US Pat. No. 9,809,583

OXAZOLIDINE-BASED COMPOUND AND SELECTIVE ANDROGEN RECEPTOR AGONIST COMPRISING SAME

DONG-A ST CO., LTD., (KR...

1. A compound represented by the following Chemical Formula 1, an isomer thereof, or a pharmaceutically acceptable salt thereof:

in Chemical Formula 1,
R1 is a substituent represented by the following Chemical Formula 2 or Chemical Formula 3,

R2 is hydrogen, oxo, or C1-C6 alkyl,

R3 and R4 each independently is a substituent selected from the group consisting of hydrogen and C1-C6 alkyl,

R5 and R6 each independently is a substituent selected from the group consisting of hydrogen, halogen, and C1-C6 alkyl,

R7 is halogen, cyano or nitro,

the C1-C6 alkyl is substituted with one or more substituents selected from the group consisting of hydrogen, hydroxy, and halogen;

—X(CH2)nR8  [Chemical Formula 2]

in Chemical Formula 2, X is O, N(R), S or S(O)2,

R is hydrogen,
R8 is hydrogen, C3-C7 heterocycle having a nitrogen atom, aryl, or heteroaryl having a nitrogen atom which has one or two rings,

the heterocycle, aryl or heteroaryl each independently is substituted with one or more substituents selected from the group
consisting of hydrogen, hydroxy, halogen, C1-C6 alkyl, C1-C6 alkoxy, a cyano group, a nitro group, a hydroxyimino group, a C1-C6 alkoxyimino group, (CH2)pNR10R11, (CH2)pNC(O)R10, (CH2)pNC(O)OR10, (CH2)pNC(O)NR10R11, (CH2)pC(O)NR10R11, (CH2)pNS(O)2R10, (CH2)pS(O)2R10(CH2)pC(O)OR10,


p is an integer of 0 or 1,
R10 and R11 each independently is a substituent selected from the group consisting of hydrogen, C1-C6 alkyl, pyrrolidinyl, and phenyl,

the C1-C6 alkyl is substituted with one or more substituents selected from the group consisting of hydrogen, hydroxy, amino, cyano and
halogen,

n is 0 or 1;

in Chemical Formula 3, Y is C or N,
m is an integer of 0, 1 or 2,
R9 is a substituent selected from the group consisting of hydrogen, oxo, hydroxy, C1-C6 alkyl, cyano, C(O)R12, C(O)OR12, C(O)NR12R13, S(O)2R12, NC(O)R13, NR12R13, and NC(O)OR12,

R12 and R13 each independently is a substituent selected from the group consisting of hydrogen, hydroxy and C1-C6 alkyl, and

the C1-C6 alkyl is substituted with one or more substituents selected from the group consisting of hydrogen, hydroxy, halogen and cyano.

US Pat. No. 9,163,043

OXAZOLIDINONE DERIVATIVES

DONG-A ST CO., LTD., Seo...

1. An oxazolidinone derivative of Formula I, or a pharmaceutically acceptable salt thereof;
wherein,
Het is pyrrolyl, imidazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, pyrazolyl, pyrrolidinyl, oxazolyl, isoxazolyl, or thiazolyl;
X is carbon;
ring A is unsubstituted or has at least one fluorine substituent;
R7 is H, PO(OH)2, or PO(O)2?2(M+)2, wherein M+ is a pharmaceutically acceptable metal cation;

wherein Het is unsubstituted or optionally substituted with one or more R3, wherein R3 is at least one C1-4 alkyl group that is unsubstituted, or substituted with cyano, —(CH2)m-OR7 or ketone; and

m is 0, 1, 2, 3, or 4.
US Pat. No. 9,822,174

ANTI-VEGF ANTIBODY, AND PHARMACEUTICAL COMPOSITION FOR PREVENTING, DIAGNOSING OR TREATING CANCER OR ANGIOGENESIS-RELATED DISEASES, CONTAINING SAME

DONG-A SOCIO HOLDINGS CO....

