IP Library › Granted Patent US 10,131,650
Granted Patent B2
US 10,131,650 · App. 15/326,422 · Granted Nov 20, 2018

Alpha-helix analog having triazine-piperazine backbone and method for preparing same

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Quick Facts
Patent No.
US 10,131,650
App. No.
15/326,422
Granted
Nov 20, 2018
Kind
B2
Abstract

The alpha-helix mimetic containing a triazine-piperazine scaffold is provided. The alpha-helix mimetic compound can mimic efficiently the alpha-helix structure of protein secondary structure and act as an inhibitor for the protein interaction being specific to various diseases mediated by alpha-helix. Therefore, the compound can be used as a biological probe and have a high potential of drug treating diseases.

Claims (218)

1. A compound or a pharmaceutically acceptable salt thereof, wherein the compound is selected from the group consisting of the compounds of Chemical formula 4 to Chemical formula 8:

2. A compound or a pharmaceutically acceptable salt thereof,

wherein the compound is the compound of Chemical formula 9:

wherein, in Chemical formula 9,

R 1 and R 4 are independently —NR 8 R 9 ,

R 8 and R 9 are independently hydrogen, (C 1 -C 6 ) alkyl, —(CH 2 ) r NH 2 , —(CH 2 ) r N(H)C(═NH)NH 2 , —(CH 2 ) r C(═O)OH, or —(CH 2 ) r OH, and

r is an integer of 1 to 6.

3. A compound or a pharmaceutically acceptable salt thereof, wherein the compound is the compound of Chemical formula 3:

wherein R 1 , R 2 , R 3 , R 6 and R 7 in Chemical formula 3 are independently selected from the groups represented by the following chemical structures:

R1

R2

R3

R6

R7

NHEt

NHiPr

iBu

NHEt

NH 2

NHEt

NHiBu

iBu

NHEt

NH 2

NHEt

NHBn

iBu

NHEt

NH 2

NHEt

NHNaph

iBu

NHEt

NH 2

NHEt

NHiPr

Bn

NHEt

NH 2

NHEt

NHiBu

Bn

NHEt

NH 2

NHEt

NHBn

Bn

NHEt

NH 2

NHEt

NHNaph

Bn

NHEt

NH 2

NHEt

NHiPr

Me

NHEt

NH 2

NHEt

NHiBu

Me

NHEt

NH 2

NHEt

NHBn

Me

NHEt

NH 2

NHEt

NHNaph

Me

NHEt

NH 2

NHEt

NHiPr

iBu

NHiBu

NH 2

NHEt

NHiBu

iBu

NHiBu

NH 2

NHEt

NHBn

iBu

NHiBu

NH 2

NHEt

NHNaph

iBu

NHiBu

NH 2

NHEt

NHiPr

Bn

NHiBu

NH 2

NHEt

NHiBu

Bn

NHiBu

NH 2

NHEt

NHBn

Bn

NHiBu

NH 2

NHEt

NHNaph

Bn

NHiBu

NH 2

NHEt

NHiPr

Me

NHiBu

NH 2

NHEt

NHiBu

Me

NHiBu

NH 2

NHEt

NHBn

Me

NHiBu

NH 2

NHEt

NHNaph

Me

NHiBu

NH 2

NHEt

NHiPr

iBu

NHBn

NH 2

NHEt

NHiBu

iBu

NHBn

NH 2

NHEt

NHBn

iBu

NHBn

NH 2

NHEt

NHNaph

iBu

NHBn

NH 2

NHEt

NHiPr

Bn

NHBn

NH 2

NHEt

NHiBu

Bn

NHBn

NH 2

NHEt

NHBn

Bn

NHBn

NH 2

NHEt

NHNaph

Bn

NHBn

NH 2

NHEt

NHiPr

Me

NHBn

NH 2

NHEt

NHiBu

Me

NHBn

NH 2

NHEt

NHBn

Me

NHBn

NH 2

NHEt

NHNaph

Me

NHBn

NH 2

4. The compound or a pharmaceutically acceptable salt thereof according to claim 3 , wherein the compound is the compound of Chemical formula 10:

5. A composition, comprising a compound or a pharmaceutically acceptable salt thereof according to claim 1 , and

pharmaceutically acceptable carriers, excipients or diluents.

6. A pharmaceutical composition, comprising:

pharmaceutically acceptable carriers, excipients or diluents; and

a compound selected from the group consisting of the compounds of Chemical formula 4 to Chemical formula 6, and Chemical formula 9 and Chemical formula 10, or a pharmaceutically acceptable salt thereof:

wherein in Chemical formula 9,

R 1 and R 4 are independently —NR 8 R 9 where R 8 and R 9 are independently hydrogen, (C 1 -C 6 ) alkyl, —(CH 2 ) r NH 2 , —(CH 2 ) r N(H)C(═NH)NH 2 , —(CH 2 ) r C(═O)OH, or —(CH 2 ) r OH, and

r is an integer of 1 to 6.

7. The pharmaceutical composition according to claim 6 , wherein the compound is the compound of Chemical formula 9;

and

wherein in Chemical formula 9,

R 1 and R 4 are independently —NR 8 R 9 where R 8 and R 9 are independently hydrogen, (C 1 -C 6 ) alkyl, —(CH 2 ) r NH 2 , —(CH 2 ) r N(H)C(═NH)NH 2 , —(CH 2 ) r C(═O)OH, or —(CH 2 ) r OH, and

r is an integer of 1 to 6.

8. A pharmaceutical composition, comprising:

pharmaceutically acceptable carriers, excipients or diluents; and

a compound selected from the group consisting of the compounds of Chemical formula 7 to Chemical formula 8, or a pharmaceutically acceptable salt thereof:

9. The pharmaceutical composition according to claim 6 , wherein the compound is the compound of Chemical formula 10:

10. A composition, comprising a compound or a pharmaceutically acceptable salt thereof according to claim 2 , and

pharmaceutically acceptable carriers, excipients or diluents.

11. A composition, comprising a compound or a pharmaceutically acceptable salt thereof according to claim 3 , and

pharmaceutically acceptable carriers, excipients or diluents.

12. A composition, comprising a compound or a pharmaceutically acceptable salt thereof according to claim 4 , and

pharmaceutically acceptable carriers, excipients or diluents.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 4, 2023
From: POSCO HOLDINGS INC.; POSTECH ACADEMY-INDUSTRY FOUNDATION
To: POSCO CO., LTD; POSTECH ACADEMY-INDUSTRY FOUNDATION
Reel/Frame 063254/0853 →
CHANGE OF NAME Recorded Sep 28, 2022
From: POSCO
To: POSCO HOLDINGS INC.
Reel/Frame 061562/0041 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 13, 2017
From: LIM, HYUN-SUK; OH, MISOOK; HOANG, QUYEN Q.; WANG, WEI
To: POSCO; POSTECH ACADEMY-INDUSTRY FOUNDATION
Reel/Frame 041001/0327 →