 365.32.

Example 157: 4-Fluoro-2-(2-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.14 - 13.93 (m, 1H), 8.49 (d, J = 1.38 Hz, 1H), 8.35 - 8.42 (m, 1H), 7.75 (d, J = 1.50) Hz, 1H), 7.61 (dd, J = 1.44, 5.32 Hz, 1H), 7.46 - 7.54 (m, 1H), 3.87 - 3.98 (m, 3H);

[M+1]: 348.32.

Example 158: 2-(2-methyl-5-(4-(trifluoromethyl)pyrimidin-2-ylamino)benzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 10.32 (s, 1 H) 8.83 (d, J = 4.88 Hz, 1 H) 8.52 (d, J = 1.25 Hz, 1 H) 8.00 (dd, J = 8.38, 1.63 Hz, 1 H) 7.96 (d, J = 2.13 Hz, 1 H) 7.82 (dd, J = 8.38, 2.13 Hz, 1 H) 7.71 (d, J = 8.38 Hz, 1 H) 7.25 - 7.31 (m, 2 H) 2.39 (s, 5 H);

[M+1]: 474.43.

Example 159: 2-(6-oxo-1,6-dihydropyridine-2-carboxamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 11.80 - 12.47 (m, 2 H) 8.68 (d, J = 1.63 Hz, 1 H) 8.03 (d, J = 1.75 Hz, 1 H) 7.84 - 7.89 (m, 2 H) 7.48 - 7.67 (m, 1 H) 6.87 - 6.99 (m, 1 H);

[M+1]: 316.3.

Example 160: 2-(3-(1H-imidazol-1-yl)benzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 8.56 (d, J = 1.00 Hz, 1 H) 8.40 (br d, J = 16.51 Hz, 1 H) 8.10 (d, J = 8.00 Hz, 1 H ) 7.17 (s, 1 H) 7.98 (dd, J = 8.50, 1.75 Hz, 1 H) 7.91 (dd, J = 1.00 Hz, 1 H) 7.87 (t, J = 1.00 Hz, 1 H) 7.76 (d, J = 1.00 Hz, 1 H) 7.69 (t, J = 7.88 Hz, 1 H);

[M+1]: 365.38.

Example 161: 2-(2-Chloro-5-(4-methylpyrimidin-2-ylamino)benzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 9.85 - 9.94 (m, 1 H) 8.60 (br s, 1 H) 8.39 (d, J = 5.00 Hz, 1 H) 8.10 (d, J = 1.00 Hz, 1 H) 8.00 (dd, J = 1.00 Hz, 1 H) 7.96 (dd, J = 8.88, 2.63 Hz, 1 H) 7.78 (d, J = 1.00 Hz, 1 H) 7.46 (d, J = 1.00 Hz, 1 H) 6.78 - 6.83 (m, 1 H) 2.37 (s, 3 H);

[M+1]: 440.87.

Example 162: 2-(4-carboxybenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 8.65 (d, J = 1.25 Hz, 1 H) 8.23 (d, J = 8.63 Hz, 2 H) 8.09 (d, J = 8.63 Hz, 2 H) 8.03 (dd, J = 8.51, 1.75 Hz, 1 H) 7.84 (d, J = 8.38 Hz, 1 H);

[M+1]: 343.33.

Example 163: 2-(8-hydroxyquinoline-2-carboxamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 8.65 (d, J = 1.25 Hz, 1 H) 8.23 (d, J = 8.63 Hz, 2 H) 8.09 (d, J = 8.63 Hz, 2 H) 8.03 (dd, J = 8.51, 1.75 Hz, 1 H) 7.84 (d, J = 8.38 Hz, 1 H);

[M+1]: 343.33.

Example 164: 2-(4-chloro-2-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 13.61 (s, 1 H) 11.83 - 13.39 (m, 1 H) 10.80 (s, 1 H) 8.72 (d, J = 1.50 Hz, 1 H) 8.63 (d, J = 8.63 Hz, 1 H) 8.31 (d, J = 8.63 Hz, 1 H) 8.07 (dd, J = 8.50, 1.75 Hz, 1 H) 7.91 (d, J = 8.51 Hz, 1 H) 7.64 - 7.69 (m, 1 H) 7.55 (dd, J = 8.07, 0.94 Hz, 1 H) 7.24 (dd, J = 7.69, 1.06 Hz, 1 H);

[M+1]: 363.79.

Example 165: 2-(3,4-dimethoxybenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 11.25 - 14.46 (m, 2 H) 8.64 (d, J = 1.38 Hz, 1 H) 8.03 (dd, J = 8.38, 1.75 Hz, 1 H) 7.78 - 7.86 (m, 3 H) 7.14 (d, J = 8.63 Hz, 1 H) 3.88 (s, 3 H) 3.87 (s, 3 H);

[M+1]: 359.37.

Example 166: 2-(2-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 12.37 - 14.09 (m, 2 H) 8.67 (d, J = 1.38 Hz, 1 H) 8.38 - 8.42 (m, 1 H) 8.05 (dd, J = 8.51, 1.75 Hz, 1 H) 7.86 (d, J = 8.50 Hz, 1 H) 7.60 (dd, J = 5.32, 1.44 Hz, 1 H) 7.50 (s, 1 H) 3.93 (s, 3 H);

[M+1]: 330.33.

Example 167: 2-(4-chloro-3-fluorobenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 8.27 - 8.29 (m, 1H) 7.98 - 8.07 (m, 2 H) 7.83 (dd, J = 8.38, 1.75 Hz, 1 H) 7.64 (t, J = 7.82 Hz, 1 H) 7.50 (d, J = 8.38 Hz, 1 H);

[M+1]: 351.75.

Example 168: 2-(4-fluoro-3-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 12.45 - 13.73 (m, 2 H) 8.66 (d, J = 1.63 Hz, 1 H) 8.04 (dd, J = 8.51, 1.75 Hz, 1 H) 8.00 (dd, J = 8.25, 2.13 Hz, 1 H) 7.84 (d, J = 8.50 Hz, 1 H) 7.76 - 7.81 (m, 1 H) 7.43 (dd, J = 11.13, 8.50 Hz, 1 H) 3.95 - 4.01 (m, 4 H);

[M+1]: 347.33.

Example 169: 2-(3-fluoro-4-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 11.96 - 13.89 (m, 2 H) 8.64 (d, J = 1.38 Hz, 1 H) 8.01 - 8.08 (m, 3 H) 7.83 (d, J = 8.50 Hz, 1 H) 7.34 - 7.40 (m, 1 H) 3.96 (s, 3 H);

[M+1]: 347.33.

Example 170: 2-(4-cyanobenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 12.70 - 13.51 (m, 2 H) 8.65 - 8.68 (m, 1 H) 8.27 (s, 3 H) 8.07 (d, J = 8.63 Hz, 3 H ) 7.85 (br d, J = 8.38 Hz, 1 H);

[M+1]: 324.33.

Example 171: 2-(3-cyanobenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 11.18 - 13.94 (m, 2 H) 8.65 - 8.68 (m, 1 H) 8.58 (t, J = 1.44 Hz, 1 H) 8.39 - 8.43 (m, 1 H) 8.14 (dt, J = 7.88, 1.31 Hz, 1 H) 8.05 (dd, J = 8.51, 1.75 Hz, 1 H) 7.86 (d, J = 8.50 Hz, 1 H) 7.80 (t, J = 8.00 Hz, 1 H);

[M+1]: 324.33.

Example 172: 2-(3-hydroxybenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 12.42 - 13.46 (m, 2 H) 9.90 (s, 1 H) 8.64 - 8.68 (m, 1 H) 8.03 (dd, J = 8.50, 1.75 Hz, 1 H) 7.84 (d, J = 8.50 Hz, 1 H) 7.61 (d, J = 7.88 Hz, 1 H) 7.49 (t, J = 1.88 Hz, 1 H) 7.37 (s, 1 H) 7.04 - 7.08 ( m, 1 H) 3.36 (s, 90 H) 2.47 - 2.54 (m, 31 H);

[M+1]: 315.32.

Example 173: 2-(3-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 12.35 - 13.42 (m, 2 H) 8.66 (d, J = 1.38 Hz, 1 H) 8.04 (dd, J = 8.38, 1.75 Hz, 1 H) 7.85 (d, J = 8.50 Hz, 1 H) 7.74 (ddd, J = 3.75, 2.50, 1.13 Hz, 2 H) 7.50 (t, J = 8.19 Hz, 1 H) 7.24 (ddd, J = 8.29, 2.47, 0.88 Hz, 1 H) 3.87 (s, 3 H);

[M+1]: 329.34.

Example 174: 2-(4-methylcyclohexanecarboxamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 12.35 - 12.58 (m, 1 H) 8.59 (d, J = 1.75 Hz, 1 H) 8.25 (d, J = 1.50 Hz, 1 H) 7.99 (dd , J = 8.38, 1.75 Hz, 1 H) 7.75 - 7.85 (m, 2 H) 7.35 (d, J = 8.50 Hz, 1 H) 2.65 - 2.72 (m, 1 H) 2.09 (s, 1 H) 1.85 ( td, J = 8.47, 3.94 Hz, 3 H) 1.76 (s, 1 H) 1.47 - 1.70 (m, 6 H) 1.32 - 1.46 (m, 3 H) 0.91 - 0.95 (m, 3 H);

[M+1]: 319.39.

Example 175: 2-(5-bromo-2-methoxynicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 12.61 - 12.84 (m, 1 H) 8.62 - 8.79 (m, 1 H) 8.53 (d, J = 2.38 Hz, 1 H) 8.32 (d, J = 2.38 Hz, 1 H) 7.96 - 8.17 (m, 1 H) 7.87 (d, J = 8.50 Hz, 1 H) 4.36 (br d, J = 7.13 Hz, 2 H) 3.98 (s, 3 H) 1.36 (t , J = 7.07 Hz, 3 H);

[M+1]: 409.23.

Example 176: 2-(2-tert-butylisonicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, MeOH-d ₄ ) δ ppm 8.70 (dd, J = 5.07, 0.81 Hz, 1 H) 8.52 (d, J = 1.75 Hz, 1 H) 7.97 - 8.11 (m, 2 H) 7.72 - 7.81 (m, 2 H) 4.39 (q, J = 7.13 Hz, 2 H) 1.44 (s, 9 H) 1.39 - 1.43 (m, 3 H);

[M+1]: 356.41.

Example 177: 5-Chloro-2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 13.19 - 13.78 (m, 1 H) 11.17 (br s, 1H) 8.10 - 8.24 (m, 2 H) 7.88 - 8.02 (m, 2 H) 7.75 ( d, J = 8.00 Hz, 1 H) 7.35 - 7.45 (m, 2 H) 7.00 - 7.15 (m, 2 H) 6.08 (br s, 1 H) 3.69 - 3.80 (m, 2 H) 2.59 (br s, 2H);

[M+1]: 402.75.

Example 178: 5-methoxy-2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 13.30 - 13.53 (m, 1 H) 9.39 (s, 1 H) 8.72 (dd, J = 8.19, 1.81 Hz, 1 H) 8.38 (s, 1 H) ) 8.15 (d, J = 8.13 Hz, 1 H) 7.37 - 7.49 (m, 1 H) 3.91 (s, 3 H) 3.82 (s, 3 H) 3.81 (s, 1 H);

[M+1]: 398.33.

Example 179: 5-Hydroxy-2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 9.39 (s, 1H), 8.68 - 8.75 (m, 1H), 8.53 (s, 1H), 8.14 (d, J = 8.25 Hz, 1H),7.24 ( s, 1H);

[M+1]: 384.3.

Example 180: 2-(5-fluoro-2-methoxynicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 12.46 - 12.82 (m, 1 H) 8.67 (s, 1 H) 8.43 (d, J = 2.63 Hz, 1 H) 8.09 - 8.27 (m, 1 H) ) 8.03 (br d, J = 8.51 Hz, 1 H) 7.86 (d, J = 8.38 Hz, 1 H) 3.99 (s, 3 H);

[M+1]: 348.32.

Example 181: 2-(5-bromo-2-methylnicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 12.70 - 13.51 (m, 2 H) 8.76 (d, J = 2.38 Hz, 1 H) 8.67 (d, J = 1.38 Hz, 1 H) 8.37 (d , J = 2.38 Hz, 1 H) 8.04 (dd, J = 8.50, 1.75 Hz, 1 H) 7.85 (d, J = 8.38 Hz, 1 H) 2.57 - 2.60 (m, 3 H);

[M+1]: 393.23.

Example 182: 2-(6-bromonicotinamido)-5-methoxybenzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 13.20 - 13.40 (m, 1 H) 9.05 (s, 1 H) 8.33 - 8.39 (m, 2 H) 7.89 (d, J = 8.38 Hz, 1 H ) 7.38 - 7.51 (m, 1 H) 3.91 (s, 3 H);

[M+1]: 409.23.

Example 183: 2-(2-Aminoisonicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 12.90 - 13.96 (m, 1 H) 8.67 (d, J = 1.50 Hz, 1 H) 8.29 - 8.52 (m, 2 H) 8.13 (d, J = 6.50 Hz, 1 H) 8.06 (dd, J = 8.50, 1.75 Hz, 1 H) 7.84 (d, J = 8.50 Hz, 1H) 7.56 (s, 1 H) 7.34 (dd, J = 6.57, 1.56 Hz, 1 H);

[M+1]: 315.32.

Example 184: 2-(2-bromo-6-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 13.02 - 13.35 (m, 1 H) 8.66 (d, J = 1.38 Hz, 1 H) 8.04 (dd, J = 8.44, 1.69 Hz, 1 H) 7.78 - 7.88 (m, 2 H) 7.49 (d, J = 0.88 Hz, 1 H) 3.93 (s, 3 H);

[M+1]: 409.23.

Example 185: 2-(6-bromo-2-chloronicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.94 - 13.18 (m, 1H), 8.70 (d, J = 1.50 Hz, 1H), 8.20 (d, J = 8.00 Hz, 1H), 8.04 (dd, J = 1.75, 8.50 Hz, 1H), 7.92 (d, J = 8.00 Hz, 1H), 7.87 (d, J = 8.50 Hz, 1H);

[M+1]: 413.65.

Example 186: 2-(6-tert-butylnicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.97 - 13.40 (m, 1H), 9.20 (dd, J = 0.75, 2.38 Hz, 1H), 8.66 (d, J = 1.50 Hz, 1H), 8.42 ( dd, J = 2.50, 8.38 Hz, 1H), 8.04 (dd, J = 1.75, 8.51 Hz, 1H), 7.85 (d, J = 8.38 Hz, 1H), 7.65 (dd, J = 0.63, 8.38 Hz, 1H) ), 1.36 (s, 9H);

[M+1]: 356.41.

Example 187: 2-(5,6-dichloronicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 13.05 - 13.46 (m, 1H), 9.03 (d, J = 2.00 Hz, 1H), 8.75 (d, J = 1.75 Hz, 1H), 8.65 (s, 1H), 8.04 (dd, J = 1.56, 8.44 Hz, 1H), 7.83 (br d, J = 8.38 Hz, 1H);

[M+1]: 369.19.

Example 188: 2-(5-vinylnicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 13.09 - 13.38 (m, 1H), 9.12 (d, J = 2.00 Hz, 1H), 8.89 (d, J = 1.88 Hz, 1H), 8.61 - 8.71 ( m, 2H), 8.05 (dd, J = 1.63, 8.51 Hz, 1H), 7.86 (d, J = 8.50 Hz, 1H), 6.89 (dd, J = 11.07, 17.70 Hz, 1H), 6.17 (d, J) = 17.64 Hz, 1H), 5.55 (d, J = 11.26 Hz, 1H);

[M+1]: 326.34.

Example 189: 2-(5-(furan-3-yl)nicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 13.10 - 13.34 (m, 1H), 9.13 (dd, J = 2.06, 12.44 Hz, 2H), 8.65 - 8.76 (m, 2H), 8.40 - 8.49 (m , 1H), 8.06 (dd, J = 1.69, 8.44 Hz, 1H), 7.83 - 7.90 (m, 2H), 7.18 (dd, J = 0.81, 1.81 Hz, 1H);

[M+1]: 366.36.

