Nucleic acid-containing lipid nanoparticle

Abstract

The present invention provides a nucleic acid- containing lipid nanoparticle comprising an analog of a fatty acid ester of glycerol, and a nucleic acid, wherein the analog is not hydrolyzable by a lipase.

Description

A ... Description Title of Invention: NUCLEIC ACID-CONTAINING LIPID NANOPARTICLE Technical Field

[0001] The present invention relates to a nucleic acid- containing lipid nanoparticle. Background Art

[0002] In order to achieve gene therapy, carriers have been developed for efficiently delivering nucleic acids such as plasmid DNA (pDNA), antisense oligodeoxynucleic acid (ODN) and short interfering RNA (siRNA) to target cells in vivo. A method which involves allowing lipid particles to contain nucleic acids in order to protect the nucleic acids from in vivo nucleases and the like, and administering the complexes is known as an approach thereof.

[0003] Patent Literature 1 and Non Patent Literature 1 have reported, as a method for producing a liposome containing a nucleic acid or the like, for example, a method for producing a liposome containing siRNA by dissolving a dried cationic lipid, an aqueous sodium citrate solution Y .................................... 1 of siRNA and a neutral lipid, and a polyethylene glycolated phospholipid in HEPES [N-(2- hydroxyethyl)piperazine-N'-(2-ethanesulfonic acid)] buffered saline (hereinafter, referred to as "HBS") and ethanol, adding the resulting solution to diethyl ether to form a water-in-oil (W / O) emulsion, then mixing the solution, and treating the solution by a reverse-phase evaporation method.

[0004] Patent Literature 2 and Non Patent Literature 2 have reported a method for producing a liposome containing ODN by dissolving ODN in an aqueous citric acid solution of pH 3.8, adding a solution of a lipid in ethanol to the solution, decreasing the ethanol concentration to 20 v / v% to prepare a liposome containing ODN, filtering the solution through a sizing membrane, removing an excess of ethanol by dialysis, and then further dialyzing the sample at pH 7.5 to remove ODN attached to the liposome surface.

[0005] Patent Literature 3 has reported, for example, a method for producing a liposome containing pDNA by mixing a solution containing pDNA dissolved in an aqueous citric acid solution with a solution containing a lipid dissolved in ethanol using a T-shaped mixer, decreasing the ethanol concentration to 45 v / v%, then further adding thereto a citrate buffer solution so that the ethanol 4 j 3 concentration is decreased to 20 v / v% to prepare a liposome containing pDNA, removing residual pDNA through an anion-exchange resin, and removing an excess of ethanol by ultrafiltration.

[0006] Patent Literature 4 has reported a method for producing a liposome containing pDNA by complexing pDNA with a cationic lipid as micelle in an organic solvent containing water, further adding a lipid thereto, and then removing the organic solvent by dialysis.

[0007] Patent Literature 5 has reported a method for producing a liposome containing pDNA by complexing pDNA with a cationic lipid as micelle in an aqueous solution of a surfactant, further adding a lipid thereto, and then removing the surfactant by dialysis.

[0008] Meanwhile, Non Patent Literature 3 has reported that in a test using lipid nanoparticles containing doxorubicin, the contents are efficiently released by hydrolyzing an ester bond at position sn-2 of phospholipid with phospholipase A2 (hereinafter, also referred to as "PLA2"). This means that when phospholipid, a constituent of the lipid nanoparticles, is metabolized with phospholipase A2 in vivo, the stability of the particles carrying a drug is reduced. When the drug is a low-molecular drug, the reduced 9 4 . stability of the particles facilitates smoothly releasing the drug so that the drug exhibits activity. On the other hand, when the contents are a nucleic acid, the nucleic acid is poorly taken up into cells even after release and is enzymatically degraded, leading to the disappearance of its activity. Nanoparticles containing the nucleic acid mentioned above generally employ a lipid served as a substrate of PLA2. Thus, it has been difficult to prepare a lipid particle having high stability.

[0009] Patent Literature 6 discloses that 1,2-di-O- hexadecyl-sn-glycero-3-phosphocholine is used in a composition for the oral administration and transport of bioactive drugs, and states that such a composition is stable against acids. However, the literature does not state that this composition was used for nucleic acid transport. Citation List Patent Literature

[0010] Patent Literature 1: U.S. Patent Application Publication No. 2013 / 0149374 Patent Literature 2: Japanese Unexamined Patent Application Publication (Translation of PCT Application) No. 2002-501511 5 5 • • Patent Literature 3: WO 2004 / 002453 Patent Literature 4: WO 96 / 40964 Patent Literature 5: U.S. Patent Application Publication No. 2010 / 0041152 Patent Literature 6: WO 2014 / 143806 Non Patent Literature

[0011] Non Patent Literature 1: Biochimica et Biophysica Acta, 2012, Vol. 1818, p. 1633-1641 Non Patent Literature 2: Biochimica et Biophysica Acta, 2001, Vol. 1510, p. 152-166 Summary of Invention Technical Problem

[0012] An object of the present invention is to provide a nucleic acid-containing lipid nanoparticle that is useful as a medicament and is more stable than conventional particles. Solution to Problem

[0013] The present invention relates to the following: [1] A nucleic acid-containing lipid nanoparticle comprising an analog of a fatty acid ester of glycerol, and 8 J Ç . a nucleic acid, wherein the analog is not hydrolyzable by a lipase. [2] The nucleic acid-containing lipid nanoparticle according to [1], wherein the analog of the fatty acid ester of glycerol is an analog of a glycerophospholipid. [3] The nucleic acid-containing lipid nanoparticle according to [1] or [2], wherein the lipase is phospholipase A2. [4] The nucleic acid-containing lipid nanoparticle according to any one of [1] to [3], wherein the analog of the fatty acid ester of glycerol is a lipid represented by the following formula (1) or (2): [Image disponible dans le document PDF, Image available in the PDF document] (1) wherein Rx1 and Rx2 are the same or different and are each optionally substituted linear or branched C7-C23 alkyl, C7-C23 alkenyl or C7-C23 alkynyl; and Rx3 is a negative charge, a hydrogen atom, or any of the following groups: . 4 . 4 • ₹ NH<com:Sub>3< / com:Sub>, ₹ OH [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] and [Image disponible dans le document PDF, Image available in the PDF document] (2) wherein . Rx4 is optionally substituted linear or branched C8- C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl or Rx41-CO-; Rx41 is optionally substituted linear or branched C7- C23 alkyl, C7-C23 alkenyl or C7-C23 alkynyl; Rx<com:Sup>5< / com:Sup> is optionally substituted linear or branched C8- C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; and Rx6 is a negative charge, a hydrogen atom, or any of the following groups: [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] 4 . . N. • [5] The nucleic acid-containing lipid nanoparticle according to any one of [1] to [4], wherein a content of the analog of the fatty acid ester of glycerol is 0.001- fold molar amount or more with respect to the molar number of total lipid. [6] The nucleic acid-containing lipid nanoparticle according to any one of [1] to [5], further comprising a cationic lipid. [7] The nucleic acid-containing lipid nanoparticle according to [6], wherein the cationic lipid is lipid A represented by at least one of formulas (I), (II), (IV), (V') and (V'') given below, and / or lipid B represented by at least one of formulas (CL-I), (CL-II), (CL-III), (CL-IV), (CL-V), (CL-VI), (CL-VII), (CL-VIII), (CL-IX), (CL-XI), (CL-XII), (CL-XIII), (CL-XIV), (CL-XV), (CL-XVI), (CL-XVII), (CL-XVIII) and (CL-XIX) given below (wherein the formulas (I), (II), (III), (IV), (V') and (V'') are represented by structures described in Description of Embodiments mentioned later, and the formulas (CL-I), (CL-II), (CL-III), (CL-IV), (CL-V), (CL- VI), (CL-VII), (CL-VIII), (CL-IX), (CL-X), (CL-XI), (CL- XII), (CL-XIII), (CL-XIV), (CL-XV), (CL-XVI), (CL-XVII), (CL-XVIII) and (CL-XIX) are represented by structures 4 . described in Description of Embodiments mentioned later; the same holds true for the description below). [8] The nucleic acid-containing lipid nanoparticle according to [7], wherein the cationic lipid is the lipid В. [9] The nucleic acid-containing lipid nanoparticle according to any one of [1] to [8], further comprising a lipid derivative or a fatty acid derivative of a water- soluble polymer.

[10] The nucleic acid-containing lipid nanoparticle according to [9], wherein the water-soluble polymer moiety of the lipid derivative or the fatty acid derivative of the water-soluble polymer is selected from the group consisting of polyethylene glycol, polyglycerin, polyethyleneimine, polyvinyl alcohol, polyacrylic acid and polyacrylamide.

[11] The nucleic acid-containing lipid nanoparticle according to any one of [1] to

[10] , further comprising a neutral lipid.

[12] The nucleic acid-containing lipid nanoparticle according to

[11] , wherein the neutral lipid is selected á . . from the group consisting of phospholipid, sterol, glyceroglycolipid, sphingoglycolipid and sphingoid.

[13] The nucleic acid-containing lipid nanoparticle according to any one of [1] to

[12] , wherein the nucleic acid is a nucleic acid having a silencing effect on a target gene through the use of RNA interference (RNAi).

[14] The nucleic acid-containing lipid nanoparticle according to

[13] , wherein the target gene is a gene related to tumor or inflammation.

[15] A method for stabilizing a nucleic acid-containing lipid nanoparticle using an analog of a fatty acid ester of glycerol, wherein the analog is not hydrolyzable by a lipase. Here, the analog may be the analog referred in any of [1] to [5], and the nucleic acid-containing lipid nanoparticle may be the nucleic acid-containing lipid nanoparticle according to any of [1] to

[14] .

[16] A method for introducing a nucleic acid into a cell using the nucleic acid-containing lipid nanoparticle according to any one of [1] to

[14] .

[17] The method according to

[16] , wherein the cell is a cell residing at a mammalian tumor or inflammation site.

[18] . p. The method according to

[16] or

[17] , wherein the cell is a cell residing in the mammalian liver, stomach, lung, kidney, pancreas or spleen.

[19] The method according to any one of

[16] to

[18] , wherein a method for the introduction into the cell is a method of introduction into the cell by intravenous administration or subcutaneous administration.

[20] A method for treating a cancer or an inflammatory disease, comprising administering the nucleic acid- containing lipid nanoparticle according to any one of [1] to

[14] to a mammal.

[21] The method for treating method according to

[20] , wherein the administration is intravenous administration or subcutaneous administration.

[22] A medicament comprising the nucleic acid-containing lipid nanoparticle according to any one of [1] to

[14] .

[23] The medicament according to

[22] , wherein the medicament is intended for intravenous administration or subcutaneous administration.

[24] . . A therapeutic agent for a cancer or an inflammatory disease comprising the nucleic acid-containing lipid nanoparticle according to any one of [1] to

[14] .

[25] The therapeutic agent according to

[24] , wherein the therapeutic agent is intended for intravenous administration or subcutaneous administration.

[26] A compound represented by formula (CL-XVIII), or a pharmaceutically acceptable salt thereof (the cationic lipid): [Image disponible dans le document PDF, Image available in the PDF document] (CL-XVIII) wherein R<com:Sup>137< / com:Sup> and R<com:Sup>138< / com:Sup> are the same or different and are each linear or branched C8-C24 alkyl, C8-C24 alkenyl, C8-C24 alkynyl, C8-C24 alkylthioethyl, C8-24 alkenylthioethyl, or C8-C24 alkynylthioethyl; and X<com:Sup>135< / com:Sup> is a hydrogen atom, C1-C3 alkyl, hydroxy C2-C4 alkyl, formula (C): [Image disponible dans le document PDF, Image available in the PDF document] 4 wherein <com:Math><semantics>X136<annotation encoding="application / x-tex">X^{136}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X137<annotation encoding="application / x-tex">X^{137}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or C1-C3 alkyl, or <com:Math><semantics>X136<annotation encoding="application / x-tex">X^{136}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X137<annotation encoding="application / x-tex">X^{137}< / annotation>< / semantics>< / com:Math> optionally form a C2-C6 nitrogen-containing hetero ring together with the nitrogen atom to which they are bonded; <com:Math><semantics>L132<annotation encoding="application / x-tex">L^{132}< / annotation>< / semantics>< / com:Math> is S or O; and <com:Math><semantics>p115<annotation encoding="application / x-tex">p^{115}< / annotation>< / semantics>< / com:Math> is an integer from 2 to 4, formula (D): [Image disponible dans le document PDF, Image available in the PDF document] (D) wherein <com:Math><semantics>X138<annotation encoding="application / x-tex">X^{138}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X139<annotation encoding="application / x-tex">X^{139}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or C1 to C3 alkyl, or <com:Math><semantics>X138<annotation encoding="application / x-tex">X^{138}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X139<annotation encoding="application / x-tex">X^{139}< / annotation>< / semantics>< / com:Math> optionally form a C3-C6 nitrogen-containing hetero ring together with the nitrogen atom to which they are bonded; and <com:Math><semantics>p116<annotation encoding="application / x-tex">p^{116}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 4, or formula (E): [Image disponible dans le document PDF, Image available in the PDF document] (E) wherein <com:Math><semantics>X140<annotation encoding="application / x-tex">X^{140}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X141<annotation encoding="application / x-tex">X^{141}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or C1 to C3 alkyl, or <com:Math><semantics>X140<annotation encoding="application / x-tex">X^{140}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X141<annotation encoding="application / x-tex">X^{141}< / annotation>< / semantics>< / com:Math> optionally form a C3-C6 nitrogen-containing hetero ring together with the nitrogen atom to which they are bonded; and <com:Math><semantics>p117<annotation encoding="application / x-tex">p^{117}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 4.

[27] 4 A compound represented by formula (CL-XIX), or a pharmaceutically acceptable salt thereof (the cationic lipid): [Image disponible dans le document PDF, Image available in the PDF document] wherein R<com:Sup>139< / com:Sup> and R<com:Sup>140< / com:Sup> are the same or different and are each linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; [Image disponible dans le document PDF, Image available in the PDF document] X<com:Sup>142< / com:Sup> is a hydrogen atom, C1-C3 alkyl, hydroxy C2-C4 alkyl, formula (F): [Image disponible dans le document PDF, Image available in the PDF document] (F) wherein <com:Math><semantics>X143<annotation encoding="application / x-tex">X^{143}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X144<annotation encoding="application / x-tex">X^{144}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or C1-C3 alkyl, or <com:Math><semantics>X143<annotation encoding="application / x-tex">X^{143}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X144<annotation encoding="application / x-tex">X^{144}< / annotation>< / semantics>< / com:Math> optionally form a C2-C6 nitrogen-containing hetero ring together with the nitrogen atom to which they are bonded; <com:Math><semantics>L134<annotation encoding="application / x-tex">L^{134}< / annotation>< / semantics>< / com:Math> is S or O; and <com:Math><semantics>p118<annotation encoding="application / x-tex">p^{118}< / annotation>< / semantics>< / com:Math> is an integer from 2 to 4, or formula (G): [Image disponible dans le document PDF, Image available in the PDF document] (G) wherein <com:Math><semantics>X145<annotation encoding="application / x-tex">X^{145}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X146<annotation encoding="application / x-tex">X^{146}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or C1 to C3 alkyl, or <com:Math><semantics>X145<annotation encoding="application / x-tex">X^{145}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X146<annotation encoding="application / x-tex">X^{146}< / annotation>< / semantics>< / com:Math> optionally form a C3-C6 nitrogen-containing hetero ring together with the nitrogen atom to which they are bonded; and p<com:Sup>119< / com:Sup> is an integer from 1 to 4. Advantageous Effects of Invention

[0014] The present invention can provide a nucleic acid- containing lipid nanoparticle that is useful as a medicament and is more stable than conventional particles. Brief Description of Drawings

[0015] [Figure 1] Figure 1 shows a graph showing the amount of lipids remaining in each preparation. The ordinate of the graph depicts the amount of lipids remaining (%) with that in a PLA2-untreated group defined as 1. The abscissa depicts each preparation. [Figure 2] Figure 2 shows a graph showing the amount of lipids remaining in each preparation. The ordinate of the graph depicts the amount of lipids remaining (%) with that in a PLA2-untreated group defined as 1. The abscissa depicts each preparation. [Figure 3] Figure 3 shows a graph showing the amount of lipids remaining in each preparation. The ordinate of the graph depicts the amount of lipids remaining (%) with • that in a PLA2-untreated group defined as 1. The abscissa depicts each preparation. Description of Embodiments

[0016] Hereinafter, the mode for carrying out the present invention will be described in detail. The embodiments described below do not limit the present invention.

[0017] The nucleic acid-containing lipid nanoparticle of the present invention comprises an analog of a fatty acid ester of glycerol, and a nucleic acid. The analog is not hydrolyzable by a lipase. The nucleic acid-containing lipid nanoparticle of the present invention can be stably present even if contacted with a lipase, because the lipid in the particle resists degradation.

[0018] In a lipid having a fatty acid ester structure of glycerol (hereinafter, also referred to as a natural glycerol lipid), at least one hydroxy group of glycerol, and a fatty acid form an ester bond. This ester bond is hydrolyzed by the action of a lipase. The analog of the fatty acid ester of glycerol according to the present invention is a lipid having a structure modified from a partial structure in the 4 . natural glycerol lipid, and is not hydrolyzable by a lipase.

[0019] In the present invention, the phrase "not hydrolyzable by a lipase" means that when the nucleic acid-containing lipid nanoparticle of the present invention is contacted with a lipase, usually 30% or more, preferably 50% or more, more preferably 70% or more, further preferably 90% or more, still further preferably 99% or more, is not degraded with respect to the total amount of the analog of the fatty acid ester of glycerol present in the nucleic acid-containing lipid nanoparticle. The bringing into contact the analog with the lipase is performed under conditions of usually 30 to 45°C, preferably 35 to 42°C, more preferably 37°C, and usually 0 minutes to 48 hours, preferably 1 minute to 36 hours, more preferably 1 minute to 24 hours.

[0020] The analog of the fatty acid ester of glycerol according to the present invention is preferably structurally modified in the range of preferably 10 angstroms (angstrom: <com:Math><semantics>10−10<annotation encoding="application / x-tex">10^{-10}< / annotation>< / semantics>< / com:Math> m) or less, more preferably 8 angstroms or less, further preferably 6 angstroms or less, from the carbon atom at position sn-2 of a glycerol skeleton in a natural glycerol lipid represented by formula (NL1) given below. When the structural modification is in the range of 10 angstroms or less from 4 4 i i the carbon atom at position sn-2, the nucleic acid- containing lipid nanoparticle tends to resist the hydrolytic effect of a lipase and is thus stabilized. The lower limit value of the structural modification range is not particularly limited as long as the lower limit value is 0 angstroms or more. The range of 0 angstroms from the carbon atom at position sn-2 refers to the carbon atom at position <com:Math><semantics>sn−2<annotation encoding="application / x-tex">sn-2< / annotation>< / semantics>< / com:Math>.

[0021] In this context, the structural modification means that a structure near the glycerol skeleton of the natural glycerol lipid is changed, and is not particularly limited as long as the structural modification reduces interaction with an active site of a lipase. Examples thereof include: the inversion of the asymmetric center of the natural glycerol lipid, i.e., the conversion of an L form to a D form; the replacement of the ester bond between the glycerol skeleton and the fatty acid with a bond such as an ether bond (-0-), a thioether bond <com:Math><semantics>(−S−)<annotation encoding="application / x-tex">(-S-)< / annotation>< / semantics>< / com:Math>, an amino bond <com:Math><semantics>(−N(Rp)−<annotation encoding="application / x-tex">(-N(R^p)-< / annotation>< / semantics>< / com:Math> (wherein <com:Math><semantics>Rp<annotation encoding="application / x-tex">R^p< / annotation>< / semantics>< / com:Math> is a hydrogen atom or an organic group) or an amide bond (-NHCO-); the replacement of hydrogen at any one or more of positions sn-1, sn-2 and sn-3 with an organic group; and the introduction of an organic group to position <com:Math><semantics>α<annotation encoding="application / x-tex">\alpha< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>β<annotation encoding="application / x-tex">\beta< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>γ<annotation encoding="application / x-tex">\gamma< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>δ<annotation encoding="application / x-tex">\delta< / annotation>< / semantics>< / com:Math> of an acyl group mentioned later. Examples of the organic group include hydroxy, alkoxy, alkoxycarbonyl, nitro, cyano, fluoro, chloro and 4 • • . bromo. Among these substituents, the alkyl moiety in alkoxy and alkoxycarbonyl is a C1-C4 alkyl such as methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl or cyclopropylmethyl.

[0022] [Image disponible dans le document PDF, Image available in the PDF document] (NL1)

[0023] a and b are each independently an acyl group given below, and c is an acyl group, a phosphoric acid group, a sugar or the like. However, when both a and c are acyl groups, these acyl groups differ in the number of carbon atoms, structure, etc. and are not the same.

[0024] [Image disponible dans le document PDF, Image available in the PDF document]

[0025] Examples of R'xx in the acyl group include optionally substituted linear or branched C7-C23 alkyl, C7-C23 alkenyl and C7-C23 alkynyl.

[0026] . • The analog of the fatty acid ester of glycerol according to the present invention, i.e., the analog of the natural glycerol lipid represented by formula (NL1), is preferably a glycerophospholipid analog.

[0027] The glycerophospholipid can be represented by, for example, the following formula (NL2), and the glycerophospholipid analog is a structurally modified form of the lipid represented by the following formula <com:Math><semantics>(NL2)<annotation encoding="application / x-tex">(NL2)< / annotation>< / semantics>< / com:Math>:

[0028] [Image disponible dans le document PDF, Image available in the PDF document] • (NL2)

[0029] In formula (NL2), Rxx<com:Sup>1< / com:Sup> and Rxx<com:Sup>2< / com:Sup> are the same or different and are each optionally substituted linear or branched C7-C23 alkyl, C7-C23 alkenyl or C7-C23 alkynyl. Examples of Rxx3 include a hydrogen atom, and the following groups:

[0030] * [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document]

[0031] Examples of the linear or branched C7-C23 alkyl in formulas (NL1) and (NL2) include heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, 2,6,10- trimethylundecyl, pentadecyl, 3,7,11-trimethyldodecyl, hexadecyl, heptadecyl, octadecyl, 6,10,14- trimethylpentadecan-2-yl, nonadecyl, 2,6,10,14- tetramethylpentadecyl, icosyl, 3,7,11,15- tetramethylhexadecyl, henicosyl, docosyl, tricosyl and tetracosyl.

[0032] The linear or branched C7-C23 alkenyl in formulas (NL1) and (NL2) can be linear or branched C7-C23 alkenyl containing one to three double bonds. Examples thereof include (Z)-tridec-8-enyl, (Z)-tetradec-9-enyl, (Z)- pentadec-8-enyl, (Z)-hexadec-9-enyl, (Z)-heptadec-5-enyl, (Z)-octadec-6-enyl, (Z)-heptadec-8-enyl, (Z)-octadec-9- enyl, (E)-heptadec-8-enyl, (E)-octadec-9-enyl, (Z)- heptadec-10-enyl, (Z)-octadec-11-enyl, (8Z,11Z)- heptadeca-8,11-dienyl, (92,122)-octadeca-9,12-dienyl, . - E (8Z,11Z,14Z)-octadeca-8,11,14-trienyl, (9Z,12Z,15Z)- octadeca-9,12,15-trienyl, (Z)-nonadec-10-enyl, (Z)-icos- 11-enyl, (10Z,13Z)-nonadeca-10,13-dienyl, (11Z,14Z)- icosa-11,14-dienyl, 2,6,10-trimethylundeca-1,5,9-trienyl, 3,7,11-trimethyldodeca-2,6,10-trienyl, 2,6,10,14- tetramethylpentadec-1-enyl and 3,7,11,15- tetramethylhexadec-2-enyl, preferably (Z)-pentadec-8-enyl, (Z)-hexadec-9-enyl, (Z)-heptadec-5-enyl, (Z)-octadec-6- enyl, (Z)-heptadec-8-enyl, (Z)-octadec-9-enyl, (8Z,11Z)- heptadeca-8,11-dienyl and (9Z,12Z)-octadeca-9,12-dienyl, more preferably (Z)-heptadec-8-enyl, (Z)-octadec-9-enyl, (8Z,11Z)-heptadeca-8,11-dienyl and (9Z,12Z)-octadeca- 9,12-dienyl.

[0033] The linear or branched C7-C23 alkynyl in formulas (NL1) and (NL2) can be linear or branched C8-24 alkynyl containing one to three triple bonds. Examples thereof include dodec-11-ynyl, tridec-12-ynyl, pentadec-6-ynyl, hexadec-7-ynyl, pentadeca-4,6-diynyl, hexadeca-5,7-diynyl, heptadec-8-ynyl and octadec-9-ynyl, preferably pentadec- 6-ynyl, hexadec-7-ynyl, pentadeca-4,6-diynyl, hexadeca- 5,7-diynyl, heptadec-8-ynyl and octadec-9-ynyl, more preferably heptadec-8-ynyl and octadec-9-ynyl.

[0034] Examples of the substituent for the optionally substituted linear or branched C7-C23 alkyl, C7-C23 alkenyl or C7-C23 alkynyl in formulas (NL1) and (NL2) . . include hydroxy, alkoxy, alkoxycarbonyl, nitro, cyano, fluoro, chloro and bromo. Among these substituents, the alkyl moiety in alkoxy and alkoxycarbonyl is C1-C4 alkyl such as methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl or cyclopropylmethyl.

[0035] Examples of the glycerophospholipid represented by formula (NL2) include, but are not limited to, natural or synthetic phospholipids such as phosphatidylcholines (PCs) (specifically, soybean phosphatidylcholine, egg phosphatidylcholine (EPC), distearoyl phosphatidylcholine, 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC), dipalmitoyl phosphatidylcholine, 1,2-dipalmitoyl-sn- glycero-3-phosphocholine (DPPC), palmitoyl oleoyl phosphatidylcholine (POPC), dimyristoyl phosphatidylcholine (DMPC), dioleoyl phosphatidylcholine (DOPC), etc.), phosphatidylethanolamines (specifically distearoyl phosphatidylethanolamine (DSPE), dipalmitoyl phosphatidylethanolamine (DPPE), dioleoyl phosphatidylethanolamine (DOPE), dimyristoyl phospoethanolamine (DMPE), 16-0-monomethyl PE, 16-0- dimethyl PE, 18-1-trans PE, palmitoyl oleoyl- phosphatidylethanolamine (POPE), 1-stearoyl-2-oleoyl- phosphatidylethanolamine (SOPE), etc.), glycerophospholipids (specifically, phosphatidylserine, phosphatidic acid, phosphatidylglycerol, 4 phosphatidylinositol, palmitoyl oleoyl phosphatidylglycerol (POPG), lysophosphatidylcholine, etc.), sphingophospholipids (specifically, sphingomyelin, ceramide phosphoethanolamine, ceramide phosphoglycerol, ceramide phosphoglycerophosphoric acid, etc.), glycerophosphonolipids, sphingophosphonolipids, natural lecithins (specifically, egg lecithin, soybean lecithin, etc.) and hydrogenated phospholipids (specifically, hydrogenated soybean phosphatidylcholine, etc.).

[0036] The lipase according to the present invention is not particularly limited as long as the enzyme hydrolyzes the fatty acid ester contained in the natural glycerol lipid represented by formula (NL1). Examples of the lipase include phospholipase. Examples of the phospholipase specifically include phospholipase A1, phospholipase A2, phospholipase B, lysophospholipase, phospholipase C and phospholipase D. The analog of the fatty acid ester of glycerol according to the present invention is preferably an analog of a fatty acid ester of glycerol, and the analog is not hydrolyzable by phospholipase A2.

[0037] The glycerophospholipid analog has a structure modified from a partial structure of the glycerophospholipid represented by formula (NL2) described above. Specifically, the glycerophospholipid • 5 4 . analog is preferably a lipid represented by the following formula (1) or (2):

[0038] [Image disponible dans le document PDF, Image available in the PDF document] (1)

[0039] wherein Rx1 and Rx2 are the same or different and are each optionally substituted linear or branched C7-C23 alkyl, C7-C23 alkenyl or C7-C23 alkynyl; and Rx<com:Sup>3< / com:Sup> is a negative charge, a hydrogen atom, or any of the following groups: [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] or

[0040] ٠ ø. 4 1 [Image disponible dans le document PDF, Image available in the PDF document] (2)

[0041] wherein Rx4 is optionally substituted linear or branched C8- C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl or Rx41-CO-; Rx41 is optionally substituted linear or branched C7- C23 alkyl, C7-C23 alkenyl or C7-C23 alkynyl; Rx<com:Sup>5< / com:Sup> is optionally substituted linear or branched C8- C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; and Rx6 is a negative charge, a hydrogen atom, or any of the following groups: [Image disponible dans le document PDF, Image available in the PDF document]

[0042] Examples of the linear or branched C7-C23 alkyl, C7- C23 alkenyl and C7-C23 alkenyl in formulas (1) and (2) can include the same as those listed about C7-C23 alkyl, C7-C23 alkenyl and C7-C23 alkenyl in formula (NL2).

[0043] 1 4 • Examples of the linear or branched C8-C24 alkyl include heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, 2,6,10-trimethylundecyl, pentadecyl, 3,7,11-trimethyldodecyl, hexadecyl, heptadecyl, octadecyl, 6,10,14-trimethylpentadecan-2-yl, nonadecyl, 2,6,10,14- tetramethylpentadecyl, icosyl, 3,7,11,15- tetramethylhexadecyl, henicosyl, docosyl, tricosyl and tetracosyl.

[0044] The linear or branched C8-C24 alkenyl can be linear or branched C8-24 alkenyl containing one to three double bonds. Examples thereof include (Z)-tridec-8-enyl, (Z)- tetradec-9-enyl, (Z)-pentadec-8-enyl, (Z)-hexadec-9-enyl, (Z)-heptadec-5-enyl, (Z)-octadec-6-enyl, (Z)-heptadec-8- enyl, (Z)-octadec-9-enyl, (E)-heptadec-8-enyl, (E)- octadec-9-enyl, (Z)-heptadec-10-enyl, (Z)-octadec-11-enyl, (8Z,11Z)-heptadeca-8,11-dienyl, (9Z,12Z)-octadeca-9,12- dienyl, (8Z,11Z,14Z)-octadeca-8,11,14-trienyl, (9Z,12Z,15Z)-octadeca-9,12,15-trienyl, (Z)-nonadec-10- enyl, (Z)-icos-11-enyl, (10Z,13Z)-nonadeca-10,13-dienyl, (11Z,14Z)-icosa-11,14-dienyl, 2,6,10-trimethylundeca- 1,5,9-trienyl, 3,7,11-trimethyldodeca-2,6,10-trienyl, 2,6,10,14-tetramethylpentadec-1-enyl and 3,7,11,15- tetramethylhexadec-2-enyl, preferably (Z)-pentadec-8-enyl, (Z)-hexadec-9-enyl, (Z)-heptadec-5-enyl, (Z)-octadec-6- enyl, (Z)-heptadec-8-enyl, (Z)-octadec-9-enyl, (8Z,11Z)- heptadeca-8,11-dienyl and (9Z,12Z)-octadeca-9,12-dienyl, 4 4 4 1 more preferably (Z)-heptadec-8-enyl, (Z)-octadec-9-enyl, (8Z,11Z)-heptadeca-8,11-dienyl and (9Z,12Z)-octadeca- 9,12-dienyl.

[0045] The linear or branched C8-C24 alkynyl can be linear or branched C8-24 alkynyl containing one to three triple bonds. Examples thereof include dodec-11-ynyl, tridec- 12-ynyl, pentadec-6-ynyl, hexadec-7-ynyl, pentadeca-4,6- diynyl, hexadeca-5,7-diynyl, heptadec-8-ynyl and octadec- 9-ynyl, preferably pentadec-6-ynyl, hexadec-7-ynyl, pentadeca-4,6-diynyl, hexadeca-5,7-diynyl, heptadec-8- ynyl and octadec-9-ynyl, more preferably heptadec-8-ynyl and octadec-9-ynyl.

[0046] Examples of the substituent for the optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl, C8-C24 alkynyl, C7-C23 alkyl, C7-C23 alkenyl and C7-C23 alkynyl in formulas (1) and (2) include hydroxy, alkoxy, alkoxycarbonyl, nitro, cyano, fluoro, chloro and bromo. Among these substituents, the alkyl moiety in alkoxy and alkoxycarbonyl is C1-C4 alkyl such as methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl or cyclopropylmethyl.

[0047] The analog of the fatty acid ester of glycerol according to the present invention may be a salt. When the analog of the fatty acid ester of glycerol is a salt, 1 the salt is not particularly limited as long as the salt is pharmaceutically acceptable. For example, when each of Rx3 and Rx6 in formulas (1) and (2) is a hydrogen atom,

[0048] [Image disponible dans le document PDF, Image available in the PDF document] 1 a salt of an alkali metal such as sodium or potassium, or ammonium salt (NH4<com:Sup>+< / com:Sup> salt) is preferred. Each of Rx<com:Sup>3< / com:Sup> and Rx<com:Sup>6< / com:Sup> may be a negative charge. The negative charge represented by Rx3 or Rx6 means that hydrogen corresponding to <com:Math><semantics>Rx3<annotation encoding="application / x-tex">Rx^3< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>Rx6<annotation encoding="application / x-tex">Rx^6< / annotation>< / semantics>< / com:Math> is deprotonated. Specifically, the negative charge means that a phosphoric acid ester group in formulas (1) and (2) may be <com:Math><semantics>−PO42−<annotation encoding="application / x-tex">-PO_4^{2-}< / annotation>< / semantics>< / com:Math>.

[0049] The lipid represented by formula (2) may be a single substance of any one optical isomer as to asymmetric carbon having a configuration that is not shown herein, or may be a mixture containing such optical isomers at an arbitrary ratio.

[0050] Specifically, an inositol skeleton in Rxx3, Rx3 and Rx<com:Sup>6< / com:Sup> in formula (NL2) and formulas (1) and (2) is derived from any inositol given below. In the following inositol structures, a hydroxy group to form a bond to phosphoric acid is not particularly limited. - . * 4 ٦

[0051] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document]

[0052] When each of Rxx<com:Sup>3< / com:Sup>, Rx<com:Sup>3< / com:Sup> and Rx<com:Sup>6< / com:Sup> is an inositol skeleton, the inositol skeleton is preferably represented by the following formula:

[0053] [Image disponible dans le document PDF, Image available in the PDF document]

[0054] Examples of the C7-C23 alkyl, the C7-C23 alkenyl, the C7-C23 alkynyl, the C8-C24 alkyl, the C8-C24 alkenyl and the C8-C24 alkynyl in formulas (1) and (2) can include the same as those listed about their respective groups in formulas (NL1) and (NL2). Preferred examples . . • • thereof can include the same as those listed about the respective groups in formulas (NL1) and (NL2). The groups in each of formulas (1), (2), (NL1) and (NL2) may be arbitrarily combined as described about the respective groups or may be a combination of preferred groups.

[0055] Examples of the analog of the fatty acid ester of glycerol in the nucleic acid-containing nanoparticle of the present invention can specifically include the following compounds:

[0056] [Image disponible dans le document PDF, Image available in the PDF document] (D-DPPC) [Image disponible dans le document PDF, Image available in the PDF document] (D-DSPC) [Image disponible dans le document PDF, Image available in the PDF document] The analog of the fatty acid ester of glycerol according to the present invention may be a commercially available product or may be synthesized by use of an organic synthesis approach.

[0058] The lipid represented by formula (1) can be produced, for example, as follows, though the production method is not particularly limited.

[0059] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document]

[0060] wherein PG represents a protective group; and Rx1, <com:Math><semantics>Rx2<annotation encoding="application / x-tex">Rx^2< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>Rx3<annotation encoding="application / x-tex">Rx^3< / annotation>< / semantics>< / com:Math> are as defined in <com:Math><semantics>Rx1<annotation encoding="application / x-tex">Rx^1< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>Rx2<annotation encoding="application / x-tex">Rx^2< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>Rx3<annotation encoding="application / x-tex">Rx^3< / annotation>< / semantics>< / com:Math> in formula <com:Math><semantics>(1)<annotation encoding="application / x-tex">(1)< / annotation>< / semantics>< / com:Math>.

[0061] Specifically, a hydroxy group of acetal X1 known in the art which is obtained from a sugar such as mannitol is protected with a protective group (PG group), and an isopropylidene group is hydrolyzed to prepare diol X3. Alternatively, diol X3 may be obtained as a commercially available product such as (S)-3-(benzyloxy)propane-1,2- diol. Subsequently, diol X3 is reacted with an acid chloride represented by <com:Math><semantics>Rx1<annotation encoding="application / x-tex">Rx^1< / annotation>< / semantics>< / com:Math>-CO-Cl, <com:Math><semantics>Rx2<annotation encoding="application / x-tex">Rx^2< / annotation>< / semantics>< / com:Math>-CO-Cl or the like to obtain compound X4. Further, the protective group (PG • . . group) is removed, and the resulting hydroxy group can be reacted with phosphorus (V) oxychloride in the presence of a base such as triethylamine and further reacted with a compound represented by Rx3-OH to obtain the lipid represented by formula (1). The reaction for the conversion of diol X3 to compound X4 may be performed by protecting any of a primary alcohol and a secondary alcohol with a protective group. The protective group for use in the synthesis of the lipid represented by formula (1) can be selected on the basis of reaction conditions or a substrate with reference to, for example, Protective Groups in Organic Synthesis, third edition, T.W. Greene, John Wiley & Sons Inc. (1999).

[0062] The lipid represented by formula (2) can be produced, for example, as follows, though the production method is not particularly limited.

[0063] [Image disponible dans le document PDF, Image available in the PDF document]

[0064] • F á wherein PG represents a protective group; Rx<com:Sup>0< / com:Sup> represents optionally substituted linear or branched C7- C23 alkyl, C7-C23 alkenyl or C7-C23 alkynyl; X represents a halogen atom such as chlorine, bromine or iodine, OMs, or OTs; and Rx4, Rx5, Rx6 and Rx41 are as defined in Rx4, <com:Math><semantics>Rx5<annotation encoding="application / x-tex">Rx^5< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>Rx6<annotation encoding="application / x-tex">Rx^6< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>Rx41<annotation encoding="application / x-tex">Rx^{41}< / annotation>< / semantics>< / com:Math> in formula (2).

[0065] Specifically, a hydroxy group of acetal X6 known in the art which is obtained from a sugar such as mannitol is protected with a protective group (PG group), and an isopropylidene group is hydrolyzed to prepare diol X8. Subsequently, diol X8 can be reacted with an electrophile represented by, for example, <com:Math><semantics>Rx0−CH2−X<annotation encoding="application / x-tex">Rx^0-CH_2-X< / annotation>< / semantics>< / com:Math> (reaction conditions of Williamson etherification can be referred to and applied thereto) to obtain diether X9. Alternatively, diol X8 can be reacted with an acid chloride represented by Rx42-CO-Cl or the like and subsequently reacted with an electrophile represented by <com:Math><semantics>Rx0−CH2−X<annotation encoding="application / x-tex">Rx^0-CH_2-X< / annotation>< / semantics>< / com:Math> to obtain compound X9. Further, the protective group (PG group) is removed, and the resulting hydroxy group can be reacted with phosphorus (V) oxychloride in the presence of a base such as triethylamine and further reacted with a compound represented by Rx3-OH to obtain the lipid represented by formula (2). The reaction for the conversion of diol X3 to compound X4 may be performed by protecting any of a ¥ • primary alcohol and a secondary alcohol with a protective group. The protective group for use in the synthesis of the lipid represented by formula (2) can be selected on the basis of reaction conditions or a substrate with reference to, for example, Protective Groups in Organic Synthesis, third edition, T.W. Greene, John Wiley & Sons Inc. (1999).

[0066] The nucleic acid-containing lipid nanoparticle of the present invention preferably further comprises a cationic lipid. The cationic lipid is not particularly limited as long as the cationic lipid is an amphipathic molecule having a lipophilic region containing one or more optionally substituted hydrocarbon groups, and a cationic hydrophilic region containing at least one primary amino group, secondary amino group, tertiary amino group and / or quaternary ammonium group. Examples thereof can include a lipid having a hydrophilic unit having one quaternary ammonium group and optionally substituted three independent hydrocarbon groups (lipid A), and a lipid having a hydrophilic unit having optionally substituted one amino group or one quaternary ammonium group and a hydrophobic unit having optionally substituted two independent hydrocarbon groups (lipid B).

[0067] A á • In the present invention, the nucleic acid- containing lipid nanoparticle is prepared using the lipid having a hydrophilic unit having one quaternary ammonium group and optionally substituted three independent hydrocarbon groups (lipid A) with a lipid derivative or a fatty acid derivative of a water-soluble polymer, and a nucleic acid. The obtained nucleic acid-containing lipid nanoparticle can have much better physicochemical stability and physiological activity.