1. An antibody that binds to vascular endothelial growth factor (VEGF), the antibody comprising:
1) a light chain variable region comprising complementarity determining region (CDR)1, CDR2 and CDR3, wherein the CDR1 is
represented by an amino acid sequence selected from the group consisting of SEQ ID NOs: 4-14; the CDR2 is represented by the
amino acid sequence of SEQ ID NO: 1; and the CDR3 is represented by the amino acid sequence of SEQ ID NO: 2; and

2) a heavy chain variable region comprising CDR1, CDR2 and CDR3, wherein the CDR1 is represented by an amino acid sequence
selected from the group consisting of SEQ ID NOs: 15-34; the CDR 2 is represented an the amino acid sequence selected from
the group consisting of SEQ ID NOs: 35-50; and the CDR3 is represented by the amino acid sequence of SEQ ID NO: 3,

wherein the antibody is selected from the group consisting of:
(i) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of SEQ
ID NO: 4, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence of
SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO: 15,
CDR 2 represented by the amino acid sequence of SEQ ID NO: 35 and CDR3 represented by the amino acid sequence of SEQ ID NO:
3;

(ii) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of SEQ
ID NO: 5, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence of
SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO: 16,
CDR 2 represented by the amino acid sequence of SEQ ID NO: 36 and CDR3 represented by the amino acid sequence of SEQ ID NO:
3;

(iii) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of SEQ
ID NO: 5, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence of
SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO: 17,
CDR 2 represented by the amino acid sequence of SEQ ID NO: 37 and CDR3 represented by the amino acid sequence of SEQ ID NO:
3;

(iv) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of SEQ
ID NO: 5, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence of
SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO: 18,
CDR 2 represented by the amino acid sequence of SEQ ID NO: 38 and CDR3 represented by the amino acid sequence of SEQ ID NO:
3;

(v) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of SEQ
ID NO: 5, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence of
SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO: 19,
CDR 2 represented by the amino acid sequence of SEQ ID NO: 39 and CDR3 represented by the amino acid sequence of SEQ ID NO:
3;

(vi) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of SEQ
ID NO: 5, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence of
SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO: 20,
CDR 2 represented by the amino acid sequence of SEQ ID NO: 40 and CDR3 represented by the amino acid sequence of SEQ ID NO:
3;

(vii) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of SEQ
ID NO: 6, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence of
SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO: 21,
CDR 2 represented by the amino acid sequence of SEQ ID NO: 38 and CDR3 represented by the amino acid sequence of SEQ ID NO:
3;

(viii) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of
SEQ ID NO: 6, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence
of SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO:
22, CDR 2 represented by the amino acid sequence of SEQ ID NO: 38 and CDR3 represented by the amino acid sequence of SEQ ID
NO: 3;

(ix) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of SEQ
ID NO: 7, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence of
SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO: 23,
CDR 2 represented by the amino acid sequence of SEQ ID NO: 41 and CDR3 represented by the amino acid sequence of SEQ ID NO:
3;

(x) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of SEQ
ID NO: 6, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence of
SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO: 24,
CDR 2 represented by the amino acid sequence of SEQ ID NO: 38 and CDR3 represented by the amino acid sequence of SEQ ID NO:
3;

(xi) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of SEQ
ID NO: 6, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence of
SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO: 25,
CDR 2 represented by the amino acid sequence of SEQ ID NO: 38 and CDR3 represented by the amino acid sequence of SEQ ID NO:
3;

(xii) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of SEQ
ID NO: 8, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence of
SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO: 26,
CDR 2 represented by the amino acid sequence of SEQ ID NO: 42 and CDR3 represented by the amino acid sequence of SEQ ID NO:
3;

(xiii) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of
SEQ ID NO: 6, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence
of SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO:
27, CDR 2 represented by the amino acid sequence of SEQ ID NO: 38 and CDR3 represented by the amino acid sequence of SEQ ID
NO: 3;

(xiv) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of SEQ
ID NO: 9, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence of
SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO: 28,
CDR 2 represented by the amino acid sequence of SEQ ID NO: 43 and CDR3 represented by the amino acid sequence of SEQ ID NO:
3;

(xv) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of SEQ
ID NO: 5, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence of
SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO: 29,
CDR 2 represented by the amino acid sequence of SEQ ID NO: 44 and CDR3 represented by the amino acid sequence of SEQ ID NO:
3;

(xvi) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of SEQ
ID NO: 10, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence of
SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO: 30,
CDR 2 represented by the amino acid sequence of SEQ ID NO: 45 and CDR3 represented by the amino acid sequence of SEQ ID NO:
3;

