Xanthene protective agent

Patent metadata

Field	Value
Publication number	US-10508124-B2
Application number	US-201716319581-A
Country	US
Kind code	B2
Filing date	Jul 24, 2017
Priority date	Jul 25, 2016
Publication date	Dec 17, 2019
Grant date	Dec 17, 2019

Abstract

To develop a protecting group that facilitates separation and purification, after reaction, of a compound including a protected functional group, without solidifying or insolubilizing the compound.
A xanthene compound of by General Formula (1)

(wherein Y is —OR 17 (R 17 is a hydrogen atom or an active ester-protecting group), —NHR 18 (R 18 is a hydrogen atom, or a linear or branched C 1 -C 6 alkyl group or aralkyl group), an azide, a halogen atom, or a carbonyl group formed together with a methylene group;
at least one of R 1 to R 8 is represented by Formula (2);

—O—R 9 —X-A  (2)

and a residue is a hydrogen atom, a halogen atom, a C 1 -C 4 alkyl group, or a C 1 -C 4 alkoxy group,
wherein R 9 is a linear or branched C 1 -C 16 alkylene group;
X is O or CONR 19 (R 19 is a hydrogen atom or a C 1 -C 4 alkyl group); and
A is represented by Formula (3) or the like

(wherein R 10 , R 11 , and R 12 , the same or different, are a linear or branched C 1 -C 6 alkyl group or an aryl group optionally including a substituent;
R 13 is a single bond or a linear or branched C 1 -C 3 alkylene group; and
R 14 , R 15 , and R 16 are a linear or branched C 1 -C 3 alkylene group)).

First claim

The invention claimed is:

1. A xanthene compound of General Formula (1)

wherein:
Y is:
—OR 17 , wherein R 17 is a hydrogen atom or an active ester-protecting group,
—NHR 18 , wherein R 18 is a hydrogen atom, or a linear or branched C 1 -C 6 alkyl group or aralkyl group,
an azide,
a halogen atom, or
a carbonyl group formed together with a methylene group;
at least one of R 1 to R 8 is represented by Formula (2),
—O—R 9 —X-A  (2)

and each of the remaining R 1 to R 8 independently is a hydrogen atom, a halogen atom, a C 1 -C 4 alkyl group, or a C 1 -C 4 alkoxy group,
wherein R 9 is a linear or branched C 1 -C 16 alkylene group;
X is O or CONR 19 , wherein R 19 is a hydrogen atom or a C 1 -C 4 alkyl group; and
A is represented by Formula (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), or (13)

wherein R 10 , R 11 , and R 12 are each independently a linear or branched C 1 -C 6 alkyl group or an aryl group optionally including a substituent;
R 13 is a single bond or a linear or branched C 1 -C 3 alkylene group; and
R 14 , R 15 , and R 16 are each independently a linear or branched C 1 -C 3 alkylene group.

2. The xanthene compound according to claim 1 , wherein Y is:
—OR 17 , wherein R 17 is a hydrogen atom or an active ester-protecting group,
—NHR 18 , wherein R 18 is a hydrogen atom, or a linear or branched C 1 -C 6 alkyl group or aralkyl group,
an azide, or
a halogen atom.

3. The xanthene compound according to claim 1 , wherein Y is:
—OR 17 , wherein R 17 is a hydrogen atom or an active ester-protecting group), or
—NHR 18 , wherein R 18 is a hydrogen atom, or a linear or branched C 1 -C 6 alkyl group or aralkyl group.

4. The xanthene compound according to claim 1 , wherein Y is:
—OR 17 , wherein R 17 is a hydrogen atom,
—NHR 18 , wherein R 18 is a hydrogen atom, or
a carbonyl group formed together with a methylene group.

5. The xanthene compound according to claim 1 , wherein Y is:
—OR 17 , wherein R 17 is a hydrogen atom, or
—NHR 18 , wherein R 18 is a hydrogen atom.

6. The xanthene compound according to claim 1 , wherein at least one of R 1 to R 8 is a group represented by Formula (2), and each of the remaining R 1 to R 8 independently is a hydrogen atom, a C 1 -C 4 alkyl group, or a C 1 -C 4 alkoxy group.

7. The xanthene compound according to claim 1 , wherein R 9 is a linear or branched C 2 -C 16 alkylene group.

8. The xanthene compound according to claim 1 , wherein R 9 is a linear or branched C 6 -C 16 alkylene group.

9. The xanthene compound according to claim 1 , wherein R 13 is a single bond or a methylene group, and R 14 , R 15 , and R 16 are each a methylene group.

10. A protective agent for protecting a carboxy group, a hydroxy group, a diol group, an amino group, an amide group, or a mercapto group, wherein the protective agent comprises the xanthene compound according to claim 1 .

11. A method for producing a compound with a protective agent for protecting a carboxy group, a hydroxy group, a diol group, an amino group, an amide group, or a mercapto group, the method comprising reacting the carboxy group, hydroxy group, diol group, amino group, amide group, or mercapto group, with the protective agent, wherein the protective agent comprises the xanthene compound according to claim 1 .

12. A method for producing a peptide with a protective agent for protecting a carboxy group, a hydroxy group, a diol group, an amino group, an amide group, or a mercapto group, the method comprising reacting the carboxy group, hydroxy group, diol group, amino group, amide group, or mercapto group, with the protective agent, wherein the protective agent comprises the xanthene compound according to claim 1 .

Assignees

• Sekisui Medical Co Ltd

Inventors

• Yano Shinya
• Mori Toshihiro
• Kubota Hideki

Classifications

• C07K1/08

  using activating agents {(C07K1/003, C07K1/006 take precedence)} · CPC title

• C07F7/18

  Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages · CPC title

• Y02P20/55

  Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups · CPC title

• C07K1/062

  for alpha- or omega-carboxy functions · CPC title

• C07K1/066

  for omega-amido functions · CPC title