Example 190: 2-(5-cyclopentenylnicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 13.06 - 13.42 (m, 1H), 9.08 (d, J = 2.00 Hz, 1H), 8.95 (d, J = 2.00 Hz, 1H), 8.67 (d, J = 1.50 Hz, 1H), 8.55 (t, J = 2.06 Hz, 1H), 8.05 (dd, J = 1.69, 8.44 Hz, 1H), 7.86 (d, J = 8.38 Hz, 1H), 6.63 (t, J = 1.88 Hz, 1H), 2.72 - 2.82 (m, 2H), 2.53 - 2.60 (m, 2H), 2.02 (quin, J = 7.54 Hz, 2H);

[M+1]: 366.41.

Example 191: 2-(5-(2-methylprop-1-enyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 13.03 - 13.34 (m, 1H), 9.08 (d, J = 2.00 Hz, 1H), 8.61 - 8.71 (m, 2H), 8.30 (br t, J = 1.94 Hz, 1H), 8.05 (dd, J = 1.69, 8.44 Hz, 1H), 7.86 (br d, J = 8.50 Hz, 1H), 6.35 (s, 1H), 1.96 (s, 3H), 1.91 (s) , 3H);

[M+1]: 354.39.

Example 192: 2-(2,6-dibromonicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.88 - 13.13 (m, 1H), 8.69 (d, J = 1.50 Hz, 1H), 8.13 (d, J = 7.88 Hz, 1H), 8.04 (dd, J = 1.75, 8.50 Hz, 1H), 7.93 (d, J = 8.00 Hz, 1H), 7.87 (d, J = 8.38 Hz, 1H);

[M+1]: 458.1.

Example 193: 2-(6-amino-5-bromonicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.82 - 12.94 (m, 1H), 8.77 (d, J = 2.13 Hz, 1H), 8.63 (d, J = 1.50 Hz, 1H), 8.47 (d, J = 2.00 Hz, 1H), 8.02 (dd, J = 1.75, 8.38 Hz, 1H), 7.82 (d, J = 8.50 Hz, 1H), 7.10 - 7.31 (m, 2H);

[M+1]: 394.22.

Example 194: 2-(2-iodoisonicotinamido)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 13.27 (br s, 1H), 8.67 (d, J = 1.50 Hz, 1H), 8.61 (d, J = 5.13 Hz, 1H), 8.48 (d, J = 0.63 Hz, 1H), 7.98 - 8.08 (m, 2H), 7.85 (br d, J = 8.38 Hz, 1H);

[M+1]: 426.2.

Example 195: 2-(2-methylisonicotinamido)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 13.12 - 13.49 (m, 1H), 8.63 - 8.74 (m, 2H), 8.05 (dd, J = 1.38, 8.38 Hz, 1H), 7.92 (s, 1H) ), 7.80 - 7.90 (m, 2H), 2.60 (s, 3H);

[M+1]: 314.33.

Example 196: 2-(5-fluoronicotinamido)benzo[d]thiazole-5-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 9.14 (t, J = 1.50 Hz, 1H), 8.84 (d, J = 2.75 Hz, 1H), 8.63 (d, J = 1.50 Hz, 1H), 8.37 (d, J = 9.44 Hz, 1H), 8.02 (dd, J = 1.69, 8.44 Hz, 1H), 7.82 (d, J = 8.38 Hz, 1H), 3.52 - 3.79 (m, 3H), 2.53 - 2.58 ( m, 1H);

[M+1]: 318.3.

Example 197: 2-(5-chloronicotinamido)benzo[d]thiazole-5-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 9.19 (d, J = 1.63 Hz, 1H), 8.90 (s, 1H), 8.67 (s, 1H), 8.60 (s, 1H), 8.05 (d, J = 8.50 Hz, 1H), 7.86 (br d, J = 8.25 Hz, 1H), 3.10 - 3.26 (m, 2H), 2.53 - 2.59 (m, 1H);

[M+1]: 334.8.

Example 198: 2-(isonicotinamido)benzo[d]thiazole-5-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.91 (d, J = 5.09 Hz, 2H), 8.69 (d, J = 1.38 Hz, 1H), 8.14 (d, J = 5.13 Hz, 2H), 8.06 (dd, J = 1.69, 8.44 Hz, 1H), 7.86 (d, J = 8.50 Hz, 1H), 3.57 - 3.85 (m, 9H);

[M+1]: 300.3.

Example 199: 2-(3-fluoro-4-(trifluoromethyl)benzamido)benzo[d]thiazole-5-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.67 (d, J = 1.38 Hz, 1H), 8.23 (d, J = 11.51 Hz, 1H), 8.15 (d, J = 8.50 Hz, 1H), 8.00 - 8.07 (m, 2H), 7.86 (br d, J = 8.38 Hz, 1H), 3.49 - 3.62 (m, 1H);

[M+1]: 385.3.

Example 200: 2-(2-chloroisonicotinamido)benzo[d]thiazole-5-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.68 (s, 1H), 8.68 (d, J = 5.12 Hz, 2H), 8.16 (s, 1H), 8.01 - 8.07 (m, 2H), 7.81 - 7.90 (m, 1H), 3.49 - 3.72 (m, 4H), 3.03 - 3.30 (m, 3H), 2.53 - 2.59 (m, 1H);

[M+1]: 334.8.

Example 201: 2-(nicotinamido)benzo[d]thiazole-5-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 9.32 (s, 1H), 8.90 (dd, J = 1.63, 5.00 Hz, 1H), 8.67 (d, J = 1.25 Hz, 1H), 8.63 (td, J = 1.72, 8.07 Hz, 1H), 8.05 (dd, J = 1.69, 8.44 Hz, 1H), 7.85 (d, J = 8.50 Hz, 1H), 7.77 (dd, J = 5.00, 7.88 Hz, 1H), 3.30 - 3.57 (m, 10H), 2.53 - 2.69 (m, 1H);

[M+1]: 300.3.

Example 202: 2-(6-oxo-1,6-dihydropyridine-2-carboxamido)benzo[d]thiazole-5-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.68 (d, J = 1.38 Hz, 1H), 8.04 (dd, J = 1.75, 8.51 Hz, 1H), 7.81 - 7.90 (m, 2H), 7.58 ( br d, J = 6.38 Hz, 1H), 6.95 (br d, J = 8.13 Hz, 1H), 3.54 - 3.82 (m, 4H), 2.98 - 3.26 (m, 4H), 2.53 - 2.60 (m, 1H) , 2.35 - 2.47 (m, 1H);

[M+1]: 316.3.

Example 203: 2-(3,4,5-trifluorobenzamido)benzo[d]thiazole-5-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.66 (s, 1H), 7.96 - 8.18 (m, 3H), 7.85 (br d, J = 8.50 Hz, 1H), 3.41 - 3.62 (m, 3H) , 3.03 - 3.29 (m, 2H), 2.53 - 2.58 (m, 1H);

[M+1]: 353.3.

Example 204: 2-(3-fluoro-4-methylbenzamido)benzo[d]thiazole-5-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.12 (d, J = 1.25 Hz, 1H), 7.84 - 7.91 (m, 1H), 7.79 (dd, J = 1.38, 11.26 Hz, 1H), 7.71 - 7.77 (m, 1H), 7.33 (d, J = 8.13 Hz, 1H), 7.23 - 7.30 (m, 1H), 2.23 - 2.29 (m, 3H);

[M+1]: 331.3.

Example 205: 2-(2-ethoxyisonicotinamido)benzo[d]thiazole-5-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.66 (d, J = 1.75 Hz, 1H), 8.36 - 8.43 (m, 1H), 8.04 (dd, J = 1.75, 8.50 Hz, 1H), 7.81 - 7.90 (m, 1H), 7.51 - 7.64 (m, 1H), 7.49 - 7.57 (m, 1H), 7.44 (dd, J = 0.75, 1.38 Hz, 1H), 4.30 - 4.47 (m, 3H), 1.35 ( t, J = 7.00 Hz, 3H);

[M+1]: 344.4.

Example 206: 2-(2-morpholinoisonicotinamido)benzo[d]thiazole-5-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.67 (d, J = 1.75 Hz, 1H), 8.31 (d, J = 5.38 Hz, 1H), 8.05 (dd, J = 1.75, 8.50 Hz, 1H) , 7.86 (d, J = 8.50 Hz, 1H), 7.60 (s, 1H), 7.26 (dd, J = 1.19, 5.32 Hz, 1H), 3.75 (br s, 5H), 3.60 (br d, J = 5.25 Hz, 8H);

[M+1]: 385.4.

Example 207: 2-(6-chloro-5-fluoropicolinamido)benzo[d]thiazole-5-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.66 (d, J = 1.38 Hz, 1H), 8.23 (d, J = 8.38 Hz, 1H), 8.04 (dd, J = 1.81, 8.44 Hz, 1H) , 7.86 - 7.91 (m, 1H), 7.77 - 7.86 (m, 1H);

[M+1]: 352.7.

Example 208: 2-(5-carboxypicolinamido)benzo[d]thiazole-5-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 9.22 (dd, J = 0.88, 2.00 Hz, 1H), 8.68 (d, J = 1.75 Hz, 1H), 8.55 (dd, J = 2.13, 8.13 Hz, 2H), 8.32 (br dd, J = 0.75, 8.13 Hz, 2H), 8.04 (dd, J = 1.75, 8.50 Hz, 2H), 7.89 (d, J = 8.76 Hz, 1H), 3.16 (s, 7H) , 2.53 - 2.80 (m, 6H);

[M+1]: 344.3.

Example 209: 2-(2-Chloro-6-methoxyisonicotinamido)benzo[d]thiazole-5-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.65 (d, J = 1.38 Hz, 1H), 8.01 - 8.07 (m, 1H), 7.83 - 7.87 (m, 1H), 7.67 (d, J = 1.13) Hz, 1H), 7.46 (d, J = 1.13 Hz, 1H), 3.92 - 3.94 (m, 4H);

[M+1]: 364.8.

Example 210: 2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-5-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 12.65 - 13.90 (m, 2 H) 9.40 (d, J = 1.88 Hz, 1 H) 8.73 (dd, J = 8.07, 1.81 Hz, 1 H) 8.69 (d, J = 1.50 Hz, 1 H) 8.15 (d, J = 8.25 Hz, 1 H) 8.06 (dd, J = 8.44, 1.69 Hz, 1 H) 7.86 (br d, J = 8.38 Hz, 1 H) ;

[M+1]: 368.3.

Example 211: 2-(2-(trifluoromethyl)isonicotinamido)benzo[d]thiazole-5-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 12.36 - 13.98 (m, 2 H) 9.04 (d, J = 5.00 Hz, 1 H) 8.56 (s, 1 H) 8.69 (d, J = 1.38 Hz) , 1 H) 8.33 (dd, J = 4.94, 1.19 Hz, 1 H) 8.06 (dd, J = 8.44, 1.69 Hz, 1 H) 7.86 (br d, J = 8.13 Hz, 1 H);

[M+1]: 368.3.

Example 212: 2-(2-methoxyisonicotinamido)benzo[d]thiazole-5-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 13.26 (br s, 1 H) 8.68 (d, J = 1.50 Hz, 1 H) 8.40 (dd, J = 5.25, 0.63 Hz, 1 H) 8.05 ( dd, J = 8.38, 1.75 Hz, 1 H) 7.86 (d, J = 8.50 Hz, 1 H) 7.60 (dd, J = 5.25, 1.50 Hz, 1 H) 7.50 (dd, J = 1.38, 0.75 Hz, 1 H) 3.93 (s, 3 H);

[M+1]: 330.3.

Example 213: 2-(3-fluoro-4-methoxybenzamido)benzo[d]thiazole-5-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 12.99 (brs, 1 H) 8.65 (d, J = 1.50 Hz, 1 H) 8.01 - 8.08 (m, 3 H) 7.84 (d, J = 8.50 Hz) , 1 H) 7.37 (t, J = 8.18 Hz, 1 H) 3.95 (s, 3 H);

[M+1]: 347.3.

Example 214: Preparation of 2-(4-(4-methoxyphenyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid

(a) potassium carbonate, N,N-dimethylformamide, rt, 6h;

(b) 1N NaOH, THF, MeOH, rt, 24 h.

Step 214-1: Preparation of ethyl 2-(4-(4-methoxyphenyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylate

Ethyl 2-chlorobenzo[d]thiazole-6-carboxylate (200 mg, 0.82 mmol), K ₂ CO ₃ (228 mg, 1.65 mmol) and 1 -(4-Methoxyphenyl)piperazine (329 mg, 1.71 mmol) was dissolved in DMF (2 mL) using a 20 mL vial. The mixture was stirred at room temperature for 6 hours. Then 1N HCl, water and a little methanol were added to produce a solid. The resulting solid was purified through a filter to obtain the title compound (255 mg, 0.69 mmol) as a white solid (yield 77%).

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 1.33 (t, J = 7.13 Hz, 3 H) 3.11 - 3.24 (m, 4 H) 3.70 (s, 3 H) 3.73 - 3.82 (m, 4 H) ) 4.31 (d, J = 7.13 Hz, 2 H) 6.86 (br d, J = 9.01 Hz, 2 H) 6.98 (br d, J = 9.13 Hz, 2 H) 7.52 (d, J = 8.38 Hz, 1 H) ) 7.89 (dd, J = 8.44, 1.69 Hz, 1 H) 8.43 (d, J = 1.63 Hz, 1 H);

[M+1]: 397.49.

Step 214-2: Preparation of 2-(4-(4-methoxyphenyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid

Ethyl 2-(4-(4-methoxyphenyl)piperazin-1-yl instead of ethyl 2-(6-(trifluoromethyl)ticotinamido)benzo[d]thiazole-6-carboxylate ) The title compound (110 mg, 0.29 mmol) was obtained by reacting in a similar manner to steps 1-2 of Example 1, except for using benzo[d]thiazole-6-carboxylate.

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 8.41 (d, J = 1.63 Hz, 1 H) 7.88 (dd, J = 8.44, 1.69 Hz, 1 H) 7.51 (d, J = 8.38 Hz, 1 H) 7.15 (br d, J = 7.13 Hz, 2 H) 6.91 (d, J = 9.01 Hz, 2 H) 3.85 (br s, 4 H) 3.70 - 3.76 (m, 3 H) 3.24 - 3.34 (m, 4H);

[M+1]: 370.44.

The compounds of Examples 215 to 266 below were synthesized in a manner similar to Example 214, but using appropriate reactants considering the structure of the title compound.

Example 215: 2-(4-(4-acetylphenyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 12.72 (br s, 1H) 8.40 (d, J = 1.38 Hz, 1 H) 7.79 - 7.95 (m, 3 H) 7.51 (d, J = 8.38 Hz) , 1 H) 7.04 (br d, J = 8.88 Hz, 2 H) 3.69 - 3.88 (m, 4 H) 3.38 - 3.64 (m, 5 H) 2.45 - 2.49 (m, 3 H);

[M+1]: 382.45.

Example 216: 2-(4-(2,3-dichlorophenyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 12.72 (br s, 1 H) 8.40 (d, J = 1.63 Hz, 1 H) 7.88 (dd, J = 8.50, 1.75 Hz, 1 H) 7.50 ( d, J = 8.38 Hz, 1 H) 7.30 - 7.41 (m, 2 H) 7.21 (dd, J = 6.57, 3.06 Hz, 1 H) 3.74 - 3.88 (m, 4 H) 3.08 - 3.23 (m, 4 H) );

[M+1]: 210.4.

Example 217: 2-(4-(4-cyanophenyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 12.61 - 12.87 (m, 1 H) 8.40 (d, J = 1.63 Hz, 1 H) 7.88 (dd, J = 8.51, 1.75 Hz, 1 H) 7.64 (d, J = 9.01 Hz, 2 H) 7.51 (d, J = 8.50 Hz, 1 H) 7.08 (d, J = 9.01 Hz, 2 H) 3.74 - 3.80 (m, 4 H) 3.54 - 3.60 (m, 4H);

[M+1]: 365.42.