[0068] In the present invention, the lipid having a hydrophilic unit having one quaternary ammonium group and optionally substituted three independent hydrocarbon groups (lipid A) is not particularly limited as long as the lipid is a molecule intramolecularly having one quaternary ammonium group as a hydrophilic unit and having optionally substituted three independent hydrocarbon groups. Lipid A is represented by, for example, any of structural formulas (A) to (C) given below. In structural formulas (A) to (C) given below, the "hydrophilic unit" represents a hydrophilic unit having one quaternary ammonium group, and the three "hydrophobic units" represent optionally substituted three independent hydrocarbon groups.

[0069] Zero to three out of the four bonds of the quaternary ammonium group constituting the "hydrophilic A . • • unit" are attached to any 0 to 3 of the hydrocarbon groups constituting the "hydrophobic unit", and the remaining bond(s) is attached to an optionally substituted chain and / or cyclic hydrocarbon group, etc. The optionally substituted chain and / or cyclic hydrocarbon group constituting the "hydrophilic unit" can be any group composed of carbon and hydrogen atoms and is preferably a group having 1 to 10 carbon atoms, more preferably a group having 1 to 6 carbon atoms, further preferably a group having 1 to 3 carbon atoms.

[0070] The "hydrophilic unit" may have one or more ethers, esters, amides or the like via a carbon atom in the optionally substituted chain and / or cyclic hydrocarbon group, etc. constituting this hydrophilic unit. Examples of the substituent for the optionally substituted chain and / or cyclic hydrocarbon group, etc. include carbamate, amino, monoalkylamino, dialkylamino, pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin-2-yl, piperidin-3-yl, Ý piperidin-4-yl, morpholin-2-yl, morpholin-3-yl, hydroxy, alkoxy, alkoxycarbonyl, hydroxycarbonyl, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, nitro, cyano, fluoro, chloro, and bromo.

[0071] The hydrocarbon group constituting the "hydrophobic unit" can be any group consisting of 8 to 24 carbon atoms and hydrogen atoms. Hydrocarbon groups can be classified . 4 . from the viewpoint of topology. Examples thereof include linear hydrocarbon groups, branched hydrocarbon groups and cyclic hydrocarbon groups (e.g., a cholesteryl group). A linear or branched hydrocarbon group is preferred. Also, hydrocarbon groups can be classified on the basis of the presence or absence of an unsaturated bond (double bond or triple bond). Hydrocarbon groups having an unsaturated bond can also be classified on the basis of the presence or absence of aromaticity. A hydrocarbon group having only a saturated bond (alkyl) or a hydrocarbon group having an unsaturated bond and lacking aromaticity (e.g., alkenyl or alkynyl) is preferred. The hydrocarbon group in lipid A is preferably linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl.

[0072] Each hydrocarbon group constituting the "hydrophobic unit" may be bonded directly to the quaternary ammonium group of the "hydrophilic unit", or may be bonded to the quaternary ammonium group via an ether, ester or amide bond, etc. and the optionally substituted chain and / or cyclic hydrocarbon group, etc. constituting the "hydrophilic unit". As shown in structural formula (B) or (C), the hydrocarbon groups constituting two or three "hydrophobic units" may be bonded via a carbon atom, and this carbon atom may be bonded either directly to the quaternary ammonium group of the "hydrophilic unit" or to the quaternary ammonium group via an ether, ester or . . 4 • amide bond, etc. and the optionally substituted chain and / or cyclic hydrocarbon group, etc. constituting the "hydrophilic unit".

[0073] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document]

[0074] Examples of lipid A can include lipids represented by the following formulas (I) to (IV), (V') and (V''):

[0075] formula (I)

[0076] [Image disponible dans le document PDF, Image available in the PDF document] (I) 6 • wherein R<com:Sup>1< / com:Sup> to R<com:Sup>3< / com:Sup> are the same or different and are each optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; L<com:Sup>1< / com:Sup> to L<com:Sup>3< / com:Sup> are the same or different and are each absent, or <com:Math><semantics>−Z1−(CY1Y2)p1−<annotation encoding="application / x-tex">-Z^{1}-(CY^{1}Y^{2})_{p1}-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−Z2−(CY3Y4)p2−Z3−(CY5Y6)p3−<annotation encoding="application / x-tex">-Z^{2}-(CY^{3}Y^{4})_{p2}-Z^{3}-(CY^{5}Y^{6})_{p3}-< / annotation>< / semantics>< / com:Math> wherein Y1 to Y6 are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; Z1 to <com:Math><semantics>Z3<annotation encoding="application / x-tex">Z^3< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−O−<annotation encoding="application / x-tex">-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY7A−<annotation encoding="application / x-tex">-NY^{7A}-< / annotation>< / semantics>< / com:Math>, -CO-O-, -O-CO-, -CO-NY<com:Math><semantics>7B<annotation encoding="application / x-tex">^{7B}< / annotation>< / semantics>< / com:Math>-, -NY<com:Math><semantics>7C<annotation encoding="application / x-tex">^{7C}< / annotation>< / semantics>< / com:Math>-CO- or -NY<com:Math><semantics>7D<annotation encoding="application / x-tex">^{7D}< / annotation>< / semantics>< / com:Math>-CO-O- wherein Y<com:Sup>7A< / com:Sup> to Y<com:Sup>7D< / com:Sup> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; and p<com:Sup>1< / com:Sup> to p<com:Sup>3< / com:Sup> are the same or different and are each an integer from 1 to 5; X<com:Sup>1< / com:Sup> is optionally substituted C1-C4 alkyl; and A' is a pharmaceutically acceptable anion, formula (II)

[0077] [Image disponible dans le document PDF, Image available in the PDF document] (II) wherein R<com:Sup>4< / com:Sup> to R<com:Sup>6< / com:Sup> are the same or different and are each optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; L4 to L6 are the same or different and are each absent, or <com:Math><semantics>−Z4−(CY8Y9)p4<annotation encoding="application / x-tex">-Z^4 - (CY^8Y^9)_{p4}< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−Z5−(CY10Y11)p5−Z6−(CY12Y13)p6<annotation encoding="application / x-tex">-Z^5 - (CY^{10}Y^{11})_{p5} - Z^6 - (CY^{12}Y^{13})_{p6}< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y8<annotation encoding="application / x-tex">Y^8< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y13<annotation encoding="application / x-tex">Y^{13}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; Z4 to <com:Math><semantics>Z6<annotation encoding="application / x-tex">Z^6< / annotation>< / semantics>< / com:Math> are the same or different and are each -O-, -NY<com:Sup>14A< / com:Sup>-, [Image disponible dans le document PDF, Image available in the PDF document] wherein <com:Math><semantics>Y14A<annotation encoding="application / x-tex">Y^{14A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y14D<annotation encoding="application / x-tex">Y^{14D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; p4 is an integer from 0 to 5; <com:Math><semantics>p5<annotation encoding="application / x-tex">p^5< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; and <com:Math><semantics>p6<annotation encoding="application / x-tex">p^6< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] wherein <com:Math><semantics>Y15<annotation encoding="application / x-tex">Y^{15}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y26<annotation encoding="application / x-tex">Y^{26}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; Z7 to <com:Math><semantics>Z9<annotation encoding="application / x-tex">Z^9< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−O−<annotation encoding="application / x-tex">-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY27A−<annotation encoding="application / x-tex">-NY^{27A}-< / annotation>< / semantics>< / com:Math>, [Image disponible dans le document PDF, Image available in the PDF document] wherein <com:Math><semantics>Y27A<annotation encoding="application / x-tex">Y^{27\text{A}}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y27D<annotation encoding="application / x-tex">Y^{27\text{D}}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; p7 is an integer from 1 to 5; p8 is an integer from 0 to 5; p<com:Sup>9< / com:Sup> is an integer from 1 to 5; p<com:Sup>10< / com:Sup> is an integer from 0 to 5; p<com:Sup>11< / com:Sup> is an integer from 1 to 5; and p<com:Sup>12< / com:Sup> is an integer from 1 to 5; <com:Math><semantics>B1<annotation encoding="application / x-tex">B^1< / annotation>< / semantics>< / com:Math> is [Image disponible dans le document PDF, Image available in the PDF document] 4 4 wherein <com:Math><semantics>X2<annotation encoding="application / x-tex">X^2< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X3<annotation encoding="application / x-tex">X^3< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted C1-C4 alkyl, or together form an optionally substituted C4-C6 hetero ring with the adjacent nitrogen atom; X4 is optionally substituted C1- C4 alkyl; <com:Math><semantics>X5<annotation encoding="application / x-tex">X^5< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X6<annotation encoding="application / x-tex">X^6< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted C1-C4 alkyl, or together form an optionally substituted C4-C6 hetero ring with the adjacent nitrogen atom; X7 is optionally substituted C1- C4 alkyl; <com:Math><semantics>Y28<annotation encoding="application / x-tex">Y^{28}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y37<annotation encoding="application / x-tex">Y^{37}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; Z10 and Z11 are the same or different and are each <com:Math><semantics>−O−<annotation encoding="application / x-tex">-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY38A−<annotation encoding="application / x-tex">-NY^{38A}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−NY38B−<annotation encoding="application / x-tex">-CO-NY^{38B}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY38C−CO−<annotation encoding="application / x-tex">-NY^{38C}-CO-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−<annotation encoding="application / x-tex">-< / annotation>< / semantics>< / com:Math> NY<com:Sup>38D< / com:Sup>-CO-O- wherein Y<com:Sup>38A< / com:Sup> to Y<com:Sup>38D< / com:Sup> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>p13<annotation encoding="application / x-tex">p^{13}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; and <com:Math><semantics>p14<annotation encoding="application / x-tex">p^{14}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>p17<annotation encoding="application / x-tex">p^{17}< / annotation>< / semantics>< / com:Math> are the same or different and are each an integer from 1 to 5; and A<com:Sup>2< / com:Sup> is a pharmaceutically acceptable anion, formula (III)

[0078] [Image disponible dans le document PDF, Image available in the PDF document] (III) wherein 1 R<com:Sup>7< / com:Sup> to R<com:Sup>9< / com:Sup> are the same or different and are each optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; L<com:Sup>8< / com:Sup> to L<com:Sup>10< / com:Sup> are the same or different and are each absent, or <com:Math><semantics>−Z12<annotation encoding="application / x-tex">-Z^{12}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>(CY39Y40)p18<annotation encoding="application / x-tex">(CY^{39}Y^{40})_{p18}< / annotation>< / semantics>< / com:Math>- or <com:Math><semantics>−Z13<annotation encoding="application / x-tex">-Z^{13}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>(CY41Y42)p19<annotation encoding="application / x-tex">(CY^{41}Y^{42})_{p19}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>Z14<annotation encoding="application / x-tex">Z^{14}< / annotation>< / semantics>< / com:Math>- <com:Math><semantics>(CY43Y44)p20<annotation encoding="application / x-tex">(CY^{43}Y^{44})_{p20}< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y39<annotation encoding="application / x-tex">Y^{39}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y44<annotation encoding="application / x-tex">Y^{44}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z12<annotation encoding="application / x-tex">Z^{12}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Z14<annotation encoding="application / x-tex">Z^{14}< / annotation>< / semantics>< / com:Math> are the same or different and are each -O-, -NY45A-, -CO-O-, -O-CO-, -CO-NY45B-, -NY45C-CO-, - <com:Math><semantics>NY45D<annotation encoding="application / x-tex">NY^{45D}< / annotation>< / semantics>< / com:Math>-CO-O- or -CO- wherein <com:Math><semantics>Y45A<annotation encoding="application / x-tex">Y^{45A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y45D<annotation encoding="application / x-tex">Y^{45D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; p18 is an integer from 0 to 5; p<com:Sup>19< / com:Sup> is an integer from 1 to 5; and p<com:Sup>20< / com:Sup> is an integer from 0 to 5; [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] wherein Y46 to Y57 are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z15<annotation encoding="application / x-tex">Z^{15}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Z17<annotation encoding="application / x-tex">Z^{17}< / annotation>< / semantics>< / com:Math> are the same or different and are each -O-, - <com:Math><semantics>NY58A<annotation encoding="application / x-tex">NY^{58A}< / annotation>< / semantics>< / com:Math>-, -CO-O-, -O-CO-, -CO-<com:Math><semantics>NY58B<annotation encoding="application / x-tex">NY^{58B}< / annotation>< / semantics>< / com:Math>-, -<com:Math><semantics>NY58C<annotation encoding="application / x-tex">NY^{58C}< / annotation>< / semantics>< / com:Math>-CO-, -<com:Math><semantics>NY58D<annotation encoding="application / x-tex">NY^{58D}< / annotation>< / semantics>< / com:Math>-CO-O- or -CO- wherein Y<com:Sup>58A< / com:Sup> to Y<com:Sup>58D< / com:Sup> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; p<com:Sup>21< / com:Sup> is an integer from 1 to 5; p<com:Sup>22< / com:Sup> is an integer from 0 to 5; <com:Math><semantics>p23<annotation encoding="application / x-tex">p^{23}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; <com:Math><semantics>p24<annotation encoding="application / x-tex">p^{24}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; p<com:Sup>25< / com:Sup> is an integer from 1 to 5; and p<com:Sup>26< / com:Sup> is an integer from 1 to 5; • . [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] wherein Y<com:Sup>59< / com:Sup> to Y<com:Sup>70< / com:Sup> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z18<annotation encoding="application / x-tex">Z^{18}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Z20<annotation encoding="application / x-tex">Z^{20}< / annotation>< / semantics>< / com:Math> are the same or different and are each -O-, - [Image disponible dans le document PDF, Image available in the PDF document] or -CO- wherein Y<com:Sup>71A< / com:Sup> to Y<com:Sup>71D< / com:Sup> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; p<com:Sup>27< / com:Sup> is an integer from 1 to 5; p<com:Sup>28< / com:Sup> is an integer from 0 to 5; <com:Math><semantics>p29<annotation encoding="application / x-tex">p^{29}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>p30<annotation encoding="application / x-tex">p^{30}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; p<com:Sup>31< / com:Sup> is an integer from 1 to 5; and <com:Math><semantics>p32<annotation encoding="application / x-tex">p^{32}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>J1<annotation encoding="application / x-tex">J^1< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>J2<annotation encoding="application / x-tex">J^2< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>CY72<annotation encoding="application / x-tex">CY^{72}< / annotation>< / semantics>< / com:Math> or N wherein Y<com:Sup>72< / com:Sup> is a hydrogen atom, hydroxy, optionally substituted C1-C4 alkyl, optionally substituted C1-C4 alkoxy, or optionally substituted C1-C4 acyloxy; <com:Math><semantics>B2<annotation encoding="application / x-tex">B^2< / annotation>< / semantics>< / com:Math> is [Image disponible dans le document PDF, Image available in the PDF document] wherein <com:Math><semantics>X8<annotation encoding="application / x-tex">X^8< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X9<annotation encoding="application / x-tex">X^9< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted C1-C4 alkyl, or together form an optionally substituted C4-C6 hetero ring with the adjacent nitrogen atom; X10 is optionally substituted C1- C4 alkyl; <com:Math><semantics>X11<annotation encoding="application / x-tex">X^{11}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X12<annotation encoding="application / x-tex">X^{12}< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted C1-C4 alkyl, or together form .... • 4 an optionally substituted C4-C6 hetero ring with the adjacent nitrogen atom; X13 is optionally substituted C1- C4 alkyl; Y73 to Y82 are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z21<annotation encoding="application / x-tex">Z^{21}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>Z22<annotation encoding="application / x-tex">Z^{22}< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−O−<annotation encoding="application / x-tex">-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY83A−<annotation encoding="application / x-tex">-NY^{83A}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−NY83B−<annotation encoding="application / x-tex">-CO-NY^{83B}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY83C−CO−<annotation encoding="application / x-tex">-NY^{83C}-CO-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−<annotation encoding="application / x-tex">-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>NY83D<annotation encoding="application / x-tex">NY^{83D}< / annotation>< / semantics>< / com:Math>-CO-O- wherein <com:Math><semantics>Y83A<annotation encoding="application / x-tex">Y^{83A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y83D<annotation encoding="application / x-tex">Y^{83D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>p33<annotation encoding="application / x-tex">p^{33}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; and <com:Math><semantics>p34<annotation encoding="application / x-tex">p^{34}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>p37<annotation encoding="application / x-tex">p^{37}< / annotation>< / semantics>< / com:Math> are the same or different and are each an integer from 1 to 5; and A<com:Sup>3< / com:Sup> is a pharmaceutically acceptable anion, formula (IV)

[0079] [Image disponible dans le document PDF, Image available in the PDF document] (IV) wherein R<com:Sup>10< / com:Sup> to R<com:Sup>12< / com:Sup> are the same or different and are each optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; <com:Math><semantics>L13<annotation encoding="application / x-tex">L^{13}< / annotation>< / semantics>< / com:Math> is absent, or <com:Math><semantics>−Z23−(CY84Y85)p38−<annotation encoding="application / x-tex">-Z^{23}-(CY^{84}Y^{85})_{p38}-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−Z24−(CY86Y87)p39−<annotation encoding="application / x-tex">-Z^{24}-(CY^{86}Y^{87})_{p39}-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>Z25<annotation encoding="application / x-tex">Z^{25}< / annotation>< / semantics>< / com:Math>-(<com:Math><semantics>CY88Y89<annotation encoding="application / x-tex">CY^{88}Y^{89}< / annotation>< / semantics>< / com:Math>)<com:Sub>p40< / com:Sub>- wherein <com:Math><semantics>Y84<annotation encoding="application / x-tex">Y^{84}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y89<annotation encoding="application / x-tex">Y^{89}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z23<annotation encoding="application / x-tex">Z^{23}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Z25<annotation encoding="application / x-tex">Z^{25}< / annotation>< / semantics>< / com:Math> are the same or . 4 different and are each <com:Math><semantics>−0−<annotation encoding="application / x-tex">-0-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY90A−<annotation encoding="application / x-tex">-NY^{90A}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−<annotation encoding="application / x-tex">-CO-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>NY90B<annotation encoding="application / x-tex">NY^{90B}< / annotation>< / semantics>< / com:Math>-, <com:Math><semantics>−NY90C<annotation encoding="application / x-tex">-NY^{90C}< / annotation>< / semantics>< / com:Math>-CO- or <com:Math><semantics>−NY90D<annotation encoding="application / x-tex">-NY^{90D}< / annotation>< / semantics>< / com:Math>-CO-O- wherein <com:Math><semantics>Y90A<annotation encoding="application / x-tex">Y^{90A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y90D<annotation encoding="application / x-tex">Y^{90D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; and p38 to p40 are the same or different and are each an integer from 1 to 5; L<com:Sup>14< / com:Sup> and L<com:Sup>15< / com:Sup> are the same or different and are each [Image disponible dans le document PDF, Image available in the PDF document] <com:Math><semantics>(CY95Y96)p43<annotation encoding="application / x-tex">(CY^{95}Y^{96})_{p43}< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y91<annotation encoding="application / x-tex">Y^{91}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y96<annotation encoding="application / x-tex">Y^{96}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z26<annotation encoding="application / x-tex">Z^{26}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Z28<annotation encoding="application / x-tex">Z^{28}< / annotation>< / semantics>< / com:Math> are the same or different and are each -O-, -NY<com:Sup>97A< / com:Sup>-, -CO-O-, -O-CO-, -CO-NY<com:Sup>97B< / com:Sup>-, -NY<com:Sup>97C< / com:Sup>-CO-, - <com:Math><semantics>NY97D<annotation encoding="application / x-tex">NY^{97D}< / annotation>< / semantics>< / com:Math>-CO-O- or -CO- wherein <com:Math><semantics>Y97A<annotation encoding="application / x-tex">Y^{97A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y97D<annotation encoding="application / x-tex">Y^{97D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; p41 is an integer from 0 to 5; p42 is an integer from 1 to 5; and p43 is an integer from 0 to 5; <com:Math><semantics>L16<annotation encoding="application / x-tex">L^{16}< / annotation>< / semantics>< / com:Math> is absent, or <com:Math><semantics>−(CY98Y99)p44<annotation encoding="application / x-tex">-(CY^{98}Y^{99})_{p44}< / annotation>< / semantics>< / com:Math>-, <com:Math><semantics>−(CY100Y101)p45<annotation encoding="application / x-tex">-(CY^{100}Y^{101})_{p45}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>Z29<annotation encoding="application / x-tex">Z^{29}< / annotation>< / semantics>< / com:Math>- [Image disponible dans le document PDF, Image available in the PDF document] <com:Math><semantics>(CY108Y109)p49<annotation encoding="application / x-tex">(CY^{108}Y^{109})_{p49}< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y98<annotation encoding="application / x-tex">Y^{98}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y109<annotation encoding="application / x-tex">Y^{109}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; Z<com:Sup>29< / com:Sup> to Z<com:Sup>31< / com:Sup> are the same or different and are each -O-, -NY<com:Sup>110A< / com:Sup>-, -CO-O-, -O-CO-, -CO-NY<com:Sup>110B< / com:Sup>-, -NY<com:Sup>110C< / com:Sup>-CO-, <com:Math><semantics>−NY110D−CO−O−<annotation encoding="application / x-tex">-NY^{110D}-CO-O-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−CO−<annotation encoding="application / x-tex">-CO-< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y110A<annotation encoding="application / x-tex">Y^{110A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y110D<annotation encoding="application / x-tex">Y^{110D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; p44 is an integer from 1 to 5; p<com:Sup>45< / com:Sup> is an integer from 0 to 5; p<com:Sup>46< / com:Sup> is an integer from 1 to 4 1 • 5; p47 is an integer from 0 to 5; p48 is an integer from 1 to 5; and p<com:Sup>49< / com:Sup> is an integer from 1 to 5; <com:Math><semantics>J3<annotation encoding="application / x-tex">J^3< / annotation>< / semantics>< / com:Math> is <com:Math><semantics>CY111<annotation encoding="application / x-tex">CY^{111}< / annotation>< / semantics>< / com:Math> or N wherein <com:Math><semantics>Y111<annotation encoding="application / x-tex">Y^{111}< / annotation>< / semantics>< / com:Math> is a hydrogen atom, hydroxy, optionally substituted C1-C4 alkyl, optionally substituted C1-C4 alkoxy, or optionally substituted C1-C4 acyloxy; X<com:Sup>14< / com:Sup> and X<com:Sup>15< / com:Sup> are the same or different and are each optionally substituted C1-C4 alkyl, or together form an optionally substituted C4-C6 hetero ring with the adjacent nitrogen atom; and A4 is a pharmaceutically acceptable anion, and formula (V') or formula (V'')

[0080] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] (V') (V") or wherein <Formule mathématique disponible dans le document PDF, Math available in the PDF document>${\bf R}^{13}$ to <Formule mathématique disponible dans le document PDF, Math available in the PDF document>${\bf R}^{18}$ are the same or different and are each optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; <com:Math><semantics>Y112<annotation encoding="application / x-tex">Y^{112}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y115<annotation encoding="application / x-tex">Y^{115}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom, hydroxy or optionally substituted C1-C4 alkyl; <com:Math><semantics>𝙻17<annotation encoding="application / x-tex">\texttt{L}^{17}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>𝙻19<annotation encoding="application / x-tex">\texttt{L}^{19}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>𝙻22<annotation encoding="application / x-tex">\texttt{L}^{22}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>𝙻24<annotation encoding="application / x-tex">\texttt{L}^{24}< / annotation>< / semantics>< / com:Math> are the same or different and are each absent, or <com:Math><semantics>−Z32−(CY116Y117)p51−<annotation encoding="application / x-tex">-Z^{32}-(CY^{116}Y^{117})_{p51}-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−Z33−(CY118Y119)p52−<annotation encoding="application / x-tex">-Z^{33}-(CY^{118}Y^{119})_{p52}-< / annotation>< / semantics>< / com:Math> 4 • <com:Math><semantics>Z34<annotation encoding="application / x-tex">Z^{34}< / annotation>< / semantics>< / com:Math>-(<com:Math><semantics>CY120Y121<annotation encoding="application / x-tex">CY^{120}Y^{121}< / annotation>< / semantics>< / com:Math>)<com:Sub>p53< / com:Sub>- wherein <com:Math><semantics>Y116<annotation encoding="application / x-tex">Y^{116}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y121<annotation encoding="application / x-tex">Y^{121}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z32<annotation encoding="application / x-tex">Z^{32}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Z34<annotation encoding="application / x-tex">Z^{34}< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−O−<annotation encoding="application / x-tex">-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY122A−<annotation encoding="application / x-tex">-NY^{122A}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−<annotation encoding="application / x-tex">-CO-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>NY122B<annotation encoding="application / x-tex">NY^{122B}< / annotation>< / semantics>< / com:Math>-, <com:Math><semantics>−NY122C<annotation encoding="application / x-tex">-NY^{122C}< / annotation>< / semantics>< / com:Math>-CO-, <com:Math><semantics>−NY122D<annotation encoding="application / x-tex">-NY^{122D}< / annotation>< / semantics>< / com:Math>-CO-O- or -CO- wherein <com:Math><semantics>Y122A<annotation encoding="application / x-tex">Y^{122A}< / annotation>< / semantics>< / com:Math> to Y<com:Sup>122D< / com:Sup> are the same or different and are each a hydrogen atom or optionally substituted <com:Math><semantics>C1−C4<annotation encoding="application / x-tex">C1-C4< / annotation>< / semantics>< / com:Math> alkyl; <com:Math><semantics>p51<annotation encoding="application / x-tex">p^{51}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; p<com:Sup>52< / com:Sup> is an integer from 1 to 5; and p<com:Sup>53< / com:Sup> is an integer from 0 to 5; <com:Math><semantics>𝙻20<annotation encoding="application / x-tex">\texttt{L}^{20}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>𝙻25<annotation encoding="application / x-tex">\texttt{L}^{25}< / annotation>< / semantics>< / com:Math> are the same or different and are each absent, or <com:Math><semantics>−(CY123Y124)p54<annotation encoding="application / x-tex">-(CY^{123}Y^{124})_{p54}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−(CY125Y126)p55<annotation encoding="application / x-tex">-(CY^{125}Y^{126})_{p55}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−Z35<annotation encoding="application / x-tex">-Z^{35}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−(CY127Y128)p56<annotation encoding="application / x-tex">-(CY^{127}Y^{128})_{p56}< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−(CY129Y130)p57−Z36−(CY131Y132)p58−Z37−(CY133Y134)p59<annotation encoding="application / x-tex">-(CY^{129}Y^{130})_{p57}-Z^{36}-(CY^{131}Y^{132})_{p58}-Z^{37}-(CY^{133}Y^{134})_{p59}< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y123<annotation encoding="application / x-tex">Y^{123}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y134<annotation encoding="application / x-tex">Y^{134}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; Z35 to <com:Math><semantics>Z37<annotation encoding="application / x-tex">Z^{37}< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−O−<annotation encoding="application / x-tex">-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY135A−<annotation encoding="application / x-tex">-NY^{135A}-< / annotation>< / semantics>< / com:Math>, -CO-O-, -O-CO-, -CO-NY<com:Sup>135B< / com:Sup>-, -NY<com:Sup>135C< / com:Sup>-CO-, -NY<com:Sup>135D< / com:Sup>-CO-O- or - CO- wherein <com:Math><semantics>Y135A<annotation encoding="application / x-tex">Y^{135\text{A}}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y135D<annotation encoding="application / x-tex">Y^{135\text{D}}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; p<com:Sup>54< / com:Sup> is an integer from 1 to 5; p<com:Sup>55< / com:Sup> is an integer from 0 to 5; <com:Math><semantics>p56<annotation encoding="application / x-tex">p^{56}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; <com:Math><semantics>p57<annotation encoding="application / x-tex">p^{57}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>p58<annotation encoding="application / x-tex">p^{58}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; and p<com:Sup>59< / com:Sup> is an integer from 1 to 5; <com:Math><semantics>𝙻21<annotation encoding="application / x-tex">\texttt{L}^{21}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>𝙻26<annotation encoding="application / x-tex">\texttt{L}^{26}< / annotation>< / semantics>< / com:Math> are the same or different and are each absent, or <com:Math><semantics>−(CY136Y137)p60<annotation encoding="application / x-tex">-(CY^{136}Y^{137})_{p60}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−(CY138Y139)p61<annotation encoding="application / x-tex">-(CY^{138}Y^{139})_{p61}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−Z38<annotation encoding="application / x-tex">-Z^{38}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−(CY140Y141)p62<annotation encoding="application / x-tex">-(CY^{140}Y^{141})_{p62}< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−(CY142Y143)p63−Z39−(CY144Y145)p64−Z40−(CY146Y147)p65<annotation encoding="application / x-tex">-(CY^{142}Y^{143})_{p63}-Z^{39}-(CY^{144}Y^{145})_{p64}-Z^{40}-(CY^{146}Y^{147})_{p65}< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>𝒀136<annotation encoding="application / x-tex">\mathbf{Y}^{136}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>𝒀147<annotation encoding="application / x-tex">\mathbf{Y}^{147}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; Z38 . to <com:Math><semantics>Z40<annotation encoding="application / x-tex">Z^{40}< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−O−<annotation encoding="application / x-tex">-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY148A−<annotation encoding="application / x-tex">-NY^{148A}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−NY148B−<annotation encoding="application / x-tex">-CO-NY^{148B}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NR148C−CO−<annotation encoding="application / x-tex">-NR^{148C}-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY148D−CO−O−<annotation encoding="application / x-tex">-NY^{148D}-CO-O-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−<annotation encoding="application / x-tex">-< / annotation>< / semantics>< / com:Math> CO- wherein <com:Math><semantics>Y148A<annotation encoding="application / x-tex">Y^{148A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y148D<annotation encoding="application / x-tex">Y^{148D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; p<com:Sup>60< / com:Sup> is an integer from 1 to 5; p<com:Sup>61< / com:Sup> is an integer from 0 to 5; <com:Math><semantics>p62<annotation encoding="application / x-tex">p^{62}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>p63<annotation encoding="application / x-tex">p^{63}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; p<com:Sup>64< / com:Sup> is an integer from 1 to 5; and p<com:Sup>65< / com:Sup> is an integer from 0 to 5; B<com:Sup>3< / com:Sup> and B<com:Sup>4< / com:Sup> are the same or different and are each [Image disponible dans le document PDF, Image available in the PDF document] wherein <com:Math><semantics>X16<annotation encoding="application / x-tex">X^{16}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X17<annotation encoding="application / x-tex">X^{17}< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted C1-C4 alkyl, or together form an optionally substituted C4-C6 hetero ring with the adjacent nitrogen atom; X18 is optionally substituted C1- C4 alkyl; X19 and X20 are the same or different and are each optionally substituted C1-C4 alkyl, or together form an optionally substituted C4-C6 hetero ring with the adjacent nitrogen atom; X21 is optionally substituted C1- C4 alkyl; Y149 to Y158 are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z41<annotation encoding="application / x-tex">Z^{41}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>Z42<annotation encoding="application / x-tex">Z^{42}< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−O−<annotation encoding="application / x-tex">-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY159A−<annotation encoding="application / x-tex">-NY^{159A}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−NY159B−<annotation encoding="application / x-tex">-CO-NY^{159B}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY159C−CO−<annotation encoding="application / x-tex">-NY^{159C}-CO-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−<annotation encoding="application / x-tex">-< / annotation>< / semantics>< / com:Math> NY<com:Sup>159D< / com:Sup>-CO-O- wherein Y<com:Sup>159A< / com:Sup> to Y<com:Sup>159D< / com:Sup> are the same or different ¥ and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>p66<annotation encoding="application / x-tex">p^{66}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; and <com:Math><semantics>p67<annotation encoding="application / x-tex">p^{67}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>p70<annotation encoding="application / x-tex">p^{70}< / annotation>< / semantics>< / com:Math> are the same or different and are each an integer from 1 to 5; and A<com:Sup>5< / com:Sup> and A<com:Sup>6< / com:Sup> are the same or different and are each a pharmaceutically acceptable anion.

[0081] Hereinafter, the compounds represented by formulas (I) to (IV), (V') and (V'') are also referred to as compounds (I) to (IV), (V') and (V''), respectively. The same holds true for compounds of other formula numbers.

[0082] The definition of each group in formulas (I) to (V'') will be described below. Examples of the linear or branched C8-C24 alkyl include octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, 2,6,10-trimethylundecyl, pentadecyl, 3,7,11- trimethyldodecyl, hexadecyl, heptadecyl, octadecyl, 6,10,14-trimethylpentadecan-2-yl, nonadecyl, 2,6,10,14- tetramethylpentadecyl, icosyl, 3,7,11,15- tetramethylhexadecyl, henicosyl, docosyl, tricosyl and tetracosyl, preferably nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl and octadecyl, more preferably undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl and hexadecyl.

[0083] .4 . Examples of the linear or branched C9-C18 alkyl include nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, 2,6,10-trimethylundecyl, pentadecyl, 3,7,11- trimethyldodecyl, hexadecyl, heptadecyl, octadecyl and 6,10,14-trimethylpentadecan-2-yl, preferably nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl and octadecyl, more preferably undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl and hexadecyl.

[0084] The linear or branched C8-C24 alkenyl can be linear or branched C8-24 alkenyl containing one to three double bonds. Examples thereof include (Z)-tridec-8-enyl, (Z)- tetradec-9-enyl, (Z)-pentadec-8-enyl, (Z)-hexadec-9-enyl, (Z)-heptadec-5-enyl, (Z)-octadec-6-enyl, (Z)-heptadec-8- enyl, (Z)-octadec-9-enyl, (E)-heptadec-8-enyl, (E)- octadec-9-enyl, (Z)-heptadec-10-enyl, (Z)-octadec-11-enyl, (8Z,11Z)-heptadeca-8,11-dienyl, (9Z,12Z)-octadeca-9,12- dienyl, (8Z,11Z,14Z)-octadeca-8,11,14-trienyl, (9Z,12Z,15Z)-octadeca-9,12,15-trienyl, (Z)-nonadec-10- enyl, (Z)-icos-11-enyl, (10Z,13Z)-nonadeca-10,13-dienyl, (11Z,14Z)-icosa-11,14-dienyl, 2,6,10-trimethylundeca- 1,5,9-trienyl, 3,7,11-trimethyldodeca-2,6,10-trienyl, 2,6,10,14-tetramethylpentadec-1-enyl and 3,7,11,15- tetramethylhexadec-2-enyl, preferably (Z)-pentadec-8-enyl, (Z)-hexadec-9-enyl, (Z)-heptadec-5-enyl, (Z)-octadec-6- enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-heptadec-8-enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-octadec-9-enyl, <com:Math><semantics>(8Z,11Z)<annotation encoding="application / x-tex">(8Z,11Z)< / annotation>< / semantics>< / com:Math>- 3 heptadeca-8,11-dienyl and (9Z,12Z)-octadeca-9,12-dienyl, more preferably (Z)-heptadec-8-enyl, (Z)-octadec-9-enyl, (8Z,11Z)-heptadeca-8,11-dienyl and (9Z,12Z)-octadeca- 9,12-dienyl.

[0085] Examples of the linear or branched C15-C20 alkenyl include (Z)-pentadec-8-enyl, (Z)-hexadec-9-enyl, (Z)- heptadec-5-enyl, (Z)-octadec-6-enyl, (Z)-heptadec-8-enyl, (Z)-octadec-9-enyl, (E)-heptadec-8-enyl, (E)-octadec-9- enyl, (Z)-heptadec-10-enyl, (Z)-octadec-11-enyl, (8Z,11Z)-heptadeca-8,11-dienyl, (9Z,12Z)-octadeca-9,12- dienyl, (8Z,11Z,14Z)-octadeca-8,11,14-trienyl, (9Z,12Z,15Z)-octadeca-9,12,15-trienyl, (Z)-nonadec-10- enyl, (Z)-icos-11-enyl, (10Z,13Z)-nonadeca-10,13-dienyl, <com:Math><semantics>(11Z,14Z)<annotation encoding="application / x-tex">(11Z, 14Z)< / annotation>< / semantics>< / com:Math>-icosa-11,14-dienyl and 3,7,11,15- tetramethylhexadec-2-enyl, preferably (Z)-pentadec-8-enyl, (Z)-hexadec-9-enyl, (Z)-heptadec-5-enyl, (Z)-octadec-6- enyl, (Z)-heptadec-8-enyl, (Z)-octadec-9-enyl, (8Z,11Z)- heptadeca-8,11-dienyl and (9Z,12Z)-octadeca-9,12-dienyl, more preferably (Z)-heptadec-8-enyl, (Z)-octadec-9-enyl, (8Z,11Z)-heptadeca-8,11-dienyl and (9Z,12Z)-octadeca- <com:Math><semantics>9,12<annotation encoding="application / x-tex">9,12< / annotation>< / semantics>< / com:Math>-dienyl.

[0086] In the present invention, a group having a cyclopropane ring formed by adding formally a methylene biradical to a double bond of the optionally substituted linear or branched C8-C24 alkenyl is also included in the • * ٠ C8-C24 alkenyl. Examples thereof include groups having the following cyclopropane rings corresponding to (Z)- hexadec-9-enyl, (9Z,12Z)-octadeca-9,12-dienyl and (8Z,11Z) -heptadeca-8,11-dienyl:

[0087] [Image disponible dans le document PDF, Image available in the PDF document]

[8800] ٦, [Image disponible dans le document PDF, Image available in the PDF document] and

[0089] [Image disponible dans le document PDF, Image available in the PDF document]

[0090] The linear or branched C8-C24 alkynyl can be linear or branched C8-24 alkynyl containing one to three triple bonds. Examples thereof include dodec-11-ynyl, tridec- 12-ynyl, pentadec-6-ynyl, hexadec-7-ynyl, pentadeca-4,6- diynyl, hexadeca-5,7-diynyl, heptadec-8-ynyl and octadec- 9-ynyl, preferably pentadec-6-ynyl, hexadec-7-ynyl, pentadeca-4,6-diynyl, hexadeca-5,7-diynyl, heptadec-8- ynyl and octadec-9-ynyl, more preferably heptadec-8-ynyl and octadec-9-ynyl.

[0091] Examples of the C1-C4 alkyl include methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, isobutyl, sec- ⋖ + butyl, tert-butyl, cyclobutyl and cyclopropylmethyl, preferably methyl and ethyl, more preferably methyl.

[0092] The alkyl moiety in the optionally substituted C1-C4 alkoxy is as defined in the C1-C4 alkyl.

[0093] Examples of the substituent for the optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl include hydroxy, alkoxy, alkoxycarbonyl, nitro, cyano, fluoro, chloro and bromo. Among these substituents, the alkyl moiety in alkoxy and alkoxycarbonyl is as defined in the C1-C4 alkyl.

[0094] Examples of the substituent for the optionally substituted C1-C4 alkyl include amino, monoalkylamino, dialkylamino, pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, morpholin-2-yl, morpholin-3-yl, hydroxy, alkoxy, alkoxycarbonyl, hydroxycarbonyl, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, nitro, cyano, fluoro, chloro and bromo. Among these substituents, the alkyl moiety in monoalkylamino, dialkylamino, alkoxy, alkoxycarbonyl, monoalkylcarbamoyl and dialkylcarbamoyl is as defined in the C1-C4 alkyl. Two alkyl moieties in dialkylamino and dialkylcarbamoyl may be the same as or different from each other.

[0095] ¥ • In the present invention, each of the pyrrolidin-2- yl, the pyrrolidin-3-yl, the piperidin-2-yl, the piperidin-3-yl, the piperidin-4-yl, the morpholin-2-yl and the morpholin-3-yl includes a group formed by adding C1-C3 alkyl such as methyl or ethyl to a nitrogen atom in a ring. Examples of the C1-C3 alkyl include methyl, ethyl, propyl, isopropyl and cyclopropyl, preferably methyl and ethyl, more preferably methyl.

[0096] Examples of the C4-C6 hetero ring together formed by X<com:Sup>2< / com:Sup> and X<com:Sup>3< / com:Sup> with the adjacent nitrogen atom include pyrrolidine, piperidine, morpholine and azepane, preferably pyrrolidine and piperidine. Examples of the substituent for the optionally substituted C4-C6 hetero ring together formed by X2 and X3 with the adjacent nitrogen atom include optionally substituted C1-C4 alkyl (as defined above), amino, monoalkylamino, dialkylamino, pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, morpholin-2-yl, morpholin-3-yl, hydroxy, alkoxy, alkoxycarbonyl, hydroxycarbonyl, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, nitro, cyano, fluoro, chloro and bromo. Among these substituents, the alkyl moiety in monoalkylamino, dialkylamino, alkoxy, alkoxycarbonyl, monoalkylcarbamoyl and dialkylcarbamoyl is as defined in the C1-C4 alkyl. Two alkyl moieties in dialkylamino and * ٠ dialkylcarbamoyl may be the same as or different from each other.

[0097] The hetero ring moiety and the substituent moiety in the optionally substituted C4-C6 hetero ring together formed by X<com:Sup>5< / com:Sup> and X<com:Sup>6< / com:Sup> with the adjacent nitrogen atom are each as defined above.

[0098] The hetero ring moiety and the substituent moiety in the optionally substituted C4-C6 hetero ring together formed by X<com:Sup>8< / com:Sup> and X<com:Sup>9< / com:Sup> with the adjacent nitrogen atom are each as defined above. .

