# US 2026/0076918 A1 · Heterotelechelic compounds

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- Number: US 2026/0076918 A1
- Document ID: US20260076918A1
- Status: Published application
- Kind: A1
- Application number: 19/109,632
- Filed: 2023-09-08
- Published: 2026-03-19
- Earliest claimed: 2022-09-09
- Assignees: Kawasaki Institute of Industrial Promotion
- Applicants: Kawasaki Institute of Industrial Promotion
- Inventors: Joachim VAN GUYSE; Saed ABBASI; Kazunori KATAOKA; Satoshi UCHIDA
- Web page: https://patentgrep.com/patent/US20260076918A1

## CPC

- A61K 9/5146: {obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyamines, polyanhydrides}
- C08G 73/0233: {Polyamines derived from (poly)oxazolines, (poly)oxazines or having pendant acyl groups}
- A61K 9/1272: comprising non-phosphatidyl surfactants as bilayer-forming substances, e.g. cationic lipids or non-phosphatidyl liposomes coated or grafted with polymers (lipids as modifying agents {A61K47/543})
- A61K 9/5123: {Organic compounds, e.g. fats, sugars}
- A61K 31/7088: Compounds having three or more nucleosides or nucleotides
- A61K 39/385: Haptens or antigens, bound to carriers
- A61K 47/34: Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers (A61K47/10 takes precedence)
- A61K 49/0002: {General or multifunctional contrast agents, e.g. chelated agents}
- C08G 69/48: Polymers modified by chemical after-treatment
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

The present invention relates to biocompatible polymers suitable for drugs and gene delivery, and producing methods thereof. The present invention also enables the creation of compounds with diverse structures by a concise method. The present invention relates to polycyclic iminoether compounds having different functional groups in both sides, such as a pentafluorophenyl group at one end and an azide group at the other end, derivatives thereof and producing methods thereof.

