Asymmetric auxiliary group

• US 10,167,309 B2
• Filed: 10/14/2016
• Issued: 01/01/2019
• Est. Priority Date: 07/13/2012
• Status: Active Grant

• Current Assignee: WAVE Life Sciences Ltd.
• Original Assignee: WAVE Life Sciences Ltd.
• Inventors: Shimizu, Mamoru, Wada, Takeshi
• Primary Examiner(s): Berry, Layla D
• Application Number:
  US15/294,602
• Publication Number:
  US 20170029445A1
• Time in Patent Office: 809 Days
• Field of Search: None
• CPC Class Codes: C07B 53/00 Asymmetric syntheses
• CPC Class Codes: C07D 207/08 with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
• CPC Class Codes: C07D 405/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 473/18 one oxygen and one nitrogen atom, e.g. guanine
• CPC Class Codes: C07D 473/34 attached in position 6, e.g. adenine
• CPC Class Codes: C07F 7/0812 comprising a heterocyclic ring
• CPC Class Codes: C07H 1/00 Processes for the preparation of sugar derivatives
• CPC Class Codes: C07H 19/10 with the saccharide radical esterified by phosphoric or polyphosphoric acids
• CPC Class Codes: C07H 19/11 containing cyclic phosphate
• CPC Class Codes: C07H 19/207 the phosphoric or polyphosphoric acids being esterified by a further hydroxylic compound, e.g. flavine adenine dinucleotide or nicotinamide-adenine dinucleotide
• CPC Class Codes: C07H 19/213 containing cyclic phosphate
• CPC Class Codes: C07H 21/04 with deoxyribosyl as saccharide radical
• CPC Class Codes: C07H 23/00 Compounds containing boron, silicon, or a metal, e.g. chelates, vitamin B12 esters with inorganic acids C07H11/00; metal salts, see parent compounds

Abstract

To provide a chiral reagent or a salt thereof.

The chiral reagent has following chemical formula (I). In the formula (I), G¹ and G² are independently a hydrogen atom, a nitro group (—NO₂), a halogen atom, a cyano group (—CN), a group of formula (II) or (III), or both G¹ and G² taken together to form a group of formula (IV).

Claims

1. A chiral reagent or a salt thereof, wherein the chiral reagent has the structure of the following chemical formula (I′

);

2. The chiral reagent or a salt thereof in accordance with claim 1, wherein G¹ is a hydrogen atom.

3. The chiral reagent or a salt thereof in accordance with claim 1, wherein G¹ is a nitro group.

4. The chiral reagent or a salt thereof in accordance with claim 1, wherein G¹ is a halogen atom.

5. The chiral reagent or a salt thereof in accordance with claim 1, wherein G¹ is a cyano group.

6. The chiral reagent or a salt thereof in accordance with claim 1, wherein G¹ is a group of formula (II).

7. The chiral reagent or a salt thereof in accordance with claim 1, wherein G¹ is a group of formula (III).

8. The chiral reagent or a salt thereof in accordance with claim 1, wherein G¹ is a group of formula (V).

9. The chiral reagent or a salt thereof in accordance with claim 1, wherein G² is a nitro group.

10. The chiral reagent or a salt thereof in accordance with claim 1, wherein G² is a cyano group.

11. The chiral reagent or a salt thereof in accordance with claim 1, wherein G² is a group of formula (III).

12. The chiral reagent or a salt thereof in accordance with claim 1, wherein G² is a group of formula (III), wherein G³¹ to G³³ are independently C_1-4 alkyl group, C_6-14 aryl group, C_7-14 aralkyl group, C_1-4 alkyl C_6-14 aryl group, C_1-4 alkoxy C_6-14 aryl group, or C_6-14 aryl C_1-4 alkyl group.

13. The chiral reagent or a salt thereof in accordance with claim 1, wherein G² is a group of formula (III), wherein G³¹ to G³³ are independently C_1-4 alkyl group, C₆ aryl group, C_7-10 aralkyl group, C_1-4 alkyl C₆ aryl group, C_1-4 alkoxy C₆ aryl group, or C₆ aryl C_1-4 alkyl group.

14. The chiral reagent or a salt thereof in accordance with claim 1, wherein G² is a group of formula (III), wherein G³¹ to G³³ are independently C_1-4 alkyl group, or C₆ aryl group.

15. The chiral reagent or a salt thereof in accordance with claim 1, wherein G² is a group of formula (III), wherein G³¹ to G³³ are independently C_1-4 alkyl group.

16. The chiral reagent or a salt thereof in accordance with claim 1, wherein G² is a group of formula (III), wherein G³¹ and G³³ are C₆ aryl group and G³² is C_1-4 alkyl group.

17. The chiral reagent or a salt thereof in accordance with claim 1, wherein G² is a group of formula (V).

18. The chiral reagent or a salt thereof in accordance with claim 1, wherein G² is a group of formula (V), wherein each of G⁵¹ and G⁵² is a hydrogen atom and G⁵³ is a 4-methyl group.

19. A compound having the structure of

20. A compound having the structure of