# US 11,993,570 B2 · Cationic lipids

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- Number: US 11,993,570 B2
- Document ID: US11993570B2
- Status: Granted
- Kind: B2
- Application number: 17/900,412
- Filed: 2022-08-31
- Published: 2023-08-17
- Granted: 2024-05-28
- Earliest claimed: 2017-12-28
- Assignees: Takeda Pharmaceutical Company Limited
- Applicants: Takeda Pharmaceutical Company Limited
- Inventors: Satoru Matsumoto; Yoshimasa Omori; Masahiro Mineno; Yasutaka Hoashi
- Web page: https://patentgrep.com/patent/US11993570B2

## CPC

- C07C 69/533: Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C12N 15/88: using microencapsulation, e.g. using {amphiphile} liposome vesicle
- A61K 9/127: Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K 9/1617: {Organic compounds, e.g. phospholipids, fats}
- A61K 31/7105: Natural ribonucleic acids, i.e. containing only riboses attached to adenine, guanine, cytosine or uracil and having 3'-5' phosphodiester links
- A61K 31/713: Double-stranded nucleic acids or oligonucleotides
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- C07C 229/12: to carbon atoms of acyclic carbon skeletons
- C12N 15/113: Non-coding nucleic acids modulating the expression of genes, e.g. antisense oligonucleotides; {Antisense DNA or RNA; Triplex- forming oligonucleotides; Catalytic nucleic acids, e.g. ribozymes; Nucleic acids used in co-suppression or gene silencing (when used in plants C12N15/8218)}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention provides a technique that enables introduction of active ingredients, in particular, nucleic acids, into cells with superior efficiency; and cationic lipids, etc., for use in the technique. The compound or a salt thereof according to the present invention is a compound represented by formula (I) or a salt thereof. In formula (I), n represents an integer of 2 to 5, R represents a linear C1-5 alkyl group, a linear C7-11 alkenyl group, or a linear C11 alkadienyl group, and wavy lines each independently represent a cis-bond or a trans-bond.

## Claims

### Claim 1

A compound represented by formula (I):
wherein:
n represents an integer of 2 to 5;
R represents a linear C1-5 alkyl group, a linear C7-11 alkenyl group, or a linear C11 alkadienyl group; and
wavy lines each independently represent a cis-bond or a trans-bond, or a salt thereof.

### Claim 2

3-((4-(Dimethylamino)butanoyl)oxy)-2,2-bis(((9Z)-tetradec-9-enoyloxy)methyl)propyl (9Z)-tetradec-9-enoate or a salt thereof.

### Claim 3

3-((5-(Dimethylamino)pentanoyl)oxy)-2,2-bis(((9Z)-tetradec-9-enoyloxy)methyl)propyl (9Z)-tetradec-9-enoate or a salt thereof.

### Claim 4

3-((6-(Dimethylamino)hexanoyl)oxy)-2,2-bis(((9Z)-tetradec-9-enoyloxy)methyl)propyl (9Z)-tetradec-9-enoate or a salt thereof.

### Claim 5 (depends on 1)

A lipid particle comprising the compound or a salt thereof according to claim 1.

### Claim 6 (depends on 5)

A composition for nucleic acid introduction comprising a nucleic acid and the lipid particle according to claim 5.

### Claim 7 (depends on 6)

The composition according to claim 6, wherein the nucleic acid is an RNA.

### Claim 8 (depends on 7)

The composition according to claim 7, wherein the RNA is an mRNA or an siRNA.