IP Library › Granted Patent US 12,668,566
Granted Patent B2
US 12,668,566 · App. 17/613,834 · Granted Jun 30, 2026

Preparation method for salicylamine acetate

Inventors: Ling Long (Shanghai, CN); Jianyi Ma (Shanghai, CN); Weiguo Liu (Shanghai, CN); Zhouya Liu (Shanghai, CN)
Assignee: TSI Group Co., Ltd.
C07C213/02C07C51/412
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,668,566
App. No.
17/613,834
Filed
Jun 21, 2022
Granted
Jun 30, 2026
Kind
B2
Art Unit
1692
USPC
564/414
Abstract

A preparation method for salicylamine acetate, comprising preparing an amino-protected intermediate from salicylaldehyde, and reacting the intermediate with acetic acid to prepare an acetate.

Claims (15)

1 . A method for preparing salicylamine acetate, wherein the method comprises the following steps:

(1) subjecting salicylaldehyde having a structure shown in Formula 1

to amino protection to obtain a compound having a structure shown in Formula 2

(2) reacting the compound having the structure shown in Formula 2 with acetic acid to obtain salicylamine acetate in one step, wherein the ratio of the compound of Formula 2 to acetic acid in step (2) is 1:1-20 (g/ml) and the temperature for reacting with acetic acid in step (2) is from 70° C. to the reflux temperature of acetic acid.

2 . The method according to claim 1 , wherein the reaction temperature of amino protection in step (1) is 0-50° C.

3 . The method according to claim 1 , wherein the reaction time of amino protection in step (1) is 3-18 hours.

4 . The method according to claim 1 , wherein the reaction solvent in step (1) is selected from the group consisting of tetrahydrofuran, 2-methyltetrahydrofuran, acetonitrile and 1,4-dioxane.

5 . The method according to claim 1 , wherein the ratio of the compound of Formula 2 to acetic acid in step (2) is 1:1-15 (g/mL).

6 . The method according to claim 1 , wherein the ratio of the compound of Formula 2 to acetic acid in step (2) is 1:3-10 (g/mL).

7 . The method according to claim 1 , wherein the method comprises the following steps:

(1) protecting the salicylaldehyde having the structure shown in Formula 1 with an amino group to obtain the compound having the structure shown in Formula 2;

(2) reacting the compound having the structure shown in Formula 2 with acetic acid, and lowering the temperature to room temperature after the reaction is complete, to obtain crude salicylamine acetate;

(3) mixing the obtained crude salicylamine acetate with an organic solvent and crystallizing to obtain pure salicylamine acetate; wherein the organic solvent is selected from the group consisting of ethyl acetate, isopropyl ether, absolute ethanol and methyl tert-butyl ether.

8 . The method according to claim 1 , wherein the time for reacting with acetic acid in step (2) is 5-70 hours.

9 . The method according to claim 1 , wherein the time for reacting with acetic acid in step (2) is 5-60 hours.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 3, 2026
From: LONG, LING; MA, JIANYI; LIU, WEIGOU; LIU, ZHOUYA
To: TSI GROUP CO., LTD.
Reel/Frame 074837/0115 →
CHANGE OF NAME Recorded May 12, 2022
From: JIANGYIN TSI PHARMACEUTICAL CO., LTD.
To: TSI GROUP, CO. LTD.
Reel/Frame 059985/0402 →
Priority Claims (1)
CN 201910440439.9 · May 24, 2019 · national
Continuity (1)
Related Publication 20220315524A1 · Oct 6, 2022
References Cited (23)
US 11512044B2 · Long · 2022 [cited by examiner]
US 20070203214A1 · Salvatore et al. · 2007 [cited by applicant]
US 20210053907A1 · Long · 2021 [cited by examiner]
BR 112020010618B1 · 2020 [cited by applicant]
CN 102295594 · 2011 [cited by examiner]
CN 102295594B · 2011 [cited by applicant]
EP 3719002A1 · 2020 [cited by applicant]
JP H07330702 · 1995 [cited by applicant]
WO 2019105324A1 · 2019 [cited by applicant]
WO WO2019105324 · 2019 [cited by examiner]
Mestichelli et al. (Concise Copper-Catalyzed Synthesis of Tricyclic Biaryl Ether-Linked Aza-Heterocyclic Ring Systems. Organic Letters, vol. 15, No. 21, pp. 5448-5451, Published Oct. 2013) (Year: 2013). [cited by examiner]
Mestichelli et al. Supporting Information 276 pages (Year: 2013). [cited by examiner]
Fuller et al. (Food and Chemical Toxicology, 121, pp. 541-548, Published 2018) (Year: 2018). [cited by examiner]
Greene (Greene's Protective Groups in Organic Synthesis, fourth edition, pp. 696, 707, 725-735 and 748-756, Published 2007) (Year: 2007). [cited by examiner]
CN 102295594 translation (Year: 2011). [cited by examiner]
Zagol-Ikapitte et al. (Characterization of Scavengers of Gamma-Ketoaldehydes That Do Not Inhibit Prostaglandin Biosynthesis, Chem. Res. Toxicol., 23, pp. 240-250, Published 2010) (Year: 2010). [cited by examiner]
Gopal Das, Braja , et al., “The direct reductive amination of electron-deficient amines with aldehydes: the unique reactivity of the Re2O7 catalyst”, Chemical Communications, vol. 48, No. 66, Jan. 1, 2012. [cited by applicant]
Mestichelli, Paola , et al., “Concise Copper-Catalyzed Synthesis of Tricyclic Biaryl Ether-Linked Aza-Heterocyclic Ring Systems”, Organic Letters, vol. 15, No. 21, Oct. 17, 2013. [cited by applicant]
Plattner, Jacob J, et al., “[(Aminomethyl)aryloxy]acetic Acid Esters. A New Class of High-Ceiling Diuretics. 3. Variation in the Bridge between the Aromatic Rings to Complete Mapping of the Receptor”, Journal of Medicin… [cited by applicant]
Zagol-Ikapitte, Irene , et al., “Characterization of Scavengers of y-Ketoaldeydes That Do Not Inhibit Prostaglandin Biosynthesis”, Chemical Research in Toxicology, vol. 23, No. 1, Jan. 18, 2010. [cited by applicant]
“Cbz-Protected Amino Groups”, < URL: https://www.organic-chemistry.org/protectivegroups/amino/cbz-amino.htm >. [cited by applicant]
Fuller, John C., et al., “In vitro safety pharmacology evaluation of 2-hydroxybenzylamine acetate”, Food and Chemical Toxicology, vol. 121, 2018, 541-548. [cited by applicant]
Lee, Chanhyo , et al., “Colorimetric anion sensing by porphyrin-based anion receptors”, Tetrahedron Letters, vol. 42, 2001, 8665-8668. [cited by applicant]