Example 218: 2-(4-(pyridin-4-yl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.42 (d, J = 1.50 Hz, 1H), 8.29 (br s, 2H), 7.89 (dd, J = 1.63, 8.38 Hz, 1H), 7.52 (d , J = 8.50 Hz, 1H), 7.11 - 7.25 (m, 2H), 3.82 - 3.88 (m, 8H);

[M+1]: 341.4.

Example 219: 2-(4-(pyridin-3-yl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.40 (d, J = 1.63 Hz, 2H), 8.01 - 8.10 (m, 1H), 7.88 (dd, J = 1.75, 8.38 Hz, 1H), 7.51 ( d, J = 8.50 Hz, 1H), 7.40 (dd, J = 2.06, 8.32 Hz, 1H), 7.27 (br s, 1H), 3.77 - 3.81 (m, 4H), 3.39 (br d, J = 5.13 Hz) , 4H);

[M+1]: 341.4.

Example 220: 2-(4-(2,4-difluorophenyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 8.40 (d, J = 1.63 Hz, 1H), 7.87 (dd, J = 1.81, 8.44 Hz, 1H), 7.50 (d, J = 8.51 Hz, 1H) , 7.22 - 7.29 (m, 1H), 7.15 (dt, J = 6.07, 9.41 Hz, 1H), 7.00 - 7.06 (m, 1H), 3.74 - 3.84 (m, 4H), 3.09 - 3.17 (m, 4H) ;

[M+1]: 376.4.

Example 221: 2-(4-(3-methoxyphenyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.70 (br s, 1H), 8.39 (s, 1H), 7.87 (br d, J = 8.25 Hz, 1H), 7.50 (d, J = 8.13 Hz, 1H), 7.16 (br t, J = 8.00 Hz, 1H), 6.60 (br d, J = 8.25 Hz, 1H), 6.53 (br s, 1H), 6.43 (br d, J = 8.13 Hz, 1H), 3.69 - 3.81 (m, 7H);

[M+1]: 370.4.

Example 222: 2-(4-(3-phenylpropanoyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.40 (d, J = 1.75 Hz, 1H), 7.87 (dd, J = 1.81, 8.44 Hz, 1H), 7.50 (d, J = 8.76 Hz, 1H) , 7.23 - 7.32 (m, 4H), 7.11 - 7.23 (m, 1H), 3.63 - 3.69 (m, 2H), 2.77 - 2.92 (m, 2H), 2.64 - 2.76 (m, 2H), 2.53 - 2.57 ( m, 1H);

[M+1]: 396.47.

Example 223: 2-(4-(2-phenylacetyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.40 (d, J = 1.50 Hz, 1H), 7.87 (dd, J = 1.81, 8.44 Hz, 1H), 7.50 (d, J = 8.38 Hz, 1H) , 7.21 - 7.36 (m, 4H), 3.54 - 3.77 (m, 7H);

[M+1]: 382.45.

Example 224: 2-(4-(3-chloro-4-fluorophenylsulfonyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 12.50 - 12.94 (m, 1H), 8.37 (d, J = 1.63 Hz, 1H), 7.85 (dd, J = 1.75, 8.50 Hz, 1H), 7.76 ( d, J = 2.25 Hz, 1H), 7.70 - 7.75 (m, 1H), 7.46 (d, J = 8.50 Hz, 1H), 7.38 (d, J = 8.76 Hz, 1H), 3.95 (s, 3H), 3.68 - 3.80 (m, 5H), 3.09 (br t, J = 4.94 Hz, 5H);

[M+1]: 456.91.

Example 225: 2-(4-(thiophen-2-ylsulfonyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 12.58 - 12.81 (m, 1H), 8.38 (d, J = 1.50 Hz, 1H), 8.04 - 8.15 (m, 1H), 7.80 - 7.92 (m, 1H) ), 7.62 - 7.74 (m, 1H), 7.41 - 7.56 (m, 1H), 7.23 - 7.34 (m, 1H), 3.72 - 3.80 (m, 4H), 3.05 - 3.16 (m, 4H);

[M+1]: 410.5.

Example 226: 2-(4-(2-(4-fluorophenyl)acetyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.40 (d, J = 1.75 Hz, 1H), 7.87 (dd, J = 1.81, 8.44 Hz, 1H), 7.50 (d, J = 8.50 Hz, 1H) , 7.28 (t, J = 6.14 Hz, 2H), 7.14 (t, J = 8.94 Hz, 2H), 3.57 - 3.73 (m, 9H), 2.53 - 2.56 (m, 1H);

[M+1]: 400.44.

Example 227: 2-(4-(3-cyclopentylpropanoyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.39 (d, J = 1.75 Hz, 1H), 7.87 (dd, J = 1.75, 8.50 Hz, 1H), 7.49 (d, J = 8.63 Hz, 1H) , 3.60 - 3.69 (m, 9H), 2.35 - 2.41 (m, 1H), 2.31 - 2.41 (m, 2H), 1.68 - 1.79 (m, 3H), 1.41 - 1.64 (m, 1H), 1.38 - 1.65 ( m, 6H), 1.02 - 1.17 (m, 2H);

[M+1]: 388.5.

Example 228: 2-(4-(benzylsulfonyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 8.19 - 8.31 (m, 1H), 7.81 - 7.86 (m, 1H), 7.42 (br d, J = 1.88 Hz, 2H), 7.39 (d, J = 3.75 Hz, 2H), 7.37 (br d, J = 1.88 Hz, 2H), 4.47 (s, 2H), 3.60 - 3.66 (m, 5H), 3.30 (br d, J = 5.00 Hz, 6H);

[M+1]: 418.5.

Example 229: 2-(4-(3,4-difluorophenylsulfonyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 8.33 (d, J = 1.50 Hz, 1H), 7.81 - 7.87 (m, 1H), 7.59 (s, 2H), 7.44 (d, J = 8.50 Hz, 2H), 3.70 - 3.75 (m, 5H), 3.05 - 3.11 (m, 4H);

[M+1]: 440.46.

Example 230: 2-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 12.54 - 12.82 (m, 1H), 8.36 (d, J = 1.75 Hz, 1H), 7.86 (dd, J = 1.75, 8.50 Hz, 1H), 7.52 - 7.57 (m, 2H), 7.46 (d, J = 8.50 Hz, 1H), 7.35 - 7.40 (m, 2H), 5.42 (s, 1H), 3.96 - 4.07 (m, 2H), 3.57 - 3.65 (m, 4H), 2.05 (br d, J = 4.63 Hz, 2H), 1.76 - 1.80 (m, 2H);

[M+1]: 389.87.

Example 231: 2-(3H-spiro[benzofuran-2,4'-piperidin]-1'-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 12.59 - 12.88 (m, 1H), 8.37 (d, J = 1.63 Hz, 1H), 7.87 (dd, J = 1.75, 8.38 Hz, 1H), 7.47 ( d, J = 8.50 Hz, 1H), 7.23 - 7.34 (m, 4H), 5.07 (s, 2H), 4.12 (br d, J = 11.13 Hz, 2H), 3.52 - 3.59 (m, 2H), 2.13 - 2.14 (m, 1H), 2.06 (br dd, J = 8.32, 13.20 Hz, 2H), 1.74 - 1.81 (m, 2H);

[M+1]: 367.43.

Example 232: 2-(4-(4-fluorophenyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) δ 12.63 - 12.78 (m, 1H), 8.36 (d, J = 1.50 Hz, 1H), 7.86 (dd, J = 1.81, 8.44 Hz, 1H), 7.47 ( d, J = 8.63 Hz, 1H), 7.33 (dd, J = 5.63, 8.76 Hz, 2H), 7.10 - 7.17 (m, 1H), 7.12 (t, J = 8.94 Hz, 1H), 4.14 - 4.25 (m , 2H), 3.20 - 3.30 (m, 2H), 2.86 - 2.92 (m, 1H), 1.89 (br s, 2H), 1.67 - 1.79 (m, 2H);

[M+1]: 357.41.

Example 233: 2-(4-hydroxy-4-phenylpiperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 12.45 - 12.90 (m, 1 H) 8.36 (d, J = 1.50 Hz, 1 H) 7.86 (dd, J = 8.44, 1.81 Hz, 1 H) 7.40 - 7.59 (m, 3H) 7.30 - 7.38 (m, 2 H) 7.20 - 7.29 (m, 1 H) 5.30 (s, 1 H) 3.93 - 4.09 (m, 2 H) 3.54 -3.67 (m, 2 H) 2.53 - 2.61 (m, 1 H) 1.93 - 2.18 (m, 2 H) 1.70 - 1.83 (m, 2 H);

[M+1]: 355.42.

Example 234: 2-(4-(2-methoxypyridin-4-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) δ ppm 12.68 (br s, 1 H) 8.36 (d, J = 1.63 Hz, 1 H) 8.08 (d, J = 5.25 Hz, 1 H) 7.86 (dd, J = 8.50, 1.63 Hz, 1 H) 7.47 (d, J = 8.38 Hz, 1 H) 6.94 (d, J = 5.38 Hz, 1 H) 6.72 (s, 1 H) 4.20 (br d, J = 12.76 Hz, 2 H) 3.83 (s, 3 H) 2.83 - 2.99 (m, 1H) 1.92 (br d, J = 12.38 Hz, 2 H) 1.67 - 1.82 (m, 2 H);

[M+1]: 370.44.

Example 235: 2-(4-hydroxy-4-(pyridin-4-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.67 (br s, 1H), 8.58 (br s, 1H), 8.37 (d, J = 1.63 Hz, 1H), 8.22 - 8.85 (m, 1H), 7.86 (dd, J = 1.75, 8.38 Hz, 1H), 7.56 (br s, 2H), 7.47 (d, J = 8.38 Hz, 1H), 5.58 (s, 1H), 4.04 (br d, J = 10.88 Hz) , 2H), 3.55 - 3.66 (m, 2H), 2.08 (dt, J = 4.69, 13.04 Hz, 2H), 1.74 (br d, J = 13.13 Hz, 2H);

[M+1]: 356.41.

Example 236: 2-(4-(pyridin-4-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.68 (br s, 1H), 8.40 - 8.40 (m, 1H), 8.50 (br s, 1H), 8.37 (d, J = 1.63 Hz, 1H), 7.86 (dd, J = 1.69, 8.44 Hz, 1H), 7.47 (d, J = 8.51 Hz, 1H), 7.33 (br s, 2H), 4.22 (br d, J = 12.38 Hz, 2H), 3.35 - 3.41 (m, 2H), 2.86 - 2.97 (m, 1H), 1.94 (br d, J = 12.38 Hz, 2H), 1.75 (dq, J = 4.13, 12.55 Hz, 2H);

[M+1]: 340.41.

Example 237: 2-(4-(3-(trifluoromethyl)phenyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.67 (br s, 1H), 8.37 (d, J = 1.63 Hz, 1H), 7.86 (dd, J = 1.75, 8.38 Hz, 1H), 7.53 - 7.66 (m, 4H), 7.47 (d, J = 8.38 Hz, 1H), 4.23 (br d, J = 13.01 Hz, 2H), 3.34 - 3.40 (m, 2H), 2.88 - 3.09 (m, 1H), 1.90 - 1.99 (m, 2H), 1.74 - 1.87 (m, 2H);

[M+1]: 407.42.

Example 238: 2-(4-hydroxy-4-(pyridin-3-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.67 (br s, 1H), 8.37 (d, J = 1.63 Hz, 1H), 7.86 (dd, J = 1.75, 8.38 Hz, 1H), 7.53 - 7.66 (m, 4H), 7.47 (d, J = 8.38 Hz, 1H), 4.23 (br d, J = 13.01 Hz, 2H), 3.34 - 3.40 (m, 2H), 2.88 - 3.09 (m, 1H), 1.90 - 1.99 (m, 2H), 1.74 - 1.87 (m, 2H);

[M+1]: 407.42.

Example 239: 2-(4-(pyridin-3-yloxy)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.68 (br s, 1H), 8.37 (d, J = 1.63 Hz, 2H), 8.21 (br s, 1H), 7.86 (dd, J = 1.69, 8.44 Hz, 1H), 7.44 - 7.53 (m, 2H), 7.37 (br s, 1H), 4.77 - 4.85 (m, 1H), 3.87 - 3.97 (m, 2H), 3.54 - 3.67 (m, 3H), 2.11 (ddd, J = 3.13, 6.57, 9.69 Hz, 2H), 1.73 - 1.80 (m, 2H);

[M+1]: 356.41.

Example 240: 2-(4-((pyridin-3-yloxy)methyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.35 (d, J = 1.63 Hz, 1H), 8.25 - 8.41 (m, 1H), 8.10 - 8.25 (m, 1H), 7.85 (dd, J = 1.81 , 8.44 Hz, 1H), 7.45 (d, J = 8.50 Hz, 1H), 7.39 - 7.42 (m, 1H), 7.35 (br s, 1H), 4.13 (br d, J = 12.76 Hz, 2H), 3.97 (d, J = 6.38 Hz, 2H), 3.27 (br d, J = 2.25 Hz, 2H), 2.07 - 2.18 (m, 1H), 1.93 (br d, J = 11.88 Hz, 2H), 1.41 (dt, J = 8.44, 12.23 Hz, 2H);

[M+1]: 370.44.

Example 241: 2-(4-(pyridin-3-ylmethyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.43 (br s, 2H), 8.31 (d, J = 1.38 Hz, 1H), 7.83 (dd, J = 1.56, 8.44 Hz, 1H), 7.64 (br d, J = 7.88 Hz, 1H), 7.42 (d, J = 8.50 Hz, 1H), 7.33 (dd, J = 4.88, 7.63 Hz, 1H), 4.06 (br d, J = 12.38 Hz, 2H), 3.12 - 3.19 (m, 2H), 2.56 - 2.62 (m, 2H), 1.87 (dt, J = 3.69, 7.16 Hz, 1H), 1.65 - 1.77 (m, 2H), 1.21 - 1.34 (m, 2H);

[M+1]: 354.44.

Example 242: 2-(4-(thiazol-2-ylmethyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.32 - 8.35 (m, 1H), 7.84 (dd, J = 1.38, 8.38 Hz, 1H), 7.72 (d, J = 3.25 Hz, 1H), 7.59 ( d, J = 3.25 Hz, 1H), 7.44 (d, J = 8.50 Hz, 1H), 4.06 (br d, J = 12.51 Hz, 2H), 3.16 - 3.27 (m, 2H), 2.99 (d, J = 7.00 Hz, 2H), 2.08 (br d, J = 3.63 Hz, 1H), 1.80 (br d, J = 11.88 Hz, 2H), 1.28 - 1.40 (m, 2H);

[M+1]: 360.47.

Example 243: 2-(4-((4-methyl-1H-pyrazol-1-yl)methyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.33 (d, J = 1.63 Hz, 1H), 7.84 (dd, J = 1.81, 8.44 Hz, 1H), 7.42 - 7.48 (m, 2H), 7.23 ( s, 1H), 4.06 (br d, J = 12.13 Hz, 2H), 3.96 (d, J = 7.13 Hz, 2H), 3.14 - 3.22 (m, 2H), 2.05 - 2.17 (m, 1H), 2.00 ( s, 3H), 1.60 (br d, J = 10.88 Hz, 2H), 1.20 - 1.33 (m, 2H);

[M+1]: 357.44.

Example 244: 2-(4-((4H-1,2,4-triazol-4-yl)methyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.53 (s, 2H), 8.34 (d, J = 1.38 Hz, 1H), 7.84 (dd, J = 1.63, 8.38 Hz, 1H), 7.45 (d, J = 8.50 Hz, 1H), 3.92 - 4.17 (m, 6H), 3.18 (dt, J = 2.19, 12.60 Hz, 1H), 1.61 (br d, J = 12.01 Hz, 2H), 1.23 - 1.32 (m, 2H);

[M+1]: 344.40.