(xvii) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of
SEQ ID NO: 11, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence
of SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO:
31, CDR 2 represented by the amino acid sequence of SEQ ID NO: 42 and CDR3 represented by the amino acid sequence of SEQ ID
NO: 3;

(xviii) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of
SEQ ID NO: 11, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence
of SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO:
20, CDR 2 represented by the amino acid sequence of SEQ ID NO: 39 and CDR3 represented by the amino acid sequence of SEQ ID
NO: 3;

(xix) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of SEQ
ID NO: 11, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence of
SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO: 32,
CDR 2 represented by the amino acid sequence of SEQ ID NO: 46 and CDR3 represented by the amino acid sequence of SEQ ID NO:
3;

(xx) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of SEQ
ID NO: 5, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence of
SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO: 33,
CDR 2 represented by the amino acid sequence of SEQ ID NO: 45 and CDR3 represented by the amino acid sequence of SEQ ID NO:
3;

(xxi) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of SEQ
ID NO: 5, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence of
SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO: 34,
CDR 2 represented by the amino acid sequence of SEQ ID NO: 47 and CDR3 represented by the amino acid sequence of SEQ ID NO:
3;

(xxii) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of
SEQ ID NO: 6, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence
of SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO:
25, CDR 2 represented by the amino acid sequence of SEQ ID NO: 48 and CDR3 represented by the amino acid sequence of SEQ ID
NO: 3;

(xxiii) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of
SEQ ID NO: 12, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence
of SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO:
31, CDR 2 represented by the amino acid sequence of SEQ ID NO: 38 and CDR3 represented by the amino acid sequence of SEQ ID
NO: 3;

(xxiv) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of
SEQ ID NO: 9, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence
of SEQ ID NO: 2 and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO:
31, CDR 2 represented by the amino acid sequence of SEQ ID NO: 46 and CDR3 represented by the amino acid sequence of SEQ ID
NO: 3;

(xxv) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of SEQ
ID NO: 10, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence of
SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO: 17,
CDR 2 represented by the amino acid sequence of SEQ ID NO: 42 and CDR3 represented by the amino acid sequence of SEQ ID NO:
3;

(xxvi) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of
SEQ ID NO: 13, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence
of SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO:
34, CDR 2 represented by the amino acid sequence of SEQ ID NO: 49 and CDR3 represented by the amino acid sequence of SEQ ID
NO: 3; and

(xxvii) the antibody comprising 1) a light chain variable region comprising CDR1 represented by the amino acid sequence of
SEQ ID NO: 14, CDR 2 represented by the amino acid sequence of SEQ ID NO: 1 and CDR3 represented by the amino acid sequence
of SEQ ID NO: 2; and 2) a heavy chain variable region comprising CDR1 represented by the amino acid sequence of SEQ ID NO:
17, CDR 2 represented by the amino acid sequence of SEQ ID NO: 50 and CDR3 represented by the amino acid sequence of SEQ ID
NO: 3.

US Pat. No. 9,375,483

STABLE LIQUID PHARMACEUTICAL COMPOSITION CONTAINING PIROXICAM OR ITS PHARMACEUTICALLY ACCEPTABLE SALT AND HYALURONIC ACID OR ITS PHARMACEUTICALLY ACCEPTABLE SALT AND THE MANUFACTURING METHOD THEREOF

DONG-A ST CO., LTD., Seo...

1. An anti-inflammatory, analgesic pharmaceutical composition, consisting of (1) piroxicam or a pharmaceutically acceptable
salt thereof and hyaluronic acid or a pharmaceutically acceptable salt thereof as active ingredients; (2) ?-cyclodextrin or
its derivative and polyethylene glycol as stabilizing agents; and (3) a pharmaceutically acceptable carrier for administration
of the pharmaceutical composition by injection.

US Pat. No. 9,834,550

PYRIDOPYRIMIDINONE COMPOUNDS FOR MODULATING THE CATALYTIC ACTIVITY OF HISTONE LYSINE DEMETHYLASES (KDMS)

DONG-A ST CO., LTD., Seo...

