Granted Patent B1

US 12,661,349 · App. 18/555,209 · Granted Jun 23, 2026

Inventors: Seul Ah Chun (Seoul, KR); Sung Wook Kim (Seoul, KR); Ji Yoon Kim (Seoul, KR); Sung Won Kim (Seoul, KR); Ki Sook Park (Cheongju-si, KR)

Assignee: LG CHEM, LTD.

A61K31/454C07D401/12

Abstract

Claims (14)

1 . A potassium salt of 1-[1-chloro-6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-3,4-dihydro-naphthalen-2-ylmethyl]-piperidine-4-carboxylic acid, which has 3 or more characteristic peaks (2Θ) selected from the following X-ray diffraction pattern spectrum: 6.14±0.2°, 9.59±0.2°, 10.23±0.2°, 11.25±0.2°, 12.32±0.2°, 12.98±0.2°, 15.39±0.2°, 16.18±0.2°, 18.47±0.2° 18.89±0.2° 19.22±0.2°, 20.57±0.2°, 21.14±0.2°, 21.91±0.2°, 22.50±0.2°, 23.34±0.2°, 24.16±0.2° 24.70±0.2° 26.12±0.2° and 27.03±0.2°.

2 . The potassium salt according to claim 1 , which is in a crystalline form.

3 . The potassium salt according to claim 1 , which has 3 or more characteristic peaks (2Θ) selected from the following X-ray diffraction pattern spectrum: 6.14±0.1°, 9.59±0.1°, 10.23±0.1°, 11.25±0.1°, 12.32±0.1°, 12.98±0.1°, 15.39±0.1°, 16.18±0.1°, 18.47±0.1°, 18.89±0.1°, 19.22±0.1°, 20.57±0.1°, 21.14±0.1°, 21.91±0.1°, 22.50±0.1°, 23.34±0.1°, 24.16±0.1°, 24.70±0.1°, 26.12±0.1° and 27.03±0.1°.

4 . A methanesulfonic acid salt (mesylate) of 1-[1-chloro-6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-3,4-dihydro-naphthalen-2-ylmethyl]-piperidine-4-carboxylic acid, which has 3 or more characteristic peaks (2Θ) selected from the following X-ray diffraction pattern spectrum: 13.16±0.2°, 13.65±0.2°, 14.62±0.2°, 15.71±0.2°, 17.95±0.2°, 18.21±0.2° 19.73±0.2°, 20.70±0.2°, 22.31±0.2°, 22.49±0.2°, 22.92±0.2°, 24.23±0.2°, 24.95±0.2°, 25.35±0.2°, 29.52±0.2° and 31.78±0.2°.

5 . The methanesulfonic acid salt according to claim 4 , which is in a crystalline form.

6 . The methanesulfonic acid salt according to claim 4 , which has 3 or more characteristic peaks (2Θ) selected from the following X-ray diffraction pattern spectrum: 13.16±0.1°, 13.65±0.1°, 14.62±0.1°, 15.71±0.1°, 17.95±0.1°, 18.21±0.1°, 19.73±0.1°, 20.70±0.1°, 22.31±0.1°, 22.49±0.1°, 22.92±0.1°, 24.23±0.1°, 24.95±0.1°, 25.35±0.1°, 29.52±0.1° and 31.78±0.1°.

7 . A pharmaceutical composition for the treatment of autoimmune disease including multiple sclerosis, which comprises a potassium salt of 1-[1-chloro-6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-3,4-dihydro-naphthalen-2-ylmethyl]-piperidine-4-carboxylic acid as defined in claim 1 , together with a pharmaceutically acceptable carrier.

8 . A pharmaceutical composition for the prevention or treatment of a disease caused by undesired lymphocyte infiltration related to sphingosine-1-phosphate, which comprises a potassium salt of 1-[1-chloro-6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-3,4-dihydro-naphthalen-2-ylmethyl]-piperidine-4-carboxylic acid as defined in claim 1 , together with a pharmaceutically acceptable carrier.

9 . A pharmaceutical composition for the prevention or treatment of immunoregulation disorder, which comprises a potassium salt of 1-[1-chloro-6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-3,4-dihydro-naphthalen-2-ylmethyl]-piperidine-4-carboxylic acid as defined in claim 1 , together with a pharmaceutically acceptable carrier.

10 . The pharmaceutical composition according to claim 9 , wherein the immunoregulation disorder is autoimmune disease or chronic inflammatory disease selected from the group consisting of systemic lupus erythematosus, chronic rheumatoid arthritis, inflammatory bowel diseases, multiple sclerosis, amyotrophic lateral sclerosis (ALS), arteriosclerosis, atherosclerosis, scleroderma and autoimmune hepatitis.

11 . A pharmaceutical composition for the treatment of autoimmune disease including multiple sclerosis, which comprises a methanesulfonic acid salt (mesylate) of 1-[1-chloro-6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-3,4-dihydro-naphthalen-2-ylmethyl]-piperidine-4-carboxylic acid as defined in claim 4 , together with a pharmaceutically acceptable carrier.

12 . A pharmaceutical composition for the prevention or treatment of a disease caused by undesired lymphocyte infiltration related to sphingosine-1-phosphate, which comprises a methanesulfonic acid salt (mesylate) of 1-[1-chloro-6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-3,4-dihydro-naphthalen-2-ylmethyl]-piperidine-4-carboxylic acid as defined in claim 4 , together with a pharmaceutically acceptable carrier.

13 . A pharmaceutical composition for the prevention or treatment of immunoregulation disorder, which comprises a methanesulfonic acid salt (mesylate) of 1-[1-chloro-6-(3-chloro-1-isopropyl-1H-indazol-5-ylmethoxy)-3,4-dihydro-naphthalen-2-ylmethyl]-piperidine-4-carboxylic acid as defined in claim 4 , together with a pharmaceutically acceptable carrier.

14 . The pharmaceutical composition according to claim 13 , wherein the immunoregulation disorder is autoimmune disease or chronic inflammatory disease selected from the group consisting of systemic lupus erythematosus, chronic rheumatoid arthritis, inflammatory bowel diseases, multiple sclerosis, amyotrophic lateral sclerosis (ALS), arteriosclerosis, atherosclerosis, scleroderma and autoimmune hepatitis.

Assignments (1)

Priority Claims (1)

References Cited (29)