[0099] The hetero ring moiety and the substituent moiety in the optionally substituted C4-C6 hetero ring together formed by X11 and X12 with the adjacent nitrogen atom are each as defined above.

[0100] The hetero ring moiety and the substituent moiety in the optionally substituted C4-C6 hetero ring together formed by X14 and X15 with the adjacent nitrogen atom are each as defined above.

[0101] The hetero ring moiety and the substituent moiety in the optionally substituted C4-C6 hetero ring together formed by X16 and X17 with the adjacent nitrogen atom are each as defined above. , • *

[0102] The hetero ring moiety and the substituent moiety in the optionally substituted C4-C6 hetero ring together formed by X19 and X20 with the adjacent nitrogen atom are each as defined above.

[0103] Examples of the acyl in the C1-C4 acyloxy include formyl, acetyl, propanoyl, 2-methylpropanoyl, cyclopropanoyl and butanoyl, preferably acetyl.

[0104] Examples of the substituent for the optionally substituted C1-C4 acyloxy include amino, monoalkylamino, dialkylamino, pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, morpholin-2-yl, morpholin-3-yl, hydroxy, alkoxy, alkoxycarbonyl, hydroxycarbonyl, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, nitro, cyano, fluoro, chloro and bromo. Among these substituents, the alkyl moiety in monoalkylamino, dialkylamino, alkoxy, alkoxycarbonyl, monoalkylcarbamoyl and dialkylcarbamoyl is as defined in the C1-C4 alkyl. Two alkyl moieties in dialkylamino and dialkylcarbamoyl may be the same as or different from each other.

[0105] The quaternary ammonium group means a group having a nitrogen atom having four covalent bonds to four carbon atoms. Unlike a hydrogen atom added to primary to b • . tertiary amines, the quaternary ammonium group always has a positive charge irrespective of ambient pH.

[0106] Examples of the pharmaceutically acceptable anion include, but are not limited to: inorganic ions such as chloride ions, bromide ions, iodide ions, nitrate ions, sulfate ions and phosphate ions; and organic acid ions such as acetate ions, oxalate ions, maleate ions, fumarate ions, citrate ions, benzoate ions and methanesulfonate ions.

[0107] In formula (I), <com:Math><semantics>R1<annotation encoding="application / x-tex">R^1< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>R3<annotation encoding="application / x-tex">R^3< / annotation>< / semantics>< / com:Math> are preferably the same linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl, more preferably the same linear or branched C8- C24 alkyl or C8-C24 alkenyl, further preferably the same linear or branched C15-C20 alkenyl or the same linear or branched C9-C18 alkyl, most preferably the same linear C15-C20 alkenyl or the same linear C9-C18 alkyl.

[0108] L<com:Sup>1< / com:Sup> to L<com:Sup>3< / com:Sup> are the same or different and are each absent, or <com:Math><semantics>−Z1−(CY1Y2)p1−<annotation encoding="application / x-tex">-Z^{1}-(CY^{1}Y^{2})_{p1}-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−Z2−(CY3Y4)p2−Z3−(CY5Y6)p3−<annotation encoding="application / x-tex">-Z^{2}-(CY^{3}Y^{4})_{p2}-Z^{3}-(CY^{5}Y^{6})_{p3}-< / annotation>< / semantics>< / com:Math>, preferably <com:Math><semantics>−Z1−(CY1Y2)p1−.<annotation encoding="application / x-tex">-Z^1-(CY^1Y^2)_{p1}-.< / annotation>< / semantics>< / com:Math> <com:Math><semantics>Y1<annotation encoding="application / x-tex">Y^1< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y6<annotation encoding="application / x-tex">Y^6< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl, preferably a hydrogen atom. Z1 to <com:Math><semantics>Z3<annotation encoding="application / x-tex">Z^3< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−O−<annotation encoding="application / x-tex">-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY7A−<annotation encoding="application / x-tex">-NY^{7A}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−NY7B−<annotation encoding="application / x-tex">-CO-NY^{7B}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY7C−CO−<annotation encoding="application / x-tex">-NY^{7C}-CO-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−NY7D−CO−O−<annotation encoding="application / x-tex">-NY^{7D}-CO-O-< / annotation>< / semantics>< / com:Math>, preferably -O-, -CO-O-, -O-CO-, -CO-NY<com:Sup>7B< / com:Sup>- or -NY<com:Sup>7C< / com:Sup>-CO-. 4 <com:Math><semantics>Y7A<annotation encoding="application / x-tex">Y^{7A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y7D<annotation encoding="application / x-tex">Y^{7D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl, preferably a hydrogen atom or methyl. p1 to p3 are the same or different and are each an integer from 1 to 5, preferably 1 or 2.

[0109] L<com:Sup>1< / com:Sup> to L<com:Sup>3< / com:Sup> are preferably the same or different and are each <com:Math><semantics>−O−(CY1Y2)p1−<annotation encoding="application / x-tex">-O-(CY^1Y^2)_{p1}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−O−(CY1Y2)p1−<annotation encoding="application / x-tex">-CO-O-(CY^1Y^2)_{p1}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−(CY1Y2)p1−<annotation encoding="application / x-tex">-O-CO-(CY^1Y^2)_{p1}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−<annotation encoding="application / x-tex">-CO-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>NY7B−(CY1Y2)p1−<annotation encoding="application / x-tex">NY^{7B}-(CY^{1}Y^{2})_{p1}-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−NY7C−CO−(CY1Y2)p1−<annotation encoding="application / x-tex">-NY^{7C}-CO-(CY^{1}Y^{2})_{p1}-< / annotation>< / semantics>< / com:Math>, more preferably are the same or different and are each <com:Math><semantics>−CO−O−(CY1Y2)p1−<annotation encoding="application / x-tex">-CO-O-(CY^1Y^2)_{p1}-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−O−<annotation encoding="application / x-tex">-O-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>CO−(CY1Y2)p1−<annotation encoding="application / x-tex">CO-(CY^1Y^2)_{p1}-< / annotation>< / semantics>< / com:Math>, further preferably are the same and <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>(CH2)2−.<annotation encoding="application / x-tex">(CH_2)_2 - .< / annotation>< / semantics>< / com:Math>

[0110] In formula (I), preferably, one or more of <com:Math><semantics>L1<annotation encoding="application / x-tex">L^1< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>L3<annotation encoding="application / x-tex">L^3< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−CO−O−(CY1Y2)p1−<annotation encoding="application / x-tex">-CO-O-(CY^{1}Y^{2})_{p1}-< / annotation>< / semantics>< / com:Math> or -O-CO-<com:Math><semantics>(CY1Y2)p1<annotation encoding="application / x-tex">(CY^1Y^2)_{p1}< / annotation>< / semantics>< / com:Math>-, and <com:Math><semantics>R1<annotation encoding="application / x-tex">R^1< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>R3<annotation encoding="application / x-tex">R^3< / annotation>< / semantics>< / com:Math> are the same linear C15-C20 alkenyl or the same linear C9-C18 alkyl.

[0111] When at least one of <com:Math><semantics>L1<annotation encoding="application / x-tex">L^1< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>L3<annotation encoding="application / x-tex">L^3< / annotation>< / semantics>< / com:Math> is absent, or <com:Math><semantics>−0<annotation encoding="application / x-tex">-0< / annotation>< / semantics>< / com:Math>- <com:Math><semantics>(CY1Y2)p1<annotation encoding="application / x-tex">(CY^{1}Y^{2})_{p1}< / annotation>< / semantics>< / com:Math>-, -O-CO-<com:Math><semantics>(CY1Y2)p1<annotation encoding="application / x-tex">(CY^{1}Y^{2})_{p1}< / annotation>< / semantics>< / com:Math>- or -NY<com:Sup>7C< / com:Sup>-CO-<com:Math><semantics>(CY1Y2)p1<annotation encoding="application / x-tex">(CY^{1}Y^{2})_{p1}< / annotation>< / semantics>< / com:Math>-, R<com:Sup>1< / com:Sup> to R<com:Sup>3< / com:Sup> bonded to the positively charged nitrogen atom <com:Math><semantics>(N+)<annotation encoding="application / x-tex">(N^+)< / annotation>< / semantics>< / com:Math>, -O- <com:Math><semantics>(CY1Y2)p1<annotation encoding="application / x-tex">(CY^{1}Y^{2})_{p1}< / annotation>< / semantics>< / com:Math>-, -O-CO-<com:Math><semantics>(CY1Y2)p1<annotation encoding="application / x-tex">(CY^{1}Y^{2})_{p1}< / annotation>< / semantics>< / com:Math>- or -NR<com:Sup>6< / com:Sup>-CO-<com:Math><semantics>(CY1Y2)p1<annotation encoding="application / x-tex">(CY^{1}Y^{2})_{p1}< / annotation>< / semantics>< / com:Math>- are the same or different and are each more preferably octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, icosyl, docosyl, tetracosyl, (Z)-tetradec-9-enyl, (Z)-hexadec-9- enyl, (Z)-octadec-6-enyl, (Z)-octadec-9-enyl, (E)- octadec-9-enyl, (Z)-octadec-11-enyl, (9Z,12Z)-octadeca- 4 • 1 • 9,12-dienyl, (9Z,12Z,15Z)-octadeca-9,12,15-trienyl, (Z)- icos-11-enyl, (11Z,14Z)-icosa-11,14-dienyl, 3,7,11- trimethyldodeca-2,6,10-trienyl, 3,7,11,15- tetramethylhexadec-2-enyl or the like, further preferably dodecyl, tetradecyl, hexadecyl, (Z)-hexadec-9-enyl, (Z)- octadec-6-enyl, (Z)-octadec-9-enyl, (9Z,12Z)-octadeca- 9,12-dienyl or the like.

[0112] When at least one of <com:Math><semantics>L1<annotation encoding="application / x-tex">L^1< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>L3<annotation encoding="application / x-tex">L^3< / annotation>< / semantics>< / com:Math> is <com:Math><semantics>−CO−O−(CY1Y2)p1<annotation encoding="application / x-tex">-CO-O-(CY^1Y^2)_{p1}< / annotation>< / semantics>< / com:Math> or - <com:Math><semantics>CO−NY7B−(CY1Y2)p1−<annotation encoding="application / x-tex">CO-NY^{7B}-(CY^{1}Y^{2})_{p1}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>R1<annotation encoding="application / x-tex">R^{1}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>R3<annotation encoding="application / x-tex">R^{3}< / annotation>< / semantics>< / com:Math> bonded to <com:Math><semantics>−CO−O−(CY1Y2)p1−<annotation encoding="application / x-tex">-CO-O-(CY^{1}Y^{2})_{p1}-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−<annotation encoding="application / x-tex">-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>CO−NY7B−(CY1Y2)p1−<annotation encoding="application / x-tex">CO-NY^{7B}-(CY^{1}Y^{2})_{p1}-< / annotation>< / semantics>< / com:Math> are the same or different and are each more preferably nonyl, undecyl, tridecyl, pentadecyl, heptadecyl, nonadecyl, henicosyl, tricosyl, (Z)-tridec-8- enyl, (Z)-pentadec-8-enyl, (Z)-heptadec-5-enyl, (Z)- heptadec-8-enyl, (E)-heptadec-8-enyl, (Z)-heptadec-10- enyl, (8Z,11Z)-heptadeca-8,11-dienyl, (8Z,11Z,14Z)- octadeca-8,11,14-trienyl, (Z)-nonadec-10-enyl, (10Z,13Z)- nonadeca-10,13-dienyl, (11Z,14Z)-icosa-11,14-dienyl, 2,6,10-trimethylundeca-1,5,9-trienyl, 2,6,10,14- tetramethylpentadec-1-enyl or the like, further preferably undecyl, tridecyl, pentadecyl, (Z)-pentadec-8- enyl, (Z)-heptadec-5-enyl, (Z)-heptadec-8-enyl, (8Z,11Z)- heptadeca-8,11-dienyl or the like.

[0113] X<com:Sup>1< / com:Sup> is preferably methyl, hydroxypropyl or hydroxyethyl, more preferably methyl.

[0114] 4 4 . In formula (II), <com:Math><semantics>R4<annotation encoding="application / x-tex">R^4< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>R6<annotation encoding="application / x-tex">R^6< / annotation>< / semantics>< / com:Math> are preferably the same linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl, more preferably the same linear or branched C8- C24 alkyl or C8-C24 alkenyl, further preferably the same linear or branched C15-C20 alkenyl or the same linear or branched C9-C18 alkyl, most preferably the same linear C15-C20 alkenyl or the same linear C9-C18 alkyl.

[0115] L4 to L6 are the same or different and are each absent, or <com:Math><semantics>−Z4−(CY8Y9)p4<annotation encoding="application / x-tex">-Z^4 - (CY^8Y^9)_{p4}< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−Z5−(CY10Y11)p5−Z6−(CY12Y13)p6<annotation encoding="application / x-tex">-Z^5 - (CY^{10}Y^{11})_{p5} - Z^6 - (CY^{12}Y^{13})_{p6}< / annotation>< / semantics>< / com:Math>, preferably <com:Math><semantics>−Z4−(CY8Y9)p4<annotation encoding="application / x-tex">-Z^4 - (CY^8Y^9)_{p4}< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−Z5−(CY10Y11)p5−Z6−(CY12Y13)p6<annotation encoding="application / x-tex">-Z^5 - (CY^{10}Y^{11})_{p5} - Z^6 - (CY^{12}Y^{13})_{p6}< / annotation>< / semantics>< / com:Math>, more preferably <com:Math><semantics>−Z4−(CY8Y9)p4−<annotation encoding="application / x-tex">-Z^4-(CY^8Y^9)_{p4}-< / annotation>< / semantics>< / com:Math>. <com:Math><semantics>Y8<annotation encoding="application / x-tex">Y^8< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y13<annotation encoding="application / x-tex">Y^{13}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl, preferably a hydrogen atom. Z4 to <com:Math><semantics>Z6<annotation encoding="application / x-tex">Z^6< / annotation>< / semantics>< / com:Math> are the same or different and are each -O-, -NY<com:Sup>14A< / com:Sup>-, [Image disponible dans le document PDF, Image available in the PDF document] preferably <com:Math><semantics>−0−<annotation encoding="application / x-tex">-0-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−NY14B−<annotation encoding="application / x-tex">-CO-NY^{14B}-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−NY14C−CO−<annotation encoding="application / x-tex">-NY^{14C}-CO-< / annotation>< / semantics>< / com:Math>. Y<com:Sup>27A< / com:Sup> to Y<com:Sup>27D< / com:Sup> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl, preferably a hydrogen atom or methyl. p4 is an integer from 0 to 5. <com:Math><semantics>p5<annotation encoding="application / x-tex">p^5< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5. <com:Math><semantics>p6<annotation encoding="application / x-tex">p^6< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5. All of <com:Math><semantics>p4<annotation encoding="application / x-tex">p^4< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>p6<annotation encoding="application / x-tex">p^6< / annotation>< / semantics>< / com:Math> are preferably 1 or 2.

[0116] L4 to L6 are preferably the same or different and are [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] 4 • or <com:Math><semantics>−0−CO−(CY10Y11)p5−Z6−(CY12Y13)p6<annotation encoding="application / x-tex">-0-CO-(CY^{10}Y^{11})_{p5}-Z^6-(CY^{12}Y^{13})_{p6}< / annotation>< / semantics>< / com:Math>, more preferably are the same or different and are each <com:Math><semantics>−CO−O−(CY8Y9)p4−<annotation encoding="application / x-tex">-CO-O-(CY^8Y^9)_{p4}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>(CY8Y9)p4<annotation encoding="application / x-tex">(CY^{8}Y^{9})_{p4}< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−O−CO−(CY10Y11)p5−O−(CY12Y13)p6<annotation encoding="application / x-tex">-O-CO-(CY^{10}Y^{11})_{p5}-O-(CY^{12}Y^{13})_{p6}< / annotation>< / semantics>< / com:Math>, further preferably are the same and <com:Math><semantics>−CO−O−CH2−<annotation encoding="application / x-tex">-CO-O-CH_2-< / annotation>< / semantics>< / com:Math>.

[0117] In formula (II), preferably, one or more of <com:Math><semantics>L4<annotation encoding="application / x-tex">L_4< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>L6<annotation encoding="application / x-tex">L_6< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−CO−O−(CY8Y9)p4<annotation encoding="application / x-tex">-CO-O-(CY^8Y^9)_{p4}< / annotation>< / semantics>< / com:Math>, - <com:Math><semantics>O−CO−(CY8Y9)p4−<annotation encoding="application / x-tex">O-CO-(CY^{8}Y^{9})_{p4}-< / annotation>< / semantics>< / com:Math>, or <com:Math><semantics>−O−CO−(CY10Y11)p5−O−(CY12Y13)p6−<annotation encoding="application / x-tex">-O-CO-(CY^{10}Y^{11})_{p5}-O-(CY^{12}Y^{13})_{p6}-< / annotation>< / semantics>< / com:Math>, and <com:Math><semantics>R4<annotation encoding="application / x-tex">R^{4}< / annotation>< / semantics>< / com:Math> to R<com:Sup>6< / com:Sup> are the same linear C15-C20 alkenyl or the same linear C9-C18 alkyl.

[0118] When at least one of <com:Math><semantics>L4<annotation encoding="application / x-tex">L^4< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>L6<annotation encoding="application / x-tex">L^6< / annotation>< / semantics>< / com:Math> is absent, or -O- <com:Math><semantics>(CY8Y9)p4<annotation encoding="application / x-tex">(CY^{8}Y^{9})_{p4}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−(CY8Y9)p4<annotation encoding="application / x-tex">-O-CO-(CY^{8}Y^{9})_{p4}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY14C−CO−(CY8Y9)p4<annotation encoding="application / x-tex">-NY^{14C}-CO-(CY^{8}Y^{9})_{p4}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY14D−CO−<annotation encoding="application / x-tex">-NY^{14D}-CO-< / annotation>< / semantics>< / com:Math> O- or <com:Math><semantics>−O−CO−(CY10Y11)p5−(CY12Y13)p6−<annotation encoding="application / x-tex">-O-CO-(CY^{10}Y^{11})_{p5}-(CY^{12}Y^{13})_{p6}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>R7<annotation encoding="application / x-tex">R^7< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>R9<annotation encoding="application / x-tex">R^9< / annotation>< / semantics>< / com:Math> bonded to the carbon atom adjacent to <com:Math><semantics>L7<annotation encoding="application / x-tex">L^7< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−(CY8Y9)p4<annotation encoding="application / x-tex">-O-(CY^8Y^9)_{p4}< / annotation>< / semantics>< / com:Math>-, <com:Math><semantics>−O−CO−(CY8Y9)p4<annotation encoding="application / x-tex">-O-CO-(CY^8Y^9)_{p4}< / annotation>< / semantics>< / com:Math>-, <com:Math><semantics>−NY14C−CO−(CY8Y9)p4−<annotation encoding="application / x-tex">-NY^{14C}-CO-(CY^8Y^9)_{p4}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY14D−CO−O−<annotation encoding="application / x-tex">-NY^{14D}-CO-O-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−O−CO−(CY10Y11)p5−Z6−<annotation encoding="application / x-tex">-O-CO-(CY^{10}Y^{11})_{p5}-Z^6-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>(CY12Y13)p6<annotation encoding="application / x-tex">(CY^{12}Y^{13})_{p6}< / annotation>< / semantics>< / com:Math> are the same or different and are each preferably octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, icosyl, docosyl, tetracosyl, (Z)-tetradec-9- enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-hexadec-9-enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-octadec-6-enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>- octadec-9-enyl, (E)-octadec-9-enyl, (Z)-octadec-11-enyl, (9Z,12Z)-octadeca-9,12-dienyl, (9Z,12Z,15Z)-octadeca- 9,12,15-trienyl, (Z)-icos-11-enyl, (11Z,14Z)-icosa-11,14- dienyl, 3,7,11-trimethyldodeca-2,6,10-trienyl, 3,7,11,15- tetramethylhexadec-2-enyl or the like, more preferably dodecyl, tetradecyl, hexadecyl, (Z)-hexadec-9-enyl, (Z)- . 4 octadec-6-enyl, (Z)-octadec-9-enyl, (9Z,12Z)-octadeca- 9,12-dienyl or the like.

[0119] When at least one of <com:Math><semantics>L4<annotation encoding="application / x-tex">L^4< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>L6<annotation encoding="application / x-tex">L^6< / annotation>< / semantics>< / com:Math> is <com:Math><semantics>−CO−O−(CY8Y9)p4<annotation encoding="application / x-tex">-CO-O-(CY^8Y^9)_{p4}< / annotation>< / semantics>< / com:Math> or - <com:Math><semantics>CO−NY14B−(CY8Y9)p4−<annotation encoding="application / x-tex">CO-NY^{14B}-(CY^8Y^9)_{p4}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>R4<annotation encoding="application / x-tex">R^4< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>R6<annotation encoding="application / x-tex">R^6< / annotation>< / semantics>< / com:Math> bonded to <com:Math><semantics>−CO−O−(CY8Y9)p4−<annotation encoding="application / x-tex">-CO-O-(CY^8Y^9)_{p4}-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−<annotation encoding="application / x-tex">-< / annotation>< / semantics>< / com:Math> CO-NY<com:Sup>14B< / com:Sup>-(CY<com:Sup>8< / com:Sup>Y<com:Sup>9< / com:Sup>)<com:Sub>p4< / com:Sub>- are the same or different and are each preferably nonyl, undecyl, tridecyl, pentadecyl, heptadecyl, nonadecyl, henicosyl, tricosyl, (Z)-tridec-8- enyl, (Z)-pentadec-8-enyl, (Z)-heptadec-5-enyl, (Z)- heptadec-8-enyl, (E)-heptadec-8-enyl, (Z)-heptadec-10- enyl, (8Z,11Z)-heptadeca-8,11-dienyl, (8Z,11Z,14Z)- octadeca-8,11,14-trienyl, (Z)-nonadec-10-enyl, (10Z,13Z)- nonadeca-10,13-dienyl, (11Z,14Z)-icosa-11,14-dienyl, 2,6,10-trimethylundeca-1,5,9-trienyl, 2,6,10,14- tetramethylpentadec-1-enyl or the like, more preferably undecyl, tridecyl, pentadecyl, (Z)-pentadec-8-enyl, (Z)- heptadec-5-enyl, (Z)-heptadec-8-enyl, (8Z,11Z)-heptadeca- 8,11-dienyl or the like.

[0120] <com:Math><semantics>L7<annotation encoding="application / x-tex">L^{7}< / annotation>< / semantics>< / com:Math> is preferably absent, or <com:Math><semantics>−(CY15Y16)p7<annotation encoding="application / x-tex">-(CY^{15}Y^{16})_{p7}< / annotation>< / semantics>< / com:Math>-, <com:Math><semantics>−(CY17Y18)p8<annotation encoding="application / x-tex">-(CY^{17}Y^{18})_{p8}< / annotation>< / semantics>< / com:Math>- O-CO-<com:Math><semantics>(CY19Y20)p9<annotation encoding="application / x-tex">(CY^{19}Y^{20})_{p9}< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−(CY17Y18)p8<annotation encoding="application / x-tex">-(CY^{17}Y^{18})_{p8}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>NY27C<annotation encoding="application / x-tex">NY^{27C}< / annotation>< / semantics>< / com:Math>-CO-<com:Math><semantics>(CY19Y20)p9<annotation encoding="application / x-tex">(CY^{19}Y^{20})_{p9}< / annotation>< / semantics>< / com:Math>, more preferably absent, or <com:Math><semantics>−(CY15Y16)p7<annotation encoding="application / x-tex">-(CY^{15}Y^{16})_{p7}< / annotation>< / semantics>< / com:Math>. In this case, <com:Math><semantics>B1<annotation encoding="application / x-tex">B^1< / annotation>< / semantics>< / com:Math> is preferably [Image disponible dans le document PDF, Image available in the PDF document] more preferably <com:Math><semantics>−N+(CH3)3<annotation encoding="application / x-tex">-N^+(CH_3)_3< / annotation>< / semantics>< / com:Math>.

[0121] • 4 • When <com:Math><semantics>L7<annotation encoding="application / x-tex">L^7< / annotation>< / semantics>< / com:Math> is <com:Math><semantics>−(CY15Y16)p7<annotation encoding="application / x-tex">-(CY^{15}Y^{16})_{p7}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>p7<annotation encoding="application / x-tex">p^7< / annotation>< / semantics>< / com:Math> is preferably 1 to 3, more preferably 1 or 2, further preferably 1. Each of Y15 and Y<com:Sup>16< / com:Sup> is preferably a hydrogen atom. B<com:Sup>1< / com:Sup> is preferably - <com:Math><semantics>N+<annotation encoding="application / x-tex">N^+< / annotation>< / semantics>< / com:Math> (CH<com:Sub>3< / com:Sub>)<com:Sub>3< / com:Sub>.

[0122] When <com:Math><semantics>L7<annotation encoding="application / x-tex">L^7< / annotation>< / semantics>< / com:Math> is <com:Math><semantics>−(CY17Y18)p8−O−CO−(CY19Y20)p9−<annotation encoding="application / x-tex">-(CY^{17}Y^{18})_{p8}-O-CO-(CY^{19}Y^{20})_{p9}-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−(CY17Y18)p8−<annotation encoding="application / x-tex">-(CY^{17}Y^{18})_{p8}-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>NY27C<annotation encoding="application / x-tex">NY^{27C}< / annotation>< / semantics>< / com:Math>-CO-(CY<com:Sup>19< / com:Sup>Y<com:Sup>20< / com:Sup>)<com:Sub>p9< / com:Sub>-, preferably, p<com:Sup>8< / com:Sup> is 0 to 3, and p<com:Sup>9< / com:Sup> is 1 to 3. More preferably, <com:Math><semantics>p8<annotation encoding="application / x-tex">p^8< / annotation>< / semantics>< / com:Math> is 0 to 1, and <com:Math><semantics>p9<annotation encoding="application / x-tex">p^9< / annotation>< / semantics>< / com:Math> is 1 to 3. Preferably, each of <com:Math><semantics>Y17<annotation encoding="application / x-tex">Y^{17}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y20<annotation encoding="application / x-tex">Y^{20}< / annotation>< / semantics>< / com:Math> is a hydrogen atom, and <com:Math><semantics>Y27C<annotation encoding="application / x-tex">Y^{27C}< / annotation>< / semantics>< / com:Math> is a hydrogen atom or methyl. <com:Math><semantics>B1<annotation encoding="application / x-tex">B^1< / annotation>< / semantics>< / com:Math> is preferably <com:Math><semantics>−N†(CH3)3<annotation encoding="application / x-tex">-N^{\dagger}(CH_3)_3< / annotation>< / semantics>< / com:Math>.

[0123] Preferably, <com:Math><semantics>X2<annotation encoding="application / x-tex">X^2< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X3<annotation encoding="application / x-tex">X^3< / annotation>< / semantics>< / com:Math> are the same or different and are each methyl or ethyl, or together form an optionally substituted C4-C6 hetero ring with the adjacent nitrogen atom. More preferably, <com:Math><semantics>X2<annotation encoding="application / x-tex">X^2< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X3<annotation encoding="application / x-tex">X^3< / annotation>< / semantics>< / com:Math> are the same and methyl, or together form pyrrolidine or piperidine with the adjacent nitrogen atom. Further preferably, X2 and X3 are the same and methyl.

[0124] X4 is preferably methyl, ethyl, hydroxypropyl, hydroxyethyl or the like, more preferably methyl. Preferably, <com:Math><semantics>X2<annotation encoding="application / x-tex">X^2< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X3<annotation encoding="application / x-tex">X^3< / annotation>< / semantics>< / com:Math> are the same or different and are each methyl or ethyl, and <com:Math><semantics>X4<annotation encoding="application / x-tex">X^4< / annotation>< / semantics>< / com:Math> is methyl, ethyl, hydroxypropyl, hydroxyethyl or the like. Each of <com:Math><semantics>X2<annotation encoding="application / x-tex">X^2< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>X4<annotation encoding="application / x-tex">X^4< / annotation>< / semantics>< / com:Math> is more preferably methyl.

[0125] 3 . In another preferred mode of the present invention, <com:Math><semantics>B1<annotation encoding="application / x-tex">B^1< / annotation>< / semantics>< / com:Math> is [Image disponible dans le document PDF, Image available in the PDF document] and <com:Math><semantics>L7<annotation encoding="application / x-tex">L^7< / annotation>< / semantics>< / com:Math> is absent, or <com:Math><semantics>−(CY15Y16)p7<annotation encoding="application / x-tex">-(CY^{15}Y^{16})_{p7}< / annotation>< / semantics>< / com:Math>-, <com:Math><semantics>−(CY17Y18)p8<annotation encoding="application / x-tex">-(CY^{17}Y^{18})_{p8}< / annotation>< / semantics>< / com:Math>-O-CO- [Image disponible dans le document PDF, Image available in the PDF document] case, more preferably, B1 is [Image disponible dans le document PDF, Image available in the PDF document] and <com:Math><semantics>L7<annotation encoding="application / x-tex">L^7< / annotation>< / semantics>< / com:Math> is absent, or <com:Math><semantics>−NH−CO−(CH2)p9−<annotation encoding="application / x-tex">-NH-CO-(CH_2)_{p9}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−(CH2)p9−<annotation encoding="application / x-tex">-O-CO-(CH_2)_{p9}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CH2−<annotation encoding="application / x-tex">-CH_2-< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document]

[0126] In formula (III), R<com:Sup>7< / com:Sup> is preferably linear or branched C8-C24 alkyl or C8-C24 alkenyl, more preferably linear or branched C15-C20 alkenyl or linear or branched C9-C18 alkyl, most preferably the same linear C15-C20 alkenyl or the same linear C9-C18 alkyl. R8 and R9 are preferably the same linear or branched C8-C24 alkyl, C8- C24 alkenyl or C8-C24 alkynyl, more preferably the same linear or branched C15-C20 alkenyl or linear or branched C9-C18 alkyl, most preferably the same linear C15-C20 alkenyl or linear C9-C18 alkyl.

[0127] A 4 [Image disponible dans le document PDF, Image available in the PDF document] <com:Math><semantics>Z14<annotation encoding="application / x-tex">Z^{14}< / annotation>< / semantics>< / com:Math>-(CY<com:Sup>43< / com:Sup>Y<com:Sup>44< / com:Sup>)<com:Sub>p20< / com:Sub>-, preferably absent or <com:Math><semantics>−Z12<annotation encoding="application / x-tex">-Z^{12}< / annotation>< / semantics>< / com:Math>-(CY<com:Sup>39< / com:Sup>Y<com:Sup>40< / com:Sup>)<com:Sub>p18< / com:Sub>-. L<com:Sup>9< / com:Sup> and L10 are the same or different and are each absent, or [Image disponible dans le document PDF, Image available in the PDF document] preferably are the same or different and are each absent or <com:Math><semantics>−Z12<annotation encoding="application / x-tex">-Z^{12}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>(CY39Y40)p18<annotation encoding="application / x-tex">(CY^{39}Y^{40})_{p18}< / annotation>< / semantics>< / com:Math>-. <com:Math><semantics>Y39<annotation encoding="application / x-tex">Y^{39}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y44<annotation encoding="application / x-tex">Y^{44}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl, preferably a hydrogen atom. <com:Math><semantics>Z12<annotation encoding="application / x-tex">Z^{12}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Z14<annotation encoding="application / x-tex">Z^{14}< / annotation>< / semantics>< / com:Math> are the same or different and are each -O-, -NY45A-, -CO-O-, - [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] <com:Math><semantics>Y45A<annotation encoding="application / x-tex">Y^{45A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y45D<annotation encoding="application / x-tex">Y^{45D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl, preferably a hydrogen atom or methyl. p18 is an integer from 0 to 5, preferably 0 or 1. p19 is an integer from 1 to 5, preferably 1 or 2. p<com:Sup>20< / com:Sup> is an integer from 0 to 5, preferably 0 or 1.

[0128] [Image disponible dans le document PDF, Image available in the PDF document] -O-CO-<com:Math><semantics>(CY39Y40)p18<annotation encoding="application / x-tex">(CY^{39}Y^{40})_{p18}< / annotation>< / semantics>< / com:Math>-, or two or more of L<com:Sup>8< / com:Sup> to L<com:Sup>10< / com:Sup> are the same or different and are each <com:Math><semantics>−CO−O−(CY39Y40)p18<annotation encoding="application / x-tex">-CO-O-(CY^{39}Y^{40})_{p18}< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>(CY39Y40)p18<annotation encoding="application / x-tex">(CY^{39}Y^{40})_{p18}< / annotation>< / semantics>< / com:Math>-, and each of <com:Math><semantics>R7<annotation encoding="application / x-tex">R^7< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>R9<annotation encoding="application / x-tex">R^9< / annotation>< / semantics>< / com:Math> is linear C15-C20 alkenyl or C9-C18 alkyl. R8 and R9 are preferably the same.

[0129] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] 4 • 4 A [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] - [Image disponible dans le document PDF, Image available in the PDF document] L<com:Sup>9< / com:Sup> and L<com:Sup>10< / com:Sup> are preferably the same or different and [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] preferably are the same or different and are each absent, [Image disponible dans le document PDF, Image available in the PDF document] preferably are the same or different and are each absent or <com:Math><semantics>−CO−O−(CH2)p18−<annotation encoding="application / x-tex">-CO-O-(CH_2)_{p18}-< / annotation>< / semantics>< / com:Math>, most preferably are the same and [Image disponible dans le document PDF, Image available in the PDF document]

[0130] In formula (III), preferably, one of <com:Math><semantics>L8<annotation encoding="application / x-tex">L^8< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>L10<annotation encoding="application / x-tex">L^{10}< / annotation>< / semantics>< / com:Math> is [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] - - of <com:Math><semantics>L8<annotation encoding="application / x-tex">L^8< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>L10<annotation encoding="application / x-tex">L^{10}< / annotation>< / semantics>< / com:Math> are the same or different and are each absent, [Image disponible dans le document PDF, Image available in the PDF document] - [Image disponible dans le document PDF, Image available in the PDF document] ... is preferably linear C15-C20 alkenyl or C9-C18 alkyl. R8 and R<com:Sup>9< / com:Sup> are preferably the same.

[0131] When at least one of <com:Math><semantics>L8<annotation encoding="application / x-tex">L^8< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>L10<annotation encoding="application / x-tex">L^{10}< / annotation>< / semantics>< / com:Math> is absent, or -O- [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] . 4 4 each preferably octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, icosyl, docosyl, tetracosyl, (Z)- tetradec-9-enyl, (Z)-hexadec-9-enyl, (Z)-octadec-6-enyl, (Z)-octadec-9-enyl, (E)-octadec-9-enyl, (Z)-octadec-11- enyl, (9Z,12Z)-octadeca-9,12-dienyl, (9Z,12Z,15Z)- octadeca-9,12,15-trienyl, (Z)-icos-11-enyl, (11Z,14Z)- icosa-11,14-dienyl, 3,7,11-trimethyldodeca-2,6,10-trienyl, 3,7,11,15-tetramethylhexadec-2-enyl or the like, more preferably dodecyl, tetradecyl, hexadecyl, (Z)-hexadec-9- enyl, (Z)-octadec-6-enyl, (Z)-octadec-9-enyl, (9Z,12Z)- octadeca-9,12-dienyl or the like.

[0132] When at least one of <com:Math><semantics>L8<annotation encoding="application / x-tex">L^8< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>L10<annotation encoding="application / x-tex">L^{10}< / annotation>< / semantics>< / com:Math> is <com:Math><semantics>−CO−O−(CY39Y40)D18−<annotation encoding="application / x-tex">-CO-O-(CY^{39}Y^{40})_{D18}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−NY45B−(CY39Y40)p18−<annotation encoding="application / x-tex">-CO-NY^{45B}-(CY^{39}Y^{40})_{p18}-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−CO−(CY39Y40)p18<annotation encoding="application / x-tex">-CO-(CY^{39}Y^{40})_{p18}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>R7<annotation encoding="application / x-tex">R^7< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>R9<annotation encoding="application / x-tex">R^9< / annotation>< / semantics>< / com:Math> bonded to <com:Math><semantics>−CO−O−(CY39Y40)p18−<annotation encoding="application / x-tex">-CO-O-(CY^{39}Y^{40})_{p18}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−NY458−(CY39Y40)p18−<annotation encoding="application / x-tex">-CO-NY^{458}-(CY^{39}Y^{40})_{p18}-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−CO−(CY39Y40)p18<annotation encoding="application / x-tex">-CO-(CY^{39}Y^{40})_{p18}< / annotation>< / semantics>< / com:Math> are the same or different and are each preferably nonyl, undecyl, tridecyl, pentadecyl, heptadecyl, nonadecyl, henicosyl, tricosyl, (Z)-tridec-8-enyl, (Z)-pentadec-8- enyl, (Z)-heptadec-5-enyl, (Z)-heptadec-8-enyl, (E)- heptadec-8-enyl, (Z)-heptadec-10-enyl, (8Z,11Z)- heptadeca-8,11-dienyl, (8Z,11Z,14Z)-octadeca-8,11,14- trienyl, (Z)-nonadec-10-enyl, (10Z,13Z)-nonadeca-10,13- dienyl, (11Z,14Z)-icosa-11,14-dienyl, 2,6,10- trimethylundeca-1,5,9-trienyl or 2,6,10,14- tetramethylpentadec-1-enyl, more preferably undecyl, tridecyl, pentadecyl, (Z)-pentadec-8-enyl, (Z)-heptadec- • • [Image disponible dans le document PDF, Image available in the PDF document] dienyl or the like.

[0133] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] <com:Math><semantics>(CY50Y51)p23<annotation encoding="application / x-tex">(CY^{50}Y^{51})_{p23}< / annotation>< / semantics>< / com:Math>-. <com:Math><semantics>Y46<annotation encoding="application / x-tex">Y^{46}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y57<annotation encoding="application / x-tex">Y^{57}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl, preferably a hydrogen atom. <com:Math><semantics>Z15<annotation encoding="application / x-tex">Z^{15}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Z17<annotation encoding="application / x-tex">Z^{17}< / annotation>< / semantics>< / com:Math> are the same or different and are each -O-, <com:Math><semantics>−NY58A<annotation encoding="application / x-tex">-NY^{58A}< / annotation>< / semantics>< / com:Math>-, -CO-O-, -O- [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] more preferably -O-CO- or -NY<com:Sup>58C< / com:Sup>-CO-. p<com:Sup>21< / com:Sup> is an integer from 1 to 5, preferably 1 to 3. <com:Math><semantics>p22<annotation encoding="application / x-tex">p^{22}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5, preferably 0 to 3. <com:Math><semantics>p23<annotation encoding="application / x-tex">p^{23}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5, preferably 1 or 2.

[0134] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] <com:Math><semantics>(CY50Y51)p23<annotation encoding="application / x-tex">(CY^{50}Y^{51})_{p23}< / annotation>< / semantics>< / com:Math>, more preferably absent or <com:Math><semantics>−(CY46Y47)p21<annotation encoding="application / x-tex">-(CY^{46}Y^{47})_{p21}< / annotation>< / semantics>< / com:Math>-, further preferably absent or <com:Math><semantics>−(CH2)p2−.<annotation encoding="application / x-tex">-(CH_2)_{p2}-.< / annotation>< / semantics>< / com:Math>

[0135] <com:Math><semantics>L12<annotation encoding="application / x-tex">L^{12}< / annotation>< / semantics>< / com:Math> is preferably absent or <com:Math><semantics>−(CY59Y60)p27<annotation encoding="application / x-tex">-(CY^{59}Y^{60})_{p27}< / annotation>< / semantics>< / com:Math>, more preferably absent or <com:Math><semantics>−(CH2)p27<annotation encoding="application / x-tex">-(CH_2)_{p27}< / annotation>< / semantics>< / com:Math>-, further preferably absent [Image disponible dans le document PDF, Image available in the PDF document]

[0136] • . <com:Math><semantics>J1<annotation encoding="application / x-tex">J^1< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>J2<annotation encoding="application / x-tex">J^2< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>CY72<annotation encoding="application / x-tex">CY^{72}< / annotation>< / semantics>< / com:Math> or N. Preferably, <com:Math><semantics>J1<annotation encoding="application / x-tex">J^1< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>J2<annotation encoding="application / x-tex">J^2< / annotation>< / semantics>< / com:Math> are the same or different and are each CH, C(OH) or N.

[0137] When <com:Math><semantics>L11<annotation encoding="application / x-tex">L^{11}< / annotation>< / semantics>< / com:Math> is absent, <com:Math><semantics>J1<annotation encoding="application / x-tex">J^{1}< / annotation>< / semantics>< / com:Math> is preferably CH.

