Compounds to provide a long-lasting odor.

Abstract

COMPOUNDS FOR PROVIDING A LASTING ODOR. The present invention relates to the field of perfumery. More specifically, it relates to compounds of formula (I) capable of providing a lasting or consistent odor to the environment. Furthermore, the present invention relates to a method for imparting a lasting odor to an environment or to surfaces, such as hard surfaces, fabrics, skin or hair. In addition, the present invention relates to the use of said compounds in perfumery, as well as to perfume compositions or perfumed articles comprising the compounds of the invention.

Description

"Compounds to provide a long-lasting odor" FIELD OF TECHNIQUE

[0001] The present invention relates to the field of perfumery. More specifically, it relates to compounds of formula (I) capable of imparting a lasting or consistent odor to the environment. Furthermore, the present invention relates to a method for imparting a lasting odor to the environment or to surfaces, such as hard surfaces, fabrics, skin or hair. In addition, the present invention relates to the use of said compounds in perfumery, as well as to perfume compositions or perfumed articles comprising the compounds of the invention. PRIOR ART

[0002] Consumers generally correlate the effectiveness of scented items to the longevity or substantivity of the fragrance's longevity. Perfumes are composed of a multitude of different volatile compounds, which are applied to a surface from which they evaporate to be inhaled. Perfume is applied to the environment or to surfaces, such as hard surfaces, fabric, skin, or hair, by means of a perfume composition or a scented consumer item, for example, fine fragrances or shower gels. Due to the high volatility of the fragrances that constitute perfumes, the odor emanating from the perfumed surface can only be perceived for a limited period of time. Specifically, the so-called top notes of a perfume evaporate very quickly. They are the most volatile compounds in the composition and represent the freshness of a perfume.Top notes typically include citrus, floral, green, and fruity notes, among others, with floral and fruity notes being particularly well-liked by consumers. Various classes of floral and fruity notes are used in perfumes. Typical examples of fruity notes are those reminiscent of peach, apricot, and exotic fruits.

[0003] Consumers seek fragrances that are stable upon application and at the same time long-lasting or consistent so that they last for several hours or even days after application. Specifically, long-lasting fruity and floral notes are desirable. Petition 870220074448, dated 08 / 18 / 2022, page 10 / 85 2 / 71

[0004] Therefore, the objective of the present invention is to provide a system that is stable for delivering a long-lasting or consistent odor, specifically a fruity and / or floral odor, to the environment. Furthermore, another objective of the present invention is to provide a method for imparting a long-lasting odor of cyclopentanone-derived perfumery ingredients known for their fruity and / or floral organoleptic properties to surfaces, such as hard surfaces, fabrics, skin, or hair, by applying the perfume composition or perfumed articles. DESCRIPTION OF THE INVENTION

[0005] It has been found that some specific compounds, namely multicyclic compounds derived from cyclopentanone-based perfume ingredients, can be advantageously employed to generate a long-lasting or consistent perfume effect, specifically a fruity and / or floral note, on a given surface in the environment and, therefore, be useful as ingredients for perfume composition or for perfumed articles.

[0006] Therefore, a first object of the present invention is a compound of the formula in the form of any one of its stereoisomers or a mixture thereof, where n is 1, 2, 3 or 4; The dotted line represents a single bond or a double bond. X is an oxygen atom or an NR group where R is a hydrogen atom, a C1 to C4 alkyl group, a phenyl group, or a benzyl group. R1 is a hydrogen atom or a C1 to C10 hydrocarbon group comprising, optionally, 1 to 5 oxygen atoms and / or a sulfur atom and / or Petition 870220074448, dated 08 / 18 / 2022, page 11 / 85 3 / 71 one, two or three nitrogen atoms; R2 and R2' are, independently of each other, a hydrogen atom, a C1 to C4 alkyl group, or a CHR1XH group, or R2 and R2' form, when taken together, a carbonyl group; R3 is a hydrogen atom, a C1 to C4 alkyl group, a phenyl group, or a benzyl group; R4 is a hydrogen atom, a COOR' group, or a C1-3 alkyl group optionally substituted by a COOR' group where R' is a C1-3 alkyl group; R5s are, independently of each other, either a hydrogen atom or a methyl group; or R and R1, when obtained together, form a C4-6 azocycloalkyl group; or R1 and R2, when obtained together, form a C5-6 cycloalkyl group; or, R2 and R3, when obtained together, form a group of formula iR1 A,.X(II) R^f'^ / ^^R^XRx A R5 In R4, the bold line is connected to the carbon atom of R2, and the dashed line is connected to the nitrogen atom of R3.