1. A compound represented by following Formula 1, an isomer thereof, or a pharmaceutically acceptable salt thereof:

wherein,
X is selected from the group consisting of hydrogen, cycloalkyl, heterocyclyl, aryl, heteroaryl, —CH(R1)NH—R2 and —CH(R1)O—R2, which cycloalkyl, heterocyclyl, aryl and heteroaryl may optionally be substituted with one or more R3;

Y is —CH2NH-A-Z—;

A is selected from the group consisting of a single bond, C1-8 alkylene, C2-8 alkenylene, C2-8 alkynylene, C3-10 cycloalkylene, heterocyclylene, —C(?O)— and —CH(R3)C(?O)—, which alkylene, alkenylene, alkynylene, cycloalkylene and heterocyclylene may optionally be substituted with one
or more R4;

Z is selected from the group consisting of hydrogen, —N(R4)(R5), C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C3-10 cycloalkyl, heterocyclyl, aryl, arylalkyl and heteroaryl, which alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, arylalkyl
and heteroaryl may optionally be substituted with one or more R3;

R1 is selected from the group consisting of hydrogen, C1-8 alkyl, C1-4 fluoroalkyl, C1-4 hydroxyalkyl, C2-8 alkenyl, C2-8 alkynyl, C3-10 cycloalkyl, arylalkyl, heterocyclyl and heteroarylalkyl, which heterocyclyl may optionally be substituted with one or more
selected from the group consisting of halogen and C1-8alkyl;

R2 is selected from the group consisting of aryl, arylalkyl and heteroaryl, which aryl, arylalkyl and heteroaryl may optionally
be substituted with one or more selected from hydrogen, halogen, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C3-10 cycloalkyl, —CF3, —CN, —NO2, —C(?O)—O(R4), —C(?O)—N(R4)(R5), —O(R4), —OCF3, —S(R4), —SO3, —SO2(R4), —N(R4)(R5), C1-8 alkoxyC1-8 alkyl, —C1-8 alkyl-C(?O)R4, —C(?O)R4, —C1-8 alkyl-R4, —NH—C(?O)R4 and —C1-8alkyl-NR4R5;

R3 is selected from the group consisting of hydrogen, C1-8 alkyl, C1-4 aminoalkyl, C1-4 hydroxyalkyl, C2-8 alkenyl, C2-8 alkynyl, C3-10 cycloalkyl, oxo, C(?O)—O(R4), —C(?O)—N(R4)(R5)—O(R4), —S(R4), —SO2(R4) and —N(R4)(R5); or, alternatively two vicinal substituents are forming aryl or heteroaryl ring, which is substituted with one or more R4,

R4 or R5 is independently selected from the group consisting of hydrogen, C1-6 alkyl, C1-4 aminoalkyl, C1-4 fluoroalkyl, C1-4 hydroxyalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, heteroarylalkyl and arylalkyl, which alkyl, alkenyl, alkynyl,
cycloalkyl, heterocyclyl, heteroaryl, aryl, cycloalkylalkyl, heterocyclylalkyl, heteroarylalkyl and arylalkyl may optionally
be substituted with one or more independently selected R1; or, alternatively germinal R4 and R5 are forming N-containing heterocyclyl, which is substituted with one or more R1.

US Pat. No. 9,771,348

METHOD FOR PREPARING BENZAMIDE DERIVATIVE, NOVEL INTERMEDIATE USED IN PREPARATION OF BENZAMIDE, AND METHOD FOR PREPARING NOVEL INTERMEDIATE

DONG-A ST CO., LTD, Seou...

1. A method for preparing a compound of Formula 3:
or a pharmaceutically acceptable salt thereof, the method comprising:
reacting a compound of Formula 1:
with a compound of Formula 2:

or a pharmaceutically acceptable salt thereof.

US Pat. No. 9,828,339

BIPHENYL DERIVATIVES AND METHODS FOR PREPARING SAME

DONG-A ST CO., LTD, Seou...