[0138] In another preferred mode of the present invention, <com:Math><semantics>L9<annotation encoding="application / x-tex">L^9< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L10<annotation encoding="application / x-tex">L^{10}< / annotation>< / semantics>< / com:Math> are absent; <com:Math><semantics>L12<annotation encoding="application / x-tex">L^{12}< / annotation>< / semantics>< / com:Math> is <com:Math><semantics>−CO−(CH2)p29−<annotation encoding="application / x-tex">-CO-(CH_2)_{p29}-< / annotation>< / semantics>< / com:Math>; <com:Math><semantics>J1<annotation encoding="application / x-tex">J^1< / annotation>< / semantics>< / com:Math> is CH; and <com:Math><semantics>J2<annotation encoding="application / x-tex">J^2< / annotation>< / semantics>< / com:Math> is N. In this case, preferably, <com:Math><semantics>L8<annotation encoding="application / x-tex">L^8< / annotation>< / semantics>< / com:Math> is -CO-NY<com:Sup>45B< / com:Sup>- <com:Math><semantics>(CH2)p18<annotation encoding="application / x-tex">(CH_2)_{p18}< / annotation>< / semantics>< / com:Math>-, and <com:Math><semantics>L11<annotation encoding="application / x-tex">L^{11}< / annotation>< / semantics>< / com:Math> is absent or <com:Math><semantics>−(CH2)p21<annotation encoding="application / x-tex">-(CH_2)_{p21}< / annotation>< / semantics>< / com:Math>-.

[0139] In an alternative preferred mode of the present invention, <com:Math><semantics>L9<annotation encoding="application / x-tex">L^9< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L10<annotation encoding="application / x-tex">L^{10}< / annotation>< / semantics>< / com:Math> are absent; <com:Math><semantics>L12<annotation encoding="application / x-tex">L^{12}< / annotation>< / semantics>< / com:Math> is <com:Math><semantics>−0−CO−(CH2)p29−<annotation encoding="application / x-tex">-0-CO-(CH_2)_{p29}-< / annotation>< / semantics>< / com:Math>; and each of <com:Math><semantics>J1<annotation encoding="application / x-tex">J^1< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>J2<annotation encoding="application / x-tex">J^2< / annotation>< / semantics>< / com:Math> is CH. In this case, preferably, <com:Math><semantics>L8<annotation encoding="application / x-tex">L^8< / annotation>< / semantics>< / com:Math> is <com:Math><semantics>−0−CO−(CH2)p18−<annotation encoding="application / x-tex">-0-CO-(CH_2)_{p18}-< / annotation>< / semantics>< / com:Math>, and <com:Math><semantics>L11<annotation encoding="application / x-tex">L^{11}< / annotation>< / semantics>< / com:Math> is absent.

[0140] B<com:Sup>2< / com:Sup> is preferably [Image disponible dans le document PDF, Image available in the PDF document] more preferably <com:Math><semantics>−N+(CH3)3<annotation encoding="application / x-tex">-N^+(CH_3)_3< / annotation>< / semantics>< / com:Math>.

[0141] <com:Math><semantics>X8<annotation encoding="application / x-tex">X^8< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>X10<annotation encoding="application / x-tex">X^{10}< / annotation>< / semantics>< / com:Math> are as defined above in <com:Math><semantics>X2<annotation encoding="application / x-tex">X^2< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>X4<annotation encoding="application / x-tex">X^4< / annotation>< / semantics>< / com:Math>, respectively.

[0142] In formula (IV), R<com:Sup>10< / com:Sup> is preferably linear or branched C8-C24 alkyl or C8-C24 alkenyl, more preferably linear or branched C15-C20 alkenyl or linear or branched C9-C18 . . alkyl, most preferably linear C15-C20 alkenyl or linear <com:Math><semantics>C9−C18<annotation encoding="application / x-tex">C9-C18< / annotation>< / semantics>< / com:Math> alkyl. <com:Math><semantics>R11<annotation encoding="application / x-tex">R^{11}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R12<annotation encoding="application / x-tex">R^{12}< / annotation>< / semantics>< / com:Math> are preferably the same linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl, more preferably the same linear or branched C15- C20 alkenyl or linear or branched C9-C18 alkyl, most preferably the same linear C15-C20 alkenyl or linear C9- C18 alkyl.

[0143] <com:Math><semantics>L13<annotation encoding="application / x-tex">L^{13}< / annotation>< / semantics>< / com:Math> is absent, or <com:Math><semantics>−Z23<annotation encoding="application / x-tex">-Z^{23}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>(CY84Y85)p38<annotation encoding="application / x-tex">(CY^{84}Y^{85})_{p38}< / annotation>< / semantics>< / com:Math>- or <com:Math><semantics>−Z24<annotation encoding="application / x-tex">-Z^{24}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>(CY86Y87)p39<annotation encoding="application / x-tex">(CY^{86}Y^{87})_{p39}< / annotation>< / semantics>< / com:Math>- <com:Math><semantics>Z25<annotation encoding="application / x-tex">Z^{25}< / annotation>< / semantics>< / com:Math>-(CY<com:Sup>88< / com:Sup>Y<com:Sup>89< / com:Sup>)<com:Sub>p40< / com:Sub>-, preferably absent, or <com:Math><semantics>−Z23<annotation encoding="application / x-tex">-Z^{23}< / annotation>< / semantics>< / com:Math>-(CY<com:Sup>84< / com:Sup>Y<com:Sup>85< / com:Sup>)<com:Sub>p38< / com:Sub>-. Y84 to Y89 are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl, preferably a hydrogen atom. <com:Math><semantics>𝒁23<annotation encoding="application / x-tex">\mathbf{Z}^{23}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>𝒁25<annotation encoding="application / x-tex">\mathbf{Z}^{25}< / annotation>< / semantics>< / com:Math> are the same or different and are each -O-, -NY90A-, -CO-O-, -O-CO-, -CO- <com:Math><semantics>NY90B<annotation encoding="application / x-tex">NY^{90B}< / annotation>< / semantics>< / com:Math>-, <com:Math><semantics>−NY90C<annotation encoding="application / x-tex">-NY^{90C}< / annotation>< / semantics>< / com:Math>-CO- or <com:Math><semantics>−NY90D<annotation encoding="application / x-tex">-NY^{90D}< / annotation>< / semantics>< / com:Math>-CO-O-, preferably -CO-O-, -O- CO-, <com:Math><semantics>−CO−NY90B<annotation encoding="application / x-tex">-CO-NY^{90B}< / annotation>< / semantics>< / com:Math>- or <com:Math><semantics>−NY90C−CO−<annotation encoding="application / x-tex">-NY^{90C}-CO-< / annotation>< / semantics>< / com:Math>, more preferably <com:Math><semantics>−CO−NY90B−<annotation encoding="application / x-tex">-CO-NY^{90B}-< / annotation>< / semantics>< / com:Math>. <com:Math><semantics>Y90A<annotation encoding="application / x-tex">Y^{90A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y90D<annotation encoding="application / x-tex">Y^{90D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl, preferably a hydrogen atom or methyl. p<com:Sup>38< / com:Sup> to p<com:Sup>40< / com:Sup> are the same or different and are each an integer from 1 to 5, preferably 1 or 2.

[0144] <com:Math><semantics>L13<annotation encoding="application / x-tex">L^{13}< / annotation>< / semantics>< / com:Math> is preferably absent, or -CO-O-(CY<com:Sup>84< / com:Sup>Y<com:Sup>85< / com:Sup>)<com:Sub>p38< / com:Sub>-, -O- <com:Math><semantics>CO−(CY84Y85)p38−<annotation encoding="application / x-tex">CO-(CY^{84}Y^{85})_{p38}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−NY908−(CY84Y85)p38−<annotation encoding="application / x-tex">-CO-NY^{908}-(CY^{84}Y^{85})_{p38}-< / annotation>< / semantics>< / com:Math>, or <com:Math><semantics>−NY90C−CO−<annotation encoding="application / x-tex">-NY^{90C}-CO-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>(CY84Y85)p38<annotation encoding="application / x-tex">(CY^{84}Y^{85})_{p38}< / annotation>< / semantics>< / com:Math>, more preferably absent, or <com:Math><semantics>−CO−O−(CH2)p38<annotation encoding="application / x-tex">-CO-O-(CH_2)_{p38}< / annotation>< / semantics>< / com:Math>, - O-CO-<com:Math><semantics>(CH2)p38<annotation encoding="application / x-tex">(CH_2)_{p38}< / annotation>< / semantics>< / com:Math>- or -CO-NCH<com:Sub>3< / com:Sub>-<com:Math><semantics>(CH2)p38<annotation encoding="application / x-tex">(CH_2)_{p38}< / annotation>< / semantics>< / com:Math>-, further preferably absent, or <com:Math><semantics>−CO−NCH3−(CH2)p38−.<annotation encoding="application / x-tex">-CO-NCH_3-(CH_2)_{p38}-.< / annotation>< / semantics>< / com:Math> .

[0145] L<com:Sup>14< / com:Sup> and L<com:Sup>15< / com:Sup> are the same or different and are each absent, or <com:Math><semantics>−Z26<annotation encoding="application / x-tex">-Z^{26}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>(CY91Y92)p41<annotation encoding="application / x-tex">(CY^{91}Y^{92})_{p41}< / annotation>< / semantics>< / com:Math>- or <com:Math><semantics>−Z27<annotation encoding="application / x-tex">-Z^{27}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>(CY93Y94)p42<annotation encoding="application / x-tex">(CY^{93}Y^{94})_{p42}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>Z28<annotation encoding="application / x-tex">Z^{28}< / annotation>< / semantics>< / com:Math>- <com:Math><semantics>(CY95Y96)p43<annotation encoding="application / x-tex">(CY^{95}Y^{96})_{p43}< / annotation>< / semantics>< / com:Math>, preferably absent, or <com:Math><semantics>−Z26<annotation encoding="application / x-tex">-Z^{26}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>(CY91Y92)p41<annotation encoding="application / x-tex">(CY^{91}Y^{92})_{p41}< / annotation>< / semantics>< / com:Math>-. <com:Math><semantics>Y91<annotation encoding="application / x-tex">Y^{91}< / annotation>< / semantics>< / com:Math> to Y96 are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl, preferably a hydrogen atom. <com:Math><semantics>Z26<annotation encoding="application / x-tex">Z^{26}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Z28<annotation encoding="application / x-tex">Z^{28}< / annotation>< / semantics>< / com:Math> are the same or different and [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] <com:Math><semantics>NY97B<annotation encoding="application / x-tex">NY^{97B}< / annotation>< / semantics>< / com:Math>-, <com:Math><semantics>−NY97C<annotation encoding="application / x-tex">-NY^{97C}< / annotation>< / semantics>< / com:Math>-CO-, or -CO-. <com:Math><semantics>Y97A<annotation encoding="application / x-tex">Y^{97A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y97D<annotation encoding="application / x-tex">Y^{97D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl, preferably a hydrogen atom or methyl. <com:Math><semantics>p41<annotation encoding="application / x-tex">p^{41}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5, preferably 0 to 2. <com:Math><semantics>p42<annotation encoding="application / x-tex">p^{42}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5, preferably 1 or 2. <com:Math><semantics>p43<annotation encoding="application / x-tex">p^{43}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5, preferably 0 to 2.

[0146] L<com:Sup>14< / com:Sup> and L<com:Sup>15< / com:Sup> are preferably the same or different and are each absent, or <com:Math><semantics>−CO−O−(CY91Y92)p41−<annotation encoding="application / x-tex">-CO-O-(CY^{91}Y^{92})_{p41}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−(CY91Y92)p41−<annotation encoding="application / x-tex">-O-CO-(CY^{91}Y^{92})_{p41}-< / annotation>< / semantics>< / com:Math>, [Image disponible dans le document PDF, Image available in the PDF document] (CY91Y92)<com:Sub>p41< / com:Sub>-, more preferably are the same or different and are each absent, or <com:Math><semantics>−CO−O−(CY91Y92)p41−<annotation encoding="application / x-tex">-CO-O-(CY^{91}Y^{92})_{p41}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>(CY91Y92)p41<annotation encoding="application / x-tex">(CY^{91}Y^{92})_{p41}< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−CO−(CY91Y92)p41<annotation encoding="application / x-tex">-CO-(CY^{91}Y^{92})_{p41}< / annotation>< / semantics>< / com:Math>, further preferably are the same or different and are each absent, or -CO-O- [Image disponible dans le document PDF, Image available in the PDF document]

[0147] In formula (IV), more preferably, <com:Math><semantics>L13<annotation encoding="application / x-tex">L^{13}< / annotation>< / semantics>< / com:Math> is -CO-O- [Image disponible dans le document PDF, Image available in the PDF document] . • [Image disponible dans le document PDF, Image available in the PDF document] - [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] - [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] the same or different and are each <com:Math><semantics>−CO−O−(CY91Y92)p41−<annotation encoding="application / x-tex">-CO-O-(CY^{91}Y^{92})_{p41}-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−<annotation encoding="application / x-tex">-< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] branched C15-C20 alkenyl or C9-C18 alkyl. R<com:Sup>11< / com:Sup> and R<com:Sup>12< / com:Sup> are preferably the same.

[0148] When <com:Math><semantics>L13<annotation encoding="application / x-tex">L^{13}< / annotation>< / semantics>< / com:Math> is absent, or <com:Math><semantics>−O−(CY84Y85)p38−<annotation encoding="application / x-tex">-O-(CY^{84}Y^{85})_{p38}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY90A−<annotation encoding="application / x-tex">-NY^{90A}-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>(CY84Y85)p38<annotation encoding="application / x-tex">(CY^{84}Y^{85})_{p38}< / annotation>< / semantics>< / com:Math>-, <com:Math><semantics>−O−CO−(CY84Y85)p38<annotation encoding="application / x-tex">-O-CO-(CY^{84}Y^{85})_{p38}< / annotation>< / semantics>< / com:Math>-, <com:Math><semantics>−NY90C−CO−(CY84Y85)p38<annotation encoding="application / x-tex">-NY^{90C}-CO-(CY^{84}Y^{85})_{p38}< / annotation>< / semantics>< / com:Math>- or - <com:Math><semantics>NY90D<annotation encoding="application / x-tex">NY^{90D}< / annotation>< / semantics>< / com:Math>-CO-O-(<com:Math><semantics>CY84Y85<annotation encoding="application / x-tex">CY^{84}Y^{85}< / annotation>< / semantics>< / com:Math>)<com:Sub>p38< / com:Sub>-, <com:Math><semantics>R10<annotation encoding="application / x-tex">R^{10}< / annotation>< / semantics>< / com:Math> is preferably octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, icosyl, . docosyl, tetracosyl, (Z)-tetradec-9-enyl, (Z)-hexadec-9- enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-octadec-6-enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-octadec-9-enyl, <com:Math><semantics>(E)<annotation encoding="application / x-tex">(E)< / annotation>< / semantics>< / com:Math>- octadec-9-enyl, (Z)-octadec-11-enyl, (9Z,12Z)-octadeca- 9,12-dienyl, (9Z,12Z,15Z)-octadeca-9,12,15-trienyl, (Z)- icos-11-enyl, (11Z,14Z)-icosa-11,14-dienyl, 3,7,11- trimethyldodeca-2,6,10-trienyl or 3,7,11,15- tetramethylhexadec-2-enyl, more preferably dodecyl, tetradecyl, hexadecyl, (Z)-hexadec-9-enyl, (Z)-octadec-6- enyl, (Z)-octadec-9-enyl or (9Z,12Z)-octadeca-9,12-dienyl.

[0149] * 4 When <com:Math><semantics>L13<annotation encoding="application / x-tex">L^{13}< / annotation>< / semantics>< / com:Math> is <com:Math><semantics>−CO−O−(CY84Y85)p38<annotation encoding="application / x-tex">-CO-O-(CY^{84}Y^{85})_{p38}< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−CO−NY90B−(CY84Y85)p38<annotation encoding="application / x-tex">-CO-NY^{90B}-(CY^{84}Y^{85})_{p38}< / annotation>< / semantics>< / com:Math>, R<com:Sup>10< / com:Sup> is more preferably nonyl, undecyl, tridecyl, pentadecyl, heptadecyl, nonadecyl, henicosyl, tricosyl, (Z)-tridec-8-enyl, (Z)-pentadec-8-enyl, (Z)-heptadec-5- enyl, (Z)-heptadec-8-enyl, (E)-heptadec-8-enyl, (Z)- heptadec-10-enyl, (8Z,11Z)-heptadeca-8,11-dienyl, (8Z,11Z,14Z)-octadeca-8,11,14-trienyl, (Z)-nonadec-10- enyl, (10Z,13Z)-nonadeca-10,13-dienyl, (11Z,14Z)-icosa- 11,14-dienyl, 2,6,10-trimethylundeca-1,5,9-trienyl or 2,6,10,14-tetramethylpentadec-1-enyl, further preferably undecyl, tridecyl, pentadecyl, (Z)-pentadec-8-enyl, (Z)- heptadec-5-enyl, (Z)-heptadec-8-enyl or (8Z,11Z)- heptadeca-8,11-dienyl.

[0150] When at least one of <com:Math><semantics>𝙻14<annotation encoding="application / x-tex">\texttt{L}^{14}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>𝙻15<annotation encoding="application / x-tex">\texttt{L}^{15}< / annotation>< / semantics>< / com:Math> is absent, or -O- <com:Math><semantics>(CY91Y92)p41−<annotation encoding="application / x-tex">(CY^{91}Y^{92})_{p41}^{-}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY97A<annotation encoding="application / x-tex">-NY^{97A}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>(CY91Y92)p41−<annotation encoding="application / x-tex">(CY^{91}Y^{92})_{p41}^{-}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−(CY91Y92)p41−<annotation encoding="application / x-tex">-O-CO-(CY^{91}Y^{92})_{p41}^{-}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY97C<annotation encoding="application / x-tex">-NY^{97C}< / annotation>< / semantics>< / com:Math>- <com:Math><semantics>CO−(CY91Y92)p41−or−NY97D−CO−O−(CY91Y92)p41−,R11andR12<annotation encoding="application / x-tex">CO-(CY^{91}Y^{92})_{p41}- or -NY^{97D}-CO-O-(CY^{91}Y^{92})_{p41}-, R^{11} and R^{12}< / annotation>< / semantics>< / com:Math> bonded to <com:Math><semantics>J3<annotation encoding="application / x-tex">J^3< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−(CY91Y92)p41−<annotation encoding="application / x-tex">-O-(CY^{91}Y^{92})_{p41}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY97A−(CY91Y92)p41−<annotation encoding="application / x-tex">-NY^{97A}-(CY^{91}Y^{92})_{p41}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>(CY91Y92)p41<annotation encoding="application / x-tex">(CY^{91}Y^{92})_{p41}< / annotation>< / semantics>< / com:Math>-, <com:Math><semantics>−NY97C<annotation encoding="application / x-tex">-NY^{97C}< / annotation>< / semantics>< / com:Math>-CO-<com:Math><semantics>(CY91Y92)p41<annotation encoding="application / x-tex">(CY^{91}Y^{92})_{p41}< / annotation>< / semantics>< / com:Math>- or <com:Math><semantics>−NY97D<annotation encoding="application / x-tex">-NY^{97D}< / annotation>< / semantics>< / com:Math>-CO-O- <com:Math><semantics>(CY91Y92)p41<annotation encoding="application / x-tex">(CY^{91}Y^{92})_{p41}< / annotation>< / semantics>< / com:Math> are the same or different and are each more preferably octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, icosyl, docosyl, tetracosyl, (Z)-tetradec-9- enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-hexadec-9-enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-octadec-6-enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>- octadec-9-enyl, (E)-octadec-9-enyl, (Z)-octadec-11-enyl, (9Z,12Z)-octadeca-9,12-dienyl, (9Z,12Z,15Z)-octadeca- 9,12,15-trienyl, (Z)-icos-11-enyl, (11Z,14Z)-icosa-11,14- dienyl, 3,7,11-trimethyldodeca-2,6,10-trienyl or • 1 4 3,7,11,15-tetramethylhexadec-2-enyl, further preferably dodecyl, tetradecyl, hexadecyl, (Z)-hexadec-9-enyl, (Z)- octadec-6-enyl, (Z)-octadec-9-enyl or (9Z,12Z)-octadeca- 9,12-dienyl.

[0151] When at least one of <com:Math><semantics>L14<annotation encoding="application / x-tex">L^{14}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L15<annotation encoding="application / x-tex">L^{15}< / annotation>< / semantics>< / com:Math> is <com:Math><semantics>−CO−O−(CY91Y92)p41<annotation encoding="application / x-tex">-CO-O-(CY^{91}Y^{92})_{p41}< / annotation>< / semantics>< / com:Math>- or <com:Math><semantics>−CO−NY97B(CY91Y92)p41−<annotation encoding="application / x-tex">-CO-NY^{97B}(CY^{91}Y^{92})_{p41}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>R11<annotation encoding="application / x-tex">R^{11}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R12<annotation encoding="application / x-tex">R^{12}< / annotation>< / semantics>< / com:Math> bonded to <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>(CY91Y92)p41<annotation encoding="application / x-tex">(CY^{91}Y^{92})_{p41}< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−CO−NY97B(CY91Y92)p41<annotation encoding="application / x-tex">-CO-NY^{97B}(CY^{91}Y^{92})_{p41}< / annotation>< / semantics>< / com:Math> are the same or different and are each more preferably nonyl, undecyl, tridecyl, pentadecyl, heptadecyl, nonadecyl, henicosyl, tricosyl, (Z)-tridec-8-enyl, (Z)-pentadec-8-enyl, (Z)- heptadec-5-enyl, (Z)-heptadec-8-enyl, (E)-heptadec-8-enyl, (Z)-heptadec-10-enyl, (8Z,11Z)-heptadeca-8,11-dienyl, (8Z,11Z,14Z)-octadeca-8,11,14-trienyl, (Z)-nonadec-10- enyl, (10Z,13Z)-nonadeca-10,13-dienyl, (11Z,14Z)-icosa- 11,14-dienyl, 2,6,10-trimethylundeca-1,5,9-trienyl or 2,6,10,14-tetramethylpentadec-1-enyl, further preferably undecyl, tridecyl, pentadecyl, (Z)-pentadec-8-enyl, (Z)- heptadec-5-enyl, (Z)-heptadec-8-enyl or (8Z,11Z)- heptadeca-8,11-dienyl.

[0152] <com:Math><semantics>L16<annotation encoding="application / x-tex">L^{16}< / annotation>< / semantics>< / com:Math> is absent, or <com:Math><semantics>−(CY98Y99)p44<annotation encoding="application / x-tex">-(CY^{98}Y^{99})_{p44}< / annotation>< / semantics>< / com:Math>-, <com:Math><semantics>−(CY100Y101)p45<annotation encoding="application / x-tex">-(CY^{100}Y^{101})_{p45}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>Z29<annotation encoding="application / x-tex">Z^{29}< / annotation>< / semantics>< / com:Math>- <com:Math><semantics>(CY102Y103)p46<annotation encoding="application / x-tex">(CY^{102}Y^{103})_{p46}< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−(CY104Y105)p47<annotation encoding="application / x-tex">-(CY^{104}Y^{105})_{p47}< / annotation>< / semantics>< / com:Math> <com:Math><semantics>−Z30<annotation encoding="application / x-tex">-Z^{30}< / annotation>< / semantics>< / com:Math> <com:Math><semantics>−(CY106Y107)p48<annotation encoding="application / x-tex">-(CY^{106}Y^{107})_{p48}< / annotation>< / semantics>< / com:Math> <com:Math><semantics>−Z31<annotation encoding="application / x-tex">-Z^{31}< / annotation>< / semantics>< / com:Math> <com:Math><semantics>−<annotation encoding="application / x-tex">-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>(CY108Y109)p49<annotation encoding="application / x-tex">(CY^{108}Y^{109})_{p49}< / annotation>< / semantics>< / com:Math>, preferably absent, or <com:Math><semantics>−(CY98Y99)p44<annotation encoding="application / x-tex">-(CY^{98}Y^{99})_{p44}< / annotation>< / semantics>< / com:Math> or - <com:Math><semantics>(CY100Y101)p45−Z29−(CY102Y103)p46<annotation encoding="application / x-tex">(CY^{100}Y^{101})_{p45}-Z^{29}-(CY^{102}Y^{103})_{p46}< / annotation>< / semantics>< / com:Math>, more preferably absent, or <com:Math><semantics>−(CY98Y99)p44−,−(CY100Y101)p45−O−CO−(CY102Y103)p46−,−<annotation encoding="application / x-tex">-(CY^{98}Y^{99})_{p44}-, -(CY^{100}Y^{101})_{p45}-O-CO-(CY^{102}Y^{103})_{p46}-, -< / annotation>< / semantics>< / com:Math> . 4 [Image disponible dans le document PDF, Image available in the PDF document] further preferably absent, or <com:Math><semantics>−(CH2)p44<annotation encoding="application / x-tex">-(CH_2)_{p44}< / annotation>< / semantics>< / com:Math>- or <com:Math><semantics>−CO−(CH2)p46<annotation encoding="application / x-tex">-CO-(CH_2)_{p46}< / annotation>< / semantics>< / com:Math>-.

[0153] <com:Math><semantics>J3<annotation encoding="application / x-tex">J^3< / annotation>< / semantics>< / com:Math> is <com:Math><semantics>CY111<annotation encoding="application / x-tex">CY^{111}< / annotation>< / semantics>< / com:Math> or N, preferably CH or N. When <com:Math><semantics>J3<annotation encoding="application / x-tex">J^3< / annotation>< / semantics>< / com:Math> is N, more preferably, <com:Math><semantics>L14<annotation encoding="application / x-tex">L^{14}< / annotation>< / semantics>< / com:Math> is absent; <com:Math><semantics>L15<annotation encoding="application / x-tex">L^{15}< / annotation>< / semantics>< / com:Math> is -CO-; and <com:Math><semantics>L16<annotation encoding="application / x-tex">L^{16}< / annotation>< / semantics>< / com:Math> is absent, or <com:Math><semantics>−(CY98Y99)p44<annotation encoding="application / x-tex">-(CY^{98}Y^{99})_{p44}< / annotation>< / semantics>< / com:Math>, or <com:Math><semantics>L14<annotation encoding="application / x-tex">L^{14}< / annotation>< / semantics>< / com:Math> is absent; <com:Math><semantics>L15<annotation encoding="application / x-tex">L^{15}< / annotation>< / semantics>< / com:Math> is absent; and <com:Math><semantics>L16<annotation encoding="application / x-tex">L^{16}< / annotation>< / semantics>< / com:Math> is <com:Math><semantics>−CO−(CY102Y103)p46−.<annotation encoding="application / x-tex">-CO-(CY^{102}Y^{103})_{p46}-.< / annotation>< / semantics>< / com:Math>

[0154] <com:Math><semantics>X14<annotation encoding="application / x-tex">X^{14}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X15<annotation encoding="application / x-tex">X^{15}< / annotation>< / semantics>< / com:Math> are as defined above in <com:Math><semantics>X2<annotation encoding="application / x-tex">X^{2}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X3<annotation encoding="application / x-tex">X^{3}< / annotation>< / semantics>< / com:Math>, respectively.

[0155] In formula (V'), R<com:Sup>13< / com:Sup> is preferably linear or branched C8-C24 alkyl or C8-C24 alkenyl, more preferably linear or branched C15-C20 alkenyl or linear or branched C9-C18 alkyl, most preferably linear C15-C20 alkenyl or linear C9-C18 alkyl. R<com:Sup>14< / com:Sup> and R<com:Sup>15< / com:Sup> are preferably the same linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl, more preferably the same linear or branched C15- C20 alkenyl or linear or branched C9-C18 alkyl, most preferably the same linear C15-C20 alkenyl or linear C9- C18 alkyl.

[0156] L<com:Sup>17< / com:Sup> to L<com:Sup>19< / com:Sup> are the same or different and are each absent, or <com:Math><semantics>−Z32<annotation encoding="application / x-tex">-Z^{32}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>(CY116Y117)p51<annotation encoding="application / x-tex">(CY^{116}Y^{117})_{p51}< / annotation>< / semantics>< / com:Math>- or <com:Math><semantics>−Z33<annotation encoding="application / x-tex">-Z^{33}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>(CY118Y119)p52<annotation encoding="application / x-tex">(CY^{118}Y^{119})_{p52}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>Z34<annotation encoding="application / x-tex">Z^{34}< / annotation>< / semantics>< / com:Math>- <com:Math><semantics>(CY120Y121)p53<annotation encoding="application / x-tex">(CY^{120}Y^{121})_{p53}< / annotation>< / semantics>< / com:Math>-, preferably <com:Math><semantics>−Z32<annotation encoding="application / x-tex">-Z^{32}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>(CY116Y117)p51<annotation encoding="application / x-tex">(CY^{116}Y^{117})_{p51}< / annotation>< / semantics>< / com:Math>-, more preferably <com:Math><semantics>−O−(CY116Y117)p51−<annotation encoding="application / x-tex">-O-(CY^{116}Y^{117})_{p51}-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−CO−O−(CY116Y117)p51−<annotation encoding="application / x-tex">-CO-O-(CY^{116}Y^{117})_{p51}-< / annotation>< / semantics>< / com:Math>, further preferably -O- or -CO-O-. 4 ٤

[0157] In formula (V'), preferably, <com:Math><semantics>L17<annotation encoding="application / x-tex">L^{17}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>L19<annotation encoding="application / x-tex">L^{19}< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−0−<annotation encoding="application / x-tex">-0-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−C0−0−<annotation encoding="application / x-tex">-C0-0-< / annotation>< / semantics>< / com:Math>, and each of <com:Math><semantics>R13<annotation encoding="application / x-tex">R^{13}< / annotation>< / semantics>< / com:Math> to R<com:Sup>15< / com:Sup> is linear C15-C20 alkenyl or C9-C18 alkyl. In this case, preferably, <com:Math><semantics>L17<annotation encoding="application / x-tex">L^{17}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>L19<annotation encoding="application / x-tex">L^{19}< / annotation>< / semantics>< / com:Math> are the same and -O- or -CO- O-, and <com:Math><semantics>R13<annotation encoding="application / x-tex">R^{13}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>R15<annotation encoding="application / x-tex">R^{15}< / annotation>< / semantics>< / com:Math> are the same and linear C15-C20 alkenyl or C9-C18 alkyl.

[0158] When at least one of <com:Math><semantics>L17<annotation encoding="application / x-tex">L^{17}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>L19<annotation encoding="application / x-tex">L^{19}< / annotation>< / semantics>< / com:Math> is absent, or -O- <com:Math><semantics>(CY116Y117)p51<annotation encoding="application / x-tex">(CY^{116}Y^{117})_{p51}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−(CY116Y117)p51<annotation encoding="application / x-tex">-O-CO-(CY^{116}Y^{117})_{p51}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY122C−CO−(CY116Y117)p51<annotation encoding="application / x-tex">-NY^{122C}-CO-(CY^{116}Y^{117})_{p51}< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−NY122D−CO−O−(CY116Y117)p51−<annotation encoding="application / x-tex">-NY^{122D}-CO-O-(CY^{116}Y^{117})_{p51}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>R13<annotation encoding="application / x-tex">R^{13}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>R15<annotation encoding="application / x-tex">R^{15}< / annotation>< / semantics>< / com:Math> bonded to carbon adjacent to the furanose ring or <com:Math><semantics>L20<annotation encoding="application / x-tex">L^{20}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−(CY116Y117)p51−<annotation encoding="application / x-tex">-O-(CY^{116}Y^{117})_{p51}-< / annotation>< / semantics>< / com:Math>, - O-CO-<com:Math><semantics>(CY116Y117)p51<annotation encoding="application / x-tex">(CY^{116}Y^{117})_{p51}< / annotation>< / semantics>< / com:Math>-, <com:Math><semantics>−NY122C<annotation encoding="application / x-tex">-NY^{122C}< / annotation>< / semantics>< / com:Math>-CO-<com:Math><semantics>(CY116Y117)p51<annotation encoding="application / x-tex">(CY^{116}Y^{117})_{p51}< / annotation>< / semantics>< / com:Math>- or <com:Math><semantics>−NY122D<annotation encoding="application / x-tex">-NY^{122D}< / annotation>< / semantics>< / com:Math>-CO-O- <com:Math><semantics>(CY116Y117)p51<annotation encoding="application / x-tex">(CY^{116}Y^{117})_{p51}< / annotation>< / semantics>< / com:Math> are the same or different and are each preferably octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, icosyl, docosyl, tetracosyl, (Z)-tetradec-9- enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-hexadec-9-enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-octadec-6-enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>- octadec-9-enyl, (E)-octadec-9-enyl, (Z)-octadec-11-enyl, (9Z,12Z)-octadeca-9,12-dienyl, (9Z,12Z,15Z)-octadeca- 9,12,15-trienyl, (Z)-icos-11-enyl, (11Z,14Z)-icosa-11,14- dienyl, 3,7,11-trimethyldodeca-2,6,10-trienyl, 3,7,11,15- tetramethylhexadec-2-enyl or the like, more preferably dodecyl, tetradecyl, hexadecyl, (Z)-hexadec-9-enyl, (Z)- octadec-6-enyl, (Z)-octadec-9-enyl, (9Z,12Z)-octadeca- 9,12-dienyl or the like.

[0159] . • 4. [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] - - - - - - - - - - - - - - - - - - - [Image disponible dans le document PDF, Image available in the PDF document] . [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] . [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] tetramethylpentadec-1-enyl, more preferably undecyl, [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] dienyl or the like.

[0160] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document]

[0161] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] . [Image disponible dans le document PDF, Image available in the PDF document]

[0162] • ٠ <com:Math><semantics>B3<annotation encoding="application / x-tex">B^3< / annotation>< / semantics>< / com:Math> is preferably [Image disponible dans le document PDF, Image available in the PDF document] more preferably <com:Math><semantics>−N+(CH3)3<annotation encoding="application / x-tex">-N^+(CH_3)_3< / annotation>< / semantics>< / com:Math>.

[0163] <com:Math><semantics>Y112<annotation encoding="application / x-tex">Y^{112}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>Y113<annotation encoding="application / x-tex">Y^{113}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom, hydroxy or optionally substituted C1-C4 alkyl, preferably are the same or different and are each a hydrogen atom or hydroxy, more preferably are the same and a hydrogen atom.

[0164] In formula (V''), <com:Math><semantics>R16<annotation encoding="application / x-tex">R^{16}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>R18<annotation encoding="application / x-tex">R^{18}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>L22<annotation encoding="application / x-tex">L^{22}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>L26<annotation encoding="application / x-tex">L^{26}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>B4<annotation encoding="application / x-tex">B^4< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>Y114<annotation encoding="application / x-tex">Y^{114}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y115<annotation encoding="application / x-tex">Y^{115}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>A6<annotation encoding="application / x-tex">A^6< / annotation>< / semantics>< / com:Math> are as defined in <com:Math><semantics>R13<annotation encoding="application / x-tex">R^{13}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>R15<annotation encoding="application / x-tex">R^{15}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>L17<annotation encoding="application / x-tex">L^{17}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>L21<annotation encoding="application / x-tex">L^{21}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>B3<annotation encoding="application / x-tex">B^3< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>Y112<annotation encoding="application / x-tex">Y^{112}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y113<annotation encoding="application / x-tex">Y^{113}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>A5<annotation encoding="application / x-tex">A^5< / annotation>< / semantics>< / com:Math>, respectively.

[0165] In formula <com:Math><semantics>(V′)<annotation encoding="application / x-tex">(V')< / annotation>< / semantics>< / com:Math>, when <com:Math><semantics>Y112<annotation encoding="application / x-tex">Y^{112}< / annotation>< / semantics>< / com:Math> is a hydrogen atom, four substituents on the pyran ring are preferably added on different carbon atoms, respectively, on the pyran ring. Formula (V') is more preferably [Image disponible dans le document PDF, Image available in the PDF document] In this case, further preferably, <com:Math><semantics>L17<annotation encoding="application / x-tex">L^{17}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>L19<annotation encoding="application / x-tex">L^{19}< / annotation>< / semantics>< / com:Math> are the same or different and are each -O- or -CO-O-, and each of R13 to R<com:Sup>15< / com:Sup> is linear C15-C20 alkenyl or C9-C18 alkyl. Most . . * preferably, L17 to L19 are the same or different and are each <com:Math><semantics>−0−<annotation encoding="application / x-tex">-0-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>; each of <com:Math><semantics>R13<annotation encoding="application / x-tex">R^{13}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>R15<annotation encoding="application / x-tex">R^{15}< / annotation>< / semantics>< / com:Math> is linear C15-C20 alkenyl or C9-C18 alkyl; <com:Math><semantics>L17<annotation encoding="application / x-tex">L^{17}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L21<annotation encoding="application / x-tex">L^{21}< / annotation>< / semantics>< / com:Math> are absent; and <com:Math><semantics>Y113<annotation encoding="application / x-tex">Y^{113}< / annotation>< / semantics>< / com:Math> is a hydrogen atom or hydroxy.

[0166] In formula (V''), four substituents on the furan ring are preferably added on different carbon atoms, respectively, on the furan ring. Formula (V'') is more preferably [Image disponible dans le document PDF, Image available in the PDF document] In this case, further preferably, <com:Math><semantics>L22<annotation encoding="application / x-tex">L^{22}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>L24<annotation encoding="application / x-tex">L^{24}< / annotation>< / semantics>< / com:Math> are the same or different and are each -O- or -CO-O-, and each of R16 to R<com:Sup>18< / com:Sup> is linear C15-C20 alkenyl or C9-C18 alkyl. Most preferably, L<com:Sup>22< / com:Sup> to L<com:Sup>24< / com:Sup> are the same or different and are each <com:Math><semantics>−0−<annotation encoding="application / x-tex">-0-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>; each of <com:Math><semantics>R16<annotation encoding="application / x-tex">R^{16}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>R18<annotation encoding="application / x-tex">R^{18}< / annotation>< / semantics>< / com:Math> is linear C15-C20 alkenyl or C9-C18 alkyl; <com:Math><semantics>L22<annotation encoding="application / x-tex">L^{22}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L26<annotation encoding="application / x-tex">L^{26}< / annotation>< / semantics>< / com:Math> are absent; and <com:Math><semantics>Y114<annotation encoding="application / x-tex">Y^{114}< / annotation>< / semantics>< / com:Math> is a hydrogen atom or hydroxy.

[0167] When <com:Math><semantics>p13<annotation encoding="application / x-tex">p^{13}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>p33<annotation encoding="application / x-tex">p^{33}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>p66<annotation encoding="application / x-tex">p^{66}< / annotation>< / semantics>< / com:Math> are 0 in the definition of each of the formulas: .1 4 [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] and [Image disponible dans le document PDF, Image available in the PDF document] in the definition of formulas <com:Math><semantics>B1<annotation encoding="application / x-tex">B^1< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>B2<annotation encoding="application / x-tex">B^2< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>B3<annotation encoding="application / x-tex">B^3< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>B4<annotation encoding="application / x-tex">B^4< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>N+<annotation encoding="application / x-tex">N^+< / annotation>< / semantics>< / com:Math> is bonded to carbon adjacent to each of <com:Math><semantics>Z10<annotation encoding="application / x-tex">Z^{10}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>Z21<annotation encoding="application / x-tex">Z^{21}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>Z41<annotation encoding="application / x-tex">Z^{41}< / annotation>< / semantics>< / com:Math>.

[0168] The nucleic acid-containing lipid nanoparticle of the present invention preferably comprises a lipid represented by formula (II) as lipid A.

[0169] The nucleic acid-containing lipid nanoparticle of the present invention may comprise a cationic lipid other than the lipid having a hydrophilic unit having one quaternary ammonium group and optionally substituted three independent hydrocarbon groups (lipid A). The cationic lipid other than lipid A used in the present invention is not particularly limited as long as the cationic lipid is an amphipathic molecule having a lipophilic region containing one or more optionally substituted hydrocarbon groups, and a cationic • à . . hydrophilic region containing at least one primary amino group, secondary amino group, tertiary amino group and / or quaternary ammonium group (except for lipid A). The cationic lipid other than lipid A is preferably a lipid having a hydrophilic unit having optionally substituted one amino group or one quaternary ammonium group and a hydrophobic unit having optionally substituted two independent hydrocarbon groups (lipid B).

[0170] In the present invention, the lipid having, in the same molecule, a hydrophilic unit having optionally substituted one amino group or one quaternary ammonium group and a hydrophobic unit having optionally substituted two independent hydrocarbon groups (lipid B) is not particularly limited as long as the lipid is a molecule intramolecularly having optionally substituted one amino group or one quaternary ammonium group as a hydrophilic unit, and having optionally substituted two independent hydrocarbon groups. Lipid B is represented by, for example, any of structural formulas (D) and (E) given below. In structural formulas (D) and (E) given below, the "hydrophilic unit" represents a hydrophilic unit having optionally substituted one amino group or one quaternary ammonium group, and the "hydrophobic unit" represents an optionally substituted independent hydrocarbon group.

