IP Library › Granted Patent US 12,269,839
Granted Patent B2
US 12,269,839 · App. 18/094,723 · Granted Apr 8, 2025

Chiral phosphoramidite auxiliaries and methods of their use

Inventors: Sukumar Sakamuri (San Diego, CA); Curt W. Bradshaw (San Diego, CA); Dingguo Liu (San Diego, CA); Laxman Eltepu (San Diego, CA)
Assignee: SIRIUS THERAPEUTICS, INC.
C07H19/11C07H19/213C07H21/04
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Quick Facts
Patent No.
US 12,269,839
App. No.
18/094,723
Granted
Apr 8, 2025
Kind
B2
Abstract

Disclosed are P-stereogenic groups that may be used in the synthesis of compounds including stereochemically enriched P-stereogenic phosphorothioates. P-stereogenic groups may be provided in nucleoside phosphoramidites including a sugar bonded to a nucleobase and to a stereochemically enriched phosphoramidite as well as methods of their use and methods of making them.

Claims (23)

1. A method of preparing a composition comprising a nucleoside phosphoramidite, the method comprising coupling an oxazaphospholane with a nucleoside, wherein the nucleoside phosphoramidite is of the following structure:

wherein

B 1 is a nucleobase;

Y 1 is H or C 1-6 alkyl;

is a single carbon-carbon bond or a double carbon-carbon bond;

each of R 1 and R 2 is independently an optionally substituted C 1-6 alkyl or optionally substituted C 6-10 aryl, or R 1 and R 2 , together with the atoms to which each is attached, combine to form an optionally substituted C 6-10 aryl; and

each of R 3 and R 4 is H;

R 5 is H, O-protected hydroxyl, optionally substituted C 1-6 alkoxy, or halogen; and

R 6 is a hydroxyl protecting group,

wherein the oxazaphospholane has a structure of Formula (VIIIA) or (VIIIB),

wherein X is halogen or pseudohalogen.

2. The method of claim 1 , wherein R 5 is hydrogen, halogen, or optionally substituted C 1-6 alkoxy.

3. The method of claim 1 , wherein R 5 is hydrogen, fluoro, or methoxy.

4. The method of claim 1 , wherein R 6 is dimethoxytrityl.

5. The method of claim 1 , wherein R 1 and R 2 , together with the atoms to which each is attached, combine to form an optionally substituted C 6-10 aryl.

6. The method of claim 5 , wherein the optionally substituted C 6-10 aryl is an optionally substituted C 6 aryl.

7. The method of claim 1 , wherein the method further comprises reacting an aminoalcohol with an electrophilic source of phosphorous to produce the oxazaphospholane, wherein the aminoalcohol is of the following structure:

8. The method of claim 7 , wherein the electrophilic source of phosphorous (III) comprises a phosphorous (III) halide.

9. The method of claim 8 , wherein the phosphorous (III) halide is PCl 3 .

10. The method of claim 8 , wherein the coupling comprises use of a sterically hindered organic base.

11. The method of claim 10 , wherein the sterically hindered organic base comprises N,N-diisopropylethylamine.

12. The method of claim 1 , wherein X is halogen.

13. The method of claim 12 , wherein X is Cl.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 10, 2024
From: CLEAR SKIES BIO LLC
To: SIRIUS THERAPEUTICS, INC.
Reel/Frame 067372/0615 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 9, 2024
From: SAKAMURI, SUKUMAR; BRADSHAW, CURT W.; LIU, DINGGUO; ELTEPU, LAXMAN
To: SOLSTICE BIOLOGICS, LTD.
Reel/Frame 067364/0332 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 9, 2024
From: SOLSTICE BIOLOGICS LIMITED
To: CLEAR SKIES BIO LLC
Reel/Frame 067364/0522 →
Continuity (3)
Continuation 16627091
Provisional Application 62527078 · Jun 30, 2017
Related Publication 20230242567A1 · Aug 3, 2023
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