[0007] For the sake of clarity, the expression any of its stereoisomers or a mixture thereof or similar means the normal meaning understood by a person skilled in the art, that is, that the compound of formula (I) may be a pure enantiomer (optically active case) or a diastereomer. In other words, the compound of formula (I) may possess several stereocenters, and each of said stereocenters may have two different stereochemistries (e.g., R or S). The compound of formula (I) may even be in the form of a pure enantiomer or in the form of a mixture of enantiomers or diastereomers. The compound of formula (I) may be in a racemic form or in a scalemic form. Therefore, Petition 870220074448, dated 08 / 18 / 2022, p. 12 / 85 4 / 71 the compound of formula (I) may be a stereoisomer or may be in the form of a composition of matter comprising or consisting of several stereoisomers.

[0008] For the sake of clarity, the expression “dashed line represents a single bond or a double bond” or similar has the normal meaning understood by a person skilled in the art, namely, that every bond (solid line and dashed line) between carbon atoms linked by said dashed line is a single or double carbon-carbon bond.

[0009] It should be understood that “... hydrocarbon group...” means that said group consists of hydrogen and carbon atoms and may be in the form of an aliphatic hydrocarbon, i.e., a linear or branched saturated hydrocarbon (e.g., alkyl group), a linear or branched unsaturated hydrocarbon (e.g., alkenyl or alkynyl group), a saturated cyclic hydrocarbon (e.g., cycloalkyl) or an unsaturated cyclic hydrocarbon (e.g., cycloalkenyl or cycloalkynyl) or may be in the form of an aromatic hydrocarbon, i.e., an aryl group, or may also be in the form of a mixture of said types of groups, for example, a specific group may comprise a linear alkyl, a branched alkenyl (e.g., having one or more carbon-carbon double bonds), a (poly)cycloalkyl and an aryl chemical moiety, except where a specific limitation applies to only one type. for mention.Similarly, in all embodiments of the invention, when a group is mentioned as being in the form of more than one type of topology (e.g., linear, cyclic, or branched) and / or as saturated or unsaturated (e.g., alkyl, aromatic, or alkenyl), this also means a group that may comprise chemical moieties that have any of said topologies or that are saturated or unsaturated, as explained above. Similarly, in all embodiments of the invention, when a group is mentioned as being in the form of a saturated or unsaturated type (e.g., alkyl), it means that said group may be in any type of topology (e.g., linear, cyclic, or branched) or with multiple moieties with multiple topologies.

[0010] It is understood that with the terms ... a hydrocarbon group that Petition 870220074448, dated 08 / 18 / 2022, p. 13 / 85 5 / 71 optionally comprises... and ... a hydrocarbon group optionally substituted by...” said hydrocarbon group optionally comprises alcohol, ketone, aldehyde, ether, thioether, ester, carboxylic acid, amine, amide, carbamate, nitrile or thiol groups. These groups may substitute either a hydrogen atom of the hydrocarbon group and then be laterally attached to said hydrocarbon or may substitute a carbon atom (if chemically feasible) of the hydrocarbon group and then be inserted into the hydrocarbon chain.For example, a -CH2-CH2-CHOH-CH2- group represents a C4 hydrocarbon group comprising an alcohol group (substitution of a hydrogen atom), a -CH2-CH2-COO-CH2-CH2-OCO-CH2-CH2- group represents a C6 hydrocarbon group comprising two ester groups (substitution of carbon atoms / insertion into the hydrocarbon chain), and similarly, a CH2-CH2-O-CH2-CH2-O-CH2-CH2- group represents a C6 hydrocarbon group comprising two ether groups.