## Claims

### Claim 1

A compound of formula (I)
wherein X is halogen, —SR2, —OR2, —CN, —NHR2, —NR2 R3, —NHNHR2, —N═NR2, —N3, —C≡C—R2, —NHOR2, —ONR2R3, heteroaryl which may be substituted, a group which can form lipid based nano-particle (e.g., a formulation containing a lipid nano-particle (LNP), liposome, or lipoplex) or micelle including polycationic group, polyanionic group, or lipid soluble groups such as groups derived from fatty acid, preferably F, —SR2, —OR2, —CN, —NHR2, —N3,
Y is SR2, —OR2 (provided that when X is F, it is not —OH), —CN, —NHR2, —NR2 R3, —NHNHR2, —N═NR2, —N3, or heteroaryl which may be substituted, preferably —SR2, —OR2 (provided that when X is F, it is not —OH), —NHR2, —NR2 R3, —N3, or
more preferably —SR2, —OR2 (provided that when X is F, it is not —OH), —NHR2, or
wherein repeating unit
is independent of each occurrence and may be identical or different;
R1 is selected from the group consisting of alkyl group having 1-40 carbon atoms which may be substituted, alkenyl group having 2-40 carbon atoms which may be substituted, alkynyl group having 2-40 carbon atoms which may be substituted, aryl which may be substituted, heteroaryl which may be substituted;
R2 and R3 are, independent of each other, selected from the group consisting of hydrogen, alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted, carbocyclyl which may be substituted, heterocyclyl which may be substituted, aryl which may be substituted, heteroaryl which may be substituted, —C(═O)RB, —C(═O)ORB, —C(═O)N(RB)2, —S(═O)RB, —S(═O)2RB, —CH2CH(ORC)CH2ORC, sugar derivatives, and repeating unit or in the case of —NR2 R3, R2 and R3 may be linked together to form heterocyclyl which may be substituted, preferably —CH2CH(ORC)CH2ORC,
RA, RAA and RAAA are, independent of each other, selected from the group consisting of hydrogen, alkyl group having 1-20 carbon atoms which may be substituted, alkenyl group having 2-20 carbon atoms which may be substituted, and alkynyl group having 2-20 carbon atoms which may be substituted, or RA and RAA may be linked together to form ring, such as carbocycle, heterocycle, aryl, heterocyclyl, lactone, or lactam, and RA, RAA and/or RAAA may be further linked to functional molecules such as labels, or biofunctional molecules including proteins, nucleic acid, etc.;
RB is selected from the group consisting of hydrogen, alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted;
RC is selected from the group consisting of hydrogen, lipid soluble groups such as alkyl group having 1-20 carbon atoms which may be substituted, alkenyl group having 2-20 carbon atoms which may be substituted, and alkynyl group having 2-20 carbon atoms which may be substituted, and oxygen protective groups including acyl groups such as acetyl, ether groups such as methoxymethyl etc.;
said alkyl, alkenyl and alkynyl is straight chain, branched chain or cyclic chain;
m is integer from 1 to 3;
and
n is integer from 1 to 2000,
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound according to claim 1,
wherein X is halogen, —SR2, —OR2, —NHR2, —NR2 R3, —NHNHR2, —N═NR2, —N3, —NHOR2, —ONR2R3, heteroaryl which may be substituted,
Y is SR2, —OR2, —NHR2, —NR2 R3, —NHNHR2, —N═NR2, —N3, or
more preferably —SR2, —OR2, —NHR2, or
wherein
R1 is selected from the group consisting of alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted, aryl which may be substituted, heteroaryl which may be substituted;
R2 and R3 are, independent of each other, selected from the group consisting of hydrogen, alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted, carbocyclyl which may be substituted, heterocyclyl which may be substituted, aryl which may be substituted, heteroaryl which may be substituted, —C(═O)RB, —C(═O)ORB, —C(═O)N(RB)2, —S(═O)RB, —S(═O)2RB, —CH2CH(ORC)CH2ORC, sugar derivatives, and repeating unit, or in the case of —NR2 R3, R2 and R3 may be linked together to form heterocyclyl which may be substituted, preferably —CH2CH(ORC)CH2ORC,
RA, and RAA are, independent of each other, selected from the group consisting of hydrogen, alkyl group having 1-20 carbon atoms which may be substituted, alkenyl group having 2-20 carbon atoms which may be substituted, and alkynyl group having 2-20 carbon atoms which may be substituted, or RA and RAA may be linked together to form carbocycle, heterocycle, aryl, heterocyclyl, lactone, or lactam, and RA and/or RAA may be further linked to labels, or biofunctional molecules including proteins, nucleic acid, etc.;
RB is selected from the group consisting of hydrogen, alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted;
RC is selected from the group consisting of hydrogen, lipid soluble groups such as alkyl group having 1-20 carbon atoms which may be substituted, alkenyl group having 2-20 carbon atoms which may be substituted, and alkynyl group having 2-20 carbon atoms which may be substituted, and oxygen protective groups;
said alkyl, alkenyl and alkynyl is straight chain, or branched chain;
substituent(s) of alkyl, alkenyl and alkynyl is (are), independent of each other, and also not limited to, but ester group, amino group, azide group, and
n is integer from 2 to 1000,
or a pharmaceutically acceptable salt thereof.