Example 245: 2-(4-(oxazol-5-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 8.36 (d, J = 1.63 Hz, 1H), 8.25 (s, 1H), 7.85 (dd, J = 1.75, 8.50 Hz, 1H), 7.47 (d, J = 8.50 Hz, 1H), 6.96 (s, 1H), 4.11 (br d, J = 13.13 Hz, 2H), 3.56 - 3.65 (m, 3H), 2.04 - 2.12 (m, 2H), 1.67 (br dd , J = 3.56, 12.57 Hz, 2H);

[M+1]: 330.37.

Example 246: 2-(4-(1H-pyrrol-1-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 8.37 (d, J = 1.63 Hz, 1H), 7.86 (dd, J = 1.75, 8.38 Hz, 1H), 7.48 (d, J = 8.38 Hz, 1H) , 6.87 (t, J = 2.13 Hz, 2H), 5.99 (t, J = 2.13 Hz, 2H), 4.12 - 4.33 (m, 5H), 2.08 (br d, J = 9.26 Hz, 2H), 1.87 - 2.00 (m, 2H);

[M+1]: 328.40.

Example 247: 2-(4-(4-methyl-1H-pyrazol-1-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.70 (br s, 1H), 8.38 (d, J = 1.63 Hz, 1H), 7.87 (dd, J = 1.75, 8.38 Hz, 1H), 7.57 (s) , 1H), 7.48 (d, J = 8.50 Hz, 1H), 7.24 (s, 1H), 4.36 - 4.53 (m, 1H), 4.17 (br d, J = 13.13 Hz, 2H), 3.36 - 3.47 (m , 2H), 2.12 (br d, J = 9.88 Hz, 2H), 1.92 - 2.04 (m, 5H);

[M+1]: 343.42.

Example 248: 2-(4-(1H-benzo[d]imidazol-2-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.39 (d, J = 1.63 Hz, 1H), 7.87 (dd, J = 1.75, 8.50 Hz, 1H), 7.58 - 7.66 (m, 2H), 7.49 ( d, J = 8.38 Hz, 1H), 7.29 - 7.36 (m, 2H), 4.21 (br d, J = 13.01 Hz, 3H), 2.22 (br d, J = 10.51 Hz, 2H), 1.97 (dq, J = 4.13, 12.30 Hz, 2H);

[M+1]: 379.45.

Example 249: 2-(4-(6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl)piperidin-1-yl) Benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 8.39 (d, J = 1.63 Hz, 1H), 7.87 (dd, J = 1.75, 8.50 Hz, 1H), 7.58 - 7.66 (m, 2H), 7.49 ( d, J = 8.38 Hz, 1H), 7.29 - 7.36 (m, 2H), 4.21 (br d, J = 13.01 Hz, 3H), 2.22 (br d, J = 10.51 Hz, 2H), 1.97 (dq, J = 4.13, 12.30 Hz, 2H);

[M+1]: 379.45.

Example 250: 2-(4-((benzo[d]thiazol-2-yloxy)methyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 8.35 (d, J = 1.75 Hz, 1H), 7.88 (dd, J = 1.00, 8.13 Hz, 1H), 7.85 (dd, J = 8.44 Hz, 1H) , 7.66 (d, J = 7.50 Hz, 1H), 7.46 (d, J = 8.50 Hz, 1H), 7.40 (dt, J = 1.31, 7.72 Hz, 1H), 7.24 - 7.31 (m, 1H), 4.47 ( d, J = 6.63 Hz, 2H), 4.13 (br d, J = 12.88 Hz, 2H), 3.23 - 3.31 (m, 3H), 1.91 (br d, J = 10.88 Hz, 2H), 1.42 (q, J = 12.76 Hz, 1H), 1.43 (q, J = 12.30 Hz, 1H);

[M+1]: 426.52.

Example 251: 2-(2-oxospiro[indoline-3,4'-piperidin]-1'-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 10.52 (s, 1H), 8.39 (d, J = 1.75 Hz, 1H), 7.87 (dd, J = 1.75, 8.50 Hz, 1H), 7.47 - 7.52 ( m, 2H), 7.22 (dt, J = 1.13, 7.69 Hz, 1H), 6.97 (dt, J = 0.94, 7.54 Hz, 1H), 6.89 (d, J = 7.75 Hz, 1H), 3.92 - 4.07 (m , 4H), 1.84-1.93 (m, 4H);

[M+1]: 380.43.

Example 252: 2-(4-(pyridin-3-ylmethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.69 (br d, J = 8.63 Hz, 1H), 8.48 (br t, J = 5.82 Hz, 2H), 8.36 (d, J = 1.50 Hz, 1H) , 7.85 (dd, J = 1.63, 8.50 Hz, 1H), 7.64 (br d, J = 7.75 Hz, 1H), 7.46 (d, J = 8.38 Hz, 1H), 7.36 (br s, 1H), 4.30 ( d, J = 5.75 Hz, 2H), 4.10 (br d, J = 13.13 Hz, 2H), 3.21 - 3.29 (m, 2H), 2.53 - 2.58 (m, 1H), 1.88 (br d, J = 10.76 Hz) , 2H), 1.60 - 1.74 (m, 2H);

[m+1]: 397.46.

Example 253: 2-(4-(pyridin-4-ylmethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.53 - 12.77 (m, 1H), 8.53 (br t, J = 5.94 Hz, 2H), 8.36 (d, J = 1.75 Hz, 1H), 7.85 (dd , J = 1.75, 8.50 Hz, 1H), 7.46 (d, J = 8.38 Hz, 1H), 7.26 (br s, 2H), 4.30 (br d, J = 5.75 Hz, 2H), 4.11 (br d, J = 12.63 Hz, 2H), 3.23 - 3.30 (m, 2H), 2.56 - 2.62 (m, 1H), 1.91 (br dd, J = 2.13, 12.88 Hz, 2H), 1.62 - 1.76 (m, 2H);

[M+1]: 397.46.

Example 254: 2-(4-((5-fluoropyridin-3-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.68 (br s, 1H), 8.52 (br t, J = 5.88 Hz, 1H), 8.33 - 8.42 (m, 2H), 7.85 (dd, J = 1.75 , 8.38 Hz, 1H), 7.56 (br d, J = 9.26 Hz, 1H), 7.46 (d, J = 8.50 Hz, 1H), 4.35 (d, J = 5.88 Hz, 2H), 4.10 (br d, J = 13.13 Hz, 2H), 3.21 - 3.31 (m, 3H), 2.54 - 2.60 (m, 1H), 1.89 (br dd, J = 2.63, 13.13 Hz, 2H), 1.58 - 1.76 (m, 2H);

[M+1]: 415.45.

Example 255: 2-(4-((6-(trifluoromethyl)pyridin-3-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.64 - 12.75 (m, 1H), 8.66 (s, 1H), 8.58 (br t, J = 5.82 Hz, 1H), 8.36 (d, J = 1.50 Hz) , 1H), 7.82 - 7.95 (m, 3H), 7.46 (d, J = 8.38 Hz, 1H), 4.40 (br d, J = 5.75 Hz, 2H), 4.10 (br d, J = 13.51 Hz, 2H) , 3.21 - 3.30 (m, 2H), 2.56 - 2.61 (m, 1H), 1.90 (br d, J = 10.88 Hz, 2H), 1.58 - 1.74 (m, 2H);

[M+1]: 465.46.

Example 256: 2-(4-((5-chloropyridin-3-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.60 - 12.78 (m, 1H), 8.47 - 8.59 (m, 2H), 8.44 (br s, 1H), 8.36 (s, 1H), 7.85 (dd, J = 1.25, 8.50 Hz, 1H), 7.77 (s, 1H), 7.46 (d, J = 8.38 Hz, 1H), 4.32 (br d, J = 5.75 Hz, 2H), 4.10 (br d, J = 12.13 Hz, 2H), 3.19 - 3.29 (m, 2H), 2.55 - 2.59 (m, 1H), 1.89 (br d, J = 11.38 Hz, 2H), 1.59 - 1.73 (m, 2H);

[M+1]: 431.91.

Example 257: 2-(4-((2-methoxypyridin-4-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.63 - 12.81 (m, 1H), 8.49 (t, J = 6.07 Hz, 1H), 8.36 (d, J = 1.63 Hz, 1H), 8.08 (d, J = 5.25 Hz, 1H), 7.85 (dd, J = 1.81, 8.44 Hz, 1H), 7.46 (d, J = 8.50 Hz, 1H), 6.84 (dd, J = 1.25, 5.25 Hz, 1H), 6.63 ( s, 1H), 4.25 (d, J = 6.00 Hz, 2H), 4.11 (br d, J = 12.88 Hz, 2H), 3.83 (s, 3H), 3.20 - 3.30 (m, 2H), 2.55 - 2.60 ( m, 1H), 1.90 (br dd, J = 2.50, 13.13 Hz, 2H), 1.62 - 1.73 (m, 2H);

[M+1]: 427.49.

Example 258: 2-(4-carboxypiperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.55 (br s, 2H), 8.35 (d, J = 1.38 Hz, 1H), 7.85 (dd, J = 1.56, 8.44 Hz, 1H), 7.46 (d , J = 8.50 Hz, 1H), 4.01 (br d, J = 13.01 Hz, 2H), 3.25 - 3.33 (m, 2H), 2.60 (ddd, J = 3.81, 7.10, 10.72 Hz, 1H), 1.97 (br dd, J = 2.81, 13.20 Hz, 2H), 1.56 - 1.70 (m, 2H);

[M+1]: 307.34.

Example 259: 2-(4-((6-methoxypyridin-3-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.68 (br d, J = 10.51 Hz, 1H), 8.39 (t, J = 5.82 Hz, 1H), 8.35 (d, J = 1.63 Hz, 1H), 8.04 (d, J = 2.00 Hz, 1H), 7.85 (dd, J = 1.81, 8.44 Hz, 1H), 7.58 (dd, J = 2.38, 8.50 Hz, 1H), 7.46 (d, J = 8.38 Hz, 1H) ), 6.78 (d, J = 8.50 Hz, 1H), 4.21 (d, J = 5.88 Hz, 2H), 4.09 (br d, J = 13.26 Hz, 2H), 3.82 (s, 3H), 3.25 (dt, J = 2.56, 12.60 Hz, 2H), 2.55 - 2.61 (m, 1H), 1.81 - 1.93 (m, 2H), 1.58 - 1.73 (m, 2H);

[M+1]: 427.49.

Example 260: 2-(4-(cyclopropylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.61 - 12.79 (m, 1H), 8.35 (d, J = 1.50 Hz, 1H), 7.92 (br d, J = 4.00 Hz, 1H), 7.85 (dd , J = 1.69, 8.44 Hz, 1H), 7.45 (d, J = 8.50 Hz, 1H), 4.07 (br d, J = 12.88 Hz, 2H), 3.17 - 3.28 (m, 2H), 2.61 (ddd, J = 3.94, 7.44, 11.13 Hz, 2H), 1.71 - 1.86 (m, 2H), 1.55 - 1.68 (m, 2H), 0.53 - 0.65 (m, 2H), 0.33 - 0.44 (m, 2H);

[M+1]: 346.42.

Example 261: 2-(4-(3-hydroxypropylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.69 (br d, J = 4.00 Hz, 1H), 8.35 (d, J = 1.63 Hz, 1H), 7.81 - 7.88 (m, 2H), 7.46 (d , J = 8.51 Hz, 1H), 4.41 (t, J = 5.19 Hz, 1H), 4.08 (br d, J = 12.88 Hz, 2H), 3.37 - 3.44 (m, 2H), 3.24 (dt, J = 2.69 , 12.60 Hz, 2H), 3.06 - 3.14 (m, 2H), 2.44 (dt, J = 3.50, 7.38 Hz, 1H), 1.77 - 1.87 (m, 2H), 1.58 - 1.69 (m, 2H), 1.55 ( t, J = 6.75 Hz, 2H);

[M+1]: 364.43.

Example 262: 2-(4-(carboxymethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.62 (br d, J = 3.75 Hz, 2H), 8.35 (d, J = 1.63 Hz, 1H), 8.23 (t, J = 5.94 Hz, 1H), 7.85 (dd, J = 1.75, 8.50 Hz, 1H), 7.46 (d, J = 8.38 Hz, 1H), 4.08 (br d, J = 13.01 Hz, 2H), 3.74 (d, J = 6.00 Hz, 2H) , 3.22 - 3.31 (m, 2H), 2.58 (br s, 1H), 1.79 - 1.91 (m, 2H), 1.55 - 1.71 (m, 2H);

[M+1]: 364.39.

Example 263: 2-(4-((1H-pyrrol-2-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.51 - 12.84 (m, 1H), 10.55 (br s, 1H), 8.35 (d, J = 1.50 Hz, 1H), 8.17 (br t, J = 5.32 Hz, 1H), 7.85 (dd, J = 1.63, 8.38 Hz, 1H), 7.46 (d, J = 8.50 Hz, 1H), 6.63 (br d, J = 1.50 Hz, 1H), 5.81 - 5.95 (m, 2H), 4.20 (d, J = 5.38 Hz, 2H), 4.09 (br d, J = 12.76 Hz, 2H), 3.20 - 3.28 (m, 2H), 2.60 (br s, 1H), 1.79 - 1.90 (m , 2H), 1.59 - 1.73 (m, 2H);

[M+1]: 385.45.

Example 264: 2-(4-(thiazol-2-ylmethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.60 - 12.78 (m, 1H), 8.83 (t, J = 6.07 Hz, 1H), 8.36 (d, J = 1.63 Hz, 1H), 7.85 (dd, J = 1.75, 8.38 Hz, 1H), 7.72 (d, J = 3.25 Hz, 1H), 7.62 (d, J = 3.25 Hz, 1H), 7.46 (d, J = 8.50 Hz, 1H), 4.56 (d, J = 6.00 Hz, 2H), 4.10 (br d, J = 13.26 Hz, 2H), 3.23 - 3.31 (m, 2H), 2.60 (br d, J = 4.00 Hz, 1H), 1.90 (br dd, J = 2.25, 12.76 Hz, 2H), 1.61 - 1.75 (m, 2H);

[M+1]: 403.49.

Example 265: 2-(4-(2-(1H-pyrrol-1-yl)ethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

^1H NMR (400 MHz, DMSO-d ₆ ) Shift 12.62 - 12.79 (m, 1H), 8.35 (d, J = 1.63 Hz, 1H), 7.99 (br t, J = 5.44 Hz, 1H), 7.85 (dd , J = 1.69, 8.44 Hz, 1H), 7.46 (d, J = 8.38 Hz, 1H), 6.71 (t, J = 2.06 Hz, 2H), 5.98 (t, J = 2.00 Hz, 2H), 4.06 (br d, J = 12.76 Hz, 2H), 3.94 (t, J = 6.13 Hz, 2H), 3.19 - 3.29 (m, 2H), 2.41 - 2.46 (m, 1H), 1.76 - 1.84 (m, 2H), 1.56 - 1.69 (m, 2H);

[M+1]: 399.48.

Example 266: 2-(4-(2-(1H-imidazol-1-yl)ethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid

¹ H NMR (400 MHz, DMSO-d ₆ ) Shift 12.64 - 12.76 (m, 1H), 9.14 (s, 1H), 8.35 (d, J = 1.50 Hz, 2H), 7.86 (d, J = 1.75 Hz, 1H), 7.83 (d, J = 1.75 Hz, 1H), 7.75 (s, 1H), 7.64 (s, 1H), 7.45 (d, J = 8.50 Hz, 1H), 4.27 (br t, J = 5.38 Hz) , 2H), 4.05 (br d, J = 13.26 Hz, 2H), 3.47 - 3.53 (m, 2H), 3.25 (br dd, J = 2.19, 12.69 Hz, 2H), 2.44 - 2.49 (m, 1H), 1.75 - 1.82 (m, 2H), 1.49 - 1.64 (m, 2H);

[M+1]: 400.47.