[0011] The term “alkyl” is understood to comprise linear or branched alkyl groups. The term “cycloalkyl” is understood to comprise monocyclic or multicyclic alkyl groups; that is, compounds of formula (I) comprise a fused bicyclic group. The term “azocycloalkyl” is understood to comprise a ring produced from carbon atoms and a nitrogen atom.

[0012] For the sake of clarity, the expression in which the bold line is connected to the carbon atom of R2, and the dashed line to the nitrogen atom of R3 or similar has the normal meaning understood by a person skilled in the art, that is, the compound of formula (I) is of formula in the form of any of its stereoisomers or as a mixture Petition 870220074448, dated 08 / 18 / 2022, p. 14 / 85 6 / 71 of them, where the dashed line, n, X, R1, R2', R4 and R5 have the same meaning as defined above.

[0013] According to any embodiment of the invention, the compound of the invention is a compound of formula (I), as defined above, provided that 1,3dibenzyl-2'-pentilocta-hydrospiro[benzo[d]imidazol-2,1'-cyclopentane] is excluded.

[0014] According to any embodiment of the invention, each R5 can be a methyl group, or each R5 can be a hydrogen atom. In particular, each R5 can be a hydrogen atom.

[0015] According to any embodiment of the invention, R3 can be a hydrogen atom or a C1 to C4 alkyl group. Specifically, R3 can be a hydrogen atom, a methyl group, or an ethyl group.

[0016] According to any embodiment of the invention, the compound of the invention is a compound of the formula in the form of any one of its stereoisomers or a mixture thereof, where n is 1, 2, 3 or 4; The dotted line represents a single bond or a double bond. X is an oxygen atom or an NR group where R is a hydrogen atom, a C1 to C4 alkyl group, a phenyl group, or a benzyl group. R1 is a hydrogen atom or a C1 to C10 hydrocarbon group comprising, optionally, 1 to 5 oxygen atoms and / or a sulfur atom and / or one, two or three nitrogen atoms; R2e R2' are, independently of each other, a hydrogen atom, a C1 to C4 alkyl group, or a CHR1XH group, or R2e R2' form, when obtained Petition 870220074448, dated 08 / 18 / 2022, page 15 / 85 7 / 71 together, a carbonyl group; R3 is a hydrogen atom or a methyl group; R4 is a hydrogen atom, a COOR' group, or a C1-3 alkyl group optionally substituted by a COOR' group wherein R' is a C1-3 alkyl group; or R and R1, when obtained together, form a C4-6 azocycloalkyl group.

[0017] According to any embodiment of the invention, R4 may be a hydrogen atom, a methyl group, a COOCH3 group or a CH2COOCH3 group. Specifically, R4 may be a hydrogen atom.

[0018] According to any embodiment of the invention, n can be 2, 3 or 4, specifically, 2 or 3, more specifically, 3.

[0019] According to any embodiment of the invention, R3 can be a hydrogen atom.

[0020] According to any embodiment of the invention, the compound of the invention is of the formula in the form of any of its stereoisomers or as a mixture thereof, wherein the dashed line, n, R1, R2 and R2' have the same meaning as defined above.

[0021] According to any embodiment of the invention, X may be an NR group wherein R is a hydrogen atom, a methyl group or an ethyl group, specifically, R may be a hydrogen atom.

[0022] According to any embodiment of the invention, the dotted line may be a double link.