### Claim 3 (depends on 1)

The compound according to claim 1,
wherein X is F, —SR2, —OR2, —NHR2, —N3, or
Y is —SR2, —OR2, —NHR2, —N3, or
wherein
R1 is selected from the group consisting of methyl, ethyl, propyl, butyl, —CH2CH2COOCH3, —CH2CH2CH2COOCH3, —CH2CH2CH2CH2COOCH3, butenyl, butynyl, or —CH2OCH3;
R2 is selected from the group consisting of hydrogen, alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted, carbocyclyl which may be substituted, heterocyclyl which may be substituted, aryl which may be substituted, heteroaryl which may be substituted, —C(═O)RB, —C(═O)ORB, —C(═O)N(RB)2, —S(═O)RB, —S(═O)2RB—CH2CH(ORC)CH2ORC, sugar derivatives, and the repeating unit,
RA and RAA are, independent of each other, selected from the group consisting of hydrogen, alkyl group having 1-20 carbon atoms which may be substituted, alkenyl group having 2-20 carbon atoms which may be substituted, and alkynyl group having 2-20 carbon atoms which may be substituted, or RA and RAA may be linked together to form carbocycle, heterocycle, aryl, heterocyclyl, lactone, or lactam, and RA and/or RAA may be further linked to functional molecules such as labels, or biofunctional molecules including proteins, nucleic acid, etc.;
RB is selected from the group consisting of alkyl group having 1-6 carbon atoms which may be substituted;
RC is selected from the group consisting of hydrogen, alkyl group having 1-20 carbon atoms which may be substituted, and alkenyl group having 2-20 carbon atoms which may be substituted;
said alkyl, and alkenyl are straight chain; and
n is an integer from 2 to 2000,
or a pharmaceutically acceptable salt thereof.

### Claim 4 (depends on 1)

The compound according to claim 1,
wherein Y is
and RA and/or RAA may be linked to functional molecule selecting from the groups consisting of labels, or biofunctional molecules including proteins, and nucleic acid.

### Claim 5 (depends on 1)

The compound according to claim 1,
wherein X is —OR2 or —SR2,
Y is
R2 is —CH2CH(ORC)CH2ORC, and
RC is selected from the group consisting of hydrogen, alkyl group having 1-20 carbon atoms which may be substituted, and alkenyl group having 2-20 carbon atoms which may be substituted.

### Claim 6 (depends on 1)

The compound according to claim 1,
wherein X is —OR2 or —SR2,
R2 is —CH2CH(ORC)CH2ORC, and
RC is selected from the group consisting of alkyl group having 1-20 carbon atoms which may be substituted, and alkenyl group having 2-20 carbon atoms which may be substituted.

### Claim 7 (depends on 1)

The compound according to claim 1,
wherein X is —OR2 SR2, or —NHR2
R2 is —CH2CH(ORC)CH2ORC, and
RC is H.

### Claim 8 (depends on 1)

The compound according to claim 1,
wherein X is —OR2, —SR2, or —NHR2
R2 is —CH2CH(ORC)CH2ORC, and
RC is oxygen protective group.

### Claim 9 (depends on 1)

The compound according to claim 1, wherein X is a group which can form lipid based nano-particle (e.g., a formulation containing a lipid nano-particle (LNP), liposome, or lipoplex) liposome or micelle.

### Claim 10 (depends on 1)

The compound according to claim 1, wherein sugar derivative is glucose derivative.

### Claim 11 (depends on 1)

A composition comprising the compound according to claim 1.

### Claim 12 (depends on 1)

A composition comprising the compound according to claim 1, wherein the composition is vaccine.

### Claim 13 (depends on 1)

A composition comprising the compound according to claim 1, wherein the composition is used for the diagnostic probes.

### Claim 14

A compound of formula (II)
wherein repeating unit
is independent of each occurrence and may be identical or different;
R4 is selected from the group consisting of alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted, aryl which may be substituted, heteroaryl which may be substituted;
R5 is selected from the group consisting of —SR2, —OR2, —CN, —NHR2, —NR2 R3, —NHNHR2, —N═NR2, and —N3, —NHOR2, -and —ONR2R3;
R2 and R3 are, independent of each other, selected from the group consisting of hydrogen, alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, alkynyl group having 2-6 carbon atoms which may be substituted, carbocyclyl which may be substituted, heterocyclyl which may be substituted, aryl which may be substituted, heteroaryl which may be substituted, —C(═O)RB, —C(═O)ORB, —C(═O)N(RB)2, —S(═O)RB, —S(═O)2RB, —CH2CH(ORC)CH2ORC, and sugar derivatives, or in the case that R5 is —NR2 R3, R2 and R3 may be linked together to form heterocyclyl which may be substituted, preferably —CH2CH(ORC)CH2ORC;
RB is selected from the group consisting of hydrogen, alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted;
RC is selected from the group consisting of hydrogen, alkyl group having 1-20 carbon atoms which may be substituted, or alkenyl group having 2-20 carbon atoms which may be substituted;
said alkyl, and alkenyl are straight chain;
m is integer from 1 to 3;
and
n is integer from 2 to 2000.