The structural formulas of the compounds prepared according to Examples 1 to 266 are shown in Table 1 below.

Example constitutional formula Example constitutional formula One

2

3

4

5

6

7

8

9

10

11

12

13

14

15

16

17

18

19

20

21

22

23

24 25

26

27

28

29

30

31

32

33

34

35

36 37

38

39

40

41

42

43

44

45

46

47

48

49

50

51

52

53

54

55

56

57

58

59

60

61

62

63

64

65

66

67

68

69

70

71

72

73

74

75

76

77

78

79

80

81

82

83

84

85

86

87

88

89

90

91

92

93

94

95

96

97

98

99

100

101

102

103

104

105

106

107

108

109

110

111

112

113

114

115

116

117

118

119

120

121

122

123

124

125

126

127

128

129

130

131

132

133

134

135

136

137

138

139

140

141

142

143

144

145

146

147

148

149

150

151

152

153

154

155

156

157

158

159

160

161

162

163

164

165

166

167

168

169

170

171

172

173

174

175

176

177

178

179

180

181

182

183

184

185

186

187

188

189

190

191

192

193

194

195 196

197

198

199

200

201

202

203

204

205

206 207

208

209

210

211

212

213

214

215

216

217

218

219

220

221

222

223

224

225

226

227

228

229

230

231

232

233

234

235

236

237

238

239

240

241

242

243

244

245

246

247

248

249

250

251

252

253

254

255

256

257

258

259

260

261

262

263

264

265

266

Experimental Example 1: Enzyme activity inhibition ability test of 17β-HSD13 inhibitor (NAD/NADH-Glo™ assay)

To evaluate the ability of the compounds prepared according to Examples 1 to 266 to inhibit 17β-HSD13 enzyme activity, the NAD/NADH-Glo™ assay (Promega, Cat. No. G9071) was tested as follows. Specifically, each compound was prepared at a concentration of 1 μM using a buffer solution (40mM Tris, 20mM MgCl ₂ , 0.1 mg/mL bovine serum albumin in H ₂ O), and then added with 0.5mM NAD (Sigma Aldrich, Cat. No. N8285-15VL), 75 μM estradiol (Sigma Aldrich, Cat. No. E8875) and 200 ng of 17β-HSD13 enzyme (Origene, Cat. No. TP313132) at 30°C for 3 hours. I ordered it. Afterwards, an equal amount of NAD/NADH-Glo™ reagent was added and reacted at 30°C for 1 hour. When the reaction was completed, luminescence was measured using a Synergy™ NEO microplate reader (BioTEK, NEOB-1311189).

The data was analyzed using the RLU (relative light unit) value of the measured luminescence to verify the ability of each compound to inhibit 17β-HSD13 enzyme activity. Specifically, the RLU value of the sample not treated with the above compounds was set as 100% control, and the ability to inhibit 17β-HSD13 enzyme activity was confirmed by excluding the % residual activity of the 17β-HSD13 enzyme in the sample treated with the compounds. As a result, is shown in Table 2 below.

Example inhibition rate Example inhibition rate Example inhibition rate Example Inhibition rate One +++ 2 + 3 + 4 + 5 + 6 + 7 + 8 + 9 + 10 + 11 + 12 + 13 + 14 + 15 + 16 + 17 + 18 ++ 19 + 20 ++ 21 ++ 22 + 23 +++ 24 +++ 25 +++ 26 + 27 + 28 ++ 29 + 30 + 31 + 32 + 33 + 34 + 35 + 36 ++ 37 + 38 + 39 + 40 ++ 41 + 42 + 43 ++ 44 +++ 45 + 46 + 47 ++ 48 + 49 + 50 + 51 + 52 + 53 + 54 + 55 ++ 56 + 57 + 58 + 59 + 60 + 61 + 62 + 63 + 64 + 65 + 66 + 67 + 68 ++ 69 + 70 + 71 + 72 + 73 + 74 + 75 + 76 + 77 + 78 + 79 + 80 + 81 + 82 + 83 ++ 84 + 85 ++ 86 + 87 + 88 ++ 89 + 90 + 91 + 92 ++ 93 ++ 94 +++ 95 +++ 96 + 97 + 98 +++ 99 + 100 + 101 + 102 + 103 ++ 104 ++ 105 ++ 106 + 107 + 108 + 109 + 110 ++ 111 + 112 + 113 + 114 + 115 + 116 ++ 117 + 118 + 119 + 120 + 121 + 122 + 123 + 124 ++ 125 ++ 126 + 127 ++ 128 + 129 ++ 130 ++ 131 + 132 + 133 ++ 134 ^* ++ 135 + 136 + 137 + 138 + 139 + 140 + 141 ++ 142 + 143 ++ 144 ++ 145 +++ 146 +++ 147 +++ 148 +++ 149 +++ 150 + 151 + 152 + 153 + 154 ++ 155 ^* ++ 156 ^* ++ 157 ^* ++ 158 + 159 +++ 160 + 161 + 162 + 163 + 164 + 165 + 166 + 167 + 168 + 169 + 170 + 171 + 172 + 173 + 174 + 175 + 176 + 177 + 178 + 179 + 180 + 181 + 182 + 183 + 184 + 185 + 186 + 187 ++ 188 + 189 + 190 + 191 + 192 +++ 193 ++ 194 ++ 195 + 196 ++ 197 ++ 198 ++ 199 + 200 ++ 201 ++ 202 + 203 + 204 + 205 + 206 + 207 + 208 ^* ++ 209 + 210 ++ 211 ++ 212 ++ 213 ++ 214 + 215 + 216 + 217 + 218 + 219 + 220 + 221 + 222 + 223 + 224 + 225 + 226 + 227 + 228 + 229 + 230 + 231 ++ 232 + 233 + 234 + 235 + 236 + 237 + 238 + 239 + 240 + 241 + 242 + 243 + 244 + 245 + 246 + 247 + 248 + 249 + 250 + 251 + 252 + 253 + 254 + 255 + 256 + 257 + 258 + 259 + 260 + 261 + 262 + 263 + 264 + 265 + 266 +

- Based on the inhibition rate at 1 μM, + if it is less than 40. If it is between 40 and less than 70, it is marked as ++, and if it is above 70, it is marked as +++.

- In the examples marked with *, based on the IC ₅₀ value, if it is less than 0.4, it is denoted as +++, and if it is 0.4 or more but less than 2, it is denoted as ++.

From the above description, those skilled in the art to which the present invention pertains will be able to understand that the present invention can be implemented in other specific forms without changing its technical idea or essential features. In this regard, the embodiments described above should be understood in all respects as illustrative and not restrictive. The scope of the present invention should be interpreted as including the meaning and scope of the patent claims described below rather than the detailed description above, and all changes or modified forms derived from the equivalent concept thereof are included in the scope of the present invention.

Claims (15)

A compound represented by the following formula (1) or a pharmaceutically acceptable salt thereof:
[Formula 1]

In Formula 1,
X is a simple binding, -nhco- (ch ₂ ) _m- , -N (ch ₃ ) co- (ch ₂ ) _n- , -nhco- (ch ₂ ) _p -NHCO-, or -NHCO- (CH ₂ ) _q -O-,
m and n are each independently integers from 0 to 5,
p is 2,
q is 1,
R ₁ is carboxyl, or C _1-4 alkoxycarbonyl,
R ₂ is hydrogen, C _1-4 alkyl, C _1-4 alkoxy, halogen, or hydroxy,
R ₃ is phenyl, pyridinyl, furanyl, thiophenyl, indolyl, benzotriazolyl, benzothiazolyl, benzoimidazolyl, pyrrolopyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrrolyl, spiro Heptanyl, cyclobutyl, cyclohexyl, dihydropyridinyl, quinolinyl, imidazolyl, piperazinyl, or piperidinyl,
The phenyl, indolyl, benzotriazolyl, benzothiazolyl, benzoimidazolyl, pyrrolopyridinyl, pyrazinyl, pyrrolyl, spiroheptanyl, cyclobutyl, cyclohexyl, dihydropyridinyl, quinolinyl, Dazolyl, or piperidinyl, is unsubstituted or cyano, halogen, nitro, oxo, hydroxy, carboxyl, amino, C _1-4 alkyl, C _1-4 alkenyl, C _1-4 alkoxy, C _{1- 4} haloalkyl, C _1-4 haloalkoxy, C _1-4 alkoxycarbonyl, C _1-4 alkylcarbonyl, C _1-4 alkylthio, C _1-4 alkylamino, C _1-4 alkoxy-C _{1- 4} Alkoxy, C _3-10 Cycloalkyl, C _3-10 Cycloalkyl-C _1-4 Alkoxy, C _3-10 Cycloalkenyl, C _6-10 Aryloxy, C _3-10 Cycloalkyl-C _1-4 Alkyl Carbonyl, C _6-10 Aryl-C _1-4 Alkylcarbonyl, C _6-10 Arylsulfonyl, C _6-10 Aryl-C _1-4 Alkylsulfonyl, C _3-10 Cycloalkylcarbamoyl, Hydroxy -C _1-4 alkylcarbamoyl, carboxy-C _1-4 alkylcarbamoyl, 5 to 10 membered heterocyclyl, 5 to 10 membered heterocyclyloxy, 5 to 10 membered heteroaryl, 5 to 10 membered heteroaryloxy , 5 to 10 membered heteroarylamino, 5 to 10 membered heteroarylsulfonyl, 5 to 10 membered heteroaryl-C _1-4 alkyl, 5 to 10 membered heteroaryloxy-C _1-4 alkyl, 5 to 10 membered hetero. is substituted with one or more selected from the group consisting of aryl-C _1-4 alkylamino, and 5 to 10 membered heteroaryl-C _1-4 alkylcarbamoyl,
Pyridinyl, furanyl, thiophenyl, pyrimidinyl, pyridazinyl, or piperazinyl is cyano, halogen, nitro, oxo, hydroxy, carboxyl, amino, C _1-4 alkyl, C _1-4 alkyl. Kenyl, C _1-4 alkoxy, C _1-4 haloalkyl, C _1-4 haloalkoxy, C _1-4 alkoxycarbonyl, C _1-4 alkylcarbonyl, C _1-4 alkylthio, C _1-4 alkyl Amino, C _1-4 alkoxy-C _1-4 alkoxy, C _4-10 cycloalkyl, C _3-10 cycloalkyl-C _1-4 alkoxy, C _3-10 cycloalkenyl, C _6-10 aryloxy, C _3-10 cycloalkyl-C _1-4 alkylcarbonyl, C _6-10 aryl-C _1-4 alkylcarbonyl, C _6-10 arylsulfonyl, C _6-10 aryl-C _1-4 alkylsulfonyl, C _3-10 cycloalkylcarbamoyl, hydroxy-C _1-4 alkylcarbamoyl, carboxy-C _1-4 alkylcarbamoyl, 5 to 10 membered heterocyclyl, 5 to 10 membered heterocyclyloxy, 5 to 10 membered One-membered heteroaryl, 5-10 membered heteroaryloxy, 5-10 membered heteroarylamino, 5-10 membered heteroarylsulfonyl, 5-10 membered heteroaryl-C _1-4 alkyl, 5-10 membered heteroaryloxy- Substituted with one or more selected from the group consisting of C _1-4 alkyl, 5 to 10 membered heteroaryl-C _1-4 alkylamino, and 5 to 10 membered heteroaryl-C _1-4 alkylcarbamoyl.
According to paragraph 1,
X is a simple binding, -nhco-, -n (ch ₃ ) co-, -N (ch ₃ ) co- (ch ₂ )-, -NHCO- (Ch ₂ ) ₂ -NHCO-, or -NHCO- (CH ₂ ) -O-, a compound or a pharmaceutically acceptable salt thereof.
According to paragraph 1,
R ₁ is carboxyl or ethoxycarbonyl, a compound or a pharmaceutically acceptable salt thereof.
According to paragraph 1,
R ₂ is hydrogen, methyl, methoxy, fluoro, chloro, or hydroxy, or a pharmaceutically acceptable salt thereof.
A compound represented by the following formula (1) or a pharmaceutically acceptable salt thereof:
[Formula 1]

In Formula 1,
X is a simple binding, -nhco- (ch ₂ ) _m- , -N (ch ₃ ) co- (ch ₂ ) _n- , -nhco- (ch ₂ ) _p -NHCO-, or -NHCO- (CH ₂ ) _q -O-,
m and n are each independently integers from 0 to 5,
p is 2,
q is 1,
R ₁ is carboxyl, or C _1-4 alkoxycarbonyl,
R ₂ is hydrogen, C _1-4 alkyl, C _1-4 alkoxy, halogen, or hydroxy,
R ₃ is unsubstituted or cyano, fluoro, chloro, bromo, iodo, nitro, oxo, hydroxy, carboxyl, amino, methyl, tert-butyl, ethenyl, propenyl, isopropenyl, butenyl , isobutenyl, methoxy, ethoxy, propoxy, isopropoxy, isobutoxy, trifluoromethyl, difluoromethoxy, 1,1,1-trifluoroethoxy, methoxycarbonyl, methylcarbonyl , methylthio, methylamino, methoxyethoxy, cyclopropyl, cyclopropylmethoxy, cyclopentenyl, phenoxy, cyclopentylethylcarbonyl, phenylmethylcarbonyl, phenylethylcarbonyl, phenylsulfonyl, benzylsulfonyl. , carboxycyclopropyl, cyclopropylcarbamoyl, hydroxypropylcarbamoyl, carboxymethylcarbamoyl, pyrrolidinyl, morpholinyl, dihydrobenzofuran, dihydropyrrolotriazole, tetrahydropyranyloxy, furanyl, Pyridinyl, pyrrolyl, oxazolyl, pyrazolyl, benzoimidazolyl, benzothiazolyl, indolinyl, benzotriazolyloxy, pyridinyloxy, pyrazolyloxy, pyrimidinylamino, thiophenylsulfonyl, pyridinylmethyl. , pyrazolylmethyl, triazolylmethyl, thiazolylmethyl, pyridinyloxymethyl, benzothiazolyloxymethyl, pyridinylmethylamino, thiazolylmethylcarbamoyl, imidazolylethylcarbamoyl, pyrrolylmethylcarbamoyl, pyrrolyl Substituted with one or more selected from the group consisting of ethylcarbamoyl, and pyridinylmethylcarbamoyl, phenyl, indolyl, benzotriazolyl, benzothiazolyl, benzoimidazolyl, pyrrolopyridinyl, pyrazinyl, pyrrolyl , spiroheptanyl, cyclobutyl, cyclohexyl, dihydropyridinyl, quinolinyl, imidazolyl, or piperidinyl, or
Cyano, fluoro, chloro, bromo, iodo, nitro, oxo, hydroxy, carboxyl, amino, methyl, tert-butyl, ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, methoxy , ethoxy, propoxy, isopropoxy, isobutoxy, trifluoromethyl, difluoromethoxy, 1,1,1-trifluoroethoxy, methoxycarbonyl, methylcarbonyl, methylthio, methylamino. , methoxyethoxy, cyclopropylmethoxy, cyclopentenyl, phenoxy, cyclopentylethylcarbonyl, phenylmethylcarbonyl, phenylethylcarbonyl, phenylsulfonyl, benzylsulfonyl, cyclopropylcarbamoyl, hydroxypropyl Carbamoyl, carboxymethylcarbamoyl, pyrrolidinyl, morpholinyl, dihydrobenzofuran, dihydropyrrolotriazole, tetrahydropyranyloxy, furanyl, pyridinyl, pyrrolyl, oxazolyl, pyrazolyl, benzoyl. Imidazolyl, benzothiazolyl, indolinyl, benzotriazolyloxy, pyridinyloxy, pyrazolyloxy, pyrimidinylamino, thiophenylsulfonyl, pyridinylmethyl, pyrazolylmethyl, triazolylmethyl, thiazolylmethyl, A group consisting of pyridinyloxymethyl, benzothiazolyloxymethyl, pyridinylmethylamino, thiazolylmethylcarbamoyl, imidazolylethylcarbamoyl, pyrrolylmethylcarbamoyl, pyrrolylethylcarbamoyl, and pyridinylmethylcarbamoyl. substituted with one or more selected from pyridinyl, furanyl, thiophenyl, pyrimidinyl, pyridazinyl, or piperazinyl.
A compound represented by the following formula (1) or a pharmaceutically acceptable salt thereof:
[Formula 1]