[0023] According to any embodiment of the invention, R2 and R2' can be, independently of each other, a hydrogen atom, a methyl group, a group Petition 870220074448, dated 08 / 18 / 2022, page 16 / 85 8 / 71 ethyl or a CHR1XH group, or R2 and R2' form, when obtained together, a carbonyl group. Specifically, R2 and R2' can be, independently of each other, a hydrogen atom, a methyl group, an ethyl group, or a CHR1OH group, or R2 and R2' form, when obtained together, a carbonyl group. Specifically, R2 and R2' can be, independently of each other, a methyl group, an ethyl group, or a hydroxymethyl group, or R2 and R2' form, when obtained together, a carbonyl group. Specifically, R2 can be a methyl group or an ethyl group, and R2' can be a hydroxymethyl group, or R2 and R2' form, when obtained together, a carbonyl group. Specifically, R2 and R2' can be obtained together and form a carbonyl group.

[0024] According to any embodiment of the invention, the compound of the invention is of the formula in the form of any of its stereoisomers or as a mixture thereof, wherein R and R1 have the same meaning as defined above.

[0025] According to any embodiment of the invention, R1 may be a hydrogen atom or a C1-4 alkyl group optionally substituted by an amide, a guanidine, a thiol, a primary amine (i.e., NH2), a C1-3 thioether, preferably an SCH3, a phenyl, a hydroxyphenyl, a carboxylic acid, a hydroxy or a C4-8 heterocycloalkenyl group, wherein the heteroatom is one or two nitrogen atoms, such as an imidazolyl group or an indolyl group.In other words, R1 can be a hydrogen atom or a residue derived from an amino acid of the formula R1CH(NH2)COOH and, in particular, from a natural α-amino acid, such as S-alanine (R1= CH3), S-arginine [R1= (CH2)3NHC(NH)(NH2)], S-asparagine (R1= CH2CONH2), R-cysteine ​​(R1= CH2SH), S-glutamine [R1= (CH2)2CONH2], glycine (R1= H), S-histidine (R1= CH2C3N2H3), S-isoleucine [R1= C(CH3)CH2CH3], S-leucine [R1= CH2CH(CH3)2]. Petition 870220074448, dated 08 / 18 / 2022, page 17 / 85 9 / 71 S-lysine [R1= (CH2)4NH2], S-methionine [R1= (CH2)2SCH3], S-phenylalanine (R1= CH2C6H5), S-serine (R1= CH2OH), S-threonine [R1= CH(OH)CHs], S-tryptophan (R1= CH2C8H6N), S-tyrosine (R1= CH2C6H4OH), S-valine [R1= CH(CHs)2], S-aspartic acid (R1= CH2COOH), and S-glutamic acid [R1= (CH2)2COOH], or an artificial α-amino acid selected from the group of norleucine [R1= (CH2)3CH3], norvaline [R1= (CH2)2CH3], 2-phenylglycine (R1= C6H5), ornithine [R1= (CH2)sNH2], homoalanine (R1= CH2CH3), homocysteine ​​[R1= (CH2)2SH] and homoserine [R1= (CH2)2OH]. Specifically, R1 can be a hydrogen atom, a methyl group, an ethyl group, or a benzyl group. More particularly, R1 can be a hydrogen atom, a methyl group, or an ethyl group.

[0026] The term “heterocycloalkenyl” is understood to comprise 1, 2 or more olefinic double bonds and to comprise monocyclic, fused, spiro and / or bicyclic or tricyclic bridging heterocycloalkenyl groups, preferably fused monocyclic or bicyclic heterocycloalkenyl groups.

[0027] According to a specific embodiment of the invention, R and R1 can be obtained together and form a C4-5 azocycloalkyl group. Specifically, R and R1 can be obtained together and form a C4 azocycloalkyl group.

