IP Library Granted Patent US 10,858,308
Granted Patent B2
US 10,858,308 · App. 16/476,977 · Granted Dec 8, 2020

Compounds and compositions

Inventors: Gaik Babikyan (Jakarta, ID); Benjamin Jiaravanon (Singapore, SG)
Assignee: Alectrona PTE. LTD.
C07C229/16A61P31/04A61P31/10A61P31/20A61P31/22C07C227/08C07C227/40
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Quick Facts
Patent No.
US 10,858,308
App. No.
16/476,977
Granted
Dec 8, 2020
Kind
B2
Abstract

Disclosed are compounds having the following formula: (I) wherein R is an alkane chain having between 8 and 20 carbon atoms, and A is one or more anions having a total charge of −2; or R is a quaternary amine having the following formula: (Ia) wherein Ra and Rb are each an alkane chain having between 8 and 20 carbon atoms, and A is one or more anions having a total charge of −3.

Claims (45)

1. A compound having the following formula:

wherein R is an alkane chain having between 8 and 20 carbon atoms, and A is one or more anions having a total charge of −2;

or R is a quaternary amine having the following formula:

wherein R a and R b are each an alkane chain having between 8 and 20 carbon atoms, and A is one or more anions having a total charge of −3.

2. A compound according to claim 1 , wherein R is a saturated linear alkane chain having between 8 and 16 carbon atoms.

3. A compound according to claim 1 , wherein R a and R b are saturated linear alkane chains having between 8 and 16 carbon atoms.

4. A compound according to claim 1 , wherein the one or more anions are selected from chloride anions and bromide anions.

5. A compound according to claim 1 , having the following formula:

6. A compound having the following formula:

wherein R is an alkane chain having between 8 and 20 carbon atoms and A is one or more anions having a total charge of −2; or R is a quaternary amine having the following formula:

wherein R a and R b are each an alkane chain having between 8 and 20 carbon atoms, and A is one or more anions having a total charge of −3; and wherein X is 2, 4, 6, 8 or 10.

7. A compound according to claim 6 , wherein R is a saturated linear alkane chain having between 8 and 16 carbon atoms.

8. A compound according to claim 6 , wherein R a and R b are saturated linear alkane chains having between 8 and 16 carbon atoms.

9. A compound according to claim 6 , wherein the one or more anions are selected from chloride anions and bromide anions.

10. A compound according to claim 6 , having the following formula:

wherein X is 4, 8 or 10.

11. A pharmaceutical composition comprising:

the compound of claim 1 or claim 6 ; and a pharmaceutically acceptable carrier.

12. A method of treatment of Herpes virus, Human Papilloma virus, fungal infections and/or bacterial infections, comprising a step of administering to a subject a compound according to claim 1 or claim 6 .

13. A process for producing the compound of claim 1 , comprising:

i) reacting carvacrol with R 2 CH 2 COCl to form a compound having the formula:

 wherein R 2 is a halogen;

ii) reacting a compound having the formula

 with the compound having the formula

 to form the compound having the formula

wherein R is an alkane chain having between 8 and 20 carbon atoms; or

R is a quaternary amine having the following formula:

wherein R a and R b are each an alkane chain having between 8 and 20 carbon atoms;

iii) reacting thymol with R 2 CH 2 COCl to form a compound having the formula

 wherein R 2 is a halogen;

iv) reacting the compound having formula

 with the compound having the formula

 to form the final product having the formula

wherein R is an alkane chain having between 8 and 20 carbon atoms, and A is one or more anions having a total charge of −2; or R is a quaternary amine having the following formula:

wherein R a and R b are each an alkane chain having between 8 and 20 carbon atoms, and A is one or more anions having a total charge of −3.

14. A process according to claim 13 , wherein R is a saturated linear alkane chain having between 8 and 16 carbon atoms.

15. A process according to claim 13 , wherein R a and R b are each a saturated linear alkane chain having between 8 and 16 carbon atoms.

16. A process according to claim 13 , further comprising one or more steps of separation and/or extraction.

17. A process for the production of a compound according to claim 6 , comprising reacting the compound having the formula

with bromine to form a compound having the formula

wherein R is an alkane chain having between 8 and 20 carbon atoms and A is one or more anions having a total charge of −2; or R is a quaternary amine having the following formula:

wherein R a and R b are each an alkane chain having between 8 and 20 carbon atoms, and A is one or more anions having a total charge of −3; and wherein X is 2, 4, 6, 8 or 10.

18. A compound having the following formula:

wherein R is an alkane chain having between 8 and 20 carbon atoms and A is one or more anions having a total charge of −2; or R is a quaternary amine having the following formula:

wherein R a and R b are each an alkane chain having between 8 and 20 carbon atoms, and A is one or more anions having a total charge of −3; and wherein the compound is complexed with bromine.

Assignments (3)
CHANGE OF NAME Recorded Nov 10, 2021
From: ALECTRONA PTE. LTD.
To: RHEA GENETICS PTE. LTD.
Reel/Frame 058824/0635 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2019
From: BABIKYAN, GAIK; JIARAVANON, BENJAMIN
To: EPIONE RESEARCH AND DEVELOPMENT INSTITUTE, LTD
Reel/Frame 049737/0195 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2019
From: EPIONE RESEARCH AND DEVELOPMENT INSTITUTE, LTD
To: ALECTRONA PTE. LTD.
Reel/Frame 049737/0256 →
Priority Claims (1)
GB 1700404.5 · Jan 10, 2017 · national
Continuity (1)
Related Publication 20190352253A1 · Nov 21, 2019
Cited By (1)
US 12,577,196