In Formula 1,
When X is a simple combination,
R ₁ is carboxyl, or C _1-4 alkoxycarbonyl,
R ₂ is hydrogen, C _1-4 alkyl, C _1-4 alkoxy, halogen, or hydroxy,
R ₃ is unsubstituted or cyano, fluoro, chloro, bromo, iodo, nitro, oxo, hydroxy, carboxyl, amino, methyl, tert-butyl, ethenyl, propenyl, isopropenyl, butenyl , isobutenyl, methoxy, ethoxy, propoxy, isopropoxy, isobutoxy, trifluoromethyl, difluoromethoxy, 1,1,1-trifluoroethoxy, methoxycarbonyl, methylcarbonyl , methylthio, methylamino, methoxyethoxy, cyclopropylmethoxy, cyclopentenyl, phenoxy, cyclopentylethylcarbonyl, phenylmethylcarbonyl, phenylethylcarbonyl, phenylsulfonyl, benzylsulfonyl, cyclopropyl Carbamoyl, hydroxypropylcarbamoyl, carboxymethylcarbamoyl, pyrrolidinyl, morpholinyl, dihydrobenzofuran, dihydropyrrolotriazole, tetrahydropyranyloxy, furanyl, pyridinyl, pyrrolyl, oxa Zolyl, pyrazolyl, benzoimidazolyl, benzothiazolyl, indolinyl, benzotriazolyloxy, pyridinyloxy, pyrazolyloxy, pyrimidinylamino, thiophenylsulfonyl, pyridinylmethyl, pyrazolylmethyl, triazolyl. Methyl, thiazolylmethyl, pyridinyloxymethyl, benzothiazolyloxymethyl, pyridinylmethylamino, thiazolylmethylcarbamoyl, imidazolylethylcarbamoyl, pyrrolylmethylcarbamoyl, pyrrolylethylcarbamoyl, and pyridinyl. Piperazinyl, or piperidinyl substituted with one or more selected from the group consisting of methylcarbamoyl.
According to paragraph 1,
The compound is
(1) 2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid),
(2) 2-(3-phenylbutanamido)benzo[d]thiazole-6-carboxylic acid,
(4) 2-(2-methoxyisonicotinamido)benzo[d]thiazole-7-carboxylic acid (2-(2-methoxyisonicotinamido)benzo[d]thiazole-7-carboxylic acid),
(5) 2-(2-cyanoisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-cyanoisonicotinamido)benzo[d]thiazole-6-carboxylic acid),
(6) 2-(6-fluoronicotinamido)benzo[d]thiazole-6-carboxylic acid,
(7) 2-(2-methyl-5-nitrobenzamido)benzo[d]thiazole-6-carboxylic acid (2-(2-methyl-5-nitrobenzamido)benzo[d]thiazole-6-carboxylic acid),
(8) 2-(4-methylthiophene-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(4-methylthiophene-2-carboxamido)benzo[d]thiazole-6- carboxylic acid),
(9) 2-(3-nitrobenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-nitrobenzamido)benzo[d]thiazole-6-carboxylic acid),
(10) 2-(2-nitroisonicotinamido)benzo[d]thiazole-6-carboxylic acid,
(11) 2-(3-fluorobenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-fluorobenzamido)benzo[d]thiazole-6-carboxylic acid),
(12) 2-(3,5-difluorobenzamido)benzo[d]thiazole-6-carboxylic acid ,
(13) 2-(2-fluoroisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-fluoroisonicotinamido)benzo[d]thiazole-6-carboxylic acid),
(14) 2-(3,7-difluoro-1H-indole-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(3,7-difluoro-1H-indole- 2-carboxamido)benzo[d]thiazole-6-carboxylic acid),
(15) 2-(4-chloro-3-fluorobenzamido)benzo[d]thiazole-7-carboxylic acid (2-(4-chloro-3-fluorobenzamido)benzo[d]thiazole-7- carboxylic acid),
(16) 2-(benzo[d]thiazole-4-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(benzo[d]thiazole-4-carboxamido)benzo[d]thiazole -6-carboxylic acid),
(17) 2-(4-chloro-2-methoxybenzamido)benzo[d]thiazole-7-carboxylic acid (2-(4-chloro-2-methoxybenzamido)benzo[d]thiazole-7- carboxylic acid),
(18) 2-(1H-benzo[d][1,2,3]triazole-6-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(1H-benzo[d] [1,2,3]triazole-6-carboxamido)benzo[d]thiazole-6-carboxylic acid),
(19) 2-(1H-pyrrolo[2,3-b]pyridine-4-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(1H-pyrrolo[2,3-b ]pyridine-4-carboxamido)benzo[d]thiazole-6-carboxylic acid),
(20) 2-(1H-benzo[d]imidazole-5-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(1H-benzo[d]imidazole-5-carboxamido)benzo [d]thiazole-6-carboxylic acid),
(21) 2-(3-fluoro-4-methylbenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-fluoro-4-methylbenzamido)benzo[d]thiazole-6- carboxylic acid),
(22) 2-(2,6-dichloroisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2,6-dichloroisonicotinamido)benzo[d]thiazole-6-carboxylic acid),
(23) 2-(5-chloronicotinamido)benzo[d]thiazole-6-carboxylic acid,
(24) 2-(5-fluoronicotinamido)benzo[d]thiazole-6-carboxylic acid,
(25) 2-(2-chloroisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-chloroisonicotinamido)benzo[d]thiazole-6-carboxylic acid),
(26) 2-(3-chloro-4-methylbenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-chloro-4-methylbenzamido)benzo[d]thiazole-6-carboxylic acid),
(27) 2-(3,4-dichlorobenzamido)benzo[d]thiazole-6-carboxylic acid,
(28) 2-(6-ethoxynicotinamido)benzo[d]thiazole-6-carboxylic acid,
(29) 2-(6-cyanonicotinamido)benzo[d]thiazole-6-carboxylic acid,
(30) 2-(2-oxo-1,2-dihydropyridine-4-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(2-oxo-1,2-dihydropyridine- 4-carboxamido)benzo[d]thiazole-6-carboxylic acid),
(31) 2-(2-methoxypyrimidine-4-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(2-methoxypyrimidine-4-carboxamido)benzo[d]thiazole-6 -carboxylic acid),
(32) 2-(4-cyano-3-fluorobenzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-cyano-3-fluorobenzamido)benzo[d]thiazole-6 -carboxylic acid),
(33) 2-(3-cyano-4-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-cyano-4-methoxybenzamido)benzo[d]thiazole-6 -carboxylic acid),
(34) 2-(4-chloro-3-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-chloro-3-methoxybenzamido)benzo[d]thiazole-6- carboxylic acid),
(36) 2-(5-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid),
(37) 2-(2-methylpyrimidine-5-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(2-methylpyrimidine-5-carboxamido)benzo[d]thiazole-6- carboxylic acid),
(38) 2-(3-chloro-2,4,5-trifluorobenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-chloro-2,4,5-trifluorobenzamido )benzo[d]thiazole-6-carboxylic acid),
(39) 2-(6-cyanonicotinamido)benzo[d]thiazole-6-carboxylic acid,
(41) 2-(5-cyanonicotinamido)benzo[d]thiazole-6-carboxylic acid,
(42) 2-(2-(pyrrolidin-1-yl)isonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(pyrrolidin-1-yl)isonicotinamido)benzo [d]thiazole-6-carboxylic acid),
(43) 2-(2,6-difluoroisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2,6-difluoroisonicotinamido)benzo[d]thiazole-6-carboxylic acid ),
(44) 2-(3,5-difluoro-4-hydroxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3,5-difluoro-4-hydroxybenzamido)benzo[ d]thiazole-6-carboxylic acid),
(45) 2-(2-(trifluoromethyl)pyrimidine-5-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(trifluoromethyl)pyrimidine-5-carboxamido) benzo[d]thiazole-6-carboxylic acid),
(46) 2-(5-(trifluoromethyl)pyrazine-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(5-(trifluoromethyl)pyrazine-2-carboxamido)benzo [d]thiazole-6-carboxylic acid),
(47) 2-(5-methoxypyrazine-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(5-methoxypyrazine-2-carboxamido)benzo[d]thiazole-6- carboxylic acid),
(48) 2-(6-methylpyridazine-3-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(6-methylpyridazine-3-carboxamido)benzo[d]thiazole-6- carboxylic acid),
(49) 2-(2-fluoro-3-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(2-fluoro-3-(trifluoromethyl)benzamido) benzo[d]thiazole-6-carboxylic acid),
(50) 2-(4-methyl-3-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-methyl-3-(trifluoromethyl)benzamido)benzo [d]thiazole-6-carboxylic acid),
(51) 2-(4-methoxy-3-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-methoxy-3-(trifluoromethyl)benzamido) benzo[d]thiazole-6-carboxylic acid),
(52) 2-(3,5-bis(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3,5-bis(trifluoromethyl)benzamido)benzo[d ]thiazole-6-carboxylic acid),
(53) 2-(3-nitro-5-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-nitro-5-(trifluoromethyl)benzamido)benzo [d]thiazole-6-carboxylic acid),
(54) 2-(2-chloro-4-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(2-chloro-4-(trifluoromethyl)benzamido)benzo [d]thiazole-6-carboxylic acid),
(55) 2-(2-fluoro-4-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(2-fluoro-4-(trifluoromethyl)benzamido) benzo[d]thiazole-6-carboxylic acid),
(56) 2-(3-methoxy-4-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-methoxy-4-(trifluoromethyl)benzamido) benzo[d]thiazole-6-carboxylic acid),
(57) 2-(3-chloro-4-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-chloro-4-(trifluoromethyl)benzamido)benzo [d]thiazole-6-carboxylic acid),
(58) 2-(3,5-difluoro-4-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3,5-difluoro-4- (trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid),
(59) 2-(3-chloro-5-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-chloro-5-(trifluoromethyl)benzamido)benzo [d]thiazole-6-carboxylic acid),
(60) 2-(3-methoxy-5-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-methoxy-5-(trifluoromethyl)benzamido) benzo[d]thiazole-6-carboxylic acid),
(61) 2-(4-chloro-3-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-chloro-3-(trifluoromethyl)benzamido)benzo [d]thiazole-6-carboxylic acid),
(62) 2-(2,4-bis(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(2,4-bis(trifluoromethyl)benzamido)benzo[d ]thiazole-6-carboxylic acid),
(63) 2-(3-cyano-5-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-cyano-5-(trifluoromethyl)benzamido) benzo[d]thiazole-6-carboxylic acid),
(64) 2-(2-chloro-3-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(2-chloro-3-(trifluoromethyl)benzamido)benzo [d]thiazole-6-carboxylic acid),
(65) 2-(2-chloro-5-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(2-chloro-5-(trifluoromethyl)benzamido)benzo [d]thiazole-6-carboxylic acid),
(67) 2-(4-chloro-3-fluoro-N-methylbenzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-chloro-3-fluoro-N-methylbenzamido) benzo[d]thiazole-6-carboxylic acid),
(68) 2-(5-(methoxycarbonyl)picolinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-(methoxycarbonyl)picolinamido)benzo[d]thiazole-6- carboxylic acid),
(69) 2-(6-chloro-5-fluoropicolinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-chloro-5-fluoropicolinamido)benzo[d]thiazole-6 -carboxylic acid),
(70) 2-(2-chloro-6-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-chloro-6-methoxyisonicotinamido)benzo[d]thiazole-6 -carboxylic acid),
(72) 2-(2-(3,4-dichlorophenyl)acetamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(3,4-dichlorophenyl)acetamido)benzo[d ]thiazole-6-carboxylic acid),
(73) 2-(2-(3,5-difluorophenyl)acetamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(3,5-difluorophenyl)acetamido)benzo [d]thiazole-6-carboxylic acid),
(74) 2-(3-phenylpropanamido)benzo[d]thiazole-6-carboxylic acid,
(75) 2-(2-(2-fluorophenyl)acetamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(2-fluorophenyl)acetamido)benzo[d]thiazole- 6-carboxylic acid),
(76) 2-(3-(5-fluoronicotinamido)propanamido)benzo[d]thiazole-6-carboxylic acid (2-(3-(5-fluoronicotinamido)propanamido)benzo[d] thiazole-6-carboxylic acid),
(77) 2-(3-(5-chloronicotinamido)propanamido)benzo[d]thiazole-6-carboxylic acid (2-(3-(5-chloronicotinamido)propanamido)benzo[d]thiazole -6-carboxylic acid),
(78) 2-(3-(5-(trifluoromethyl)nicotinamido)propanamido)benzo[d]thiazole-6-carboxylic acid (2-(3-(5-(trifluoromethyl)nicotinamido) )propanamido)benzo[d]thiazole-6-carboxylic acid),
(79) 2-(3-(6-(trifluoromethyl)nicotinamido)propanamido)benzo[d]thiazole-6-carboxylic acid (2-(3-(6-(trifluoromethyl)nicotinamido) )propanamido)benzo[d]thiazole-6-carboxylic acid),
(80) 2-(3-(4-chloro-3-fluorophenyl)propanamido)benzo[d]thiazole-6-carboxylic acid (2-(3-(4-chloro-3-fluorophenyl) propanamido)benzo[d]thiazole-6-carboxylic acid),
(81) 2-(2-(4-chloro-3-fluorophenyl)acetamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(4-chloro-3-fluorophenyl) acetamido)benzo[d]thiazole-6-carboxylic acid),
(82) 2-(2-(4-fluorophenoxy)acetamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(4-fluorophenoxy)acetamido)benzo[d]thiazole -6-carboxylic acid),
(83) 2-(5-carboxy-1H-pyrrole-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(5-carboxy-1H-pyrrole-2-carboxamido)benzo[ d]thiazole-6-carboxylic acid),
(84) 2-(5-(trifluoromethyl)-1H-pyrrole-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(5-(trifluoromethyl)-1H-pyrrole -2-carboxamido)benzo[d]thiazole-6-carboxylic acid),
(85) 2-(2-(methylthio)isonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(methylthio)isonicotinamido)benzo[d]thiazole-6-carboxylic acid ),
(86) 2-(5-(methylthio)nicotinamido)benzo[d]thiazole-6-carboxylic acid ,
(87) 2-(2-(methylamino)isonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(methylamino)isonicotinamido)benzo[d]thiazole-6-carboxylic acid ),
(88) 2-(6-chloronicotinamido)benzo[d]thiazole-6-carboxylic acid,
(89) 2-(5-bromo-6-methoxynicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-bromo-6-methoxynicotinamido)benzo[d]thiazole-6 -carboxylic acid),
(90) 2-(6-(pyrrolidin-1-yl)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-(pyrrolidin-1-yl)nicotinamido)benzo[ d]thiazole-6-carboxylic acid),
(91) 2-(6-(2-methylprop-1-enyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-(2-methylprop-1-enyl) nicotinamido)benzo[d]thiazole-6-carboxylic acid),
(92) 2-(5-chloro-6-hydroxynicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-chloro-6-hydroxynicotinamido)benzo[d]thiazole-6- carboxylic acid),
(93) 2-(5-bromo-6-methylnicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-bromo-6-methylnicotinamido)benzo[d]thiazole-6- carboxylic acid),
(94) 2-(6-chloro-5-fluoronicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-chloro-5-fluoronicotinamido)benzo[d]thiazole-6- carboxylic acid),
(95) 2-(6-bromonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-bromonicotinamido)benzo[d]thiazole-6-carboxylic acid),
(96) 2-(6-carboxyspiro[3.3]heptane-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(6-carboxyspiro[3.3]heptane-2-carboxamido)benzo [d]thiazole-6-carboxylic acid),
(97) 2-(5-(trifluoromethyl)furan-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(5-(trifluoromethyl)furan-2-carboxamido)benzo [d]thiazole-6-carboxylic acid),
(98) 2-(5-bromonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-bromonicotinamido)benzo[d]thiazole-6-carboxylic acid),
(99) 2-(3-hydroxy-3-(trifluoromethyl)cyclobutanecarboxamido)benzo[d]thiazole-6-carboxylic acid (2-(3-hydroxy-3-(trifluoromethyl) cyclobutanecarboxamido)benzo[d]thiazole-6-carboxylic acid),
(100) 2-(3,3-difluoro-1-methylcyclobutanecarboxamido)benzo[d]thiazole-6-carboxylic acid (2-(3,3-difluoro-1-methylcyclobutanecarboxamido)benzo [d]thiazole-6-carboxylic acid),
(101) 2-(4-(2-carboxycyclopropyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-(2-carboxycyclopropyl)benzamido)benzo[d]thiazole- 6-carboxylic acid),
(102) 2-(2-(trifluoromethyl)furan-3-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(trifluoromethyl)furan-3-carboxamido)benzo [d]thiazole-6-carboxylic acid),
(103) 2-(5-carboxythiophene-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(5-carboxythiophene-2-carboxamido)benzo[d]thiazole-6- carboxylic acid),
(104) 2-(2-bromoisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-bromoisonicotinamido)benzo[d]thiazole-6-carboxylic acid),
(105) 2-(4-chloropicolinamido)benzo[d]thiazole-6-carboxylic acid,
(106) 2-(4-fluoropicolinamido)benzo[d]thiazole-6-carboxylic acid,
(107) 2-(6-chloro-5-methylpicolinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-chloro-5-methylpicolinamido)benzo[d]thiazole-6- carboxylic acid),
(108) 2-(5-chloro-3-propoxypicolinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-chloro-3-propoxypicolinamido)benzo[d]thiazole-6 -carboxylic acid),
(109) 2-(5-chloro-3-methylpicolinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-chloro-3-methylpicolinamido)benzo[d]thiazole-6- carboxylic acid),
(110) 2-(5-fluoro-6-methoxynicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-fluoro-6-methoxynicotinamido)benzo[d]thiazole-6 -carboxylic acid),
(111) 2-(4-methoxypicolinamido)benzo[d]thiazole-6-carboxylic acid,
(112) 2-(6-(trifluoromethyl)picolinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-(trifluoromethyl)picolinamido)benzo[d]thiazole-6- carboxylic acid),
(113) 2-(3-fluoropicolinamido)benzo[d]thiazole-6-carboxylic acid,
(114) 2-(4-(trifluoromethyl)picolinamido)benzo[d]thiazole-6-carboxylic acid (2-(4-(trifluoromethyl)picolinamido)benzo[d]thiazole-6- carboxylic acid),
(115) 2-(5-(trifluoromethyl)picolinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-(trifluoromethyl)picolinamido)benzo[d]thiazole-6- carboxylic acid),
(116) 2-(6-carboxynicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-carboxynicotinamido)benzo[d]thiazole-6-carboxylic acid),
(117) 2-(6-methoxypicolinamido)benzo[d]thiazole-6-carboxylic acid,
(118) 2-(6-(2-methoxyethoxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-(2-methoxyethoxy)nicotinamido)benzo[d]thiazole -6-carboxylic acid),
(119) 2-(2-methoxy-6-(trifluoromethyl)isonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-methoxy-6-(trifluoromethyl)isonicotinamido )benzo[d]thiazole-6-carboxylic acid),
(120) 2-(2-isopropoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-isopropoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid),
(121) 2-(6-ethoxy-4-fluoronicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-ethoxy-4-fluoronicotinamido)benzo[d]thiazole-6 -carboxylic acid),
(122) 2-(6-(cyclopropylmethoxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-(cyclopropylmethoxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid),
(123) 2-(6-isobutoxynicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-isobutoxynicotinamido)benzo[d]thiazole-6-carboxylic acid),
(124) 2-(2-(difluoromethoxy)isonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(difluoromethoxy)isonicotinamido)benzo[d]thiazole-6- carboxylic acid),
(125) 2-(6-(difluoromethoxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-(difluoromethoxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid),
(126) 2-(3-fluoro-4-methoxybenzamido)-4-methylbenzo[d]thiazole-6-carboxylic acid (2-(3-fluoro-4-methoxybenzamido)-4- methylbenzo[d]thiazole-6-carboxylic acid),
(127) 2-(6-methoxynicotinamido)-4-methylbenzo[d]thiazole-6-carboxylic acid (2-(6-methoxynicotinamido)-4-methylbenzo[d]thiazole-6-carboxylic acid),
(128) 2-(2-methoxyisonicotinamido)-4-methylbenzo[d]thiazole-6-carboxylic acid (2-(2-methoxyisonicotinamido)-4-methylbenzo[d]thiazole-6- carboxylic acid),
(129) 4-methyl-2-(2-(trifluoromethyl)isonicotinamido)benzo[d]thiazole-6-carboxylic acid (4-methyl-2-(2-(trifluoromethyl)isonicotinamido) benzo[d]thiazole-6-carboxylic acid),
(130) 4-methyl-2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid (4-methyl-2-(6-(trifluoromethyl)nicotinamido)benzo [d]thiazole-6-carboxylic acid),
(131) 2-(5-fluoro-2-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-fluoro-2-methoxyisonicotinamido)benzo[d]thiazole- 6-carboxylic acid),
(132) 2-(5-chloro-2-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-chloro-2-methoxyisonicotinamido)benzo[d]thiazole-6 -carboxylic acid),
(133) 2-(3-chloro-2-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(3-chloro-2-methoxyisonicotinamido)benzo[d]thiazole-6 -carboxylic acid),
(134) 2-(6-(tetrahydro-2H-pyran-4-yloxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-(tetrahydro-2H-pyran- 4-yloxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid),
(135) 2-(6-phenoxynicotinamido)benzo[d]thiazole-6-carboxylic acid,
(136) 2-(2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-6-methoxynicotinamido)benzo[d]thiazole-6-carboxyl Acid (2-(2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-6-methoxynicotinamido)benzo[d]thiazole-6-carboxylic acid),