[0028] In accordance with any one of the above embodiments, so that the compound of formula (I) can be 6-(5-hexenil)-1,4-diazaespiro[4.4]nonan-2-ona, 2-(5hexenil)tetra-hidroespiro[cyclopentano-1,3'-pyrrolo[1,2-c]imidazol]-1 '(2'H)-ona, 6-(hex5-en-1-il)-3-methyl-1,4-diazaespiro[4.4]nonan-2-ona, 3-benzil-6-(hex-5-en-1-il)-1,4diazaespiro[4.4]nonan-2-ona, 2-(hex-5-en-1-il)tetra-hidro-2H-espiro[ciclopentano1,3'-imidazo[1,5-a]piridin]-1 '(5'H)-ona, 6-petil-1,4-diazaespiro[4.4]nonan-2-ona, 3metil-6-petil-1,4-diazaespiro[4.4]nonan-2-ona, 3-benzil-6-petil-1,4diazaespiro[4.4]nonan-2-ona, 2-petiltetra-hidroespiro[ciclopentano-1,3'-pirrolo[1,2c]imidazol]-1 '(2'H)-ona, 2-petiltetra-hidro-2H-espiro[ciclopentano-1,3'-imidazo[1,5a]piridin]-1 '(5'H)-ona, 7-metil-6-petil-1,4-diazaespiro[4.4]nonan-2-ona, 6-hexil-1,4diazaespiro[4.4]nonan-2-ona, 2-hexiltetra-hidroespiro[ciclopentano-1,3'-pirrolo[1,2c]imidazol]-1'(2'H)-ona, 6-heptil-1,4-diazaespiro[4.4]nonan-2-one, 2-heptyltetrahydroespiro[cyclopentane-1,3'-pyrrole[1,2-c]imidazole]-1 '(2H)-one, 6-(but-3-en-1 -yl)Petição 870220074448, de 18 / 02 / 2020, p. 18 / 85. 10 / 71 6,9,9-trimethyl-1,4-diazaespiro[4.4]nonan-2-one, 2-(2-oxo-6-petyl-1,4diazaespiro[4.4]nonan-7-yl)methyl acetate, (6-(hex-5-en-1-yl)-3-methyl-1-oxa-4azaespiro[4.4]nonan-3-yl)methanol, (6-(hex-5-en-1-yl)-1-oxa-4-azaespiro[4.4]nonan-3yl)methanol, (3-methyl-6-pethyl-1 -oxa-4-azaespiro[4.4]nonan-3-yl)methanol, (6-petyl-1 -oxa-4azaespiro[4.4]nonan-3-yl)methanol, (6-hexyl-3-methyl-1-oxa-4-azaespiro[4.4]nonan-3-yl)methanol, (6-hexyl-1 -oxa-4-azaespiro[4.4]nonan-3-yl)methanol, (6-heptyl-3-methyl-1 -oxa4-azaespiro[4.4]nonan-3-yl)methanol or (6-heptyl-1 -oxa-4-azaespiro[4.4]nonan-3yl)methanol in the form of several humid esters. Preferably, the compound of Formula (I) can be 2-(5-hexenyl)tetra-hydrospiro[cyclopentano-1,3'pyrrole[1,2-c]imidazole]-1 '(2'H)-one or 2-petyltetra-hydroespiro[cyclopentane-1,3'pyrrole[1,2-c]imidazole]-1'(2'H)-one. Specifically, the compound of Formula (I) can be 2-(5-hexenyl)tetra-hydrospiro[cyclopentane-1,3'-pyrrole[1,2-c]imidazole]1'(2'H)-one.

[0029] Compounds according to formula (I) have the ability to slowly generate a cyclopentanone derivative of formula (VI) over time O)5(VI) FT in the form of any of its stereoisomers or as a mixture thereof, wherein the dashed line, n, R4 and R5 have the same meaning as defined above.

[0030] The compounds of formula (I) are non-volatile and essentially odorless. At the same time, they are relatively stable in perfume compositions or in perfumed items. When exposed to a surface under environmental conditions, it is possible that compounds (VI) are formed by reaction with ambient moisture. The generation of these compounds can be further triggered by the presence of oxygen in the air, by changes in pH, by exposure to light, in particular UV-A light, the presence of enzymes or increased temperature, or by other types of mechanisms or by a combination of several Petition 870220074448, dated 08 / 18 / 2022, page 19 / 85 11 / 71 mechanisms.