[0171] . . Zero to two out of the three bonds of the amino group constituting the "hydrophilic unit" are attached to any 0 to 2 of the hydrocarbon groups constituting the "hydrophobic unit", and the remaining bond(s) is attached to hydrogen or an optionally substituted chain and / or cyclic hydrocarbon group, etc. Zero to two out of the four bonds of the quaternary ammonium group constituting the "hydrophilic unit" are attached to any 0 to 2 of the hydrocarbon groups constituting the "hydrophobic unit", and the remaining bonds are attached to hydrogen or an optionally substituted chain and / or cyclic hydrocarbon group, etc. The optionally substituted chain and / or cyclic hydrocarbon group constituting the "hydrophilic unit" can be any group composed of carbon and hydrogen atoms and is preferably a group having 1 to 10 carbon atoms, more preferably a group having 1 to 6 carbon atoms, further preferably a group having 1 to 3 carbon atoms.

[0172] The "hydrophilic unit" may have one or more ethers, esters, amides or the like via a carbon atom in the optionally substituted chain and / or cyclic hydrocarbon group, etc. constituting this hydrophilic unit. Examples of the substituent for the optionally substituted chain and / or cyclic hydrocarbon group, etc. include carbamate, amino, monoalkylamino, dialkylamino, pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin-2-yl, piperidin-3-yl, . 4 . piperidin-4-yl, morpholin-2-yl, morpholin-3-yl, hydroxy, alkoxy, alkoxycarbonyl, hydroxycarbonyl, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, nitro, cyano, fluoro, chloro, and bromo.

[0173] The hydrocarbon group constituting the "hydrophobic unit" can be any group consisting of 8 to 24 carbon atoms and hydrogen atoms. Hydrocarbon groups can be classified from the viewpoint of topology. Examples thereof include linear hydrocarbon groups, branched hydrocarbon groups and cyclic hydrocarbon groups (e.g., a cholesteryl group). A linear or branched hydrocarbon group is preferred. Also, hydrocarbon groups can be classified on the basis of the presence or absence of an unsaturated bond (double bond or triple bond). Hydrocarbon groups having an unsaturated bond can also be classified on the basis of the presence or absence of aromaticity. The hydrocarbon group is preferably a hydrocarbon group having only a saturated bond (alkyl) or a hydrocarbon group having an unsaturated bond and lacking aromaticity (e.g., alkenyl or alkynyl). The hydrocarbon group in lipid A is preferably linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl.

[0174] Each hydrocarbon group constituting the "hydrophobic unit" may be bonded directly to the amino group or the quaternary ammonium group of the "hydrophilic unit", or 4 . $ b may be bonded to the amino group or the quaternary ammonium group via an ether, ester or amide bond, etc. and the optionally substituted chain and / or cyclic hydrocarbon group, etc. constituting the "hydrophilic unit". As shown in structural formula (E), the hydrocarbon groups constituting two "hydrophobic units" may be bonded via a carbon atom, and this carbon atom may be bonded either directly to the amino group or the quaternary ammonium group of the "hydrophilic unit" or to the amino group or the quaternary ammonium group via an ether, ester or amide bond, etc. and the optionally substituted chain and / or cyclic hydrocarbon group, etc. constituting the "hydrophilic unit".

[0175] [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document]

[0176] The cationic lipid in the nucleic acid-containing lipid nanoparticle of the present invention may be lipid . . 4 * A alone or lipid B alone and preferably comprises both lipid A and lipid B.

[0177] Examples of the cationic lipid other than lipid A used in the present invention include cationic lipids described in WO 2013 / 089151, WO 2011 / 136368, WO 2014 / 007398, WO 2010 / 042877 and WO 2010 / 054401.

[0178] Examples of lipid B used in the present invention can include lipids represented by the following formulas <com:Math><semantics>(CL−I)<annotation encoding="application / x-tex">(CL-I)< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>(CL−XIX)<annotation encoding="application / x-tex">(CL-XIX)< / annotation>< / semantics>< / com:Math>:

[0179] formula (CL-I)

[0180] [Image disponible dans le document PDF, Image available in the PDF document] (CL-I) wherein R<com:Sup>101< / com:Sup> and R<com:Sup>102< / com:Sup> are the same or different and are each linear or branched C10-C24 alkyl, C10-C24 alkenyl or C10- C24 alkynyl; L<com:Sup>101< / com:Sup> and L<com:Sup>102< / com:Sup> are each a hydrogen atom, or together form a single bond or C1-C3 alkylene; . . <com:Math><semantics>L103<annotation encoding="application / x-tex">L^{103}< / annotation>< / semantics>< / com:Math> is a single bond, -CO- or -CO-O-; when <com:Math><semantics>L103<annotation encoding="application / x-tex">L^{103}< / annotation>< / semantics>< / com:Math> is a single bond, <com:Math><semantics>X101<annotation encoding="application / x-tex">X^{101}< / annotation>< / semantics>< / com:Math> is a hydrogen atom, C1-C6 alkyl, C3-C6 alkenyl, pyrrolidin-3-yl, piperidin-3-yl, piperidin-4-yl, or C1-C6 alkyl or C3-C6 alkenyl substituted with one to three same or different substituents selected from amino, monoalkylamino, dialkylamino, trialkylammonio, hydroxy, alkoxy, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, pyrrolidinyl, piperidyl and morpholinyl; and when <com:Math><semantics>L103<annotation encoding="application / x-tex">L^{103}< / annotation>< / semantics>< / com:Math> is -CO- or -CO-O-, X<com:Sup>101< / com:Sup> is pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, morpholin-2-yl, morpholin-3-yl, or C1-C6 alkyl or C3-C6 alkenyl substituted with one to three same or different substituents selected from amino, monoalkylamino, dialkylamino, trialkylammonio, hydroxy, alkoxy, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, pyrrolidinyl, piperidyl and morpholinyl, and at least one of the substituents is amino, monoalkylamino, dialkylamino, trialkylammonio, pyrrolidinyl, piperidyl or morpholinyl, formula (CL-II)

[0181] [Image disponible dans le document PDF, Image available in the PDF document] (CL-II) ١. wherein <com:Math><semantics>R103<annotation encoding="application / x-tex">R^{103}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R104<annotation encoding="application / x-tex">R^{104}< / annotation>< / semantics>< / com:Math> are the same or different and are each linear or branched C12-C24 alkyl, C12-C24 alkenyl or C12- C24 alkynyl; p<com:Sup>101< / com:Sup> and p<com:Sup>102< / com:Sup> are the same or different and are each an integer from 0 to 3; L<com:Sup>106< / com:Sup> and L<com:Sup>107< / com:Sup> are each a hydrogen atom, or together form a single bond or C2-C8 alkylene; <com:Math><semantics>𝙻104<annotation encoding="application / x-tex">\texttt{L}^{104}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>𝙻105<annotation encoding="application / x-tex">\texttt{L}^{105}< / annotation>< / semantics>< / com:Math> are the same or different and are each - O-, -CO-O- or -O-CO-; <com:Math><semantics>L108<annotation encoding="application / x-tex">L^{108}< / annotation>< / semantics>< / com:Math> is a single bond, -CO- or -CO-O-; when <com:Math><semantics>L108<annotation encoding="application / x-tex">L^{108}< / annotation>< / semantics>< / com:Math> is a single bond, X<com:Sup>102< / com:Sup> is a hydrogen atom, C1-C6 alkyl, C3-C6 alkenyl, pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin-3-yl, piperidin-4-yl, or C1-C6 alkyl or C3-C6 alkenyl substituted with one to three same or different substituents selected from amino, monoalkylamino, dialkylamino, trialkylammonio, hydroxy, alkoxy, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, pyrrolidinyl, piperidyl and morpholinyl; and when <com:Math><semantics>L108<annotation encoding="application / x-tex">L^{108}< / annotation>< / semantics>< / com:Math> is -CO- or -CO-O-, X<com:Sup>102< / com:Sup> is pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, morpholin-2-yl, morpholin-3-yl, or C1-C6 alkyl or C3-C6 alkenyl substituted with one to three same or different substituents selected from amino, monoalkylamino, dialkylamino, trialkylammonio, hydroxy, alkoxy, carbamoyl, ٠ 4 $. monoalkylcarbamoyl, dialkylcarbamoyl, pyrrolidinyl, piperidyl and morpholinyl, and at least one of the substituents is amino, monoalkylamino, dialkylamino, trialkylammonio, pyrrolidinyl, piperidyl or morpholinyl, formula (CL-III)

[0182] [Image disponible dans le document PDF, Image available in the PDF document] (CL-III) wherein R<com:Sup>105< / com:Sup> is linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; R<com:Sup>106< / com:Sup> is linear or branched C8-C24 alkyl, C8-C24 alkenyl, C8-C24 alkynyl, C8-C24 alkyloxyethyl, C8-C24 alkyloxypropyl, C8-C24 alkenyloxyethyl, C8-C24 alkenyloxypropyl, C8-C24 alkynyloxyethyl or C8-C24 alkynyloxypropyl; <com:Math><semantics>X103<annotation encoding="application / x-tex">X^{103}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X104<annotation encoding="application / x-tex">X^{104}< / annotation>< / semantics>< / com:Math> are the same or different and are each C1-C3 alkyl, or together form C2-C8 alkylene, or <com:Math><semantics>X103<annotation encoding="application / x-tex">X^{103}< / annotation>< / semantics>< / com:Math> forms C2-C8 alkylene together with L111; L<com:Sup>111< / com:Sup> is a hydrogen atom, C1-C6 alkyl, C3-C6 alkenyl, amino, monoalkylamino, hydroxy, alkoxy, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, or C1-C6 alkyl or C3-C6 alkenyl substituted with one to three same or different substituents selected from amino, monoalkylamino, hydroxy, alkoxy, carbamoyl, Ġ, monoalkylcarbamoyl and dialkylcarbamoyl, or forms C2-C8 alkylene together with X<com:Sup>103< / com:Sup>; L<com:Sup>109< / com:Sup> is C1-C6 alkylene; L<com:Sup>110< / com:Sup> is a single bond, or C1-C6 alkylene, provided that the sum of the numbers of carbon atoms of <com:Math><semantics>L109<annotation encoding="application / x-tex">L^{109}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L110<annotation encoding="application / x-tex">L^{110}< / annotation>< / semantics>< / com:Math> is 7 or less; when <com:Math><semantics>L111<annotation encoding="application / x-tex">L^{111}< / annotation>< / semantics>< / com:Math> is a hydrogen atom, <com:Math><semantics>L110<annotation encoding="application / x-tex">L^{110}< / annotation>< / semantics>< / com:Math> is a single bond; and when <com:Math><semantics>L111<annotation encoding="application / x-tex">L^{111}< / annotation>< / semantics>< / com:Math> forms C2-C6 alkylene together with <com:Math><semantics>X103<annotation encoding="application / x-tex">X^{103}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>L110<annotation encoding="application / x-tex">L^{110}< / annotation>< / semantics>< / com:Math> is a single bond, or methylene or ethylene, formula (CL-IV) .

[0183] [Image disponible dans le document PDF, Image available in the PDF document] (CL-IV) wherein R<com:Sup>107< / com:Sup> is linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; R<com:Sup>108< / com:Sup> is linear or branched C8-C24 alkyl, C8-C24 alkenyl, C8-C24 alkynyl, C8-C24 alkyloxyethyl, C8-C24 alkyloxypropyl, C8-C24 alkenyloxyethyl, C8-C24 alkenyloxypropyl, C8-C24 alkynyloxyethyl, C8-C24 alkynyloxypropyl, C8-C24 alkyloxyethoxyethyl, C8-C24 alkenyloxyethoxyethyl or C8-C24 alkynyloxyethoxyethyl; X<com:Sup>105< / com:Sup> is a hydrogen atom, optionally substituted C1-C4 alkyl or <com:Math><semantics>−CO−(CH2)n−NY1Y2<annotation encoding="application / x-tex">-CO-(CH_2)_n-NY1Y2< / annotation>< / semantics>< / com:Math>; n represents an integer from 1 to 4; and • 1 4 Y1 and Y2 are the same or different and are each C1- C3 alkyl, or together form C2-C8 alkylene, formula (CL-V)

[0184] [Image disponible dans le document PDF, Image available in the PDF document] (CL-V) wherein R<com:Sup>109< / com:Sup> is linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; R<com:Sup>110< / com:Sup> is linear or branched C8-C24 alkyl, C8-C24 alkenyl, C8-C24 alkynyl, C8-C24 alkyloxyethyl, C8-C24 alkyloxypropyl, C8-C24 alkenyloxyethyl, C8-C24 alkenyloxypropyl, C8-C24 alkynyloxyethyl or C8-C24 alkynyloxypropyl; L<com:Sup>112< / com:Sup> is C1-C3 alkylene; and X<com:Sup>105< / com:Sup>' is a hydrogen atom or C1-C3 alkyl, formula (CL-VI)

[0185] [Image disponible dans le document PDF, Image available in the PDF document] (CL-VI) wherein k. R<com:Sup>111< / com:Sup> and R<com:Sup>112< / com:Sup> are the same or different and are each optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; <com:Math><semantics>X106<annotation encoding="application / x-tex">X^{106}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X107<annotation encoding="application / x-tex">X^{107}< / annotation>< / semantics>< / com:Math> are the same or different and are each C1-C3 alkyl, or together form C2-C8 alkylene; p<com:Sup>103< / com:Sup>, p<com:Sup>104< / com:Sup> and p<com:Sup>105< / com:Sup> are the same or different and are each 0 or 1, provided that <com:Math><semantics>p103<annotation encoding="application / x-tex">p^{103}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>p104<annotation encoding="application / x-tex">p^{104}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>p105<annotation encoding="application / x-tex">p^{105}< / annotation>< / semantics>< / com:Math> are not 0 at the same time; and <com:Math><semantics>L113<annotation encoding="application / x-tex">L^{113}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L114<annotation encoding="application / x-tex">L^{114}< / annotation>< / semantics>< / com:Math> are the same or different and are each O, S or NH, formula (CL-VII)

[0186] [Image disponible dans le document PDF, Image available in the PDF document] (CL-VII) wherein R<com:Sup>113< / com:Sup> and R<com:Sup>114< / com:Sup> are the same or different and are each optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; R<com:Sup>115< / com:Sup> is a hydrogen atom, hydroxy, optionally substituted C1-C4 alkyl, C1-C4 alkoxy or C1-C4 acyloxy; X<com:Sup>109< / com:Sup> and X<com:Sup>110< / com:Sup> are the same or different and are each C1-C3 alkyl, or together form C2-C8 alkylene; <com:Math><semantics>L115<annotation encoding="application / x-tex">L^{115}< / annotation>< / semantics>< / com:Math> is -CO-O-, -O-CO-, -NHCO- or -CONH-; p<com:Sup>106< / com:Sup> is an integer from 0 to 3; and p<com:Sup>107< / com:Sup> is an integer from 1 to 4, formula (CL-VIII)

[0187] [Image disponible dans le document PDF, Image available in the PDF document] wherein R<com:Sup>116< / com:Sup> and R<com:Sup>117< / com:Sup> are the same or different and are each optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl, C8-C24 alkynyl, C7-C20 alkyloxy C1-C3 alkyl, C7-C20 alkenyloxy C1-C3 alkyl or C7-C20 alkynyloxy C1-C3 alkyl, or the C8-C24 alkyl, the C8-C24 alkenyl or the C8-C24 alkynyl in which a biodegradable group is integrated, or the C8-C24 alkyl group, the C8-C24 alkenyl group or the C8-C24 alkynyl group in which a biodegradable group is present at the terminal; the biodegradable group thus integrated is -C(0)0- or -OC(O)-, and the group having the biodegradable group present at the terminal is -C(0)0-C1-C4 alkyl or -OC(0)- C1-C4 alkyl; B<com:Sup>100< / com:Sup> is a hydrogen atom, C1-C3 alkyl, hydroxy C2-C4 alkyl, C1-C3 dialkylamino C2-C4 alkyl, formula (A): [Image disponible dans le document PDF, Image available in the PDF document] • į, wherein <com:Math><semantics>X111<annotation encoding="application / x-tex">X^{111}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X112<annotation encoding="application / x-tex">X^{112}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or C1-C3 alkyl, or <com:Math><semantics>X111<annotation encoding="application / x-tex">X^{111}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X112<annotation encoding="application / x-tex">X^{112}< / annotation>< / semantics>< / com:Math> optionally form a C2-C6 nitrogen-containing hetero ring together with the nitrogen atom to which they are bonded; and <com:Math><semantics>p110<annotation encoding="application / x-tex">p^{110}< / annotation>< / semantics>< / com:Math> is an integer from 2 to 6, or formula (B): [Image disponible dans le document PDF, Image available in the PDF document] (B) wherein <com:Math><semantics>X113<annotation encoding="application / x-tex">X^{113}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X114<annotation encoding="application / x-tex">X^{114}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or C1 to C3 alkyl, or <com:Math><semantics>X113<annotation encoding="application / x-tex">X^{113}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X114<annotation encoding="application / x-tex">X^{114}< / annotation>< / semantics>< / com:Math> optionally form a C2-C6 nitrogen-containing hetero ring together with the nitrogen atom to which they are bonded; and p<com:Sup>111< / com:Sup> is an integer from 1 to 6; p<com:Sup>108< / com:Sup> is an integer from 0 to 4; p<com:Sup>109< / com:Sup> is an integer from 1 to 4, provided that when <com:Math><semantics>p108<annotation encoding="application / x-tex">p^{108}< / annotation>< / semantics>< / com:Math> is 0, <com:Math><semantics>p109<annotation encoding="application / x-tex">p^{109}< / annotation>< / semantics>< / com:Math> is not 1; L<com:Sup>116< / com:Sup> is the same or different on each carbon to which it is bonded and is a hydrogen atom or C1-C3 alkyl; and L<com:Sup>117< / com:Sup> is the same or different on each carbon to which it is bonded and is a hydrogen atom or C1-C3 alkyl, formula (CL-IX)

[0188] [Image disponible dans le document PDF, Image available in the PDF document] wherein ( ę <com:Math><semantics>𝑿115<annotation encoding="application / x-tex">\mathbf{X}^{115}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>𝑿116<annotation encoding="application / x-tex">\mathbf{X}^{116}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or C1-C3 alkyl; L<com:Sup>118< / com:Sup> and L<com:Sup>119< / com:Sup> are the same or different and are each optionally substituted linear or branched C8-C24 alkylene or C8-C24 alkenylene; <com:Math><semantics>M101<annotation encoding="application / x-tex">{M}^{101}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>M102<annotation encoding="application / x-tex">{M}^{102}< / annotation>< / semantics>< / com:Math> are the same or different and are each selected from the group consisting of <com:Math><semantics>−C=C−<annotation encoding="application / x-tex">-C=C-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−OC(O)−<annotation encoding="application / x-tex">-OC(O)-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−<annotation encoding="application / x-tex">-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>C(0)O−<annotation encoding="application / x-tex">C(0)O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−SC(0)−<annotation encoding="application / x-tex">-SC(0)-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−C(0)S−<annotation encoding="application / x-tex">-C(0)S-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−OC(S)−<annotation encoding="application / x-tex">-OC(S)-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−C(S)O−<annotation encoding="application / x-tex">-C(S)O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−SS−<annotation encoding="application / x-tex">-SS-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−<annotation encoding="application / x-tex">-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>C(R″)=N−<annotation encoding="application / x-tex">C(R'') = N-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−N=C(R″)−<annotation encoding="application / x-tex">-N=C(R'')-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−C(R″)=N−O−<annotation encoding="application / x-tex">-C(R'')=N-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−N=C(R″)−<annotation encoding="application / x-tex">-O-N=C(R'')-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−<annotation encoding="application / x-tex">-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>N(R″)C(O)−−C(O)N(R″)−−N(R″)C(S)−−C(S)N(R″)−−−<annotation encoding="application / x-tex">N(R'')C(O) - - C(O)N(R'') - - N(R'')C(S) - - C(S)N(R'') - - -< / annotation>< / semantics>< / com:Math> [Image disponible dans le document PDF, Image available in the PDF document] OC(0)0-; R' and R'' are the same or different and are each a hydrogen atom or C1-C3 alkyl; and R<com:Sup>118< / com:Sup> and R<com:Sup>119< / com:Sup> are the same or different and are each optionally substituted linear or branched C1-C16 alkyl or C2-C16 alkenyl, formula (CL-X)

[0189] [Image disponible dans le document PDF, Image available in the PDF document] (CL-X) wherein X<com:Sup>117< / com:Sup> and X<com:Sup>118< / com:Sup> are the same or different and are each a hydrogen atom, optionally substituted C1-C6 alkyl, heterocyclyl or polyamine, or <com:Math><semantics>X117<annotation encoding="application / x-tex">X^{117}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X118<annotation encoding="application / x-tex">X^{118}< / annotation>< / semantics>< / com:Math> optionally form, ₩. E 1. together with the nitrogen to which they are bonded, a 4- to 7-membered monocyclic hetero ring optionally containing one or two additional heteroatoms selected from N, O and S in addition to the nitrogen; and R<com:Sup>120< / com:Sup> and R<com:Sup>121< / com:Sup> are the same or different and are each optionally substituted linear or branched C4-C24 alkyl or C4-C24 alkenyl, formula (CL-XI)

[0190] [Image disponible dans le document PDF, Image available in the PDF document] (CL-XI) wherein <com:Math><semantics>X119<annotation encoding="application / x-tex">X^{119}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X120<annotation encoding="application / x-tex">X^{120}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom, optionally substituted linear or branched C1-C20 alkyl, C1-C20 alkenyl, C1-C20 alkynyl or C6-C20 acyl; <com:Math><semantics>R122<annotation encoding="application / x-tex">R^{122}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R123<annotation encoding="application / x-tex">R^{123}< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted linear or branched C1-C30 alkyl, C2-C30 alkenyl or C2-C30 alkynyl; and p<com:Sup>112< / com:Sup>, p<com:Sup>113< / com:Sup> and p<com:Sup>114< / com:Sup> are the same or different and are each 0, or an arbitrary positive integer, formula (CL-XII)

[0191] [Image disponible dans le document PDF, Image available in the PDF document] (CL-XII) Ĺ, wherein <com:Math><semantics>𝑿121<annotation encoding="application / x-tex">\mathbf{X}^{121}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>𝑿122<annotation encoding="application / x-tex">\mathbf{X}^{122}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom, C1-C6 alkyl, cycloalkyl or cycloalkenyl, or <com:Math><semantics>X121<annotation encoding="application / x-tex">X^{121}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X122<annotation encoding="application / x-tex">X^{122}< / annotation>< / semantics>< / com:Math> optionally form a C2-C6 nitrogen- containing hetero ring together with the nitrogen atom to which they are bonded; L<com:Sup>120< / com:Sup> and L<com:Sup>121< / com:Sup> are the same or different and are each - <com:Math><semantics>0−<annotation encoding="application / x-tex">0-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−0C(0)−or<math>−(0)C0−<annotation encoding="application / x-tex">-0C(0) - or -(0)C0-< / annotation>< / semantics>< / com:Math>; and <com:Math><semantics>R124<annotation encoding="application / x-tex">R^{124}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R125<annotation encoding="application / x-tex">R^{125}< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted linear or branched C8-C24 alkyl or C8-C24 alkenyl, formula (CL-XIII)

[0192] [Image disponible dans le document PDF, Image available in the PDF document] (CL-XIII) wherein R<com:Sup>126< / com:Sup> and R<com:Sup>127< / com:Sup> are the same or different and are each optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl, C8-C24 alkynyl, C8-C24 heteroalkyl, C8- C24 heteroalkenyl or C8-C24 heteroalkynyl; X<com:Sup>123< / com:Sup> is a hydrogen atom or optionally substituted C1- C6 alkyl; X<com:Sup>124< / com:Sup> is C1-C6 alkyl, substituted C1-C6 alkyl which is substituted with -NR<com:Sup>4a< / com:Sup>R<com:Sup>4b< / com:Sup>, or optionally substituted C3-C7 heterocyclyl; • . K R<com:Sup>4a< / com:Sup> and R<com:Sup>4b< / com:Sup> are the same or different and are each a hydrogen atom, <com:Math><semantics>−C(=NH)NH2<annotation encoding="application / x-tex">-C(=NH)NH_2< / annotation>< / semantics>< / com:Math> or optionally substituted C1-C6 alkyl, or R<com:Sup>4a< / com:Sup> and R<com:Sup>4b< / com:Sup> optionally form optionally substituted C3-C7 heterocyclyl together with the nitrogen atom to which they are bonded; <com:Math><semantics>X123<annotation encoding="application / x-tex">X^{123}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X124<annotation encoding="application / x-tex">X^{124}< / annotation>< / semantics>< / com:Math> optionally form optionally substituted C3-C7 heterocyclyl together with the nitrogen atom to which they are bonded, provided that <com:Math><semantics>X123<annotation encoding="application / x-tex">X^{123}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X124<annotation encoding="application / x-tex">X^{124}< / annotation>< / semantics>< / com:Math> do not form imidazolyl, benzimidazolyl, or succinimidyl, and only one primary amine is allowed to be present on any one of <com:Math><semantics>X123<annotation encoding="application / x-tex">X^{123}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X124<annotation encoding="application / x-tex">X^{124}< / annotation>< / semantics>< / com:Math>, or any primary amine is not present on any one of <com:Math><semantics>X123<annotation encoding="application / x-tex">X^{123}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X124<annotation encoding="application / x-tex">X^{124}< / annotation>< / semantics>< / com:Math>, and neither <com:Math><semantics>X123<annotation encoding="application / x-tex">X^{123}< / annotation>< / semantics>< / com:Math> nor <com:Math><semantics>X124<annotation encoding="application / x-tex">X^{124}< / annotation>< / semantics>< / com:Math> is substituted amide; when each of <com:Math><semantics>R126<annotation encoding="application / x-tex">R^{126}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R127<annotation encoding="application / x-tex">R^{127}< / annotation>< / semantics>< / com:Math> is C11 alkyl or C15 alkyl, X<com:Sup>123< / com:Sup> is not a hydrogen atom; when each of <com:Math><semantics>R126<annotation encoding="application / x-tex">R^{126}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R127<annotation encoding="application / x-tex">R^{127}< / annotation>< / semantics>< / com:Math> is C16 alkyl or C17 alkyl, R<com:Sup>126< / com:Sup> and R<com:Sup>127< / com:Sup> are not substituted with OH; when each of <com:Math><semantics>R126<annotation encoding="application / x-tex">R^{126}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R127<annotation encoding="application / x-tex">R^{127}< / annotation>< / semantics>< / com:Math> is C17 alkyl, <com:Math><semantics>X123<annotation encoding="application / x-tex">X^{123}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X124<annotation encoding="application / x-tex">X^{124}< / annotation>< / semantics>< / com:Math> are not substituted with OH; and when each of <com:Math><semantics>R126<annotation encoding="application / x-tex">R^{126}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R127<annotation encoding="application / x-tex">R^{127}< / annotation>< / semantics>< / com:Math> is C18 alkyl, <com:Math><semantics>X124<annotation encoding="application / x-tex">X^{124}< / annotation>< / semantics>< / com:Math> is not substituted with optionally substituted imidazolyl, formula (CL-XIV)

[0193] ₩. $- L [Image disponible dans le document PDF, Image available in the PDF document] (CL-XIV) wherein <com:Math><semantics>𝑿125<annotation encoding="application / x-tex">\mathbf{X}^{125}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>𝑿126<annotation encoding="application / x-tex">\mathbf{X}^{126}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom, optionally substituted C1-C6 alkyl, heterocyclyl or polyamine, or <com:Math><semantics>X125<annotation encoding="application / x-tex">X^{125}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X126<annotation encoding="application / x-tex">X^{126}< / annotation>< / semantics>< / com:Math> optionally form, together with the nitrogen to which they are bonded, a 4- to 7-membered monocyclic hetero ring optionally containing one or two additional heteroatoms selected from N, O and S in addition to the nitrogen; R<com:Sup>130< / com:Sup> is a hydrogen atom or C1-C6 alkyl; R<com:Sup>128< / com:Sup> and R<com:Sup>129< / com:Sup> are the same or different and are each optionally substituted linear or branched C4-C24 alkyl or C4-C24 alkenyl; Y3 and Y4 are the same or different and are each an oxygen atom or <com:Math><semantics>CH2<annotation encoding="application / x-tex">CH_2< / annotation>< / semantics>< / com:Math>; and pl15 is an integer of 0 to 2, formula (CL-XV)

[0194] [Image disponible dans le document PDF, Image available in the PDF document] (CL-XV) wherein 2 <com:Math><semantics>𝑿127<annotation encoding="application / x-tex">\mathbf{X}^{127}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>𝑿128<annotation encoding="application / x-tex">\mathbf{X}^{128}< / annotation>< / semantics>< / com:Math> are the same or different and are each C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, or <com:Math><semantics>X127<annotation encoding="application / x-tex">X^{127}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X128<annotation encoding="application / x-tex">X^{128}< / annotation>< / semantics>< / com:Math> form, together with the nitrogen atom to which they are bonded, a hetero ring having one or two nitrogen atoms; [Image disponible dans le document PDF, Image available in the PDF document] <com:Math><semantics>−OC(O)O−<annotation encoding="application / x-tex">-OC(O)O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−OC(O)N(X130)−<annotation encoding="application / x-tex">-OC(O)N(X^{130})-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−N(X130)C(O)N(X130)−<annotation encoding="application / x-tex">-N(X^{130})C(O)N(X^{130})-< / annotation>< / semantics>< / com:Math>, or <com:Math><semantics>−<annotation encoding="application / x-tex">-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>N(X130)C(0)O−;<annotation encoding="application / x-tex">N(X^{130})C(0)O-;< / annotation>< / semantics>< / com:Math> each X<com:Sup>130< / com:Sup> present is independently a hydrogen atom or C1-C3 alkyl; a is 1, 2, 3, 4, 5, or 6; b is 0, 1, 2, or 3; <com:Math><semantics>X129<annotation encoding="application / x-tex">X^{129}< / annotation>< / semantics>< / com:Math> is absent, or hydrogen or C1-C3 alkyl; R<com:Sup>131< / com:Sup> and R<com:Sup>132< / com:Sup> are the same or different and are each alkyl having 12 to 24 carbon atoms, alkenyl having 12 to 24 carbon atoms, or alkoxy having 12 to 24 carbon atoms, which has one or more biodegradable groups; the biodegradable groups are each independently integrated in the alkyl group having 12 to 24 carbon atoms, the alkenyl group having 12 to 24 carbon atoms, or the alkoxy group having 12 to 24 carbon atoms, or present at a terminal of the alkyl group having 12 to 24 carbon atoms, the alkenyl group having 12 to 24 carbon atoms, or the alkoxy group having 12 to 24 carbon atoms, wherein the biodegradable group thus integrated is -C(0)0-, <com:Math><semantics>−OC(0)<annotation encoding="application / x-tex">-OC(0)< / annotation>< / semantics>< / com:Math> -, <com:Math><semantics>−C(0)N(X130)<annotation encoding="application / x-tex">-C(0)N(X^{130})< / annotation>< / semantics>< / com:Math> -, or <com:Math><semantics>−N(X130)C(0)<annotation encoding="application / x-tex">-N(X^{130})C(0)< / annotation>< / semantics>< / com:Math> -, and the group having the biodegradable group present at the terminal is [Image disponible dans le document PDF, Image available in the PDF document] alkyl, or <com:Math><semantics>−N(X130)C(0)−C1−C4<annotation encoding="application / x-tex">-N(X^{130})C(0)-C1-C4< / annotation>< / semantics>< / com:Math> alkyl; and R<com:Sup>131< / com:Sup> and R<com:Sup>132< / com:Sup> each have at least four carbon atoms between the biodegradable group and the asterisked (*) tertiary carbon atom, formula (CL-XVI)

[0195] [Image disponible dans le document PDF, Image available in the PDF document] wherein <com:Math><semantics>𝖱133<annotation encoding="application / x-tex">{\ensuremath{\mathsf{R}}}^{133}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>𝖱134<annotation encoding="application / x-tex">{\ensuremath{\mathsf{R}}}^{134}< / annotation>< / semantics>< / com:Math> are the same or different and are each linear or branched C1-C9 alkyl, C2-C11 alkenyl or C2-C11 alkynyl; <com:Math><semantics>𝙻123<annotation encoding="application / x-tex">\texttt{L}^{123}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>𝙻124<annotation encoding="application / x-tex">\texttt{L}^{124}< / annotation>< / semantics>< / com:Math> are the same or different and are each linear C5-C18 alkylene or linear C5-C18 alkenylene, or forms a hetero ring with N to which they are bonded; <com:Math><semantics>L125<annotation encoding="application / x-tex">L^{125}< / annotation>< / semantics>< / com:Math> is a single bond or -CO-O-, and when <com:Math><semantics>L125<annotation encoding="application / x-tex">L^{125}< / annotation>< / semantics>< / com:Math> is <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−L124−CO−OR134<annotation encoding="application / x-tex">-L^{124}-CO-OR^{134}< / annotation>< / semantics>< / com:Math> is formed; <com:Math><semantics>L127<annotation encoding="application / x-tex">L^{127}< / annotation>< / semantics>< / com:Math> is S or O; L<com:Sup>126< / com:Sup> is a single bond or linear or branched C1-C6 alkylene, or forms a hetero ring with N to which they are bonded via -C(0)-; L<com:Sup>128< / com:Sup> is linear or branched C1-C6 alkylene; and - <com:Math><semantics>𝑿131<annotation encoding="application / x-tex">\mathbf{X}^{131}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>𝑿132<annotation encoding="application / x-tex">\mathbf{X}^{132}< / annotation>< / semantics>< / com:Math> are the same or different and are each . . . . . . . . . . . . . . . . . . . . hydrogen or linear or branched C1-C6 alkyl, formula (CL-XVII)

[0196] [Image disponible dans le document PDF, Image available in the PDF document] wherein [Image disponible dans le document PDF, Image available in the PDF document] <com:Math><semantics>𝙻129<annotation encoding="application / x-tex">\texttt{L}^{129}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>𝙻130<annotation encoding="application / x-tex">\texttt{L}^{130}< / annotation>< / semantics>< / com:Math> are the same or different and are each C1-C6 alkyl; R<com:Sup>135< / com:Sup> and R<com:Sup>136< / com:Sup> are the same or different and are each C10-C30 alkyl or C10-C30 alkenyl; and <com:Math><semantics>𝑿133<annotation encoding="application / x-tex">\mathbf{X}^{133}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>𝑿134<annotation encoding="application / x-tex">\mathbf{X}^{134}< / annotation>< / semantics>< / com:Math> are the same or different and are each hydrogen, C1-C6 alkyl or -CH2CH2OH, formula (CL-XVIII)

[0197] [Image disponible dans le document PDF, Image available in the PDF document]

[0198] wherein R<com:Sup>137< / com:Sup> and R<com:Sup>138< / com:Sup> are the same or different and are each 4 - 4 - 4 - 4 - 4 - 4 - 4 - 4 - 4 - 4 - linear or branched C8-C24 alkyl, C8-C24 alkenyl, C8-C24 alkynyl, C8-C24 alkylthioethyl, C8-24 alkenylthioethyl, or C8-C24 alkynylthioethyl; X<com:Sup>135< / com:Sup> is a hydrogen atom, C1-C3 alkyl, hydroxy C2-C4 alkyl, formula (C): [Image disponible dans le document PDF, Image available in the PDF document] wherein <com:Math><semantics>X136<annotation encoding="application / x-tex">X^{136}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X137<annotation encoding="application / x-tex">X^{137}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or C1-C3 alkyl, or <com:Math><semantics>X136<annotation encoding="application / x-tex">X^{136}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X137<annotation encoding="application / x-tex">X^{137}< / annotation>< / semantics>< / com:Math> optionally form a C2-C6 nitrogen-containing hetero ring together with the nitrogen atom to which they are bonded; <com:Math><semantics>L132<annotation encoding="application / x-tex">L^{132}< / annotation>< / semantics>< / com:Math> is S or O; and <com:Math><semantics>p115<annotation encoding="application / x-tex">p^{115}< / annotation>< / semantics>< / com:Math> is an integer from 2 to 4, formula (D): [Image disponible dans le document PDF, Image available in the PDF document] (D) wherein <com:Math><semantics>X138<annotation encoding="application / x-tex">X^{138}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X139<annotation encoding="application / x-tex">X^{139}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or C1 to C3 alkyl, or <com:Math><semantics>X138<annotation encoding="application / x-tex">X^{138}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X139<annotation encoding="application / x-tex">X^{139}< / annotation>< / semantics>< / com:Math> optionally form a C3-C6 nitrogen-containing hetero ring together with the nitrogen atom to which they are bonded; and <com:Math><semantics>p116<annotation encoding="application / x-tex">p^{116}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 4, or formula (E): [Image disponible dans le document PDF, Image available in the PDF document] * 3 A (E) wherein <com:Math><semantics>𝑿140<annotation encoding="application / x-tex">\mathbf{X}^{140}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>𝑿141<annotation encoding="application / x-tex">\mathbf{X}^{141}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or C1 to C3 alkyl, or <com:Math><semantics>X140<annotation encoding="application / x-tex">X^{140}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X141<annotation encoding="application / x-tex">X^{141}< / annotation>< / semantics>< / com:Math> optionally form a C3-C6 nitrogen-containing hetero ring together with the nitrogen atom to which they are bonded; and <com:Math><semantics>p117<annotation encoding="application / x-tex">p^{117}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 4, and formula (CL-XIX)

[0199] [Image disponible dans le document PDF, Image available in the PDF document] wherein <com:Math><semantics>R139<annotation encoding="application / x-tex">R^{139}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R140<annotation encoding="application / x-tex">R^{140}< / annotation>< / semantics>< / com:Math> are the same or different and are each linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; <com:Math><semantics>L133<annotation encoding="application / x-tex">L^{133}< / annotation>< / semantics>< / com:Math> is S or O; and X<com:Sup>142< / com:Sup> is a hydrogen atom, C1-C3 alkyl, hydroxy C2-C4 alkyl, formula (F): [Image disponible dans le document PDF, Image available in the PDF document] (F) wherein <com:Math><semantics>X143<annotation encoding="application / x-tex">X^{143}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X144<annotation encoding="application / x-tex">X^{144}< / annotation>< / semantics>< / com:Math> are the same or different and are 1 - 1 - K each a hydrogen atom or C1-C3 alkyl, or <com:Math><semantics>X143<annotation encoding="application / x-tex">X^{143}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X144<annotation encoding="application / x-tex">X^{144}< / annotation>< / semantics>< / com:Math> optionally form a C2-C6 nitrogen-containing hetero ring together with the nitrogen atom to which they are bonded; <com:Math><semantics>L134<annotation encoding="application / x-tex">L^{134}< / annotation>< / semantics>< / com:Math> is S or O; and <com:Math><semantics>p118<annotation encoding="application / x-tex">p^{118}< / annotation>< / semantics>< / com:Math> is an integer from 2 to 4, or formula (G): [Image disponible dans le document PDF, Image available in the PDF document] (G) wherein <com:Math><semantics>X145<annotation encoding="application / x-tex">X^{145}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X146<annotation encoding="application / x-tex">X^{146}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or C1 to C3 alkyl, or <com:Math><semantics>X145<annotation encoding="application / x-tex">X^{145}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X146<annotation encoding="application / x-tex">X^{146}< / annotation>< / semantics>< / com:Math> optionally form a C3-C6 nitrogen-containing hetero ring together with the nitrogen atom to which they are bonded; and p<com:Sup>119< / com:Sup> is an integer from 1 to 4.

[0201] One aspect of the present invention provides a compound represented by formula (CL-XVIII) or (CL-XIX), or a pharmaceutically acceptable salt thereof. In the compound represented by formula (CL-XVIII) or (CL-XIX) of the present invention, a hydrogen ion may be coordinated on a lone pair of electrons on the nitrogen atom in the structure. In this case, the hydrogen ion may form a salt with a pharmaceutically acceptable anion. In the present invention, the compound represented by formula (CL-XVIII) or (CL-XIX), or the pharmaceutically acceptable salt thereof also encompasses a cationic lipid in which a hydrogen ion may be coordinated on a lone pair 1 . . . . . . . . . . . . . . . . . . . of electrons on the nitrogen atom in the structure. In the present invention, examples of the pharmaceutically acceptable anion include: inorganic ions such as chloride ions, bromide ions, nitrate ions, sulfate ions and phosphate ions; and organic acid ions such as acetate ions, oxalate ions, maleate ions, fumarate ions, citrate ions, benzoate ions and methanesulfonate ions. Examples of the pharmaceutically acceptable salt of the compound represented by formula (CL-XVIII) or (CL- XIX) of the present invention include hydrochloride, bromate, nitrate, sulfate, phosphate, acetate, oxalate, maleate, fumarate, citrate, benzoate and methanesulfonate. Some compounds represented by formula (CL-XVIII) or (CL-XIX) of the present invention may have stereoisomers such as geometric isomers and optical isomers, tautomers, or the like. Compound (I) of the present invention encompasses all possible isomers including them, and mixtures thereof. Some or all of the atoms in formula (CL-XVIII) or (CL-XIX) of the present invention may be replaced with their corresponding isotopic atoms. The compound represented by formula (CL-XVIII) or (CL-XIX) also encompasses such a compound containing isotopic atoms replaced therefor. For example, some or all of the hydrogen atoms in compound (I) may each be a hydrogen * * atom having an atomic weight of 2 (deuterium atom). The compound derived from formula (CL-XVIII) or (CL- XIX) of the present invention by the replacement of some or all of the atoms with their corresponding isotopic atoms can be produced in the same way as in each production method described above by using commercially available building blocks. The compound derived from formula (CL-XVIII) or (CL-XIX) by the replacement of some or all of the hydrogen atoms with deuterium atoms can also be produced by use of, for example, a method which involves deuterating an alcohol, a carboxylic acid, or the like using an iridium complex as a catalyst and heavy water as a deuterium source [see J. Am. Chem. Soc., Vol. 124, No. 10, 2092 (2002)].