(137) 2-(6-(2,2,2-trifluoroethoxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-(2,2,2- trifluoroethoxy)nicotinamido)benzo[d]thiazole-6-carboxylic acid),
(138) 2-(6-isopropoxynicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-isopropoxynicotinamido)benzo[d]thiazole-6-carboxylic acid),
(139) 2-(4-chloro-3-fluorobenzamido)-4-methoxybenzo[d]thiazole-6-carboxylic acid (2-(4-chloro-3-fluorobenzamido)-4- methoxybenzo[d]thiazole-6-carboxylic acid),
(140) 2-(3-fluoro-4-methoxybenzamido)-4-methoxybenzo[d]thiazole-6-carboxylic acid (2-(3-fluoro-4-methoxybenzamido)-4 -methoxybenzo[d]thiazole-6-carboxylic acid),
(141) 4-methoxy-2-(2-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid (4-methoxy-2-(2-methoxyisonicotinamido)benzo[d]thiazole- 6-carboxylic acid),
(142) 2-(2-morpholinoisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-morpholinoisonicotinamido)benzo[d]thiazole-6-carboxylic acid),
(143) 2-(2-ethoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-ethoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid),
(144) 2-(6-methoxynicotinamido)benzo[d]thiazole-6-carboxylic acid,
(145) 2-(3-fluoro-4-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-fluoro-4-(trifluoromethyl)benzamido) benzo[d]thiazole-6-carboxylic acid),
(148) 2-(3,4,5-trifluorobenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3,4,5-trifluorobenzamido)benzo[d]thiazole-6 -carboxylic acid),
(149) 2-(2-(trifluoromethyl)isonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-(trifluoromethyl)isonicotinamido)benzo[d]thiazole-6- carboxylic acid),
(150) 2-(3-chloro-4-fluorobenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-chloro-4-fluorobenzamido)benzo[d]thiazole-6- carboxylic acid),
(151) 2-(3,4-difluorobenzamido)benzo[d]thiazole-6-carboxylic acid ,
(152) 2-(3-chloro-4-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-chloro-4-methoxybenzamido)benzo[d]thiazole-6- carboxylic acid),
(153) 2-(3-fluoro-5-(trifluoromethyl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-fluoro-5-(trifluoromethyl)benzamido) benzo[d]thiazole-6-carboxylic acid),
(154) 2-(4-chloro-3-fluorobenzamido)-4-fluorobenzo[d]thiazole-6-carboxylic acid (2-(4-chloro-3-fluorobenzamido)-4- fluorobenzo[d]thiazole-6-carboxylic acid),
(155) 2-(4-chloro-2-methoxybenzamido)-4-fluorobenzo[d]thiazole-6-carboxylic acid (2-(4-chloro-2-methoxybenzamido)-4- fluorobenzo[d]thiazole-6-carboxylic acid),
(156) 4-fluoro-2-(3-fluoro-4-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid (4-fluoro-2-(3-fluoro-4- methoxybenzamido)benzo[d]thiazole-6-carboxylic acid),
(157) 4-fluoro-2-(2-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid (4-fluoro-2-(2-methoxyisonicotinamido)benzo[d]thiazole- 6-carboxylic acid),
(158) 2-(2-methyl-5-(4-(trifluoromethyl)pyrimidin-2-ylamino)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(2 -methyl-5-(4-(trifluoromethyl)pyrimidin-2-ylamino)benzamido)benzo[d]thiazole-6-carboxylic acid),
(159) 2-(6-oxo-1,6-dihydropyridine-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(6-oxo-1,6-dihydropyridine- 2-carboxamido)benzo[d]thiazole-6-carboxylic acid),
(160) 2-(3-(1H-imidazol-1-yl)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-(1H-imidazol-1-yl)benzamido )benzo[d]thiazole-6-carboxylic acid),
(161) 2-(2-chloro-5-(4-methylpyrimidin-2-ylamino)benzamido)benzo[d]thiazole-6-carboxylic acid (2-(2-chloro-5- (4-methylpyrimidin-2-ylamino)benzamido)benzo[d]thiazole-6-carboxylic acid),
(162) 2-(4-carboxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-carboxybenzamido)benzo[d]thiazole-6-carboxylic acid),
(163) 2-(8-hydroxyquinoline-2-carboxamido)benzo[d]thiazole-6-carboxylic acid (2-(8-hydroxyquinoline-2-carboxamido)benzo[d]thiazole-6- carboxylic acid),
(164) 2-(4-chloro-2-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-chloro-2-methoxybenzamido)benzo[d]thiazole-6- carboxylic acid),
(165) 2-(3,4-dimethoxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3,4-dimethoxybenzamido)benzo[d]thiazole-6-carboxylic acid),
(166) 2-(2-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid),
(167) 2-(4-chloro-3-fluorobenzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-chloro-3-fluorobenzamido)benzo[d]thiazole-6- carboxylic acid),
(168) 2-(4-fluoro-3-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-fluoro-3-methoxybenzamido)benzo[d]thiazole-6 -carboxylic acid),
(169) 2-(3-fluoro-4-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-fluoro-4-methoxybenzamido)benzo[d]thiazole-6 -carboxylic acid),
(170) 2-(4-cyanobenzamido)benzo[d]thiazole-6-carboxylic acid (2-(4-cyanobenzamido)benzo[d]thiazole-6-carboxylic acid),
(171) 2-(3-cyanobenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-cyanobenzamido)benzo[d]thiazole-6-carboxylic acid),
(172) 2-(3-hydroxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-hydroxybenzamido)benzo[d]thiazole-6-carboxylic acid),
(173) 2-(3-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid (2-(3-methoxybenzamido)benzo[d]thiazole-6-carboxylic acid),
(174) 2-(4-methylcyclohexanecarboxamido)benzo[d]thiazole-6-carboxylic acid,
(175) 2-(5-bromo-2-methoxynicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-bromo-2-methoxynicotinamido)benzo[d]thiazole-6 -carboxylic acid),
(176) 2-(2-tert-butylisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-tert-butylisonicotinamido)benzo[d]thiazole-6-carboxylic acid),
(177) 5-chloro-2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid (5-chloro-2-(6-(trifluoromethyl)nicotinamido)benzo [d]thiazole-6-carboxylic acid),
(178) 5-methoxy-2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid (5-methoxy-2-(6-(trifluoromethyl)nicotinamido) benzo[d]thiazole-6-carboxylic acid),
(179) 5-hydroxy-2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid (5-hydroxy-2-(6-(trifluoromethyl)nicotinamido) benzo[d]thiazole-6-carboxylic acid),
(180) 2-(5-fluoro-2-methoxynicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-fluoro-2-methoxynicotinamido)benzo[d]thiazole-6 -carboxylic acid),
(181) 2-(5-bromo-2-methylnicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-bromo-2-methylnicotinamido)benzo[d]thiazole-6- carboxylic acid),
(182) 2-(6-bromonicotinamido)-5-methoxybenzo[d]thiazole-6-carboxylic acid (2-(6-bromonicotinamido)-5-methoxybenzo[d]thiazole-6- carboxylic acid),
(183) 2-(2-aminoisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-aminoisonicotinamido)benzo[d]thiazole-6-carboxylic acid),
(184) 2-(2-bromo-6-methoxyisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-bromo-6-methoxyisonicotinamido)benzo[d]thiazole- 6-carboxylic acid),
(185) 2-(6-bromo-2-chloronicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-bromo-2-chloronicotinamido)benzo[d]thiazole-6- carboxylic acid),
(186) 2-(6-tert-butylnicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-tert-butylnicotinamido)benzo[d]thiazole-6-carboxylic acid),
(187) 2-(5,6-dichloronicotinamido)benzo[d]thiazole-6-carboxylic acid,
(188) 2-(5-vinylnicotinamido)benzo[d]thiazole-6-carboxylic acid,
(189) 2-(5-(furan-3-yl)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-(furan-3-yl)nicotinamido)benzo[d] thiazole-6-carboxylic acid),
(190) 2-(5-cyclopentenylnicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-cyclopentenylnicotinamido)benzo[d]thiazole-6-carboxylic acid),
(191) 2-(5-(2-methylprop-1-enyl)nicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(5-(2-methylprop-1-enyl) nicotinamido)benzo[d]thiazole-6-carboxylic acid),
(192) 2-(2,6-dibromonicotinamido)benzo[d]thiazole-6-carboxylic acid ,
(193) 2-(6-amino-5-bromonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(6-amino-5-bromonicotinamido)benzo[d]thiazole-6- carboxylic acid),
(194) 2-(2-iodoisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-iodoisonicotinamido)benzo[d]thiazole-6-carboxylic acid),
(195) 2-(2-methylisonicotinamido)benzo[d]thiazole-6-carboxylic acid (2-(2-methylisonicotinamido)benzo[d]thiazole-6-carboxylic acid),
(196) 2-(5-fluoronicotinamido)benzo[d]thiazole-5-carboxylic acid,
(197) 2-(5-chloronicotinamido)benzo[d]thiazole-5-carboxylic acid,
(199) 2-(3-fluoro-4-(trifluoromethyl)benzamido)benzo[d]thiazole-5-carboxylic acid (2-(3-fluoro-4-(trifluoromethyl)benzamido) benzo[d]thiazole-5-carboxylic acid),
(200) 2-(2-chloroisonicotinamido)benzo[d]thiazole-5-carboxylic acid (2-(2-chloroisonicotinamido)benzo[d]thiazole-5-carboxylic acid),
(202) 2-(6-oxo-1,6-dihydropyridine-2-carboxamido)benzo[d]thiazole-5-carboxylic acid (2-(6-oxo-1,6-dihydropyridine- 2-carboxamido)benzo[d]thiazole-5-carboxylic acid),
(203) 2-(3,4,5-trifluorobenzamido)benzo[d]thiazole-5-carboxylic acid (2-(3,4,5-trifluorobenzamido)benzo[d]thiazole-5 -carboxylic acid),
(204) 2-(3-fluoro-4-methylbenzamido)benzo[d]thiazole-5-carboxylic acid (2-(3-fluoro-4-methylbenzamido)benzo[d]thiazole-5- carboxylic acid),
(205) 2-(2-ethoxyisonicotinamido)benzo[d]thiazole-5-carboxylic acid (2-(2-ethoxyisonicotinamido)benzo[d]thiazole-5-carboxylic acid),
(206) 2-(2-morpholinoisonicotinamido)benzo[d]thiazole-5-carboxylic acid (2-(2-morpholinoisonicotinamido)benzo[d]thiazole-5-carboxylic acid),
(207) 2-(6-chloro-5-fluoropicolinamido)benzo[d]thiazole-5-carboxylic acid (2-(6-chloro-5-fluoropicolinamido)benzo[d]thiazole-5 -carboxylic acid),
(208) 2-(5-carboxypicolinamido)benzo[d]thiazole-5-carboxylic acid,
(209) 2-(2-chloro-6-methoxyisonicotinamido)benzo[d]thiazole-5-carboxylic acid (2-(2-chloro-6-methoxyisonicotinamido)benzo[d]thiazole-5 -carboxylic acid),
(210) 2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-5-carboxylic acid (2-(6-(trifluoromethyl)nicotinamido)benzo[d]thiazole-5-carboxylic acid),
(211) 2-(2-(trifluoromethyl)isonicotinamido)benzo[d]thiazole-5-carboxylic acid (2-(2-(trifluoromethyl)isonicotinamido)benzo[d]thiazole-5- carboxylic acid),
(212) 2-(2-methoxyisonicotinamido)benzo[d]thiazole-5-carboxylic acid (2-(2-methoxyisonicotinamido)benzo[d]thiazole-5-carboxylic acid),
(213) 2-(3-fluoro-4-methoxybenzamido)benzo[d]thiazole-5-carboxylic acid (2-(3-fluoro-4-methoxybenzamido)benzo[d]thiazole-5 -carboxylic acid),
(214) 2-(4-(4-methoxyphenyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(4-methoxyphenyl)piperazin-1-yl )benzo[d]thiazole-6-carboxylic acid),
(215) 2-(4-(4-acetylphenyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(4-acetylphenyl)piperazin-1-yl) benzo[d]thiazole-6-carboxylic acid),
(216) 2-(4-(2,3-dichlorophenyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(2,3-dichlorophenyl)piperazin- 1-yl)benzo[d]thiazole-6-carboxylic acid),
(217) 2-(4-(4-cyanophenyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(4-cyanophenyl)piperazin-1-yl )benzo[d]thiazole-6-carboxylic acid),
(218) 2-(4-(pyridin-4-yl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(pyridin-4-yl)piperazin-1 -yl)benzo[d]thiazole-6-carboxylic acid),
(219) 2-(4-(pyridin-3-yl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(pyridin-3-yl)piperazin-1 -yl)benzo[d]thiazole-6-carboxylic acid),
(220) 2-(4-(2,4-difluorophenyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(2,4-difluorophenyl) piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(221) 2-(4-(3-methoxyphenyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(3-methoxyphenyl)piperazin-1-yl )benzo[d]thiazole-6-carboxylic acid),
(222) 2-(4-(3-phenylpropanoyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(3-phenylpropanoyl)piperazin-1- yl)benzo[d]thiazole-6-carboxylic acid),
(223) 2-(4-(2-phenylacetyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(2-phenylacetyl)piperazin-1-yl) benzo[d]thiazole-6-carboxylic acid),
(224) 2-(4-(3-chloro-4-fluorophenylsulfonyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(3-chloro -4-fluorophenylsulfonyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(225) 2-(4-(thiophen-2-ylsulfonyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(thiophen-2-ylsulfonyl)piperazin -1-yl)benzo[d]thiazole-6-carboxylic acid),
(226) 2-(4-(2-(4-fluorophenyl)acetyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(2-(4) -fluorophenyl)acetyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(227) 2-(4-(3-cyclopentylpropanoyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(3-cyclopentylpropanoyl)piperazin-1 -yl)benzo[d]thiazole-6-carboxylic acid),
(228) 2-(4-(benzylsulfonyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(benzylsulfonyl)piperazin-1-yl)benzo[d ]thiazole-6-carboxylic acid),
(229) 2-(4-(3,4-difluorophenylsulfonyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(3,4- difluorophenylsulfonyl)piperazin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(230) 2-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(4-chlorophenyl) -4-hydroxypiperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(231) 2-(3H-spiro[benzofuran-2,4'-piperidin]-1'-yl)benzo[d]thiazole-6-carboxylic acid (2-(3H-spiro[benzofuran- 2,4'-piperidine]-1'-yl)benzo[d]thiazole-6-carboxylic acid),
(232) 2-(4-(4-fluorophenyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(4-fluorophenyl)piperidin-1- yl)benzo[d]thiazole-6-carboxylic acid),
(233) 2-(4-hydroxy-4-phenylpiperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-hydroxy-4-phenylpiperidin-1-yl) benzo[d]thiazole-6-carboxylic acid),
(234) 2-(4-(2-methoxypyridin-4-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(2-methoxypyridin- 4-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(235) 2-(4-hydroxy-4-(pyridin-4-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-hydroxy-4- (pyridin-4-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(236) 2-(4-(pyridin-4-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(pyridin-4-yl)piperidin- 1-yl)benzo[d]thiazole-6-carboxylic acid),
(237) 2-(4-(3-(trifluoromethyl)phenyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(3-(trifluoromethyl) )phenyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(238) 2-(4-hydroxy-4-(pyridin-3-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-hydroxy-4- (pyridin-3-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(239) 2-(4-(pyridin-3-yloxy)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(pyridin-3-yloxy)piperidin -1-yl)benzo[d]thiazole-6-carboxylic acid),
(240) 2-(4-((pyridin-3-yloxy)methyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-((pyridin-3 -yloxy)methyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(241) 2-(4-(pyridin-3-ylmethyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(pyridin-3-ylmethyl)piperidin -1-yl)benzo[d]thiazole-6-carboxylic acid),
(242) 2-(4-(thiazol-2-ylmethyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(thiazol-2-ylmethyl) piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(243) 2-(4-((4-methyl-1H-pyrazol-1-yl)methyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4 -((4-methyl-1H-pyrazol-1-yl)methyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(244) 2-(4-((4H-1,2,4-triazol-4-yl)methyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2- (4-((4H-1,2,4-triazol-4-yl)methyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(245) 2-(4-(oxazol-5-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(oxazol-5-yl)piperidin -1-yl)benzo[d]thiazole-6-carboxylic acid),
(246) 2-(4-(1H-pyrrol-1-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(1H-pyrrol-1- yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(247) 2-(4-(4-methyl-1H-pyrazol-1-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(4 -methyl-1H-pyrazol-1-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(248) 2-(4-(1H-benzo[d]imidazol-2-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(1H -benzo[d]imidazol-2-yl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(249) 2-(4-(6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl)piperidin-1-yl)benzo [d]thiazole-6-carboxylic acid (2-(4-(6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazol-2-yl)piperidin-1 -yl)benzo[d]thiazole-6-carboxylic acid),
(250) 2-(4-((benzo[d]thiazol-2-yloxy)methyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4- ((benzo[d]thiazol-2-yloxy)methyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(251) 2-(2-oxospiro[indoline-3,4'-piperidine]-1'-yl)benzo[d]thiazole-6-carboxylic acid (2-(2-oxospiro[indoline -3,4'-piperidine]-1'-yl)benzo[d]thiazole-6-carboxylic acid),
(252) 2-(4-(pyridin-3-ylmethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(pyridin-3- ylmethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(253) 2-(4-(pyridin-4-ylmethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(pyridin-4- ylmethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(254) 2-(4-((5-fluoropyridin-3-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4 -((5-fluoropyridin-3-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(255) 2-(4-((6-(trifluoromethyl)pyridin-3-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid ( 2-(4-((6-(trifluoromethyl)pyridin-3-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(256) 2-(4-((5-chloropyridin-3-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4- ((5-chloropyridin-3-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(257) 2-(4-((2-methoxypyridin-4-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4 -((2-methoxypyridin-4-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(258) 2-(4-carboxypiperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-carboxypiperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(259) 2-(4-((6-methoxypyridin-3-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4 -((6-methoxypyridin-3-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(260) 2-(4-(cyclopropylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(cyclopropylcarbamoyl)piperidin-1-yl) benzo[d]thiazole-6-carboxylic acid),
(261) 2-(4-(3-hydroxypropylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(3-hydroxypropylcarbamoyl)piperidin -1-yl)benzo[d]thiazole-6-carboxylic acid),
(262) 2-(4-(carboxymethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(carboxymethylcarbamoyl)piperidin-1-yl) benzo[d]thiazole-6-carboxylic acid),
(263) 2-(4-((1H-pyrrol-2-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-( (1H-pyrrol-2-yl)methylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(264) 2-(4-(thiazol-2-ylmethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4-(thiazol-2 -ylmethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid),
(265) 2-(4-(2-(1H-pyrrol-1-yl)ethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-(4 -(2-(1H-pyrrol-1-yl)ethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid), or
(266) 2-(4-(2-(1H-imidazol-1-yl)ethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid (2-( 4-(2-(1H-imidazol-1-yl)ethylcarbamoyl)piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid), a compound or a pharmaceutically acceptable salt thereof.
EDCI(1-ethyl-3-(3-dimethylaminopropyl)carbodiimide), HATU(1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate, or Hexafluorophosphate Azabenzotriazole Tetramethyl Uronium), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBroP), and benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBOP); HOBt (1-hydroxybenzotriazole), or DMAP (4-dimethylaminopyridine); and one or more Hunig's bases selected from the group consisting of N,N-diisopropylethylamine (DIPEA), triethylamine (TEA), and pyridine. ; A method for producing the compound of claim 1, or a pharmaceutically acceptable salt thereof, comprising the first step of reacting the compounds represented by the following formulas (2) and (3) in the presence of:
[Formula 2]