### Claim 15 (depends on 14)

The compound according to claim 14,
R5 is —OR2, —SR2, or —NHR2,
R2 is —CH2CH(ORC)CH2ORC, and
RC is selected from the group consisting of alkyl group having 1-20 carbon atoms which may be substituted, or alkenyl group having 2-20 carbon atoms which may be substituted.

### Claim 16 (depends on 14)

The compound according to claim 14,
R5 is —OR2, —SR2, or —NHR2
R2 is —CH2CH(ORC)CH2ORC, and
RC is H.

### Claim 17 (depends on 14)

The compound according to claim 14,
R5 is —OR2 or —SR2, or —NHR2,
R2 is —CH2CH(ORC)CH2ORC, and
RC is oxygen protective group.

### Claim 18

A method for producing a compound of Formula (III),
wherein repeating unit is independent of each occurrence and may be identical or different;
R4 is selected from the group consisting of alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, alkynyl group having 2-6 carbon atoms which may be substituted, aryl which may be substituted, heteroaryl which may be substituted;
R5 is selected from the group consisting of halogen, —SR2, —OR2, —CN, —NHR2, —NR2 R3, —NHNHR2, —N═NR2, —N3, —NHOR2, -and —ONR2R3;
R2 and R3 are, independent of each other, selected from the group consisting of hydrogen, alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted, carbocyclyl which may be substituted, heterocyclyl which may be substituted, aryl which may be substituted, heteroaryl which may be substituted, —C(═O)RB, —C(═O)ORB, —C(═O)N(RB)2, —S(═O)RB, —S(═O)2RB, —CH2CH(ORC)CH2ORC, and sugar derivatives, or in the case of —NR2 R3, R2 and R3 may be linked together to form heterocyclyl which may be substituted;
RB is selected from the group consisting of hydrogen, alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted;
RC is selected from the group consisting of hydrogen, alkyl group having 1-20 carbon atoms which may be substituted, or alkenyl group having 2-20 carbon atoms which may be substituted;
said alkyl, and alkenyl are straight chain; and
n is integer from 2 to 2000,
comprising the following steps;
(a) a compound of Formula (IV)
wherein L is a leaving group;
is reacted with a compound of Formula (V)
wherein R4 is selected from the group consisting of alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted, aryl which may be substituted, heteroaryl which may be substituted;
in the presence of base to obtain a compound of Formula (II)
(b) a compound of Formula (II) is reacted with an azide reagent to obtain a compound of Formula (III).

### Claim 19 (depends on 18)

The method for producing the compound of formula (III) according to claim 18, wherein the leaving group is selected from the group consisting of halogen, OTf, ONs, and OTs.

### Claim 20 (depends on 18)

The method for producing the compound of formula (III) according to claim 18, wherein the base is selected from the group consisting of Et3N, DBU, NMP, TBD, KOH, iPr2NEt, and t-BuOK.

### Claim 21 (depends on 18)

The method for producing the compound of formula (III) according to claim 18, wherein the azide reagent is selected from the group consisting of NaN3, TMSN3, TsN3, tetrabutylammonium azide, and diphenyl phosphoryl azide.