[0202] In the definition of each group in formula (CL-I), examples of the linear or branched C10-C24 alkyl include decyl, undecyl, dodecyl, tridecyl, 6,10-dimethylundec-2- yl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, 6,10,14-trimethylpentadecan-2-yl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl and tetracosyl, preferably decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl and octadecyl, more preferably tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl and octadecyl.

[0203] The linear or branched C10-C24 alkenyl can be linear * * * or branched C10-C24 alkenyl containing one to three double bonds. Examples thereof include (Z)-dodec-7-enyl, (Z)-tetradec-7-enyl, (Z)-tetradec-9-enyl, (Z)-hexadec-4- enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-hexadec-7-enyl, <com:Math><semantics>(E)<annotation encoding="application / x-tex">(E)< / annotation>< / semantics>< / com:Math>-hexadec-7-enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>- hexadec-9-enyl, (7Z,10Z)-hexadeca-7,10-dienyl, (7Z, 10Z, 13Z) -hexadeca-7, 10, 13-trienyl, (Z) -octadec-6-enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-octadec-9-enyl, <com:Math><semantics>(E)<annotation encoding="application / x-tex">(E)< / annotation>< / semantics>< / com:Math>-octadec-9-enyl, <com:Math><semantics>(9Z,12Z)<annotation encoding="application / x-tex">(9Z,12Z)< / annotation>< / semantics>< / com:Math>- octadeca-9,12-dienyl, (Z)-octadec-11-enyl, (9Z,12Z,15Z)- octadeca-9,12,15-trienyl, (Z)-icos-11-enyl and (11Z,14Z)- icosa-11,14-dienyl, preferably (Z)-dodec-7-enyl, (Z)- tetradec-7-enyl, (Z)-hexadec-4-enyl, (Z)-hexadec-7-enyl, <com:Math><semantics>(E)<annotation encoding="application / x-tex">(E)< / annotation>< / semantics>< / com:Math>-hexadec-7-enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-hexadec-9-enyl, <com:Math><semantics>(7Z,10Z)<annotation encoding="application / x-tex">(7Z,10Z)< / annotation>< / semantics>< / com:Math>- hexadeca-7,10-dienyl, (7Z,10Z,13Z)-hexadeca-7,10,13- trienyl, (Z)-octadec-9-enyl, (9Z,12Z)-octadeca-9,12- dienyl and (11Z,14Z)-icosa-11,14-dienyl, more preferably <com:Math><semantics>(7Z,10Z)<annotation encoding="application / x-tex">(7Z, 10Z)< / annotation>< / semantics>< / com:Math>-hexadeca-7,10-dienyl and <com:Math><semantics>(9Z,12Z)<annotation encoding="application / x-tex">(9Z, 12Z)< / annotation>< / semantics>< / com:Math>-octadeca-9,12- dienyl.

[0204] The linear or branched C10-C24 alkynyl can be linear or branched C10-C24 alkynyl containing one to three triple bonds. Examples thereof include dec-9-ynyl, dodec-4-ynyl, dodec-11-ynyl, tetradec-5-ynyl, tetradec-6- ynyl, hexadec-7-ynyl, hexadeca-3,5-diynyl, hexadeca-5,7- diynyl and octadec-9-ynyl, preferably hexadec-7-ynyl and octadec-9-ynyl, more preferably octadec-9-ynyl.

[0205] In formula (CL-I), <com:Math><semantics>R101<annotation encoding="application / x-tex">R^{101}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R103<annotation encoding="application / x-tex">R^{103}< / annotation>< / semantics>< / com:Math> are preferably the 1 c 1 same linear or branched C10-C24 alkyl, C10-C24 alkenyl or C10-C24 alkynyl, more preferably the same linear or branched C10-C24 alkyl or C10-C24 alkenyl, further preferably the same linear C10-C24 alkenyl.

[0206] Examples of the C1-C3 alkylene include methylene, ethylene and propylene, preferably methylene and ethylene, more preferably methylene.

[0207] Examples of the C1-C6 alkyl include methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, isobutyl, sec- butyl, tert-butyl, cyclobutyl, cyclopropylmethyl, pentyl, isopentyl, sec-pentyl, neopentyl, tert-pentyl, cyclopentyl, hexyl and cyclohexyl, preferably methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl and hexyl, more preferably methyl, ethyl and propyl.

[0208] Examples of the C3-C6 alkenyl include allyl, 1- propenyl, butenyl, pentenyl and hexenyl, preferably allyl.

[0209] Each of the monoalkylamino and the dialkylamino can be amino substituted with one or two same or different C1-C6 alkyl (as defined above) groups, or C1-C6 alkyl (as defined above) substituted with amino, methylamino, ethylamino, dimethylamino, diethylamino, pyrrolidinyl, , e , * piperidyl or morpholinyl. Examples thereof include methylamino, ethylamino, propylamino, butylamino, pentylamino, hexylamino, dimethylamino, diethylamino, ethylmethylamino, methylpropylamino, butylmethylamino, methylpentylamino, hexylmethylamino, aminoethylamino, aminopropylamino, (aminoethyl) methylamino and bis (aminoethyl) amino, preferably methylamino, ethylamino, dimethylamino, diethylamino, aminopropylamino and bis (aminoethyl) amino, more preferably methylamino and dimethylamino.

[0210] The trialkylammonio can be ammonio substituted by three same or different C1-C6 alkyl (as defined above) groups, or C1-C6 alkyl (as defined above) substituted with amino, methylamino, ethylamino, dimethylamino, diethylamino, pyrrolidinyl, piperidyl or morpholinyl. Examples thereof include trimethylammonio, ethyldimethylammonio, diethylmethylammonio, triethylammonio, tripropylammonio, tributylammonio, tripentylammonio, trihexylammonio, tris(aminoethyl)ammonio, (aminoethyl)dimethylammonio and bis (aminoethyl) methylammonio, preferably trimethylammonio, triethylammonio, tris(aminoethyl)ammonio, (aminoethyl) dimethylammonio and bis (aminoethyl) methylammonio, more preferably trimethylammonio.

[0211] . . In compound (CL-I), the trialkylammonio may form a salt with a pharmaceutically acceptable anion (as defined above).

[0212] The alkoxy can be hydroxy substituted with C1-C6 alkyl (as defined above) or C1-C6 alkyl (as defined above) substituted with amino, methylamino, ethylamino, dimethylamino, diethylamino, pyrrolidinyl, piperidyl or morpholinyl. Examples thereof include methoxy, ethoxy, propyloxy, butyloxy, pentyloxy, hexyloxy, aminoethoxy and methylaminoethoxy, preferably methoxy, ethoxy, aminoethoxy and methylaminoethoxy, more preferably methoxy.

[0213] Each of the monoalkylcarbamoyl and the dialkylcarbamoyl can be carbamoyl substituted with one or two same or different C1-C6 alkyl (as defined above) groups, or C1-C6 alkyl (as defined above) substituted with amino, methylamino, ethylamino, dimethylamino, diethylamino, pyrrolidinyl, piperidyl or morpholinyl. Examples thereof include methylcarbamoyl, ethylcarbamoyl, propylcarbamoyl, butylcarbamoyl, pentylcarbamoyl, hexylcarbamoyl, dimethylcarbamoyl, diethylcarbamoyl, ethylmethylcarbamoyl, methylpropylcarbamoyl, butylmethylcarbamoyl, methylpentylcarbamoyl, hexylmethylcarbamoyl, aminoethylcarbamoyl, aminopropylcarbamoyl, (aminoethyl) methylcarbamoyl and • bis (aminoethyl) carbamoyl, preferably methylcarbamoyl, ethylcarbamoyl and dimethylcarbamoyl, more preferably methylcarbamoyl and dimethylcarbamoyl.

[0214] Each of <com:Math><semantics>L101<annotation encoding="application / x-tex">L^{101}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L102<annotation encoding="application / x-tex">L^{102}< / annotation>< / semantics>< / com:Math> is more preferably a hydrogen atom. In this case, R<com:Sup>101< / com:Sup> and R<com:Sup>102< / com:Sup> are the same or different and are each preferably dodecyl, tetradecyl, (Z)-dodec-7-enyl, (Z)-tetradec-7-enyl, (Z)-hexadec-4-enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-hexadec-7-enyl, <com:Math><semantics>(E)<annotation encoding="application / x-tex">(E)< / annotation>< / semantics>< / com:Math>-hexadec-7-enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-hexadec-9- enyl, (7Z,10Z)-hexadeca-7,10-dienyl, (7Z,10Z,13Z)- hexadeca-7,10,13-trienyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-octadec-9-enyl or <com:Math><semantics>(9Z,12Z)<annotation encoding="application / x-tex">(9Z,12Z)< / annotation>< / semantics>< / com:Math>- octadeca-9,12-dienyl, more preferably (Z)-tetradec-7-enyl, (Z)-hexadec-7-enyl, (7Z,10Z)-hexadeca-7,10-dienyl or (9Z,12Z)-octadeca-9,12-dienyl, further preferably are the same and (Z)-tetradec-7-enyl, (Z)-hexadec-7-enyl, (7Z,10Z)-hexadeca-7,10-dienyl or (9Z,12Z)-octadeca-9,12- dienyl. When each of <com:Math><semantics>L101<annotation encoding="application / x-tex">L^{101}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L102<annotation encoding="application / x-tex">L^{102}< / annotation>< / semantics>< / com:Math> is a hydrogen atom, <com:Math><semantics>X101<annotation encoding="application / x-tex">X^{101}< / annotation>< / semantics>< / com:Math> is more preferably a hydrogen atom, methyl, pyrrolidin-3-yl, piperidin-3-yl, piperidin-4-yl, or C1-C6 alkyl or C3-C6 alkenyl substituted with one to three same or different substituents selected from amino, monoalkylamino, dialkylamino, trialkylammonio, hydroxy, alkoxy, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, pyrrolidinyl, piperidyl and morpholinyl, further preferably a hydrogen atom, methyl, or C1-C6 alkyl or C3-C6 alkenyl substituted with one to three same or different substituents selected * c } * from amino, hydroxy and carbamoyl, still further preferably a hydrogen atom, methyl or the like.

[0215] When <com:Math><semantics>L101<annotation encoding="application / x-tex">L^{101}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L102<annotation encoding="application / x-tex">L^{102}< / annotation>< / semantics>< / com:Math> together form a single bond or C1- C3 alkylene, <com:Math><semantics>R101<annotation encoding="application / x-tex">R^{101}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R102<annotation encoding="application / x-tex">R^{102}< / annotation>< / semantics>< / com:Math> are the same or different and are each preferably tetradecyl, hexadecyl, (Z)-tetradec- 9-enyl, (Z)-hexadec-9-enyl, (Z)-octadec-6-enyl, (Z)- octadec-9-enyl, (E)-octadec-9-enyl, (Z)-octadec-11-enyl, (9Z,12Z)-octadeca-9,12-dienyl, (9Z,12Z,15Z)-octadeca- 9,12,15-trienyl, (Z)-icos-11-enyl, or (11Z,14Z)-icosa- 11,14-dienyl, more preferably (Z)-octadec-9-enyl or (9Z,12Z)-octadeca-9,12-dienyl, further preferably are the same and (Z)-octadec-9-enyl or (9Z,12Z)-octadeca-9,12- dienyl.

[0216] When <com:Math><semantics>L101<annotation encoding="application / x-tex">L^{101}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L102<annotation encoding="application / x-tex">L^{102}< / annotation>< / semantics>< / com:Math> together form a single bond or C1- C3 alkylene, X<com:Sup>101< / com:Sup> is more preferably a hydrogen atom, methyl, pyrrolidin-3-yl, piperidin-3-yl, piperidin-4-yl, or C1-C6 alkyl or C3-C6 alkenyl substituted with one to three same or different substituents selected from amino, monoalkylamino, dialkylamino, trialkylammonio, hydroxy, alkoxy, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, pyrrolidinyl, piperidyl and morpholinyl, further preferably a hydrogen atom, methyl, or C1-C6 alkyl or C3- C6 alkenyl substituted with one to three same or different substituents selected from amino, hydroxy and carbamoyl, most preferably a hydrogen atom, methyl or the A TOTAL TOTAL like.

[0217] In another more preferred mode of the present invention, when <com:Math><semantics>L101<annotation encoding="application / x-tex">L^{101}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L102<annotation encoding="application / x-tex">L^{102}< / annotation>< / semantics>< / com:Math> together form a single bond, <com:Math><semantics>L103<annotation encoding="application / x-tex">L^{103}< / annotation>< / semantics>< / com:Math> is -CO- or -CO-O-, preferably -CO-. In this case, <com:Math><semantics>X101<annotation encoding="application / x-tex">X^{101}< / annotation>< / semantics>< / com:Math> is preferably aminomethyl, 1,2-diaminoethyl, 2- aminoethyl, 1,3-diaminopropyl, 1,4-diaminobutyl, 1,5- diaminopentyl, 3-aminopropyl, 4-aminobutyl, 5-aminopentyl or the like, more preferably 1,2-diaminoethyl, 1,3- diaminopropyl, 1,4-diaminobutyl or 1,5-diaminopentyl. R<com:Sup>101< / com:Sup> and R<com:Sup>102< / com:Sup> are the same or different and are each preferably tetradecyl, hexadecyl, (Z)-tetradec-9-enyl, (Z)-hexadec-9-enyl, (Z)-octadec-6-enyl, (Z)-octadec-9- enyl, <com:Math><semantics>(E)<annotation encoding="application / x-tex">(E)< / annotation>< / semantics>< / com:Math>-octadec-9-enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-octadec-11-enyl, <com:Math><semantics>(9Z,12Z)<annotation encoding="application / x-tex">(9Z,12Z)< / annotation>< / semantics>< / com:Math>- octadeca-9,12-dienyl, (9Z,12Z,15Z)-octadeca-9,12,15- trienyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-icos-11-enyl or <com:Math><semantics>(11Z,14Z)<annotation encoding="application / x-tex">(11Z,14Z)< / annotation>< / semantics>< / com:Math>-icosa-11,14-dienyl, more preferably (Z)-octadec-9-enyl or (9Z,12Z)-octadeca- 9,12-dienyl, further preferably are the same and (Z)- octadec-9-enyl or (9Z,12Z)-octadeca-9,12-dienyl.

[0218] L<com:Sup>103< / com:Sup> is more preferably a single bond.

[0219] When <com:Math><semantics>L103<annotation encoding="application / x-tex">L^{103}< / annotation>< / semantics>< / com:Math> is a single bond, <com:Math><semantics>X101<annotation encoding="application / x-tex">X^{101}< / annotation>< / semantics>< / com:Math> is more preferably a hydrogen atom, methyl, pyrrolidin-3-yl, piperidin-3-yl, piperidin-4-yl, or C1-C6 alkyl or C3-C6 alkenyl substituted with one to three same or different substituents selected from amino, monoalkylamino, * * * dialkylamino, trialkylammonio, hydroxy, alkoxy, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, pyrrolidinyl, piperidyl and morpholinyl, or the like, further preferably a hydrogen atom, methyl, hydroxymethyl, 2- hydroxyethyl, 2,3-dihydroxypropyl, 2-hydroxypropyl, 3- hydroxypropyl, 2-hydroxy-3-methoxypropyl, aminomethyl, 2- aminoethyl, 3-aminopropyl, 4-aminobutyl, 5-aminopentyl, 2-(N, N-dimethylamino) ethyl, 3-(N, N-dimethylamino) propyl, 2-carbamoylethyl, 2-dimethylcarbamoylethyl, 1- methylpiperidin-4-yl or the like, most preferably a hydrogen atom or methyl.

[0220] When <com:Math><semantics>L103<annotation encoding="application / x-tex">L^{103}< / annotation>< / semantics>< / com:Math> is -CO- or -CO-O-, more preferably, <com:Math><semantics>X101<annotation encoding="application / x-tex">X^{101}< / annotation>< / semantics>< / com:Math> is pyrrolidin-3-yl, piperidin-3-yl, piperidin-4-yl, or C1-C6 alkyl or C3-C6 alkenyl substituted with one to three same or different substituents selected from amino, monoalkylamino, dialkylamino, trialkylammonio, hydroxy, alkoxy, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, pyrrolidinyl, piperidyl and morpholinyl, and at least one of the substituents is amino, monoalkylamino, dialkylamino, trialkylammonio, pyrrolidinyl, piperidyl, morpholinyl or the like. R<com:Sup>3< / com:Sup> is further preferably aminomethyl, 1,2-diaminoethyl, 2-aminoethyl, 1,3- diaminopropyl, 3-aminopropyl, 1,4-diaminobutyl, 4- aminobutyl, 1,5-diaminopentyl, 5-aminopentyl, (N,N- dimethylamino) methyl, 2-(N, N-dimethylamino) ethyl, 3-(N, N- dimethylamino) propyl, 1-hydroxy-2-aminoethyl, 1-amino-2- 4 4 T hydroxyethyl or the like, most preferably 1,2- diaminoethyl, 2-aminoethyl, 1,3-diaminopropyl, 3- aminopropyl, 1,4-diaminobutyl, 4-aminobutyl, 1,5- diaminopentyl, 5-aminopentyl or the like.

[0221] In an alternative more preferred mode of the present invention, <com:Math><semantics>L103<annotation encoding="application / x-tex">L^{103}< / annotation>< / semantics>< / com:Math> is a single bond, and <com:Math><semantics>X101<annotation encoding="application / x-tex">X^{101}< / annotation>< / semantics>< / com:Math> is a hydrogen atom. In this case, <com:Math><semantics>R101<annotation encoding="application / x-tex">R^{101}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R102<annotation encoding="application / x-tex">R^{102}< / annotation>< / semantics>< / com:Math> are the same or different and are each preferably dodecyl, tetradecyl, (Z)-dodec-7-enyl, (Z)-tetradec-7-enyl, (Z)-hexadec-4-enyl, (Z)-hexadec-7-enyl, (E)-hexadec-7-enyl, (Z)-hexadec-9- enyl, (7Z,10Z)-hexadeca-7,10-dienyl, (7Z,10Z,13Z)- hexadeca-7,10,13-trienyl, (Z)-octadec-9-enyl or (9Z,12Z)- octadeca-9,12-dienyl, more preferably are the same or different and are each (Z)-tetradec-7-enyl or (7Z,10Z)- hexadeca-7,10-dienyl, further preferably are the same and <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-tetradec-7-enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-hexadec-7-enyl or <com:Math><semantics>(7Z,10Z)<annotation encoding="application / x-tex">(7Z,10Z)< / annotation>< / semantics>< / com:Math>- hexadeca-7,10-dienyl.

[0222] In an alternative more preferred mode of the present invention, <com:Math><semantics>L103<annotation encoding="application / x-tex">L^{103}< / annotation>< / semantics>< / com:Math> is a single bond, and <com:Math><semantics>X101<annotation encoding="application / x-tex">X^{101}< / annotation>< / semantics>< / com:Math> is methyl. In this case, R<com:Sup>101< / com:Sup> and R<com:Sup>102< / com:Sup> are the same or different and are each preferably dodecyl, tetradecyl, (Z)-dodec-7-enyl, (Z)-tetradec-7-enyl, (Z)-hexadec-4-enyl, (Z)-hexadec-7- enyl, <com:Math><semantics>(E)<annotation encoding="application / x-tex">(E)< / annotation>< / semantics>< / com:Math>-hexadec-7-enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-hexadec-9-enyl, <com:Math><semantics>(7Z,10Z)<annotation encoding="application / x-tex">(7Z,10Z)< / annotation>< / semantics>< / com:Math>- hexadeca-7,10-dienyl, (7Z,10Z,13Z)-hexadeca-7,10,13- trienyl, (Z)-octadec-9-enyl or (9Z,12Z)-octadeca-9,12- * * dienyl, more preferably are the same or different and are each (Z)-tetradec-7-enyl, (7Z,10Z)-hexadeca-7,10-dienyl or (9Z,12Z)-octadeca-9,12-dienyl, further preferably are the same and (Z)-tetradec-7-enyl, (7Z,10Z)-hexadeca-7,10- dienyl or (9Z,12Z)-octadeca-9,12-dienyl.

[0223] In the definition of each group in formula (CL-II), examples of the linear or branched C12-C24 alkyl include dodecyl, tridecyl, tetradecyl, 2,6,10-trimethylundecyl, pentadecyl, 3,7,11-trimethyldodecyl, hexadecyl, heptadecyl, octadecyl, 6,10,14-trimethylpentadecan-2-yl, nonadecyl, 2,6,10,14-tetramethylpentadecyl, icosyl, 3,7,11,15-tetramethylhexadecyl, henicosyl, docosyl, tricosyl and tetracosyl, preferably dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and icosyl, more preferably dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl and octadecyl.

[0224] The linear or branched C12-C24 alkenyl can be linear or branched C12-C24 alkenyl containing one to three double bonds. Examples thereof include (Z)-tridec-8-enyl, (Z)-tetradec-9-enyl, (Z)-pentadec-8-enyl, (Z)-hexadec-9- enyl, (Z)-heptadec-5-enyl, (Z)-octadec-6-enyl, (Z)- heptadec-8-enyl, (Z)-octadec-9-enyl, (E)-heptadec-8-enyl, (E)-octadec-9-enyl, (Z)-heptadec-10-enyl, (Z)-octadec-11- enyl, (8Z,11Z)-heptadeca-8,11-dienyl, (9Z,12Z)-octadeca- * * * * * * * * * * * * * * * * * * * 9,12-dienyl, (8Z,11Z,14Z)-octadeca-8,11,14-trienyl, <com:Math><semantics>(9Z,12Z,15Z)<annotation encoding="application / x-tex">(9Z, 12Z, 15Z)< / annotation>< / semantics>< / com:Math> -octadeca-9, 12, 15-trienyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math> -nonadec-10- enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-icos-11-enyl, <com:Math><semantics>(10Z,13Z)<annotation encoding="application / x-tex">(10Z,13Z)< / annotation>< / semantics>< / com:Math>-nonadeca-10,13-dienyl, (11Z,14Z)-icosa-11,14-dienyl, 2,6,10-trimethylundeca- 1,5,9-trienyl, 3,7,11-trimethyldodeca-2,6,10-trienyl, 2,6,10,14-tetramethylpentadec-1-enyl and 3,7,11,15- tetramethylhexadec-2-enyl, preferably (Z)-pentadec-8-enyl, (Z)-hexadec-9-enyl, (Z)-heptadec-5-enyl, (Z)-octadec-6- enyl, (Z)-heptadec-8-enyl, (Z)-octadec-9-enyl, (8Z,11Z)- heptadeca-8,11-dienyl and (9Z,12Z)-octadeca-9,12-dienyl, more preferably (Z)-heptadec-8-enyl, (Z)-octadec-9-enyl, (8Z,11Z)-heptadeca-8,11-dienyl and (9Z,12Z)-octadeca- 9,12-dienyl.

[0225] The linear or branched C12-C24 alkynyl can be linear or branched C12-C24 alkynyl containing one to three triple bonds. Examples thereof include dodec-11-ynyl, tridec-12-ynyl, pentadec-6-ynyl, hexadec-7-ynyl, pentadeca-4,6-diynyl, hexadeca-5,7-diynyl, heptadec-8- ynyl and octadec-9-ynyl, preferably pentadec-6-ynyl, hexadec-7-ynyl, pentadeca-4,6-diynyl, hexadeca-5,7-diynyl, heptadec-8-ynyl and octadec-9-ynyl, more preferably heptadec-8-ynyl and octadec-9-ynyl.

[0226] In the definition of each group in formula (CL-II), r , • 1 the C1-C3 alkylene, the C1-C6 alkyl and the C3-C6 alkenyl are each as defined above in formula (CL-I).

[0227] The monoalkylamino, the dialkylamino, the trialkylammonio, the alkoxy, the monoalkylcarbamoyl and the dialkylcarbamoyl are each as defined above in formula <com:Math><semantics>(CL−I)<annotation encoding="application / x-tex">(CL-I)< / annotation>< / semantics>< / com:Math>.

[0228] R<com:Sup>103< / com:Sup> and R<com:Sup>104< / com:Sup> are preferably the same linear or branched C12-C24 alkyl, C12-C24 alkenyl or C12-C24 alkynyl, more preferably the same linear or branched C12- C24 alkyl or C12-C24 alkenyl.

[0229] <com:Math><semantics>L104<annotation encoding="application / x-tex">L^{104}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L105<annotation encoding="application / x-tex">L^{105}< / annotation>< / semantics>< / com:Math> are more preferably the same and -O-, - CO-O- or -O-CO-.

[0230] When at least one of <com:Math><semantics>L104<annotation encoding="application / x-tex">L^{104}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L105<annotation encoding="application / x-tex">L^{105}< / annotation>< / semantics>< / com:Math> is -O- or -O-CO-, R<com:Sup>103< / com:Sup> and R<com:Sup>104< / com:Sup> are the same or different and are each more preferably dodecyl, tetradecyl, hexadecyl, octadecyl, icosyl, docosyl, tetracosyl, (Z)-tetradec-9-enyl, (Z)- hexadec-9-enyl, (Z)-octadec-6-enyl, (Z)-octadec-9-enyl, <com:Math><semantics>(E)<annotation encoding="application / x-tex">(E)< / annotation>< / semantics>< / com:Math>-octadec-9-enyl, <com:Math><semantics>(Z)<annotation encoding="application / x-tex">(Z)< / annotation>< / semantics>< / com:Math>-octadec-11-enyl, <com:Math><semantics>(9Z,12Z)<annotation encoding="application / x-tex">(9Z,12Z)< / annotation>< / semantics>< / com:Math>- octadeca-9,12-dienyl, (9Z,12Z,15Z)-octadeca-9,12,15- trienyl, (Z)-icos-11-enyl, (11Z,14Z)-icosa-11,14-dienyl, 3,7,11-trimethyldodeca-2,6,10-trienyl or 3,7,11,15- tetramethylhexadec-2-enyl, further preferably tetradecyl, hexadecyl, octadecyl, (Z)-hexadec-9-enyl, (Z)-octadec-6- * 1 * 4 [Image disponible dans le document PDF, Image available in the PDF document]

[0231] When at least one of <com:Math><semantics>L104<annotation encoding="application / x-tex">L^{104}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L105<annotation encoding="application / x-tex">L^{105}< / annotation>< / semantics>< / com:Math> is -CO-O-, each of <com:Math><semantics>R103<annotation encoding="application / x-tex">R^{103}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R104<annotation encoding="application / x-tex">R^{104}< / annotation>< / semantics>< / com:Math> is more preferably tridecyl, pentadecyl, heptadecyl, nonadecyl, henicosyl, tricosyl, (Z)-tridec-8- enyl, (Z)-pentadec-8-enyl, (Z)-heptadec-5-enyl, (Z)- heptadec-8-enyl, (E)-heptadec-8-enyl, (Z)-heptadec-10- enyl, (8Z,11Z)-heptadeca-8,11-dienyl, (8Z,11Z,14Z)- octadeca-8,11,14-trienyl, (Z)-nonadec-10-enyl, (10Z,13Z)- nonadeca-10,13-dienyl, (11Z,14Z)-icosa-11,14-dienyl, 2,6,10-trimethylundeca-1,5,9-trienyl or 2,6,10,14- tetramethylpentadec-1-enyl, further preferably tridecyl, pentadecyl, heptadecyl, (Z)-pentadec-8-enyl, (Z)- heptadec-5-enyl, (Z)-heptadec-8-enyl or (8Z,11Z)- heptadeca-8,11-dienyl.

[0232] p<com:Sup>101< / com:Sup> and p<com:Sup>102< / com:Sup> are more preferably 0 or 1 at the same time.

[0233] L<com:Sup>106< / com:Sup> and L<com:Sup>107< / com:Sup> more preferably together form a single bond or C1-C3 alkylene. When <com:Math><semantics>L106<annotation encoding="application / x-tex">L^{106}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L107<annotation encoding="application / x-tex">L^{107}< / annotation>< / semantics>< / com:Math> together form a single bond or <com:Math><semantics>C1−C3<annotation encoding="application / x-tex">C1-C3< / annotation>< / semantics>< / com:Math> alkylene, <com:Math><semantics>X102<annotation encoding="application / x-tex">X^{102}< / annotation>< / semantics>< / com:Math> is more preferably a hydrogen atom, methyl, pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, morpholin-2-yl, morpholin-3-yl, or C1-C6 alkyl or C3-C6 alkenyl substituted with one to three same or different substituents selected from amino, monoalkylamino, 7 1 K dialkylamino, trialkylammonio, hydroxy, alkoxy, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, pyrrolidinyl, piperidyl and morpholinyl, further preferably a hydrogen atom, methyl, or C1-C6 alkyl or C3-C6 alkenyl substituted with one to three same or different substituents selected from amino, trialkylammonio, hydroxy and carbamoyl, most preferably a hydrogen atom, methyl, 2,3-dihydroxypropyl, 3-hydroxypropyl, aminomethyl, 1,2-diaminoethyl, 2- aminoethyl, 1,3-diaminopropyl, 1,4-diaminobutyl, 1,5- diaminopentyl, 3-aminopropyl, 4-aminobutyl, 5-aminopentyl or 2-carbamoylethyl. Among these substituents, the alkyl moiety in monoalkylamino, dialkylamino, trialkylammonio, alkoxy, monoalkylcarbamoyl and dialkylcarbamoyl is as defined in the C1-C4 alkyl. Two or three alkyl moieties in dialkylamino, trialkylammonio and dialkylcarbamoyl are the same as or different from each other.

[0234] When <com:Math><semantics>L106<annotation encoding="application / x-tex">L^{106}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L107<annotation encoding="application / x-tex">L^{107}< / annotation>< / semantics>< / com:Math> together form a single bond, <com:Math><semantics>L108<annotation encoding="application / x-tex">L^{108}< / annotation>< / semantics>< / com:Math> is -CO- or -CO-O-, preferably -CO-.

[0235] When <com:Math><semantics>L106<annotation encoding="application / x-tex">L^{106}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L107<annotation encoding="application / x-tex">L^{107}< / annotation>< / semantics>< / com:Math> together form a single bond, <com:Math><semantics>p101<annotation encoding="application / x-tex">p^{101}< / annotation>< / semantics>< / com:Math> and p<com:Sup>102< / com:Sup> are the same or different and are each preferably 1 to 3.

[0236] When each of <com:Math><semantics>L106<annotation encoding="application / x-tex">L^{106}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L107<annotation encoding="application / x-tex">L^{107}< / annotation>< / semantics>< / com:Math> is a hydrogen atom, <com:Math><semantics>X102<annotation encoding="application / x-tex">X^{102}< / annotation>< / semantics>< / com:Math> is preferably a hydrogen atom, methyl, pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin-2-yl, piperidin-3-yl, A Y C piperidin-4-yl, morpholin-2-yl, morpholin-3-yl or C1-C6 alkyl or C3-C6 alkenyl substituted with one to three same or different substituents selected from amino, monoalkylamino, dialkylamino, trialkylammonio, hydroxy, alkoxy, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, pyrrolidinyl, piperidyl and morpholinyl, more preferably a hydrogen atom, methyl or C1-C6 alkyl or C3-C6 alkenyl substituted with one to three same or different substituents selected from amino, trialkylammonio, hydroxy and carbamoyl, further preferably a hydrogen atom, methyl, 2,3-dihydroxypropyl, 3-hydroxypropyl, aminomethyl, 1,2-diaminoethyl, 2-aminoethyl, 1,3-diaminopropyl, 1,4- diaminobutyl, 1,5-diaminopentyl, 3-aminopropyl, 4- aminobutyl, 5-aminopentyl, 2-carbamoylethyl or the like. Among these substituents, the alkyl moiety in monoalkylamino, dialkylamino, trialkylammonio, alkoxy, monoalkylcarbamoyl and dialkylcarbamoyl is as defined in the C1-C4 alkyl. Two or three alkyl moieties in dialkylamino, trialkylammonio, and dialkylcarbamoyl are the same as or different from each other.

[0237] <com:Math><semantics>L108<annotation encoding="application / x-tex">L^{108}< / annotation>< / semantics>< / com:Math> is preferably a single bond. When <com:Math><semantics>L108<annotation encoding="application / x-tex">L^{108}< / annotation>< / semantics>< / com:Math> is a single bond, each of <com:Math><semantics>L104<annotation encoding="application / x-tex">L^{104}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L105<annotation encoding="application / x-tex">L^{105}< / annotation>< / semantics>< / com:Math> is preferably -O-.

[0238] When <com:Math><semantics>L108<annotation encoding="application / x-tex">L^{108}< / annotation>< / semantics>< / com:Math> is a single bond, <com:Math><semantics>X102<annotation encoding="application / x-tex">X^{102}< / annotation>< / semantics>< / com:Math> is preferably a hydrogen atom, methyl, pyrrolidin-3-yl, piperidin-3-yl, piperidin-4-yl or C1-C6 alkyl or C3-C6 alkenyl · F · · · · · · · · · · · · · · · · · · substituted with one to three same or different substituents selected from amino, monoalkylamino, dialkylamino, trialkylammonio, hydroxy, alkoxy, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, pyrrolidinyl, piperidyl and morpholinyl, or the like, more preferably a hydrogen atom, methyl, hydroxymethyl, 2-hydroxyethyl, 2,3-dihydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 2- hydroxy-3-methoxypropyl, aminomethyl, 2-aminoethyl, 3- aminopropyl, 4-aminobutyl, 5-aminopentyl, 2-(N,N- dimethylamino) ethyl, 3-(N, N-dimethylamino) propyl, 2- carbamoylethyl, 2-dimethylcarbamoylethyl, 1- methylpiperidin-4-yl or the like, further preferably a hydrogen atom, methyl, 2,3-dihydroxypropyl, 3- hydroxypropyl, 2-aminoethyl, 3-aminopropyl, 4-aminobutyl, 5-aminopentyl, 2-carbamoylethyl or the like. Among these substituents, the alkyl moiety in monoalkylamino, dialkylamino, trialkylammonio, alkoxy, monoalkylcarbamoyl and dialkylcarbamoyl is as defined in the C1-C4 alkyl. Two or three alkyl moieties in dialkylamino, trialkylammonio, and dialkylcarbamoyl are the same as or different from each other.

[0239] Each of <com:Math><semantics>L104<annotation encoding="application / x-tex">L^{104}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L105<annotation encoding="application / x-tex">L^{105}< / annotation>< / semantics>< / com:Math> is more preferably -0-. However, when <com:Math><semantics>L108<annotation encoding="application / x-tex">L^{108}< / annotation>< / semantics>< / com:Math> is a single bond and <com:Math><semantics>X102<annotation encoding="application / x-tex">X^{102}< / annotation>< / semantics>< / com:Math> is a hydrogen atom, <com:Math><semantics>L104<annotation encoding="application / x-tex">L^{104}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L105<annotation encoding="application / x-tex">L^{105}< / annotation>< / semantics>< / com:Math> are preferably the same and -CO-O- or -O-CO-, more preferably -CO-O-.

[0240] [Image disponible dans le document PDF, Image available in the PDF document] preferably the same and -CO-O- or -O-CO-, more preferably -CO-O-.

[0241] When <com:Math><semantics>L108<annotation encoding="application / x-tex">L^{108}< / annotation>< / semantics>< / com:Math> is -CO- or -CO-O-, <com:Math><semantics>X102<annotation encoding="application / x-tex">X^{102}< / annotation>< / semantics>< / com:Math> is preferably pyrrolidin-3-yl, piperidin-3-yl, piperidin-4-yl or C1-C6 alkyl or C3-C6 alkenyl substituted with one to three same or different substituents selected from amino, monoalkylamino, dialkylamino, trialkylammonio, hydroxy, alkoxy, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, pyrrolidinyl, piperidyl and morpholinyl, and at least one of the substituents is preferably amino, monoalkylamino, dialkylamino, trialkylammonio, pyrrolidinyl, piperidyl or morpholinyl. <com:Math><semantics>X102<annotation encoding="application / x-tex">X^{102}< / annotation>< / semantics>< / com:Math> is more preferably aminomethyl, 1,2- diaminoethyl, 2-aminoethyl, 1,3-diaminopropyl, 3- aminopropyl, 1,4-diaminobutyl, 4-aminobutyl, 1,5- diaminopentyl, 5-aminopentyl, (N, N-dimethylamino) methyl, 2-(N, N-dimethylamino) ethyl, 3-(N, N-dimethylamino) propyl, 1-amino-2-hydroxyethyl or the like, further preferably aminomethyl, 1,2-diaminoethyl, 2-aminoethyl, 1,3- diaminopropyl, 3-aminopropyl, 1,4-diaminobutyl, 4- aminobutyl, 1,5-diaminopentyl, 5-aminopentyl or the like. Among these substituents, the alkyl moiety in monoalkylamino, dialkylamino, trialkylammonio, alkoxy, monoalkylcarbamoyl and dialkylcarbamoyl is as defined in the C1-C6 alkyl. Two or three alkyl moieties in . dialkylamino, trialkylammonio and dialkylcarbamoyl are . . . the same as or different from each other.

[0242] <com:Math><semantics>𝙻104<annotation encoding="application / x-tex">\texttt{L}^{104}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>𝙻105<annotation encoding="application / x-tex">\texttt{L}^{105}< / annotation>< / semantics>< / com:Math> are preferably the same and -CO-O- or - O-CO-, more preferably -CO-O-.

[0243] In the definition of each group in formulas (CL-III), (CL-IV) and (CL-V), the linear or branched C8-C24 alkyl, C8-C24 alkenyl and C8-C24 alkynyl are each as defined above in formulas (I) to (IV), and the same groups as those described therein are preferred.

[0244] In the definition of each group in formulas (CL-III), (CL-IV) and (CL-V), examples of the alkyl moiety in C8- C24 alkyloxyethyl and C8-C24 alkyloxypropyl include those listed about the linear or branched C8-C24 alkyl.

[0245] Examples of the alkynyl moiety in alkynyloxyethyl and alkynyloxypropyl include those listed about the linear or branched C8-C24 alkynyl.

[0246] R<com:Sup>105< / com:Sup> and R<com:Sup>106< / com:Sup> are preferably the same or different and are each linear or branched C8-C24 alkyl or C8-C24 alkenyl, more preferably are the same or different and are each linear or branched C8-C24 alkenyl, further preferably are the same or different and are each linear <com:Math><semantics>C8−C24<annotation encoding="application / x-tex">C8-C24< / annotation>< / semantics>< / com:Math> alkenyl. Also, <com:Math><semantics>R105<annotation encoding="application / x-tex">R^{105}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R106<annotation encoding="application / x-tex">R^{106}< / annotation>< / semantics>< / com:Math> are more preferably the same. In this case, linear or branched C12-C24 alkyl, + + + C12-C24 alkenyl or C12-C24 alkynyl is preferred, and linear C12-C24 alkenyl is more preferred. The linear or branched C12-C24 alkyl, C12-C24 alkenyl and C12-C24 alkynyl are each as defined above in formula (CL-II).

[0247] R<com:Sup>105< / com:Sup> and R<com:Sup>106< / com:Sup> are preferably the same or different and are each linear or branched C8-C24 alkyl or C8-C24 alkenyl, more preferably are the same or different and are each linear or branched C8-C24 alkenyl, further preferably are the same or different and are each linear <com:Math><semantics>C8−C24<annotation encoding="application / x-tex">C8-C24< / annotation>< / semantics>< / com:Math> alkenyl. Also, <com:Math><semantics>R105<annotation encoding="application / x-tex">R^{105}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R106<annotation encoding="application / x-tex">R^{106}< / annotation>< / semantics>< / com:Math> are more preferably the same. In this, case, linear or branched C15-C20 alkyl, C15-C20 alkenyl or C15-C20 alkynyl is preferred, and linear C15-C20 alkenyl is more preferred. The linear or branched C15-C20 alkyl, C15-C20 alkenyl and C15-C20 alkynyl are each as defined above in formulas (I) to (IV), and the same groups as those described therein are preferred.

[0248] When <com:Math><semantics>R105<annotation encoding="application / x-tex">R^{105}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R106<annotation encoding="application / x-tex">R^{106}< / annotation>< / semantics>< / com:Math> are different, preferably, <com:Math><semantics>R105<annotation encoding="application / x-tex">R^{105}< / annotation>< / semantics>< / com:Math> is linear or branched C15-C20 alkyl, C15-C20 alkenyl or C15- C20 alkynyl, and <com:Math><semantics>R106<annotation encoding="application / x-tex">R^{106}< / annotation>< / semantics>< / com:Math> is linear or branched C8-C12 alkyl. In this context, examples of the linear or branched C8- C12 alkyl include octyl, nonyl, decyl, undecyl and dodecyl, preferably octyl, decyl and dodecyl.