[Formula 3]

In Formula 2 or 3 above,
R' is -NHR" or halogen,
R" is H or CH ₃ ,
X' is -(CH ₂ ) _m -COOH, -CONH-(CH ₂ ) _p -COOH, or -O-(CH ₂ ) _q -COOH,
m is an integer from 0 to 5,
p is 2,
q is 1,
R ₁ is carboxyl, or C _1-4 alkoxycarbonyl,
R ₂ is hydrogen, C _1-4 alkyl, C _1-4 alkoxy, halogen, or hydroxy,
R ₃ is phenyl, pyridinyl, furanyl, thiophenyl, indolyl, benzotriazolyl, benzothiazolyl, benzoimidazolyl, pyrrolopyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrrolyl, spiro heptanyl, cyclobutyl, cyclohexyl, dihydropyridinyl, quinolinyl, imidazolyl, piperazinyl, or piperidinyl,
The phenyl, indolyl, benzotriazolyl, benzothiazolyl, benzoimidazolyl, pyrrolopyridinyl, pyrazinyl, pyrrolyl, spiroheptanyl, cyclobutyl, cyclohexyl, dihydropyridinyl, quinolinyl, Dazolyl, or piperidinyl, is unsubstituted or cyano, halogen, nitro, oxo, hydroxy, carboxyl, amino, C _1-4 alkyl, C _1-4 alkenyl, C _1-4 alkoxy, C _{1- 4} haloalkyl, C _1-4 haloalkoxy, C _1-4 alkoxycarbonyl, C _1-4 alkylcarbonyl, C _1-4 alkylthio, C _1-4 alkylamino, C _1-4 alkoxy-C _{1- 4} Alkoxy, C _3-10 Cycloalkyl, C _3-10 Cycloalkyl-C _1-4 Alkoxy, C _3-10 Cycloalkenyl, C _6-10 Aryloxy, C _3-10 Cycloalkyl-C _1-4 Alkyl Carbonyl, C _6-10 Aryl-C _1-4 Alkylcarbonyl, C _6-10 Arylsulfonyl, C _6-10 Aryl-C _1-4 Alkylsulfonyl, C _3-10 Cycloalkylcarbamoyl, Hydroxy -C _1-4 alkylcarbamoyl, carboxy-C _1-4 alkylcarbamoyl, 5 to 10 membered heterocyclyl, 5 to 10 membered heterocyclyloxy, 5 to 10 membered heteroaryl, 5 to 10 membered heteroaryloxy , 5 to 10 membered heteroarylamino, 5 to 10 membered heteroarylsulfonyl, 5 to 10 membered heteroaryl-C _1-4 alkyl, 5 to 10 membered heteroaryloxy-C _1-4 alkyl, 5 to 10 membered hetero. is substituted with one or more selected from the group consisting of aryl-C _1-4 alkylamino, and 5 to 10 membered heteroaryl-C _1-4 alkylcarbamoyl,
Pyridinyl, furanyl, thiophenyl, pyrimidinyl, pyridazinyl, or piperazinyl is cyano, halogen, nitro, oxo, hydroxy, carboxyl, amino, C _1-4 alkyl, C _1-4 alkyl. Kenyl, C _1-4 alkoxy, C _1-4 haloalkyl, C _1-4 haloalkoxy, C _1-4 alkoxycarbonyl, C _1-4 alkylcarbonyl, C _1-4 alkylthio, C _1-4 alkyl Amino, C _1-4 alkoxy-C _1-4 alkoxy, C _4-10 cycloalkyl, C _3-10 cycloalkyl-C _1-4 alkoxy, C _3-10 cycloalkenyl, C _6-10 aryloxy, C _3-10 cycloalkyl-C _1-4 alkylcarbonyl, C _6-10 aryl-C _1-4 alkylcarbonyl, C _6-10 arylsulfonyl, C _6-10 aryl-C _1-4 alkylsulfonyl, C _3-10 cycloalkylcarbamoyl, hydroxy-C _1-4 alkylcarbamoyl, carboxy-C _1-4 alkylcarbamoyl, 5 to 10 membered heterocyclyl, 5 to 10 membered heterocyclyloxy, 5 to 10 membered One-membered heteroaryl, 5-10 membered heteroaryloxy, 5-10 membered heteroarylamino, 5-10 membered heteroarylsulfonyl, 5-10 membered heteroaryl-C _1-4 alkyl, 5-10 membered heteroaryloxy- Substituted with one or more selected from the group consisting of C _1-4 alkyl, 5 to 10 membered heteroaryl-C _1-4 alkylamino, and 5 to 10 membered heteroaryl-C _1-4 alkylcarbamoyl.
delete According to clause 8,
When R ₁ is C _1-4 alkoxycarbonyl, the production method further includes a second step of reacting with a base and then adding an acid to precipitate.
A pharmaceutical composition for preventing or treating liver disease, comprising the compound of claim 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
According to clause 11,
The compound is a pharmaceutical composition that inhibits 17β-HSD13 (17β-Hydroxysteroid dehydrogenase type 13 or 17β-HSD type 13).
According to clause 11,
The liver disease includes non-alcoholic steatohepatitis (NASH), nonalcoholic fatty liver disease (NAFLD), alcoholic fatty liver disease, alcoholic hepatitis, alcoholic cirrhosis, liver cirrhosis, Liver cancer, liver failure and acute liver failure, biliary tract cancer, bile duct cancer, primary biliary cholangitis, primary sclerosing cholangitis, jaundice, portal hypertension, cholelithiasis, acute or chronic cholecystitis, gallbladder polyps, gallbladder wall thickening, intrahepatic bile duct cancer, liver A pharmaceutical composition, which is at least one selected from the group consisting of hilar cholangiocarcinoma, distal cholangiocarcinoma, and biliary obstruction.
A food composition for preventing or improving liver disease, comprising the compound of claim 1 or a foodologically acceptable salt thereof as an active ingredient.
A feed composition for preventing or improving liver disease, comprising the compound of claim 1 or a feed-chemically acceptable salt thereof as an active ingredient.