5. A method for preparing a compound of Formula 1 or a pharmaceutically acceptable salt thereof:

the method comprising a step of:
reacting a compound of Formula 2:
with a compound of Formula 3:
in the presence of a carbamate synthesis reagent, wherein:
the carbamate synthesis reagent is:
a mixture of diphenylphosphoryl azide (DPPA) and triethylamine; or
a mixture of propylphosphonic anhydride (T3P), trimethylsilyl azide (TMSN3) and triethylamine; or

a mixture of sodium azide (NaN3), tetrabutylammonium bromide and zinc(II) triflate;

R1 is hydrogen, halogen, hydroxy, substituted or unsubstituted C1-C6 alkyl, or C1-C6 alkoxy;

R2, R3 and R4 are each independently hydrogen, halogen, substituted or unsubstituted amino, nitro, cyano, hydroxy, substituted or unsubstituted
C1-C6 alkyl, substituted or unsubstituted C1-C6 alkoxy, or —C(O)R6;

R5 is hydrogen or C1-C6 alkyl; and

n is 0 or 1.

US Pat. No. 9,533,977

OXAZOLIDINONE DERIVATIVE AS CETP INHIBITOR, ITS PREPARATION METHOD, AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

DONG-A ST CO., LTD., (KR...

1. A compound represented by the following Chemical Formula 1:

wherein,
X is N, Y is N or CH;
R1 is selected from the group consisting of hydrogen, cyano, halogen, halogen-substituted or unsubstituted C1 to C6 alkyl, —NR4R5, —(O)SO2R6 which is optionally substituted with C1-C4 alkyl or may not be, substituted or unsubstituted C3 to C20 cycloalkyl, substituted
or unsubstituted C3 to C20 heterocyclic, substituted or unsubstituted C6 to C40 aryl, and substituted or unsubstituted C3
to C40 heteroaryl;

R4 and R5 are independently selected from the group consisting of hydrogen, C1 to C4 alkyl, and C3 to C6 cycloalkyl with a proviso that
when R4 and R5 are independently C1 to C4 alkyl, R4 and R5 may be linked to each other to form a hetero cycle containing N;

the substituted C3 to C20 cycloalky or the C3 to C20 heterocyclic in R1 may be substituted with a functional radical selected from the group consisting of halogen, halogen-substituted or unsubstituted
C1 to C4 alkyl, C1 to C4 hydroxyalkyl, —(CH2)nCOR7, and —(CH2)nCO(O)R7;

the substituted C6 to C40 aryl in R1 may be substituted with a functional radical selected from the group consisting of halogen, cyano, nitryl, C1 to C4 alkyl,
C1 to C4 hydroxyalkyl, and C1 to C4 alkoxy;

the C3 to 40 heteroaryl in R1 may be substituted with cyano, nitryl, oxo, —NR8R9, halogen, halogen-substituted or unsubstituted C1 to C4 alkyl, C1 to C4 hydroxyalkyl, C1 to C4 alkoxy, —(CH2)nCOR10, and —(CH2)nCO(O)R10;

R2 is selected from the group consisting of hydrogen, hydroxy-substituted or unsubstituted C1 or C6 alkyl, C3 to C7 cycloalkyl,
and —(CH2)nCO(O)R11;

R3 is selected from the group consisting of C1 to C6 alkyl which may be substituted with substituted or unsubstituted C3 to C7
cycloalkyl or may not be, substituted or unsubstituted C3 to C7 cycloalkyl, substituted or unsubstituted C3 to C20 heterocyclic,
and substituted or unsubstituted C6 to C20 spirocyclic heterocyclic;

R2 and R3 may be linked to each other to form a heterocycle containing N, said heterocycle being substituted with halogen-substituted
or unsubstituted C1 to C4 alkyl or not;

the C3 to C7 cycloalkyl in R3 may be substituted with a functional radical selected from the group consisting of oxo, —NR12R13, C1 to C4 hydroxyalkyl, and —(CH2)nCO(O)R14;

the substituted C3 to C20 heterocycle and the substituted C6 to C20 spirocyclic heterocyclic in R3 may be independently substituted with a functional radical selected from the group consisting of oxo, C1 to C4 alkyl, C1 to
C4 alkoxy, (CH2)nCO(O)R15, —COR16, and —SO2R17;

R16 and R17 are independently C1 to C4 alkyl or —NR18R19;

R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R18 and R19 are independently hydrogen or C1 to C4 alkyl;

n is an integer of 0, 1 or 2; an isomer thereof, or a pharmaceutically acceptable salt thereof.

US Pat. No. 10,160,724

TETRAHYDROPYRIDINE DERIVATIVES AND THEIR USE AS ANTIBACTERIAL AGENTS

Dong-A St Co., Ltd., Seo...