[0249] More preferably, R<com:Sup>105< / com:Sup> is linear C15-C20 alkenyl, and * ( R<com:Sup>106< / com:Sup> is linear C8-C12 alkyl. Further preferably, R<com:Sup>105< / com:Sup> is (Z)-octadec-9-enyl or (9Z,12Z)-octadeca-9,12-dienyl, and <com:Math><semantics>R106<annotation encoding="application / x-tex">R^{106}< / annotation>< / semantics>< / com:Math> is octyl, decyl or dodecyl.

[0250] When <com:Math><semantics>R105<annotation encoding="application / x-tex">R^{105}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R106<annotation encoding="application / x-tex">R^{106}< / annotation>< / semantics>< / com:Math> are different, also preferably, <com:Math><semantics>R105<annotation encoding="application / x-tex">R^{105}< / annotation>< / semantics>< / co...

Claims

CLAIMS:

1. A nucleic acid-containing lipid nanoparticle comprising an analog of a fatty acid ester of glycerol, and a nucleic acid, wherein the analog is not hydrolyzable by a lipase, and is a lipid represented by the following formula (1) or (2): [Image disponible dans le document PDF, Image available in the PDF document] (1) wherein <com:Math><semantics>Rx1<annotation encoding="application / x-tex">Rx^1< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>Rx2<annotation encoding="application / x-tex">Rx^2< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted linear or branched C7-C23 alkyl, C7-C23 alkenyl or C7-C23 alkynyl; and Rx<com:Sup>3< / com:Sup> is a negative charge, a hydrogen atom, or any of the following groups: [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] or [Image disponible dans le document PDF, Image available in the PDF document] (2) wherein Rx4 is optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl or <com:Math><semantics>Rx41<annotation encoding="application / x-tex">Rx^{41}< / annotation>< / semantics>< / com:Math>-CO-; Rx<com:Sup>41< / com:Sup> is optionally substituted linear or branched C7-C23 alkyl, C7-C23 alkenyl or C7-C23 alkynyl; Rx<com:Sup>5< / com:Sup> is optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; and Rx6 is a negative charge, a hydrogen atom, or any of the following groups: [Image disponible dans le document PDF, Image available in the PDF document] • 2. The nucleic acid-containing lipid nanoparticle according to claim 1, wherein the lipase is phospholipase A2.

3. The nucleic acid-containing lipid nanoparticle according to claim 1 or 2, wherein a content of the analog of the fatty acid ester of glycerol is 0.001-fold molar amount or more with respect to the molar number of total lipid.

4. The nucleic acid-containing lipid nanoparticle according to any one of claims 1 to 3, further comprising a cationic lipid.

5. The nucleic acid-containing lipid nanoparticle according to claim 4, wherein the cationic lipid is lipid A represented by at least one of the following formulas (I) to (IV), (V') and (V''), and / or lipid B represented by at least one of the following formulas (CL-I) to (CL-XIX): formula (I) [Image disponible dans le document PDF, Image available in the PDF document] (I) wherein <com:Math><semantics>R1<annotation encoding="application / x-tex">R^1< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>R3<annotation encoding="application / x-tex">R^3< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; <com:Math><semantics>L1<annotation encoding="application / x-tex">L^1< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>L3<annotation encoding="application / x-tex">L^3< / annotation>< / semantics>< / com:Math> are the same or different and are each absent, or <com:Math><semantics>−Z1−(CY1Y2)p1−<annotation encoding="application / x-tex">-Z^{1}-(CY^{1}Y^{2})_{p1}-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−Z2−(CY3Y4)p2−Z3−(CY5Y6)p3−<annotation encoding="application / x-tex">-Z^{2}-(CY^{3}Y^{4})_{p2}-Z^{3}-(CY^{5}Y^{6})_{p3}-< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y1<annotation encoding="application / x-tex">Y^{1}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y6<annotation encoding="application / x-tex">Y^{6}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z1<annotation encoding="application / x-tex">Z^1< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Z3<annotation encoding="application / x-tex">Z^3< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−O<annotation encoding="application / x-tex">-O< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY7A<annotation encoding="application / x-tex">-NY^{7A}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO<annotation encoding="application / x-tex">-CO< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O<annotation encoding="application / x-tex">-O< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O<annotation encoding="application / x-tex">-O< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO<annotation encoding="application / x-tex">-CO< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO<annotation encoding="application / x-tex">-CO< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY7B<annotation encoding="application / x-tex">-NY^{7B}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY7C<annotation encoding="application / x-tex">-NY^{7C}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO<annotation encoding="application / x-tex">-CO< / annotation>< / semantics>< / com:Math>, or <com:Math><semantics>−NY7D−CO−O−<annotation encoding="application / x-tex">-NY^{7D}-CO-O-< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y7A<annotation encoding="application / x-tex">Y^{7A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y7D<annotation encoding="application / x-tex">Y^{7D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; and <com:Math><semantics>p1<annotation encoding="application / x-tex">p^1< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>p3<annotation encoding="application / x-tex">p^3< / annotation>< / semantics>< / com:Math> are the same or different and are each an integer from 1 to 5; <com:Math><semantics>X1<annotation encoding="application / x-tex">X^1< / annotation>< / semantics>< / com:Math> is optionally substituted C1-C4 alkyl; and <com:Math><semantics>A1<annotation encoding="application / x-tex">A^1< / annotation>< / semantics>< / com:Math> is a pharmaceutically acceptable anion, formula (II) [Image disponible dans le document PDF, Image available in the PDF document] (II) wherein <com:Math><semantics>R4<annotation encoding="application / x-tex">R^4< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>R6<annotation encoding="application / x-tex">R^6< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; <com:Math><semantics>L4<annotation encoding="application / x-tex">L^4< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>L6<annotation encoding="application / x-tex">L^6< / annotation>< / semantics>< / com:Math> are the same or different and are each absent, or <com:Math><semantics>−Z4−(CY8Y9)p4−<annotation encoding="application / x-tex">-Z^4-(CY^8Y^9)_{p4}-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−Z5−(CY10Y11)p5−Z6−(CY12Y13)p6−<annotation encoding="application / x-tex">-Z^5-(CY^{10}Y^{11})_{p5}-Z^6-(CY^{12}Y^{13})_{p6}-< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y8<annotation encoding="application / x-tex">Y^8< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y13<annotation encoding="application / x-tex">Y^{13}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z4<annotation encoding="application / x-tex">Z^4< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Z6<annotation encoding="application / x-tex">Z^6< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−O−<annotation encoding="application / x-tex">-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY14A−<annotation encoding="application / x-tex">-NY^{14A}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−NY14B−<annotation encoding="application / x-tex">-CO-NY^{14B}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY14C−CO−<annotation encoding="application / x-tex">-NY^{14C}-CO-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−NY14D−CO−O−<annotation encoding="application / x-tex">-NY^{14D}-CO-O-< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y14A<annotation encoding="application / x-tex">Y^{14A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y14D<annotation encoding="application / x-tex">Y^{14D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; p4 is an integer from 0 to 5; <com:Math><semantics>p5<annotation encoding="application / x-tex">p^5< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; and <com:Math><semantics>p6<annotation encoding="application / x-tex">p^6< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>L7<annotation encoding="application / x-tex">L^7< / annotation>< / semantics>< / com:Math> is absent, or <com:Math><semantics>−(CY15Y16)p7<annotation encoding="application / x-tex">-(CY^{15}Y^{16})_{p7}< / annotation>< / semantics>< / com:Math>-, <com:Math><semantics>−(CY17Y18)p8<annotation encoding="application / x-tex">-(CY^{17}Y^{18})_{p8}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>Z7<annotation encoding="application / x-tex">Z^7< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>(CY19Y20)p9<annotation encoding="application / x-tex">(CY^{19}Y^{20})_{p9}< / annotation>< / semantics>< / com:Math>- or <com:Math><semantics>−(CY21Y22)p10−Z8−(CY23Y24)p11−Z9−(CY25Y26)p12−<annotation encoding="application / x-tex">-(CY^{21}Y^{22})_{p10}-Z^8-(CY^{23}Y^{24})_{p11}-Z^9-(CY^{25}Y^{26})_{p12}-< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y15<annotation encoding="application / x-tex">Y^{15}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y26<annotation encoding="application / x-tex">Y^{26}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z7<annotation encoding="application / x-tex">Z^7< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Z9<annotation encoding="application / x-tex">Z^9< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−O−<annotation encoding="application / x-tex">-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY27A−<annotation encoding="application / x-tex">-NY^{27A}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−NY27B−<annotation encoding="application / x-tex">-CO-NY^{27B}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY27C−CO−<annotation encoding="application / x-tex">-NY^{27C}-CO-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−NY27D−CO−O−<annotation encoding="application / x-tex">-NY^{27D}-CO-O-< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y27A<annotation encoding="application / x-tex">Y^{27A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y27D<annotation encoding="application / x-tex">Y^{27D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted <com:Math><semantics>C1−C4<annotation encoding="application / x-tex">C1-C4< / annotation>< / semantics>< / com:Math> alkyl; <com:Math><semantics>p7<annotation encoding="application / x-tex">p^7< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; <com:Math><semantics>p8<annotation encoding="application / x-tex">p^8< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>p9<annotation encoding="application / x-tex">p^9< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; <com:Math><semantics>p10<annotation encoding="application / x-tex">p^{10}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>p11<annotation encoding="application / x-tex">p^{11}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; and <com:Math><semantics>p12<annotation encoding="application / x-tex">p^{12}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; <com:Math><semantics>𝖡1<annotation encoding="application / x-tex">\mathsf{B}^1< / annotation>< / semantics>< / com:Math> is [Image disponible dans le document PDF, Image available in the PDF document] , -- wherein <com:Math><semantics>X2<annotation encoding="application / x-tex">X^2< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X3<annotation encoding="application / x-tex">X^3< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted C1-C4 alkyl, or together form an optionally substituted C4-C6 hetero ring with the adjacent nitrogen atom; <com:Math><semantics>X4<annotation encoding="application / x-tex">X^4< / annotation>< / semantics>< / com:Math> is optionally substituted C1-C4 alkyl; <com:Math><semantics>X5<annotation encoding="application / x-tex">X^5< / annotation>< / semantics>< / com:Math> and X<com:Sup>6< / com:Sup> are the same or different and are each optionally substituted C1-C4 alkyl, or together form an optionally substituted C4-C6 hetero ring with the adjacent nitrogen atom; <com:Math><semantics>X7<annotation encoding="application / x-tex">X^7< / annotation>< / semantics>< / com:Math> is optionally substituted C1-C4 alkyl; <com:Math><semantics>Y28<annotation encoding="application / x-tex">Y^{28}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y37<annotation encoding="application / x-tex">Y^{37}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z10<annotation encoding="application / x-tex">Z^{10}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>Z11<annotation encoding="application / x-tex">Z^{11}< / annotation>< / semantics>< / com:Math> are the same or different and are each -O-, -NY<com:Sup>38A< / com:Sup>-, <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−NY38B−<annotation encoding="application / x-tex">-CO-NY^{38B}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY38C−CO−<annotation encoding="application / x-tex">-NY^{38C}-CO-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−NY38D−CO−O−<annotation encoding="application / x-tex">-NY^{38D}-CO-O-< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y38A<annotation encoding="application / x-tex">Y^{38A}< / annotation>< / semantics>< / com:Math> to Y<com:Sup>38D< / com:Sup> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>p13<annotation encoding="application / x-tex">p^{13}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; and <com:Math><semantics>p14<annotation encoding="application / x-tex">p^{14}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>p17<annotation encoding="application / x-tex">p^{17}< / annotation>< / semantics>< / com:Math> are the same or different and are each an integer from 1 to 5; and <com:Math><semantics>A2<annotation encoding="application / x-tex">A^2< / annotation>< / semantics>< / com:Math> is a pharmaceutically acceptable anion, formula (III) [Image disponible dans le document PDF, Image available in the PDF document] (III) wherein <com:Math><semantics>R7<annotation encoding="application / x-tex">R^7< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>R9<annotation encoding="application / x-tex">R^9< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; <com:Math><semantics>mL8<annotation encoding="application / x-tex">{m L}^{8}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>mL10<annotation encoding="application / x-tex">{m L}^{10}< / annotation>< / semantics>< / com:Math> are the same or different and are each absent, or <com:Math><semantics>−Z12−(CY39Y40)p18−<annotation encoding="application / x-tex">-Z^{12}-(CY^{39}Y^{40})_{p18}-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−Z13−(CY41Y42)p19−Z14−(CY43Y44)p20−<annotation encoding="application / x-tex">-Z^{13}-(CY^{41}Y^{42})_{p19}-Z^{14}-(CY^{43}Y^{44})_{p20}-< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y39<annotation encoding="application / x-tex">Y^{39}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y44<annotation encoding="application / x-tex">Y^{44}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z12<annotation encoding="application / x-tex">Z^{12}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Z14<annotation encoding="application / x-tex">Z^{14}< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−O−<annotation encoding="application / x-tex">-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY45A−<annotation encoding="application / x-tex">-NY^{45A}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−NY45B−<annotation encoding="application / x-tex">-CO-NY^{45B}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY45C−CO−<annotation encoding="application / x-tex">-NY^{45C}-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY45D−CO−O−<annotation encoding="application / x-tex">-NY^{45D}-CO-O-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−CO−<annotation encoding="application / x-tex">-CO-< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y45A<annotation encoding="application / x-tex">Y^{45A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y45D<annotation encoding="application / x-tex">Y^{45D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>p18<annotation encoding="application / x-tex">p^{18}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>p19<annotation encoding="application / x-tex">p^{19}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; and <com:Math><semantics>p20<annotation encoding="application / x-tex">p^{20}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>L11<annotation encoding="application / x-tex">L^{11}< / annotation>< / semantics>< / com:Math> is absent, or <com:Math><semantics>−(CY46Y47)p21<annotation encoding="application / x-tex">-(CY^{46}Y^{47})_{p21}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−(CY48Y49)p22<annotation encoding="application / x-tex">-(CY^{48}Y^{49})_{p22}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−Z15<annotation encoding="application / x-tex">-Z^{15}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>(CY50Y51)p23<annotation encoding="application / x-tex">(CY^{50}Y^{51})_{p23}< / annotation>< / semantics>< / com:Math>- or <com:Math><semantics>−(CY52Y53)p24−Z16−(CY54Y55)p25−Z17−(CY56Y57)p26−<annotation encoding="application / x-tex">-(CY^{52}Y^{53})_{p24}-Z^{16}-(CY^{54}Y^{55})_{p25}-Z^{17}-(CY^{56}Y^{57})_{p26}-< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y46<annotation encoding="application / x-tex">Y^{46}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y57<annotation encoding="application / x-tex">Y^{57}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z15<annotation encoding="application / x-tex">Z^{15}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Z17<annotation encoding="application / x-tex">Z^{17}< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−O−<annotation encoding="application / x-tex">-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY58A−<annotation encoding="application / x-tex">-NY^{58A}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−NY58B−<annotation encoding="application / x-tex">-CO-NY^{58B}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY58C−CO−<annotation encoding="application / x-tex">-NY^{58C}-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY58D−CO−O−<annotation encoding="application / x-tex">-NY^{58D}-CO-O-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−CO−<annotation encoding="application / x-tex">-CO-< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y58A<annotation encoding="application / x-tex">Y^{58A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y58D<annotation encoding="application / x-tex">Y^{58D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>p21<annotation encoding="application / x-tex">p^{21}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; <com:Math><semantics>p22<annotation encoding="application / x-tex">p^{22}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>p23<annotation encoding="application / x-tex">p^{23}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; <com:Math><semantics>p24<annotation encoding="application / x-tex">p^{24}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>p25<annotation encoding="application / x-tex">p^{25}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; and <com:Math><semantics>p26<annotation encoding="application / x-tex">p^{26}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; <com:Math><semantics>L12<annotation encoding="application / x-tex">L^{12}< / annotation>< / semantics>< / com:Math> is absent, or <com:Math><semantics>−(CY59Y60)p27<annotation encoding="application / x-tex">-(CY^{59}Y^{60})_{p27}< / annotation>< / semantics>< / com:Math>-, <com:Math><semantics>−(CY61Y62)p28<annotation encoding="application / x-tex">-(CY^{61}Y^{62})_{p28}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>Z18<annotation encoding="application / x-tex">Z^{18}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>(CY63Y64)p29<annotation encoding="application / x-tex">(CY^{63}Y^{64})_{p29}< / annotation>< / semantics>< / com:Math>- or <com:Math><semantics>−(CY65Y66)p30−Z19−(CY67Y68)p31−Z20−(CY69Y70)p32<annotation encoding="application / x-tex">-(CY^{65}Y^{66})_{p30}-Z^{19}-(CY^{67}Y^{68})_{p31}-Z^{20}-(CY^{69}Y^{70})_{p32}< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y59<annotation encoding="application / x-tex">Y^{59}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y70<annotation encoding="application / x-tex">Y^{70}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z18<annotation encoding="application / x-tex">Z^{18}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Z20<annotation encoding="application / x-tex">Z^{20}< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−O<annotation encoding="application / x-tex">-O< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY71A<annotation encoding="application / x-tex">-NY^{71A}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO<annotation encoding="application / x-tex">-CO< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O<annotation encoding="application / x-tex">-O< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O<annotation encoding="application / x-tex">-O< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO<annotation encoding="application / x-tex">-CO< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO<annotation encoding="application / x-tex">-CO< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY71B<annotation encoding="application / x-tex">-NY^{71B}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY71C<annotation encoding="application / x-tex">-NY^{71C}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO<annotation encoding="application / x-tex">-CO< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY71D−CO−O−<annotation encoding="application / x-tex">-NY^{71D}-CO-O-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−CO−<annotation encoding="application / x-tex">-CO-< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y71A<annotation encoding="application / x-tex">Y^{71A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y71D<annotation encoding="application / x-tex">Y^{71D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>p27<annotation encoding="application / x-tex">p^{27}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; <com:Math><semantics>p28<annotation encoding="application / x-tex">p^{28}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>p29<annotation encoding="application / x-tex">p^{29}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>p30<annotation encoding="application / x-tex">p^{30}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>p31<annotation encoding="application / x-tex">p^{31}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; and <com:Math><semantics>p32<annotation encoding="application / x-tex">p^{32}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>𝖩1<annotation encoding="application / x-tex">\mathsf{J}^1< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>𝖩2<annotation encoding="application / x-tex">\mathsf{J}^2< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>𝖢𝖸72<annotation encoding="application / x-tex">\mathsf{CY}^{72}< / annotation>< / semantics>< / com:Math> or N wherein <com:Math><semantics>Y72<annotation encoding="application / x-tex">Y^{72}< / annotation>< / semantics>< / com:Math> is a hydrogen atom, hydroxy, optionally substituted C1-C4 alkyl, optionally substituted C1-C4 alkoxy, or optionally substituted C1-C4 acyloxy; <com:Math><semantics>B2<annotation encoding="application / x-tex">B^2< / annotation>< / semantics>< / com:Math> is [Image disponible dans le document PDF, Image available in the PDF document] , UI wherein <com:Math><semantics>X8<annotation encoding="application / x-tex">X^8< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X9<annotation encoding="application / x-tex">X^9< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted C1-C4 alkyl, or together form an optionally substituted C4-C6 hetero ring with the adjacent nitrogen atom; <com:Math><semantics>X10<annotation encoding="application / x-tex">X^{10}< / annotation>< / semantics>< / com:Math> is optionally substituted C1-C4 alkyl; <com:Math><semantics>X11<annotation encoding="application / x-tex">X^{11}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X12<annotation encoding="application / x-tex">X^{12}< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted C1-C4 alkyl, or together form an optionally substituted C4-C6 hetero ring with the adjacent nitrogen atom; X<com:Sup>13< / com:Sup> is optionally substituted C1-C4 alkyl; <com:Math><semantics>Y73<annotation encoding="application / x-tex">Y^{73}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y82<annotation encoding="application / x-tex">Y^{82}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z21<annotation encoding="application / x-tex">Z^{21}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>Z22<annotation encoding="application / x-tex">Z^{22}< / annotation>< / semantics>< / com:Math> are the same or different and are each -O-, -NY<com:Sup>83A< / com:Sup>-, -CO-O-, -O-CO-, -CO-NY<com:Math><semantics>83B<annotation encoding="application / x-tex">^{83B}< / annotation>< / semantics>< / com:Math>-, -NY<com:Math><semantics>83C<annotation encoding="application / x-tex">^{83C}< / annotation>< / semantics>< / com:Math>-CO- or -NY<com:Math><semantics>83D<annotation encoding="application / x-tex">^{83D}< / annotation>< / semantics>< / com:Math>-CO-O- wherein Y<com:Math><semantics>83A<annotation encoding="application / x-tex">^{83A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y83D<annotation encoding="application / x-tex">Y^{83D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>p33<annotation encoding="application / x-tex">p^{33}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; and <com:Math><semantics>p34<annotation encoding="application / x-tex">p^{34}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>p37<annotation encoding="application / x-tex">p^{37}< / annotation>< / semantics>< / com:Math> are the same or different and are each an integer from 1 to 5; and <com:Math><semantics>A3<annotation encoding="application / x-tex">A^3< / annotation>< / semantics>< / com:Math> is a pharmaceutically acceptable anion, formula (IV) [Image disponible dans le document PDF, Image available in the PDF document] (IV) wherein <com:Math><semantics>R10<annotation encoding="application / x-tex">R^{10}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>R12<annotation encoding="application / x-tex">R^{12}< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; [Image disponible dans le document PDF, Image available in the PDF document] - <com:Math><semantics>(CY87Y88)p40<annotation encoding="application / x-tex">(CY^{87}Y^{88})_{p40}< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y83<annotation encoding="application / x-tex">Y^{83}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y88<annotation encoding="application / x-tex">Y^{88}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; Z23 to <com:Math><semantics>Z25<annotation encoding="application / x-tex">Z^{25}< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−O−<annotation encoding="application / x-tex">-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY89A−<annotation encoding="application / x-tex">-NY^{89A}-< / annotation>< / semantics>< / com:Math>, -CO-O-, -O-CO-, -CO-NY<com:Math><semantics>89B<annotation encoding="application / x-tex">^{89B}< / annotation>< / semantics>< / com:Math>-, -NY<com:Math><semantics>89C<annotation encoding="application / x-tex">^{89C}< / annotation>< / semantics>< / com:Math>-CO- or -NY<com:Math><semantics>89D<annotation encoding="application / x-tex">^{89D}< / annotation>< / semantics>< / com:Math>-CO-O- wherein Y<com:Math><semantics>89A<annotation encoding="application / x-tex">^{89A}< / annotation>< / semantics>< / com:Math> to Y<com:Sup>89D< / com:Sup> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; and <com:Math><semantics>p38<annotation encoding="application / x-tex">p^{38}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>p40<annotation encoding="application / x-tex">p^{40}< / annotation>< / semantics>< / com:Math> are the same or different and are each an integer from 1 to 5; <com:Math><semantics>mL14<annotation encoding="application / x-tex">{m L}^{14}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>mL15<annotation encoding="application / x-tex">{m L}^{15}< / annotation>< / semantics>< / com:Math> are the same or different and are each absent, or <com:Math><semantics>−Z26−(CY90Y91)p41− or −Z27−(CY92Y93)p42−Z28−(CY94Y95)p43− wherein Y90 to <annotation encoding="application / x-tex">-Z^{26}-(CY^{90}Y^{91})_{p41}- \text{ or } -Z^{27}-(CY^{92}Y^{93})_{p42}-Z^{28}-(CY^{94}Y^{95})_{p43}- \text{ wherein } Y^{90} \text{ to }< / annotation>< / semantics>< / com:Math> Y<com:Sup>95< / com:Sup> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z26<annotation encoding="application / x-tex">Z^{26}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Z28<annotation encoding="application / x-tex">Z^{28}< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−O<annotation encoding="application / x-tex">-O< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY96A<annotation encoding="application / x-tex">-NY^{96A}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−O<annotation encoding="application / x-tex">-CO-O< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO<annotation encoding="application / x-tex">-O-CO< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−NY96B<annotation encoding="application / x-tex">-CO-NY^{96B}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY96C−CO−<annotation encoding="application / x-tex">-NY^{96C}-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY96D−CO−O−<annotation encoding="application / x-tex">-NY^{96D}-CO-O-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−CO−<annotation encoding="application / x-tex">-CO-< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y96A<annotation encoding="application / x-tex">Y^{96A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y96D<annotation encoding="application / x-tex">Y^{96D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>p41<annotation encoding="application / x-tex">p^{41}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>p42<annotation encoding="application / x-tex">p^{42}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; and <com:Math><semantics>p43<annotation encoding="application / x-tex">p^{43}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>L16<annotation encoding="application / x-tex">L^{16}< / annotation>< / semantics>< / com:Math> is absent, or <com:Math><semantics>−(CY97Y98)p44<annotation encoding="application / x-tex">-(CY^{97}Y^{98})_{p44}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−(CY99Y100)p45<annotation encoding="application / x-tex">-(CY^{99}Y^{100})_{p45}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−Z29<annotation encoding="application / x-tex">-Z^{29}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>(CY101Y102)p46<annotation encoding="application / x-tex">(CY^{101}Y^{102})_{p46}< / annotation>< / semantics>< / com:Math>- or <com:Math><semantics>−(CY103Y104)p47−Z30−(CY105Y106)p48−Z31−(CY107Y108)p49<annotation encoding="application / x-tex">-(CY^{103}Y^{104})_{p47}-Z^{30}-(CY^{105}Y^{106})_{p48}-Z^{31}-(CY^{107}Y^{108})_{p49}< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y97<annotation encoding="application / x-tex">Y^{97}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y108<annotation encoding="application / x-tex">Y^{108}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z29<annotation encoding="application / x-tex">Z^{29}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Z31<annotation encoding="application / x-tex">Z^{31}< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−0<annotation encoding="application / x-tex">-0< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY109A<annotation encoding="application / x-tex">-NY^{109A}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−NY109B<annotation encoding="application / x-tex">-CO-NY^{109B}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY109C−CO−<annotation encoding="application / x-tex">-NY^{109C}-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY109D−CO−O−<annotation encoding="application / x-tex">-NY^{109D}-CO-O-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−CO−<annotation encoding="application / x-tex">-CO-< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y109A<annotation encoding="application / x-tex">Y^{109A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y109D<annotation encoding="application / x-tex">Y^{109D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>p44<annotation encoding="application / x-tex">p^{44}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; <com:Math><semantics>p45<annotation encoding="application / x-tex">p^{45}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>p46<annotation encoding="application / x-tex">p^{46}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; <com:Math><semantics>p47<annotation encoding="application / x-tex">p^{47}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>p48<annotation encoding="application / x-tex">p^{48}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; and <com:Math><semantics>p49<annotation encoding="application / x-tex">p^{49}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; <com:Math><semantics>J3<annotation encoding="application / x-tex">J^3< / annotation>< / semantics>< / com:Math> is <com:Math><semantics>CY110<annotation encoding="application / x-tex">CY^{110}< / annotation>< / semantics>< / com:Math> or N wherein <com:Math><semantics>Y110<annotation encoding="application / x-tex">Y^{110}< / annotation>< / semantics>< / com:Math> is a hydrogen atom, hydroxy, optionally substituted C1-C4 alkyl, optionally substituted C1-C4 alkoxy, or optionally substituted C1-C4 acyloxy; <com:Math><semantics>X14<annotation encoding="application / x-tex">X^{14}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X15<annotation encoding="application / x-tex">X^{15}< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted C1-C4 alkyl, or together form an optionally substituted C4-C6 hetero ring with the adjacent nitrogen atom; and <com:Math><semantics>A4<annotation encoding="application / x-tex">A^4< / annotation>< / semantics>< / com:Math> is a pharmaceutically acceptable anion, formula (V') or formula (V'') [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] (V') (V") or wherein <com:Math><semantics>R13<annotation encoding="application / x-tex">R^{13}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>R18<annotation encoding="application / x-tex">R^{18}< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; <com:Math><semantics>Y111<annotation encoding="application / x-tex">Y^{111}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y114<annotation encoding="application / x-tex">Y^{114}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom, hydroxy or optionally substituted C1-C4 alkyl; <com:Math><semantics>mL17<annotation encoding="application / x-tex">{m L}^{17}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>mL19<annotation encoding="application / x-tex">{m L}^{19}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>mL22<annotation encoding="application / x-tex">{m L}^{22}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>mL24<annotation encoding="application / x-tex">{m L}^{24}< / annotation>< / semantics>< / com:Math> are the same or different and are each absent, or <com:Math><semantics>−Z32<annotation encoding="application / x-tex">-Z^{32}< / annotation>< / semantics>< / com:Math>- <com:Math><semantics>(CY115Y116)p51<annotation encoding="application / x-tex">(CY^{115}Y^{116})_{p51}< / annotation>< / semantics>< / com:Math>- or <com:Math><semantics>−Z33<annotation encoding="application / x-tex">-Z^{33}< / annotation>< / semantics>< / com:Math>- <com:Math><semantics>(CY117Y118)p52<annotation encoding="application / x-tex">(CY^{117}Y^{118})_{p52}< / annotation>< / semantics>< / com:Math>- <com:Math><semantics>Z34<annotation encoding="application / x-tex">Z^{34}< / annotation>< / semantics>< / com:Math>- <com:Math><semantics>(CY119Y120)p53<annotation encoding="application / x-tex">(CY^{119}Y^{120})_{p53}< / annotation>< / semantics>< / com:Math>- wherein <com:Math><semantics>Y115<annotation encoding="application / x-tex">Y^{115}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y120<annotation encoding="application / x-tex">Y^{120}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z32<annotation encoding="application / x-tex">Z^{32}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Z34<annotation encoding="application / x-tex">Z^{34}< / annotation>< / semantics>< / com:Math> are the same or different and are each -O-, -NY<com:Sup>121A< / com:Sup>-, <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−NY121B−<annotation encoding="application / x-tex">-CO-NY^{121B}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY121C−CO−<annotation encoding="application / x-tex">-NY^{121C}-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY121D−CO−O−<annotation encoding="application / x-tex">-NY^{121D}-CO-O-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−CO−<annotation encoding="application / x-tex">-CO-< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y121A<annotation encoding="application / x-tex">Y^{121A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y121D<annotation encoding="application / x-tex">Y^{121D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted <com:Math><semantics>C1−C4<annotation encoding="application / x-tex">C1-C4< / annotation>< / semantics>< / com:Math> alkyl; <com:Math><semantics>p51<annotation encoding="application / x-tex">p^{51}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>p52<annotation encoding="application / x-tex">p^{52}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; and <com:Math><semantics>p53<annotation encoding="application / x-tex">p^{53}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>L20<annotation encoding="application / x-tex">L^{20}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L25<annotation encoding="application / x-tex">L^{25}< / annotation>< / semantics>< / com:Math> are the same or different and are each absent, or <com:Math><semantics>−(CY122Y123)p54−<annotation encoding="application / x-tex">-(CY^{122}Y^{123})_{p54}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−(CY124Y125)p55−Z35−(CY126Y127)p56−<annotation encoding="application / x-tex">-(CY^{124}Y^{125})_{p55}-Z^{35}-(CY^{126}Y^{127})_{p56}-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−(CY128Y129)p57−Z36−<annotation encoding="application / x-tex">-(CY^{128}Y^{129})_{p57}-Z^{36}-< / annotation>< / semantics>< / com:Math> <com:Math><semantics>(CY130Y131)p58−Z37−(CY132Y133)p59<annotation encoding="application / x-tex">(CY^{130}Y^{131})_{p58}-Z^{37}-(CY^{132}Y^{133})_{p59}< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y122<annotation encoding="application / x-tex">Y^{122}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y133<annotation encoding="application / x-tex">Y^{133}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z35<annotation encoding="application / x-tex">Z^{35}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Z37<annotation encoding="application / x-tex">Z^{37}< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−O−<annotation encoding="application / x-tex">-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY134A−<annotation encoding="application / x-tex">-NY^{134A}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−NY134B−<annotation encoding="application / x-tex">-CO-NY^{134B}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY134C−CO−<annotation encoding="application / x-tex">-NY^{134C}-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY134D−CO−O−<annotation encoding="application / x-tex">-NY^{134D}-CO-O-< / annotation>< / semantics>< / com:Math> or -CO- wherein <com:Math><semantics>Y134A<annotation encoding="application / x-tex">Y^{134A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y134D<annotation encoding="application / x-tex">Y^{134D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; p<com:Sup>54< / com:Sup> is an integer from 1 to 5; <com:Math><semantics>p55<annotation encoding="application / x-tex">p^{55}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>p56<annotation encoding="application / x-tex">p^{56}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; <com:Math><semantics>p57<annotation encoding="application / x-tex">p^{57}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>p58<annotation encoding="application / x-tex">p^{58}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; and <com:Math><semantics>p59<annotation encoding="application / x-tex">p^{59}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; <com:Math><semantics>mL21<annotation encoding="application / x-tex">{m L}^{21}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>mL26<annotation encoding="application / x-tex">{m L}^{26}< / annotation>< / semantics>< / com:Math> are the same or different and are each absent, or <com:Math><semantics>−(CY135Y136)p60<annotation encoding="application / x-tex">-(CY^{135}Y^{136})_{p60}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−(CY137Y138)p61<annotation encoding="application / x-tex">-(CY^{137}Y^{138})_{p61}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−(CY139Y140)p62<annotation encoding="application / x-tex">-(CY^{139}Y^{140})_{p62}< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−(CY141Y142)p63<annotation encoding="application / x-tex">-(CY^{141}Y^{142})_{p63}< / annotation>< / semantics>< / com:Math> <com:Math><semantics>(CY143Y144)p64−Z40−(CY145Y146)p65−<annotation encoding="application / x-tex">(CY^{143}Y^{144})_{p64}-Z^{40}-(CY^{145}Y^{146})_{p65}-< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y135<annotation encoding="application / x-tex">Y^{135}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y146<annotation encoding="application / x-tex">Y^{146}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z38<annotation encoding="application / x-tex">Z^{38}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Z40<annotation encoding="application / x-tex">Z^{40}< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−O−<annotation encoding="application / x-tex">-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY147A−<annotation encoding="application / x-tex">-NY^{147A}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−NY147B−<annotation encoding="application / x-tex">-CO-NY^{147B}-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NR147C−CO−<annotation encoding="application / x-tex">-NR^{147C}-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−NY147D−CO−O−<annotation encoding="application / x-tex">-NY^{147D}-CO-O-< / annotation>< / semantics>< / com:Math> or -CO- wherein <com:Math><semantics>Y147A<annotation encoding="application / x-tex">Y^{147A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y147D<annotation encoding="application / x-tex">Y^{147D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; p<com:Sup>60< / com:Sup> is an integer from 1 to 5; <com:Math><semantics>p61<annotation encoding="application / x-tex">p^{61}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>p62<annotation encoding="application / x-tex">p^{62}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>p63<annotation encoding="application / x-tex">p^{63}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>p64<annotation encoding="application / x-tex">p^{64}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 5; and <com:Math><semantics>p65<annotation encoding="application / x-tex">p^{65}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 5; <com:Math><semantics>B3<annotation encoding="application / x-tex">B^3< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>B4<annotation encoding="application / x-tex">B^4< / annotation>< / semantics>< / com:Math> are the same or different and are each [Image disponible dans le document PDF, Image available in the PDF document] wherein <com:Math><semantics>X16<annotation encoding="application / x-tex">X^{16}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X17<annotation encoding="application / x-tex">X^{17}< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted C1-C4 alkyl, or together form an optionally substituted C4-C6 hetero ring with the adjacent nitrogen atom; <com:Math><semantics>X18<annotation encoding="application / x-tex">X^{18}< / annotation>< / semantics>< / com:Math> is optionally substituted C1-C4 alkyl; <com:Math><semantics>X19<annotation encoding="application / x-tex">X^{19}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X20<annotation encoding="application / x-tex">X^{20}< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted C1-C4 alkyl, or together form an optionally substituted C4-C6 hetero ring with the adjacent nitrogen atom; <com:Math><semantics>X21<annotation encoding="application / x-tex">X^{21}< / annotation>< / semantics>< / com:Math> is optionally substituted C1-C4 alkyl; <com:Math><semantics>Y148<annotation encoding="application / x-tex">Y^{148}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y157<annotation encoding="application / x-tex">Y^{157}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; <com:Math><semantics>Z41<annotation encoding="application / x-tex">Z^{41}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>Z42<annotation encoding="application / x-tex">Z^{42}< / annotation>< / semantics>< / com:Math> are the same or different and are each -0-, <com:Math><semantics>−NY158A<annotation encoding="application / x-tex">-NY^{158A}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−O−<annotation encoding="application / x-tex">-CO-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−CO−<annotation encoding="application / x-tex">-O-CO-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−CO−NY158B<annotation encoding="application / x-tex">-CO-NY^{158B}< / annotation>< / semantics>< / com:Math>-, <com:Math><semantics>−NY158C<annotation encoding="application / x-tex">-NY^{158C}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>−CO−<annotation encoding="application / x-tex">-CO-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−NY158D<annotation encoding="application / x-tex">-NY^{158D}< / annotation>< / semantics>< / com:Math>-<com:Math><semantics>−CO−<annotation encoding="application / x-tex">-CO-< / annotation>< / semantics>< / com:Math> wherein <com:Math><semantics>Y158A<annotation encoding="application / x-tex">Y^{158A}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>Y158D<annotation encoding="application / x-tex">Y^{158D}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or optionally substituted C1-C4 alkyl; p<com:Sup>66< / com:Sup> is an integer from 0 to 5; and <com:Math><semantics>p67<annotation encoding="application / x-tex">p^{67}< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>p70<annotation encoding="application / x-tex">p^{70}< / annotation>< / semantics>< / com:Math> are the same or different and are each an integer from 1 to 5; and <com:Math><semantics>A5<annotation encoding="application / x-tex">A^5< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>A6<annotation encoding="application / x-tex">A^6< / annotation>< / semantics>< / com:Math> are the same or different and are each a pharmaceutically acceptable anion, formula (CL-I) [Image disponible dans le document PDF, Image available in the PDF document] (CL-I) wherein <com:Math><semantics>R101<annotation encoding="application / x-tex">R^{101}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R102<annotation encoding="application / x-tex">R^{102}< / annotation>< / semantics>< / com:Math> are the same or different and are each linear or branched C10-C24 alkyl, C10-C24 alkenyl or C10-C24 alkynyl; <com:Math><semantics>L101<annotation encoding="application / x-tex">L^{101}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L102<annotation encoding="application / x-tex">L^{102}< / annotation>< / semantics>< / com:Math> are each a hydrogen atom, or together form a single bond or C2-C8 alkylene; <com:Math><semantics>L103<annotation encoding="application / x-tex">L^{103}< / annotation>< / semantics>< / com:Math> is a single bond, -CO- or -CO-O-; when <com:Math><semantics>L103<annotation encoding="application / x-tex">L^{103}< / annotation>< / semantics>< / com:Math> is a single bond, <com:Math><semantics>X101<annotation encoding="application / x-tex">X^{101}< / annotation>< / semantics>< / com:Math> is a hydrogen atom, C1-C6 alkyl, C3-C6 alkenyl, pyrrolidin-3-yl, piperidin-3-yl, piperidin-4-yl, or C1-C6 alkyl or C3-C6 alkenyl substituted with one to three same or different substituents selected from amino, monoalkylamino, dialkylamino, trialkylammonio, hydroxy, alkoxy, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, pyrrolidinyl, piperidyl and morpholinyl; and when <com:Math><semantics>L103<annotation encoding="application / x-tex">L^{103}< / annotation>< / semantics>< / com:Math> is -CO- or -CO-O-, <com:Math><semantics>X101<annotation encoding="application / x-tex">X^{101}< / annotation>< / semantics>< / com:Math> is pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, morpholin-2-yl, morpholin-3-yl, or C1-C6 alkyl or C3-C6 alkenyl substituted with one to three same or different substituents selected from amino, monoalkylamino, dialkylamino, trialkylammonio, hydroxy, alkoxy, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, pyrrolidinyl, piperidyl and morpholinyl, and at least one of the substituents is amino, monoalkylamino, dialkylamino, trialkylammonio, pyrrolidinyl, piperidyl or morpholinyl, formula (CL-II) [Image disponible dans le document PDF, Image available in the PDF document] (CL-II) wherein <com:Math><semantics>R103<annotation encoding="application / x-tex">R^{103}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R104<annotation encoding="application / x-tex">R^{104}< / annotation>< / semantics>< / com:Math> are the same or different and are each linear or branched C12-C24 alkyl, C12-C24 alkenyl or C12-C24 alkynyl; <com:Math><semantics>p101<annotation encoding="application / x-tex">p^{101}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>p102<annotation encoding="application / x-tex">p^{102}< / annotation>< / semantics>< / com:Math> are the same or different and are each an integer from 0 to 3; <com:Math><semantics>𝙻106<annotation encoding="application / x-tex">\texttt{L}^{106}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>𝙻107<annotation encoding="application / x-tex">\texttt{L}^{107}< / annotation>< / semantics>< / com:Math> are each a hydrogen atom, or together form a single bond or C2-C8 alkylene; <com:Math><semantics>L104<annotation encoding="application / x-tex">L^{104}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L105<annotation encoding="application / x-tex">L^{105}< / annotation>< / semantics>< / com:Math> are the same or different and are each -O-, -CO-O- or -O-CO-; <com:Math><semantics>L108<annotation encoding="application / x-tex">L^{108}< / annotation>< / semantics>< / com:Math> is a single bond, -CO- or -CO-O-; when <com:Math><semantics>L108<annotation encoding="application / x-tex">L^{108}< / annotation>< / semantics>< / com:Math> is a single bond, [Image disponible dans le document PDF, Image available in the PDF document] pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin-3-yl, piperidin-4- yl, or C1-C6 alkyl or C3-C6 alkenyl substituted with one to three same or different substituents selected from amino, monoalkylamino, dialkylamino, trialkylammonio, hydroxy, alkoxy, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, pyrrolidinyl, piperidyl and morpholinyl; and when <com:Math><semantics>L108<annotation encoding="application / x-tex">L^{108}< / annotation>< / semantics>< / com:Math> is -CO- or -CO-O-, <com:Math><semantics>X102<annotation encoding="application / x-tex">X^{102}< / annotation>< / semantics>< / com:Math> is pyrrolidin-2-yl, pyrrolidin-3-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, morpholin-2-yl, morpholin-3-yl, or C1-C6 alkyl or C3-C6 alkenyl substituted with one to three same or different substituents selected from amino, monoalkylamino, dialkylamino, trialkylammonio, hydroxy, alkoxy, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, pyrrolidinyl, piperidyl and morpholinyl, and at least one of the substituents is amino, monoalkylamino, dialkylamino, trialkylammonio, pyrrolidinyl, piperidyl or morpholinyl, formula (CL-III) [Image disponible dans le document PDF, Image available in the PDF document] (CL-III) wherein <com:Math><semantics>R105<annotation encoding="application / x-tex">R^{105}< / annotation>< / semantics>< / com:Math> is linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; <com:Math><semantics>R106<annotation encoding="application / x-tex">R^{106}< / annotation>< / semantics>< / com:Math> is linear or branched C8-C24 alkyl, C8-C24 alkenyl, C8-C24 alkynyl, C8-C24 alkyloxyethyl, C8-C24 alkyloxypropyl, C8-C24 alkenyloxyethyl, C8-C24 alkenyloxypropyl, C8-C24 alkynyloxyethyl or C8-C24 alkynyloxypropyl; <com:Math><semantics>X103<annotation encoding="application / x-tex">X^{103}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X104<annotation encoding="application / x-tex">X^{104}< / annotation>< / semantics>< / com:Math> are the same or different and are each C1-C3 alkyl, or together form <com:Math><semantics>C2−C8<annotation encoding="application / x-tex">C2-C8< / annotation>< / semantics>< / com:Math> alkylene, or <com:Math><semantics>X103<annotation encoding="application / x-tex">X^{103}< / annotation>< / semantics>< / com:Math> forms <com:Math><semantics>C2−C8<annotation encoding="application / x-tex">C2-C8< / annotation>< / semantics>< / com:Math> alkylene together with <com:Math><semantics>L111<annotation encoding="application / x-tex">L^{111}< / annotation>< / semantics>< / com:Math>; <com:Math><semantics>L111<annotation encoding="application / x-tex">L^{111}< / annotation>< / semantics>< / com:Math> is a hydrogen atom, C1-C6 alkyl, C3-C6 alkenyl, amino, monoalkylamino, hydroxy, alkoxy, carbamoyl, monoalkylcarbamoyl, dialkylcarbamoyl, or C1-C6 alkyl or C3-C6 alkenyl substituted with one to three same or different substituents selected from amino, monoalkylamino, hydroxy, alkoxy, carbamoyl, monoalkylcarbamoyl and dialkylcarbamoyl, or forms C2-C8 alkylene together with <com:Math><semantics>X103<annotation encoding="application / x-tex">X^{103}< / annotation>< / semantics>< / com:Math>; <com:Math><semantics>L109<annotation encoding="application / x-tex">L^{109}< / annotation>< / semantics>< / com:Math> is C1-C6 alkylene; <com:Math><semantics>L110<annotation encoding="application / x-tex">L^{110}< / annotation>< / semantics>< / com:Math> is a single bond, or C1-C6 alkylene, provided that the sum of the numbers of carbon atoms of <com:Math><semantics>L109<annotation encoding="application / x-tex">L^{109}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L110<annotation encoding="application / x-tex">L^{110}< / annotation>< / semantics>< / com:Math> is 7 or less; when <com:Math><semantics>L111<annotation encoding="application / x-tex">L^{111}< / annotation>< / semantics>< / com:Math> is a hydrogen atom, <com:Math><semantics>L110<annotation encoding="application / x-tex">L^{110}< / annotation>< / semantics>< / com:Math> is a single bond; and when <com:Math><semantics>L111<annotation encoding="application / x-tex">L^{111}< / annotation>< / semantics>< / com:Math> forms C2-C6 alkylene together with <com:Math><semantics>X103<annotation encoding="application / x-tex">X^{103}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>L110<annotation encoding="application / x-tex">L^{110}< / annotation>< / semantics>< / com:Math> is a single bond, or methylene or ethylene, formula (CL-IV) [Image disponible dans le document PDF, Image available in the PDF document] CL-IV) wherein <com:Math><semantics>R107<annotation encoding="application / x-tex">R^{107}< / annotation>< / semantics>< / com:Math> is linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; <com:Math><semantics>R108<annotation encoding="application / x-tex">R^{108}< / annotation>< / semantics>< / com:Math> is linear or branched C8-C24 alkyl, C8-C24 alkenyl, C8-C24 alkynyl, C8-C24 alkyloxyethyl, C8-C24 alkyloxypropyl, C8-C24 alkenyloxyethyl, C8-C24 alkenyloxypropyl, C8-C24 alkynyloxyethyl, C8-C24 alkynyloxypropyl, C8-C24 alkyloxyethoxyethyl, C8-C24 alkenyloxyethoxyethyl or C8-C24 alkynyloxyethoxyethyl; and <com:Math><semantics>X105<annotation encoding="application / x-tex">X^{105}< / annotation>< / semantics>< / com:Math> is a hydrogen atom or optionally substituted C1-C4 alkyl, formula (CL-V) [Image disponible dans le document PDF, Image available in the PDF document] (CL-V) wherein R<com:Sup>109< / com:Sup> is linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; <com:Math><semantics>R110<annotation encoding="application / x-tex">R^{110}< / annotation>< / semantics>< / com:Math> is linear or branched C8-C24 alkyl, C8-C24 alkenyl, C8-C24 alkynyl, C8-C24 alkyloxyethyl, C8-C24 alkyloxypropyl, C8-C24 alkenyloxyethyl, C8-C24 alkenyloxypropyl, C8-C24 alkynyloxyethyl or C8-C24 alkynyloxypropyl; <com:Math><semantics>L112<annotation encoding="application / x-tex">L^{112}< / annotation>< / semantics>< / com:Math> is C1-C3 alkylene; and <com:Math><semantics>X105<annotation encoding="application / x-tex">X^{105}< / annotation>< / semantics>< / com:Math>' is a hydrogen atom or C1-C3 alkyl, formula (CL-VI) [Image disponible dans le document PDF, Image available in the PDF document] (CL-VI) wherein <com:Math><semantics>R111<annotation encoding="application / x-tex">R^{111}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R112<annotation encoding="application / x-tex">R^{112}< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; <com:Math><semantics>X106<annotation encoding="application / x-tex">X^{106}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X107<annotation encoding="application / x-tex">X^{107}< / annotation>< / semantics>< / com:Math> are the same or different and are each C1-C3 alkyl, or together form C2-C8 alkylene; <com:Math><semantics>p103<annotation encoding="application / x-tex">p^{103}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>p104<annotation encoding="application / x-tex">p^{104}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>p105<annotation encoding="application / x-tex">p^{105}< / annotation>< / semantics>< / com:Math> are the same or different and are each 0 or 1, provided that <com:Math><semantics>p103<annotation encoding="application / x-tex">p^{103}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>p104<annotation encoding="application / x-tex">p^{104}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>p105<annotation encoding="application / x-tex">p^{105}< / annotation>< / semantics>< / com:Math> are not 0 at the same time; and <com:Math><semantics>L113<annotation encoding="application / x-tex">L^{113}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L114<annotation encoding="application / x-tex">L^{114}< / annotation>< / semantics>< / com:Math> are the same or different and are each O, S or NH, formula (CL-VII) [Image disponible dans le document PDF, Image available in the PDF document] (CL-VII) wherein <com:Math><semantics>R113<annotation encoding="application / x-tex">R^{113}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R114<annotation encoding="application / x-tex">R^{114}< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; R<com:Sup>115< / com:Sup> is a hydrogen atom, hydroxy, optionally substituted C1-C4 alkyl, C1-C4 alkoxy or C1-C4 acyloxy; <com:Math><semantics>X109<annotation encoding="application / x-tex">X^{109}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X110<annotation encoding="application / x-tex">X^{110}< / annotation>< / semantics>< / com:Math> are the same or different and are each C1-C3 alkyl, or together form C2-C8 alkylene; <com:Math><semantics>L115<annotation encoding="application / x-tex">L^{115}< / annotation>< / semantics>< / com:Math> is -CO-O-, -O-CO-, -NHCO- or -CONH-; <com:Math><semantics>p106<annotation encoding="application / x-tex">p^{106}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 3; and <com:Math><semantics>p107<annotation encoding="application / x-tex">p^{107}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 4, formula (CL-VIII) [Image disponible dans le document PDF, Image available in the PDF document] wherein <com:Math><semantics>R116<annotation encoding="application / x-tex">R^{116}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R117<annotation encoding="application / x-tex">R^{117}< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl, C8-C24 alkynyl, C7-C20 alkyloxy C1-C3 alkyl, C7-C20 alkenyloxy C1-C3 alkyl or C7-C20 alkynyloxy C1-C3 alkyl; <com:Math><semantics>B100<annotation encoding="application / x-tex">B^{100}< / annotation>< / semantics>< / com:Math> is a hydrogen atom, C1-C3 alkyl, hydroxy C2-C4 alkyl, C1-C3 dialkylamino C2-C4 alkyl, formula (A): [Image disponible dans le document PDF, Image available in the PDF document] wherein <com:Math><semantics>X111<annotation encoding="application / x-tex">X^{111}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X112<annotation encoding="application / x-tex">X^{112}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or C1-C3 alkyl, or <com:Math><semantics>X111<annotation encoding="application / x-tex">X^{111}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X112<annotation encoding="application / x-tex">X^{112}< / annotation>< / semantics>< / com:Math> optionally form a C2-C6 nitrogen-containing hetero ring together with the nitrogen atom to which they are bonded; and <com:Math><semantics>p110<annotation encoding="application / x-tex">p^{110}< / annotation>< / semantics>< / com:Math> is an integer from 2 to 6, or formula (B): [Image disponible dans le document PDF, Image available in the PDF document] (B) wherein <com:Math><semantics>X113<annotation encoding="application / x-tex">X^{113}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X114<annotation encoding="application / x-tex">X^{114}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or C1 to C3 alkyl, or <com:Math><semantics>X113<annotation encoding="application / x-tex">X^{113}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X114<annotation encoding="application / x-tex">X^{114}< / annotation>< / semantics>< / com:Math> optionally form a C2-C6 nitrogen-containing hetero ring together with the nitrogen atom to which they are bonded; and <com:Math><semantics>p111<annotation encoding="application / x-tex">p^{111}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 6; <com:Math><semantics>P108<annotation encoding="application / x-tex">P^{108}< / annotation>< / semantics>< / com:Math> is an integer from 0 to 4; <com:Math><semantics>P109<annotation encoding="application / x-tex">P^{109}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 4, provided that when <com:Math><semantics>P108<annotation encoding="application / x-tex">P^{108}< / annotation>< / semantics>< / com:Math> is 0, <com:Math><semantics>P109<annotation encoding="application / x-tex">P^{109}< / annotation>< / semantics>< / com:Math> is not 1; <com:Math><semantics>L116<annotation encoding="application / x-tex">L^{116}< / annotation>< / semantics>< / com:Math> is the same or different on each carbon to which it is bonded and is a hydrogen atom or C1-C3 alkyl; and <com:Math><semantics>L117<annotation encoding="application / x-tex">L^{117}< / annotation>< / semantics>< / com:Math> is the same or different on each carbon to which it is bonded and is a hydrogen atom or C1-C3 alkyl, formula (CL-IX) [Image disponible dans le document PDF, Image available in the PDF document] wherein <com:Math><semantics>X115<annotation encoding="application / x-tex">X^{115}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X116<annotation encoding="application / x-tex">X^{116}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or C1-C3 alkyl; <com:Math><semantics>L118<annotation encoding="application / x-tex">L^{118}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L119<annotation encoding="application / x-tex">L^{119}< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted linear or branched C8-C24 alkylene or C8-C24 alkenylene; <com:Math><semantics>M101<annotation encoding="application / x-tex">M^{101}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>M102<annotation encoding="application / x-tex">M^{102}< / annotation>< / semantics>< / com:Math> are the same or different and are each selected from the group consisting of <com:Math><semantics>−C=C−<annotation encoding="application / x-tex">-C=C-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−OC(O)−<annotation encoding="application / x-tex">-OC(O)-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−C(O)O−<annotation encoding="application / x-tex">-C(O)O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−SC(O)−<annotation encoding="application / x-tex">-SC(O)-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−C(O)S−<annotation encoding="application / x-tex">-C(O)S-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−OC(S)−<annotation encoding="application / x-tex">-OC(S)-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−C(S)O−<annotation encoding="application / x-tex">-C(S)O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−SS−<annotation encoding="application / x-tex">-SS-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−C(R″)=N−<annotation encoding="application / x-tex">-C(R'')=N-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−N=C(R″)−<annotation encoding="application / x-tex">-N=C(R'')-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−C(R″)=N−O−<annotation encoding="application / x-tex">-C(R'') = N-O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−O−N=C(R″)−<annotation encoding="application / x-tex">-O-N=C(R'')-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−N(R″)C(O)−<annotation encoding="application / x-tex">-N(R'')C(O)-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−C(O)N(R″)−<annotation encoding="application / x-tex">-C(O)N(R'')-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−N(R″)C(S)−<annotation encoding="application / x-tex">-N(R'')C(S)-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−C(S)N(R″)−<annotation encoding="application / x-tex">-C(S)N(R'')-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−N(R″)C(O)N(R‴)−<annotation encoding="application / x-tex">-N(R'')C(O)N(R''')-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−N(R″)C(O)O−<annotation encoding="application / x-tex">-N(R'')C(O)O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−OC(0)N(R″)<annotation encoding="application / x-tex">-OC(0)N(R'')< / annotation>< / semantics>< / com:Math> - and <com:Math><semantics>−OC(0)O<annotation encoding="application / x-tex">-OC(0)O< / annotation>< / semantics>< / com:Math>-; R'' and R''' are the same or different and are each a hydrogen atom or C1-C3 alkyl; and <com:Math><semantics>R118<annotation encoding="application / x-tex">R^{118}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R119<annotation encoding="application / x-tex">R^{119}< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted linear or branched C1-C16 alkyl or C2-C16 alkenyl, formula (CL-X) [Image disponible dans le document PDF, Image available in the PDF document] (CL-X) wherein <com:Math><semantics>X117<annotation encoding="application / x-tex">X^{117}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X118<annotation encoding="application / x-tex">X^{118}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom, optionally substituted C1-C6 alkyl, heterocyclyl or polyamine, or <com:Math><semantics>X117<annotation encoding="application / x-tex">X^{117}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X118<annotation encoding="application / x-tex">X^{118}< / annotation>< / semantics>< / com:Math> optionally form, together with the nitrogen to which they are bonded, a 4- to 7-membered monocyclic hetero ring optionally containing one or two additional heteroatoms selected from N, O and S in addition to the nitrogen; and <com:Math><semantics>R120<annotation encoding="application / x-tex">R^{120}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R121<annotation encoding="application / x-tex">R^{121}< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted linear or branched C4-C24 alkyl or C4-C24 alkenyl, formula (CL-XI) [Image disponible dans le document PDF, Image available in the PDF document] (CL-XI) wherein <com:Math><semantics>X119<annotation encoding="application / x-tex">X^{119}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X120<annotation encoding="application / x-tex">X^{120}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom, optionally substituted linear or branched C1-C20 alkyl, C1-C20 alkenyl, C1-C20 alkynyl or C6-C20 acyl; <com:Math><semantics>R122<annotation encoding="application / x-tex">R^{122}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R123<annotation encoding="application / x-tex">R^{123}< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted linear or branched C1-C30 alkyl, C2-C30 alkenyl or C2-C30 alkynyl; and <com:Math><semantics>p112<annotation encoding="application / x-tex">p^{112}< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>p113<annotation encoding="application / x-tex">p^{113}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>p114<annotation encoding="application / x-tex">p^{114}< / annotation>< / semantics>< / com:Math> are the same or different and are each 0, or an arbitrary positive integer, formula (CL-XII) [Image disponible dans le document PDF, Image available in the PDF document] wherein <com:Math><semantics>X121<annotation encoding="application / x-tex">X^{121}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X122<annotation encoding="application / x-tex">X^{122}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom, C1-C6 alkyl, cycloalkyl or cycloalkenyl, or <com:Math><semantics>X121<annotation encoding="application / x-tex">X^{121}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X122<annotation encoding="application / x-tex">X^{122}< / annotation>< / semantics>< / com:Math> optionally form a C2-C6 nitrogen-containing hetero ring together with the nitrogen atom to which they are bonded; <com:Math><semantics>L120<annotation encoding="application / x-tex">L^{120}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L121<annotation encoding="application / x-tex">L^{121}< / annotation>< / semantics>< / com:Math> are the same or different and are each <com:Math><semantics>−0−<annotation encoding="application / x-tex">-0-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−0C(0)−<annotation encoding="application / x-tex">-0C(0)-< / annotation>< / semantics>< / com:Math> or <com:Math><semantics>−(0)CO−<annotation encoding="application / x-tex">-(0)CO-< / annotation>< / semantics>< / com:Math>; and <com:Math><semantics>R124<annotation encoding="application / x-tex">R^{124}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R125<annotation encoding="application / x-tex">R^{125}< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted linear or branched C8-C24 alkyl or C8-C24 alkenyl, formula (CL-XIII) [Image disponible dans le document PDF, Image available in the PDF document] (CL-XIII) wherein <com:Math><semantics>R126<annotation encoding="application / x-tex">R^{126}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R127<annotation encoding="application / x-tex">R^{127}< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl, C8-C24 alkynyl, C8-C24 heteroalkyl, C8-C24 heteroalkenyl or C8-C24 heteroalkynyl; <com:Math><semantics>X123<annotation encoding="application / x-tex">X^{123}< / annotation>< / semantics>< / com:Math> is a hydrogen atom or optionally substituted C1-C6 alkyl; <com:Math><semantics>X124<annotation encoding="application / x-tex">X^{124}< / annotation>< / semantics>< / com:Math> is C1-C6 alkyl, substituted C1-C6 alkyl which is substituted with <com:Math><semantics>−NR4aR4b<annotation encoding="application / x-tex">-NR^{4a}R^{4b}< / annotation>< / semantics>< / com:Math>, or optionally substituted C3-C7 heterocyclyl; R<com:Sup>4a< / com:Sup> and R<com:Sup>4b< / com:Sup> are the same or different and are each a hydrogen atom, <com:Math><semantics>C(=NH)NH2<annotation encoding="application / x-tex">C(=NH)NH_2< / annotation>< / semantics>< / com:Math> or optionally substituted C1-C6 alkyl, or <com:Math><semantics>R4a<annotation encoding="application / x-tex">R^{4a}< / annotation>< / semantics>< / com:Math> and R4b optionally form optionally substituted C3-C7 heterocyclyl; <com:Math><semantics>X123<annotation encoding="application / x-tex">X^{123}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X124<annotation encoding="application / x-tex">X^{124}< / annotation>< / semantics>< / com:Math> optionally form optionally substituted C3-C7 heterocyclyl together with the nitrogen atom to which they are bonded, provided that <com:Math><semantics>X123<annotation encoding="application / x-tex">X^{123}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X124<annotation encoding="application / x-tex">X^{124}< / annotation>< / semantics>< / com:Math> do not form imidazolyl, benzimidazolyl, or succinimidyl, and only one primary amine is allowed to be present on any one of <com:Math><semantics>X123<annotation encoding="application / x-tex">X^{123}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X124<annotation encoding="application / x-tex">X^{124}< / annotation>< / semantics>< / com:Math>, or any primary amine is not present on any one of <com:Math><semantics>X123<annotation encoding="application / x-tex">X^{123}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X124<annotation encoding="application / x-tex">X^{124}< / annotation>< / semantics>< / com:Math>, and neither <com:Math><semantics>X123<annotation encoding="application / x-tex">X^{123}< / annotation>< / semantics>< / com:Math> nor <com:Math><semantics>X124<annotation encoding="application / x-tex">X^{124}< / annotation>< / semantics>< / com:Math> is substituted amide; when each of <com:Math><semantics>R126<annotation encoding="application / x-tex">R^{126}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R127<annotation encoding="application / x-tex">R^{127}< / annotation>< / semantics>< / com:Math> is C11 alkyl or C15 alkyl, <com:Math><semantics>X123<annotation encoding="application / x-tex">X^{123}< / annotation>< / semantics>< / com:Math> is not a hydrogen atom; when each of <com:Math><semantics>R126<annotation encoding="application / x-tex">R^{126}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R127<annotation encoding="application / x-tex">R^{127}< / annotation>< / semantics>< / com:Math> is C16 alkyl or C17 alkyl, <com:Math><semantics>R126<annotation encoding="application / x-tex">R^{126}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R127<annotation encoding="application / x-tex">R^{127}< / annotation>< / semantics>< / com:Math> are not substituted with OH; when each of <com:Math><semantics>R126<annotation encoding="application / x-tex">R^{126}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R127<annotation encoding="application / x-tex">R^{127}< / annotation>< / semantics>< / com:Math> is C17 alkyl, <com:Math><semantics>X123<annotation encoding="application / x-tex">X^{123}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X124<annotation encoding="application / x-tex">X^{124}< / annotation>< / semantics>< / com:Math> are not substituted with OH; and when each of <com:Math><semantics>R126<annotation encoding="application / x-tex">R^{126}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R127<annotation encoding="application / x-tex">R^{127}< / annotation>< / semantics>< / com:Math> is C18 alkyl, <com:Math><semantics>X124<annotation encoding="application / x-tex">X^{124}< / annotation>< / semantics>< / com:Math> is not substituted with optionally substituted imidazolyl, formula (CL-XIV) [Image disponible dans le document PDF, Image available in the PDF document] (CL-XIV) wherein <com:Math><semantics>X125<annotation encoding="application / x-tex">X^{125}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X126<annotation encoding="application / x-tex">X^{126}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom, optionally substituted C1-C6 alkyl, heterocyclyl or polyamine, or <com:Math><semantics>X125<annotation encoding="application / x-tex">X^{125}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X126<annotation encoding="application / x-tex">X^{126}< / annotation>< / semantics>< / com:Math> optionally form, together with the nitrogen to which they are bonded, a 4- to 7-membered monocyclic hetero ring optionally containing one or two additional heteroatoms selected from N, O and S in addition to the nitrogen; <com:Math><semantics>R130<annotation encoding="application / x-tex">R^{130}< / annotation>< / semantics>< / com:Math> is a hydrogen atom or C1-C6 alkyl; and <com:Math><semantics>R128<annotation encoding="application / x-tex">R^{128}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R129<annotation encoding="application / x-tex">R^{129}< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted linear or branched C4-C24 alkyl or C4-C24 alkenyl, formula (CL-XV) [Image disponible dans le document PDF, Image available in the PDF document] (CL-XV) wherein <com:Math><semantics>X127<annotation encoding="application / x-tex">X^{127}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X128<annotation encoding="application / x-tex">X^{128}< / annotation>< / semantics>< / com:Math> are each independently C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, or <com:Math><semantics>X127<annotation encoding="application / x-tex">X^{127}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X128<annotation encoding="application / x-tex">X^{128}< / annotation>< / semantics>< / com:Math> form, together with the nitrogen atom to which they are bonded, a hetero ring having one or two nitrogen atoms; <com:Math><semantics>L122<annotation encoding="application / x-tex">L^{122}< / annotation>< / semantics>< / com:Math> is <com:Math><semantics>−C(0)O−<annotation encoding="application / x-tex">-C(0)O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−OC(0)−<annotation encoding="application / x-tex">-OC(0)-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−C(0)N(X130)−<annotation encoding="application / x-tex">-C(0)N(X^{130})-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−N(X130)C(0)−<annotation encoding="application / x-tex">-N(X^{130})C(0)-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−OC(O)O−<annotation encoding="application / x-tex">-OC(O)O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−OC(O)N(X130)−<annotation encoding="application / x-tex">-OC(O)N(X^{130})-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−N(X130)C(O)N(X130)−<annotation encoding="application / x-tex">-N(X^{130})C(O)N(X^{130})-< / annotation>< / semantics>< / com:Math>, or <com:Math><semantics>−N(X130)C(O)O−<annotation encoding="application / x-tex">-N(X^{130})C(O)O-< / annotation>< / semantics>< / com:Math>; each <com:Math><semantics>X130<annotation encoding="application / x-tex">X^{130}< / annotation>< / semantics>< / com:Math> present is independently a hydrogen atom or C1-C3 alkyl; a is 1, 2, 3, 4, 5, or 6; b is 0, 1, 2, or 3; <com:Math><semantics>X129<annotation encoding="application / x-tex">X^{129}< / annotation>< / semantics>< / com:Math> is absent, or hydrogen or C1-C3 alkyl; <com:Math><semantics>R131<annotation encoding="application / x-tex">R^{131}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R132<annotation encoding="application / x-tex">R^{132}< / annotation>< / semantics>< / com:Math> are each independently alkyl having 12 to 24 carbon atoms, alkenyl having 12 to 24 carbon atoms, or alkoxy having 12 to 24 carbon atoms, which has one or more biodegradable groups; each biodegradable group independently interrupts the alkyl group, the alkenyl group, or the alkoxy group having 12 to 24 carbon atoms, or substitutes a terminal of the alkyl group, the alkenyl group, or the alkoxy group having 12 to 24 carbon atoms (wherein the interrupting biodegradable group is <com:Math><semantics>−C(0)O−<annotation encoding="application / x-tex">-C(0)O-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−OC(0)−<annotation encoding="application / x-tex">-OC(0)-< / annotation>< / semantics>< / com:Math>, <com:Math><semantics>−C(0)N(X130)−<annotation encoding="application / x-tex">-C(0)N(X^{130})-< / annotation>< / semantics>< / com:Math>, or <com:Math><semantics>−N(X130)C(0)−<annotation encoding="application / x-tex">-N(X^{130})C(0)-< / annotation>< / semantics>< / com:Math>, and the group having the terminal biodegradable group is <com:Math><semantics>−C(0)O−C1−C4<annotation encoding="application / x-tex">-C(0)O-C1-C4< / annotation>< / semantics>< / com:Math> alkyl, <com:Math><semantics>−OC(0)−C1−C4<annotation encoding="application / x-tex">-OC(0)-C1-C4< / annotation>< / semantics>< / com:Math> alkyl, <com:Math><semantics>−C(0)N(X130)−C1−C4<annotation encoding="application / x-tex">-C(0)N(X^{130})-C1-C4< / annotation>< / semantics>< / com:Math> alkyl, or <com:Math><semantics>−N(X130)C(0)−C1−C4<annotation encoding="application / x-tex">-N(X^{130})C(0)-C1-C4< / annotation>< / semantics>< / com:Math> alkyl); and <com:Math><semantics>R131<annotation encoding="application / x-tex">R^{131}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R132<annotation encoding="application / x-tex">R^{132}< / annotation>< / semantics>< / com:Math> each have at least four carbon atoms between the biodegradable group and the asterisked (*) tertiary carbon atom, formula (CL-XVI) [Image disponible dans le document PDF, Image available in the PDF document] wherein <Formule mathématique disponible dans le document PDF, Math available in the PDF document>${\bf R}^{133}$ and <Formule mathématique disponible dans le document PDF, Math available in the PDF document>${\bf R}^{134}$ are the same or different and are each linear or branched C1-C9 alkyl, C2-C11 alkenyl or C2-C11 alkynyl; <com:Math><semantics>L123<annotation encoding="application / x-tex">L^{123}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L124<annotation encoding="application / x-tex">L^{124}< / annotation>< / semantics>< / com:Math> are the same or different and are each linear C5-C18 alkylene or linear C5-C18 alkenylene, or forms a hetero ring with N; <com:Math><semantics>L125<annotation encoding="application / x-tex">L^{125}< / annotation>< / semantics>< / com:Math> is a single bond, or -CO-O-, thereby forming <com:Math><semantics>−L124−CO−OR134<annotation encoding="application / x-tex">-L^{124}-CO-OR^{134}< / annotation>< / semantics>< / com:Math>; <com:Math><semantics>L127<annotation encoding="application / x-tex">L^{127}< / annotation>< / semantics>< / com:Math> is S or O; <com:Math><semantics>L126<annotation encoding="application / x-tex">L^{126}< / annotation>< / semantics>< / com:Math> is a single bond or linear or branched C1-C6 alkylene, or forms a hetero ring with N; <com:Math><semantics>L128<annotation encoding="application / x-tex">L^{128}< / annotation>< / semantics>< / com:Math> is linear or branched C1-C6 alkylene; and <com:Math><semantics>X131<annotation encoding="application / x-tex">X^{131}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X132<annotation encoding="application / x-tex">X^{132}< / annotation>< / semantics>< / com:Math> are the same or different and are each hydrogen or linear or branched C1-C6 alkyl, formula (CL-XVII) [Image disponible dans le document PDF, Image available in the PDF document] wherein <com:Math><semantics>L131<annotation encoding="application / x-tex">L^{131}< / annotation>< / semantics>< / com:Math> is C2-C4 alkylene or <com:Math><semantics>−CH2−S−CH2CH2−<annotation encoding="application / x-tex">-CH_2-S-CH_2CH_2-< / annotation>< / semantics>< / com:Math>; <com:Math><semantics>L129<annotation encoding="application / x-tex">L^{129}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>L130<annotation encoding="application / x-tex">L^{130}< / annotation>< / semantics>< / com:Math> are the same or different and are each C1-C6 alkyl; <com:Math><semantics>R135<annotation encoding="application / x-tex">R^{135}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R136<annotation encoding="application / x-tex">R^{136}< / annotation>< / semantics>< / com:Math> are the same or different and are each C10-C30 alkyl or C10-C30 alkenyl; and <com:Math><semantics>X133<annotation encoding="application / x-tex">X^{133}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X134<annotation encoding="application / x-tex">X^{134}< / annotation>< / semantics>< / com:Math> are the same or different and are each hydrogen, C1-C6 alkyl or <com:Math><semantics>−CH2CH2OH<annotation encoding="application / x-tex">-CH2CH2OH< / annotation>< / semantics>< / com:Math>, formula (CL-XVIII) [Image disponible dans le document PDF, Image available in the PDF document] wherein <com:Math><semantics>R137<annotation encoding="application / x-tex">R^{137}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R138<annotation encoding="application / x-tex">R^{138}< / annotation>< / semantics>< / com:Math> are the same or different and are each linear or branched C8-C24 alkyl, C8-C24 alkenyl, C8-C24 alkynyl, C8-C24 alkylthioethyl, C8-24 alkenylthioethyl, or C8-C24 alkynylthioethyl; <com:Math><semantics>X135<annotation encoding="application / x-tex">X^{135}< / annotation>< / semantics>< / com:Math> is a hydrogen atom, C1-C3 alkyl, hydroxy C2-C4 alkyl, formula (C): [Image disponible dans le document PDF, Image available in the PDF document] wherein <com:Math><semantics>X136<annotation encoding="application / x-tex">X^{136}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X137<annotation encoding="application / x-tex">X^{137}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or C1-C3 alkyl, or <com:Math><semantics>X136<annotation encoding="application / x-tex">X^{136}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X137<annotation encoding="application / x-tex">X^{137}< / annotation>< / semantics>< / com:Math> optionally form a C2-C6 nitrogen-containing hetero ring together with the nitrogen atom to which they are bonded; <com:Math><semantics>L132<annotation encoding="application / x-tex">L^{132}< / annotation>< / semantics>< / com:Math> is S or O; and <com:Math><semantics>p115<annotation encoding="application / x-tex">p^{115}< / annotation>< / semantics>< / com:Math> is an integer from 2 to 4, formula (D): [Image disponible dans le document PDF, Image available in the PDF document] (D) wherein <com:Math><semantics>X138<annotation encoding="application / x-tex">X^{138}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X139<annotation encoding="application / x-tex">X^{139}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or C1 to C3 alkyl, or <com:Math><semantics>X138<annotation encoding="application / x-tex">X^{138}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X139<annotation encoding="application / x-tex">X^{139}< / annotation>< / semantics>< / com:Math> optionally form a C3-C6 nitrogen-containing hetero ring together with the nitrogen atom to which they are bonded; and <com:Math><semantics>p116<annotation encoding="application / x-tex">p^{116}< / annotation>< / semantics>< / com:Math> is an integer from <com:Math><semantics>1<annotation encoding="application / x-tex">1< / annotation>< / semantics>< / com:Math> to <com:Math><semantics>4<annotation encoding="application / x-tex">4< / annotation>< / semantics>< / com:Math>, or formula (E): [Image disponible dans le document PDF, Image available in the PDF document] (E) wherein <com:Math><semantics>X140<annotation encoding="application / x-tex">X^{140}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X141<annotation encoding="application / x-tex">X^{141}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or C1 to C3 alkyl, or <com:Math><semantics>X140<annotation encoding="application / x-tex">X^{140}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X141<annotation encoding="application / x-tex">X^{141}< / annotation>< / semantics>< / com:Math> optionally form a C3-C6 nitrogen-containing hetero ring together with the nitrogen atom to which they are bonded; and <com:Math><semantics>p117<annotation encoding="application / x-tex">p^{117}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 4, and formula (CL-XIX) [Image disponible dans le document PDF, Image available in the PDF document] wherein <com:Math><semantics>R139<annotation encoding="application / x-tex">R^{139}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>R140<annotation encoding="application / x-tex">R^{140}< / annotation>< / semantics>< / com:Math> are the same or different and are each linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; <com:Math><semantics>L133<annotation encoding="application / x-tex">L^{133}< / annotation>< / semantics>< / com:Math> is S or O; and <com:Math><semantics>X142<annotation encoding="application / x-tex">X^{142}< / annotation>< / semantics>< / com:Math> is a hydrogen atom, C1-C3 alkyl, hydroxy C2-C4 alkyl, formula (F): [Image disponible dans le document PDF, Image available in the PDF document] (F) wherein <com:Math><semantics>X143<annotation encoding="application / x-tex">X^{143}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X144<annotation encoding="application / x-tex">X^{144}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or C1-C3 alkyl, or <com:Math><semantics>X143<annotation encoding="application / x-tex">X^{143}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X144<annotation encoding="application / x-tex">X^{144}< / annotation>< / semantics>< / com:Math> optionally form a C2-C6 nitrogen-containing hetero ring together with the nitrogen atom to which they are bonded; <com:Math><semantics>L134<annotation encoding="application / x-tex">L^{134}< / annotation>< / semantics>< / com:Math> is S or O; and <com:Math><semantics>p118<annotation encoding="application / x-tex">p^{118}< / annotation>< / semantics>< / com:Math> is an integer from 2 to 4, or formula (G): [Image disponible dans le document PDF, Image available in the PDF document] (G) wherein <com:Math><semantics>X145<annotation encoding="application / x-tex">X^{145}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X146<annotation encoding="application / x-tex">X^{146}< / annotation>< / semantics>< / com:Math> are the same or different and are each a hydrogen atom or C1 to C3 alkyl, or <com:Math><semantics>X145<annotation encoding="application / x-tex">X^{145}< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>X146<annotation encoding="application / x-tex">X^{146}< / annotation>< / semantics>< / com:Math> optionally form a C3-C6 nitrogen-containing hetero ring together with the nitrogen atom to which they are bonded; and <com:Math><semantics>p119<annotation encoding="application / x-tex">p^{119}< / annotation>< / semantics>< / com:Math> is an integer from 1 to 4.