### Claim 22

A method for producing the compound of formula (III),
wherein repeating unit is independent of each occurrence and may be identical or different;
R4 is selected from the group consisting of alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted, aryl which may be substituted, heteroaryl which may be substituted;
R5 is selected from the group consisting of halogen, —SR2, —OR2, —CN, —NHR2, —NR2 R3, —NHNHR2, —N═NR2, and —N3, —NHOR2, —ONR2R3;
R2 and R3 are, independent of each other, selected from the group consisting of hydrogen, alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted, carbocyclyl which may be substituted, heterocyclyl which may be substituted, aryl which may be substituted, heteroaryl which may be substituted, —C(═O)RB, —C(═O)ORB, —C(═O)N(RB)2, —S(═O)RB, —S(═O)2RB, —CH2CH(ORC)CH2ORC, and sugar derivatives, or in the case of —NR2 R3, R2 and R3 may be linked together to form heterocyclyl which may be substituted;
RB is selected from the group consisting of hydrogen, alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted;
RC is selected from the group consisting of hydrogen, alkyl group having 1-20 carbon atoms which may be substituted, or alkenyl group having 2-20 carbon atoms which may be substituted;
said alkyl, and alkenyl are straight chain; and
n is integer from 2 to 2000,
comprising the following steps;
(a) a compound of Formula (IIIa)
wherein R4 is selected from the group consisting of alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted, aryl which may be substituted, heteroaryl which may be substituted;
n is integer from 2 to 2000,
is reacted with a nucleophile to obtain a compound of Formula (III)
wherein R4 is selected from the group consisting of alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted, aryl which may be substituted, heteroaryl which may be substituted;
R5 is selected from the group consisting of halogen, —SR2, —OR2, —CN, —NHR2, —NR2 R3, —NHNHR2, —N═NR2, and —N3, —NHOR2, and —ONR2R3;
R2 and R3 are, independent of each other, selected from the group consisting of hydrogen, alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted, carbocyclyl which may be substituted, heterocyclyl which may be substituted, aryl which may be substituted, heteroaryl which may be substituted, —C(═O)RB, —C(═O)ORB, —C(═O)N(RB)2, —S(═O)RB, —S(═O)2RB, —CH2CH(ORC)CH2ORC, and sugar derivatives, or in the case of —NR2 R3, R2 and R3 may be linked together to form heterocyclyl which may be substituted;
RC is selected from the group consisting of hydrogen, alkyl group having 1-20 carbon atoms which may be substituted, or alkenyl group having 2-20 carbon atoms which may be substituted;
said alkyl, and alkenyl are straight chain; and
n is integer from 2 to 2000.

### Claim 23 (depends on 22)

The method for producing the compound of formula (III) according to claim 22, wherein the nucleophile is alcohol, phenol, carboxylic acid, amine, azide, thiol, cyan, or alkyne type nucleophile.

### Claim 24

The method for producing the compound of formula (VI),
wherein repeating unit is independent of each occurrence and may be identical or different;
R4 is selected from the group consisting of alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted, aryl which may be substituted, heteroaryl which may be substituted;
R5 is selected from the group consisting of halogen, —SR2, —OR2, —CN, —NHR2, —NR2 R3, —NHNHR2, —N═NR2, —N3, —NHOR2, and —ONR2R3;
R2 and R3 are, independent of each other, selected from the group consisting of hydrogen, alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted, carbocyclyl which may be substituted, heterocyclyl which may be substituted, aryl which may be substituted, heteroaryl which may be substituted, —C(═O)RB, —C(═O)ORB, —C(═O)N(RB)2, —S(═O)RB, —S(═O)2RB, —CH2CH(ORC)CH2ORC, and sugar derivatives, or in the case of —NR2 R3, R2 and R3 may be linked together to form heterocyclyl which may be substituted;
RB is selected from the group consisting of hydrogen, alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted;
RC is selected from the group consisting of hydrogen, alkyl group having 1-20 carbon atoms which may be substituted, or alkenyl group having 2-20 carbon atoms which may be substituted;
said alkyl, and alkenyl are straight chain; and
n is integer from 2 to 100,
in which a compound of formula (IIa)
wherein R4 is selected from the group consisting of alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted;
n is integer from 2 to 2000,
is reacted with nucleophile to obtain the compound of Formula (VI).