1. A tetrahydropyridine compound represented by the following formula I, a stereoisomer thereof or a pharmaceutically acceptable salt thereof:
wherein,
n is 1, 2 or 3;
R1 is C1-C6 alkyl or C1-C6 haloalkyl;
R2 is hydrogen or C1-C6 alkyl;
R3 is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, —OH or halogen;
L is C3-C7 cycloalkyl, aryl, heteroaryl or null, wherein at least one H of C3-C7 cycloalkyl, aryl or heteroaryl may be substituted with halogen, C1-C6 alkyl, C1-C6 haloalkyl, —NRARB or —OH;
D is C?C, C3-C7 cycloalkyl, aryl, heteroaryl or null, wherein at least one H of C3-C7 cycloalkyl, aryl or heteroaryl may be substituted with halogen, C1-C6 alkyl, C1-C6 haloalkyl, —NRARB or —OH;
E is C?C, C3-C7 cycloalkyl, aryl, heteroaryl or null, wherein at least one H of C3-C7 cycloalkyl, aryl or heteroaryl may be substituted with halogen, C1-C6 alkyl, C1-C6 haloalkyl, —NRARB or —OH;
G is C1-C6 alkyl, C3-C7 cycloalkyl, 4-6 membered heterocycloalkyl, aryl or heteroaryl,
wherein at least one H of C1-C6 alkyl may be substituted with halogen, —NRARB, —OH or —ORC,
at least one H of C3-C7 cycloalkyl or 4-6 membered heterocycloalkyl may be substituted with C1-C6 alkyl, C1-C6 alkyl-NRARB, C1-C6 hydroxyalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkyl-ORC, —NRARB, —OH, —(C?O)—C1-C6 alkyl or —S(?)2—C1-C6 alkyl,
at least one H of aryl or heteroaryl may be substituted with C1-C6 alkyl, C1-C6 hydroxyalkyl, C1-C6 alkyl-NRARB, halogen, nitro, cyano, —NRARB, —OH, —ORC, —S(?O)2—C1-C6 alkyl, —S(?O)2—NRARB or —N—S(?O)2—C1-C6 alkyl;
RA and RB are each independently hydrogen or C1-C6 alkyl, or RA and RB may be linked together to form 4-6 membered ring, wherein the 4-6 membered ring may have O or S atom and at least one H of the 4-6 membered ring may be substituted with halogen, —OH or C1-C6 hydroxyalkyl;
RC is C1-C6 alkyl, C1-C6 hydroxyalkyl, —(C?O)—NRDRE or —S(?O)2—C1-C6 alkyl; and
RD and RE are each independently hydrogen or C1-C6 alkyl.

US Pat. No. 10,159,667

COMPOSITION CONTAINING A DPP-IV INHIBITOR FOR PREVENTING OR TREATING RENAL DISEASES

DONG-A ST Co., Ltd, Seou...

1. A method of treating a renal disease in a subject who does not have diabetes, comprising:administering to the subject who has the renal disease who does not have diabetes a pharmaceutical composition comprising a therapeutically effective amount of a compound of Formula 1:

or a pharmaceutically acceptable salt thereof, wherein:
X is OR1 and R1 is tert-butyl; and
the renal disease is a glomerulonephritis.

US Pat. No. 10,428,055

SUBSTITUTED PIPERIDINES HAVING GPR119 AGONISTIC ACTIVITY

DONG-A ST CO., LTD., (KR...

9. A pharmaceutical composition comprising as an effective component the compound of claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof, and a pharmaceutically acceptable carrier or excipient.
US Pat. No. 10,398,747

COMPOSITION COMPRISING THE EXTRACT OF HERBAL COMBINATION FOR PREVENTING OR TREATING DIABETIC PERIPHERAL NEUROPATHY

Dong-A St Co., Ltd., Seo...

1. A pharmaceutical composition comprising an extract of a mixture of Dioscorea Rhizoma and rhizome of Dioscorea nipponica, wherein the weight ratio of the Dioscorea Rhizoma and the rhizome of Dioscorea nipponica in the mixture is 3.5:1 (w/w); and wherein the extract is obtained by extracting the mixture with 50% ethanol.