6. The nucleic acid-containing lipid nanoparticle according to claim 5, wherein the cationic lipid is the lipid B.

7. The nucleic acid-containing lipid nanoparticle according to any one of claims 1 to 6, further comprising a lipid derivative or a fatty acid derivative of a water-soluble polymer.

8. The nucleic acid-containing lipid nanoparticle according to claim 7, wherein the water-soluble polymer moiety of the lipid derivative or the fatty acid derivative of the water-soluble polymer is selected from the group consisting of polyethylene glycol, polyglycerin, polyethyleneimine, polyvinyl alcohol, polyacrylic acid and polyacrylamide.

9. The nucleic acid-containing lipid nanoparticle according to any one of claims 1 to 8, further comprising a neutral lipid.

10. The nucleic acid-containing lipid nanoparticle according to claim 9, wherein the neutral lipid is selected from the group consisting of phospholipid, sterol, glyceroglycolipid, sphingoglycolipid and sphingoid.

11. The nucleic acid-containing lipid nanoparticle according to any one of claims 1 to 10, wherein the nucleic acid is a nucleic acid having a silencing effect on a target gene through the use of RNA interference (RNAi).

12. The nucleic acid-containing lipid nanoparticle according to claim 11, wherein the target gene is a gene related to tumor or inflammation.

13. A method for stabilizing a nucleic acid-containing lipid nanoparticle using an analog of a fatty acid ester of glycerol, wherein the analog is not hydrolyzable by a lipase, and is a lipid represented by the following formula (1) or (2): [Image disponible dans le document PDF, Image available in the PDF document] (1) wherein <com:Math><semantics>Rx1<annotation encoding="application / x-tex">Rx^1< / annotation>< / semantics>< / com:Math> and <com:Math><semantics>Rx2<annotation encoding="application / x-tex">Rx^2< / annotation>< / semantics>< / com:Math> are the same or different and are each optionally substituted linear or branched C7-C23 alkyl, C7-C23 alkenyl or C7-C23 alkynyl; and Rx<com:Sup>3< / com:Sup> is a negative charge, a hydrogen atom, or any of the following groups: [Image disponible dans le document PDF, Image available in the PDF document] or [Image disponible dans le document PDF, Image available in the PDF document] (2) wherein Rx4 is optionally substituted linear or branched C8-C24 alkyl, <com:Math><semantics>C8−C24<annotation encoding="application / x-tex">C8-C24< / annotation>< / semantics>< / com:Math> alkenyl or <com:Math><semantics>C8−C24<annotation encoding="application / x-tex">C8-C24< / annotation>< / semantics>< / com:Math> alkynyl or <com:Math><semantics>Rx41−C0−<annotation encoding="application / x-tex">Rx^{41}-C0-< / annotation>< / semantics>< / com:Math>; Rx<com:Sup>41< / com:Sup> is optionally substituted linear or branched C7-C23 alkyl, C7-C23 alkenyl or C7-C23 alkynyl; Rx<com:Sup>5< / com:Sup> is optionally substituted linear or branched C8-C24 alkyl, C8-C24 alkenyl or C8-C24 alkynyl; and Rx6 is a negative charge, a hydrogen atom, or any of the following groups: [Image disponible dans le document PDF, Image available in the PDF document] [Image disponible dans le document PDF, Image available in the PDF document] • 14. Use of the nucleic acid-containing lipid nanoparticle according to any one of claims 1 to 12 for introducing a nucleic acid into a cell.

15. The use according to claim 14, wherein the cell is a cell residing at a mammalian tumor or inflammation site.

16. The use according to claim 14 or 15, wherein the cell is a cell residing in the mammalian liver, stomach, lung, kidney, pancreas or spleen.

17. The use according to any one of claims 14 to 16, wherein the nucleic acid-containing lipid nanoparticle is for intravenous administration or subcutaneous administration.

18. Use of the nucleic acid-containing lipid nanoparticle according to any one of claims 1 to 12 for treating a cancer or an inflammatory disease in a mammal.

19. The use according to claim 18, wherein the nucleic acid- containing lipid nanoparticle is for intravenous administration or subcutaneous administration.

20. A medicament comprising the nucleic acid-containing lipid nanoparticle according to any one of claims 1 to 12.

21. The medicament according to claim 20, wherein the medicament is intended for intravenous administration or subcutaneous administration.

22. A therapeutic agent for a cancer or an inflammatory disease, comprising the nucleic acid-containing lipid nanoparticle according to any one of claims 1 to 12.

23. The therapeutic agent according to claim 22, wherein the therapeutic agent is intended for intravenous administration or subcutaneous administration.