### Claim 25

A method for producing the compound of Formula (Ia)
wherein repeating unit is independent of each occurrence and may be identical or different;
R4 is selected from the group consisting of alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted, aryl which may be substituted, heteroaryl which may be substituted;
R5 is selected from the group consisting of —SR2, —OR2, —CN, —NHR2, —NR2R3, —NHNHR2, —N═NR2, —N3, —NHOR2, and —ONR2R3;
R2 and R3 are, independent of each other, selected from the group consisting of hydrogen, alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted, carbocyclyl which may be substituted, heterocyclyl which may be substituted, aryl which may be substituted, heteroaryl which may be substituted, —C(═O)RB, —C(═O)ORB, —C(═O)N(RB)2, —S(═O)RB, —S(═O)2RB, —CH2CH(ORC)CH2ORC, and sugar derivatives, or in the case of —NR2 R3, R2 and R3 may be linked together to form heterocyclyl which may be substituted, preferably —CH2CH(ORC)CH2ORC;
RA and RAA are, independent of each other, selected from the group consisting of hydrogen, alkyl group having 1-20 carbon atoms which may be substituted, alkenyl group having 2-20 carbon atoms which may be substituted, and alkynyl group having 2-20 carbon atoms which may be substituted, or RA and RAA may be linked together to form ring, such as carbocycle, heterocycle, aryl, heterocyclyl, lactone, or lactam, and RA and/or RAA may be further linked to functional molecules such as labels, biofunctional molecules including proteins, nucleic acid, etc.;
RB is selected from the group consisting of hydrogen, alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted;
RC is selected from the group consisting of hydrogen, lipid soluble groups such as alkyl group having 1-20 carbon atoms which may be substituted, alkenyl group having 2-20 carbon atoms which may be substituted, and alkynyl group having 2-20 carbon atoms which may be substituted, or oxygen protective groups including acyl groups such as acetyl, ether groups such as methoxymethyl etc.;
said alkyl, alkenyl and alkynyl is straight chain, branched chain or cyclic chain; and
n is integer from 1 to 2000,
wherein the compound of Formula (III)
wherein repeating unit is independent of each occurrence and may be identical or different;
R4 is selected from the group consisting of alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted, aryl which may be substituted, heteroaryl which may be substituted;
R5 is selected from the group consisting of halogen, —SR2, —OR2, —CN, —NHR2, —NR2 R3, —NHNHR2, —N═NR2, and —N3, —NHOR2, —ONR2R3;
R2 and R3 are, independent of each other, selected from the group consisting of hydrogen, alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted, carbocyclyl which may be substituted, heterocyclyl which may be substituted, aryl which may be substituted, heteroaryl which may be substituted, —C(═O)RB, —C(═O)ORB, —C(═O)N(RB)2, —S(═O)RB, —S(═O)2RB, —CH2CH(ORC)CH2ORC, and sugar derivatives, or in the case of —NR2 R3, R2 and R3 may be linked together to form heterocyclyl which may be substituted;
RB is selected from the group consisting of hydrogen, alkyl group having 1-6 carbon atoms which may be substituted, alkenyl group having 2-6 carbon atoms which may be substituted, and alkynyl group having 2-6 carbon atoms which may be substituted;
RC is selected from the group consisting of hydrogen, alkyl group having 1-20 carbon atoms which may be substituted, or alkenyl group having 2-20 carbon atoms which may be substituted;
said alkyl, and alkenyl are straight chain; and
n is integer from 2 to 2000
is reacted with formula (VII)
wherein RA and RAA are as shown above,
to obtain the compound of Formula (Ia).

### Claim 26 (depends on 25)

The method for producing the compound of formula (Ia) according to claim 25, wherein the reaction carried out with metal catalyst such as Cu catalyst.

### Claim 27 (depends on 25)

The method for producing the compound of formula (Ia) according to claim 25, wherein the reaction is carried out under the condition of metal catalyst free.

### Claim 28 (depends on 25)

The method for producing the compound of formula (Ia) according to claim 25, wherein the reaction is carried out in water.