IP Library › Granted Patent US 11,858,936
Granted Patent B2
US 11,858,936 · App. 17/504,443 · Granted Jan 2, 2024

Synthetic co-crystals of anhydrous guanine and process for preparing the same

Inventors: Dvir Gur (Rehovot, IL); Lia Addadi (Rehovot, IL); Stephen Weiner (Rehovot, IL)
Assignee: Dvir Gur
C07D473/18C07B2200/13
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Quick Facts
Patent No.
US 11,858,936
App. No.
17/504,443
Granted
Jan 2, 2024
Kind
B2
Abstract

This invention is directed to synthetic co-crystals of anhydrous guanine and at least one additional material, wherein the co-crystals have a high refraction index and therefore, provide products with pearlescence or whiteness with high coverage. The invention is further directed to a process for the preparation of anhydrous guanine and of the co-crystals.

Claims (25)

1. A pH-controlled process for preparing synthetic co-crystals of anhydrous guanine and at least one additional material selected from the group consisting of hypoxanthine, xanthine, uric acid, isoguanine, theobromine, isoxanthopterin, xanthopterin, thymine, cytosine, uracil, guanosine, cytidine, thymidine, uridine, adenosine, and inosine, wherein said process comprises the steps of:

preparing a basic or acidic aqueous solution of guanine and the at least one additional material;

maintaining the basic or acidic aqueous solution at a predetermined temperature range for a predetermined period of time;

adjusting the pH of the aqueous solution by adding a base or an acid over a predefined period of time until a predetermined pH value is obtained, thereby providing a synthetic co-crystal suspension comprising co-crystals;

allowing the synthetic co-crystal suspension to mature over a predetermined period of time; and

collecting the synthetic co-crystals from the crystal suspension.

2. The pH-controlled process of claim 1 , further comprising a step of filtering the basic or acidic aqueous solution prior to the step of adjusting the pH, to provide a filtrate, wherein the step of adjusting the pH comprises adjusting the pH of the filtrate.

3. The pH-controlled process of claim 1 , wherein the molar ratio between the at least one additional material and guanine is between 4:1-0.01:1.

4. The pH-controlled process of claim 1 , wherein the basic or acidic aqueous solution comprises 0.003-0.2M of guanine.

5. The pH-controlled process of claim 1 , wherein the basic or acidic aqueous solution comprises 0.003-0.2M of the at least the one additional material.

6. The pH-controlled process of claim 1 , wherein the acid is selected from the group consisting of HCl, H 2 SO 4 , H 3 PO 4 , HNO 3 , C 6 H 8 O 7 , H 2 CO 3 , H 3 BO 3 , and any combination thereof.

7. The pH-controlled process of claim 1 , wherein the pH of the acidic solution is between 0-3.

8. The pH-controlled process of claim 1 , wherein the base is selected from the group consisting of NaOH, NaHCO 3 , KOH, NH 4 OH, Ca(OH) 2 , and any combination thereof.

9. The pH-controlled process of claim 1 , wherein the pH of the basic solution is between 12-14.

10. The pH-controlled process of claim 1 , wherein the pH of the aqueous solution is adjusted by dropwise adding a base or an acid to the filtrate over a period of time of 1-20 minutes.

11. The pH-controlled process of claim 1 , wherein the predetermined pH value is between 10.5-11.5.

12. A temperature-controlled process for preparing synthetic co-crystals of anhydrous guanine and at least one additional material selected from the group consisting of hypoxanthine, xanthine, uric acid, isoguanine, theobromine, isoxanthopterin, xanthopterin, thymine, cytosine, uracil, guanosine, cytidine, thymidine, uridine, adenosine, and inosine, wherein said process comprises the steps of:

preparing a basic or acidic aqueous solution of guanine and at least one additional material;

heating the basic or acidic aqueous solution to a predetermined temperature for a predetermined length of time;

inducing co-crystallization by cooling the basic or acidic aqueous solution at a predetermined rate until reaching a predetermined temperature thereby providing a synthetic co-crystal suspension comprising co-crystals;

allowing the synthetic co-crystal suspension to mature over a predetermined period of time; and

collecting the synthetic co-crystals from the crystal suspension.

13. The temperature-controlled process of claim 12 , wherein the basic or acidic aqueous solution is heated to a temperature of between about 50-95° C.

14. The temperature-controlled process of claim 12 , wherein the co-crystallization is induced by cooling the basic or acidic aqueous solution at a predetermined rate of between about 0.1-5.0 degrees/minute.

15. The temperature-controlled process of claim 12 , wherein the basic or acidic aqueous solution is cooled to a predetermined temperature of about 4-20° C.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 5, 2024
From: GUR, DVIR
To: ECOCRYSTAL LTD.
Reel/Frame 066647/0227 →
CORRECTIVE ASSIGNMENT TO CORRECT THE SECOND INVENTOR'S NAME PREVIOUSLY RECORDED AT REEL: 65588 FRAME: 550. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT . Recorded Mar 5, 2024
From: GUR, DVIR; ADDADI, LIA; WEINER, STEPHEN
To: YEDA RESEARCH AND DEVELOPMENT CO. LTD.
Reel/Frame 066741/0839 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 16, 2023
From: GUR, DVIR; ADDAI, LIA; WEINER, STEPHEN
To: YEDA RESEARCH AND DEVELOPMENT CO. LTD.
Reel/Frame 065588/0550 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 20, 2021
From: YEDA RESEARCH AND DEVELOPMENT CO. LTD.
To: GUR, DVIR
Reel/Frame 057844/0755 →
Priority Claims (1)
IL 246428 · Jun 21, 2016 · national
Continuity (2)
Continuation 16311700
Related Publication 20220098199A1 · Mar 31, 2022
Cited By (1)
US 12,473,287