[0031] Non-volatile and essentially odorless compounds are advantageously characterized by a vapor pressure below 2.0 Pa, as obtained by calculation using EPIwin v. 3.10 software (2000, available from the U.S. Environmental Protection Agency). Preferably, said vapor pressure is below 0.2 Pa or, even more preferably, below 0.02 Pa.

[0032] Although it is not possible to provide an exhaustive list of compounds of formula (VI) that are generated from the compound of formula (I) of the invention, the following may be cited as preferred and non-limiting examples: 2-(5-hexen-1-yl)cyclopentanone, 2-hexyl-1-cyclopentanone, 2-heptyl-1-cyclopentanone, 2-petyl-1-cyclopentanone, 2,2,5-trimethyl-5-petyl-1-cyclopentanone, methyl 2-[3-oxo-2petylcyclopetyl]acetate, 3-methyl-2-petylcyclopentan-1-one, methyl 3-oxo-2petylcyclopentane-1-carboxylate or 2-(3-buten-1-yl)-2,5,5trimethylcyclopentanone. Specifically, the compound of formula (VI) may be 2(5-hexen-1-yl)cyclopentanone.

[0033] As mentioned above, the invention relates to the use of a compound of formula (I) as a perfuming ingredient to impart a lasting odor, specifically, an odor imparted by cyclopentanone-derived perfumery ingredients, to the environment. In other words, the invention relates to a method for imparting, intensifying, enhancing or modifying the odor, in particular, an odor imparted by cyclopentanone-derived perfumery ingredients (i.e., fruity and / or floral odor), of a perfuming composition or a perfumed article, the method comprising adding to said composition or article an effective amount of at least one compound of formula (I). “Use of a compound of formula (I)” must be understood in the present context as the use of any composition containing a compound of formula (I) and which can be advantageously employed in the perfumery industry.

[0034] In the present context, “fragrance ingredient” means a compound that is used in a fragrance preparation or composition to impart a hedonic effect. In other words, such a fragrance ingredient, to be considered Petition 870220074448, dated 08 / 18 / 2022, page 20 / 85 12 / 71 perfuming, it must be recognized by a person skilled in the art as having the capacity to impart or modify, in a positive or pleasant manner, the odor of a composition and not merely as having an odor.

[0035] The expression “fruity and / or floral odor” or “fruity and / or floral note” should be understood as an odor reminiscent of a floral odor, for example, the olfactory impression of roses, and fruity, specifically, notes of yellow fruits, such as, for example, notes of apricot, peach, or fruity-floral notes, such as notes of exotic fruits.

[0036] For the sake of clarity, a lasting effect is normally achieved if, after a certain period and after several hours or days, a given compound emits greater amounts of odor into the environment than a reference compound that provides the same type of odor.Thus, the expression “long-lasting odor”, when referring to the compound of formula (I) of the invention, should be understood as an increase in the duration of odor perception (release of compounds into the atmosphere that provides an olfactory impression of fruity and / or floral odor) compared to that of the molecules alone that have such an impression and measured under the same conditions, for example, after several hours (6 or 8 hours) or days (1, 3 or 7 days).

[0037] Such compositions, which can in fact be advantageously employed as perfuming ingredients, are also an object of the present invention.

[0038] Therefore, another aspect of the present invention is a fragrance composition comprising: i) a fragrance ingredient, at least one compound of formula (I) of the invention, as defined above; ii) at least one ingredient selected from the group consisting of a fragrance carrier and a fragrance base; and iii) optionally at least one fragrance adjuvant. In the present context, "perfume carrier" means a material that is practically neutral from a perfumery point of view, that is, it does not significantly alter the organoleptic properties of fragrance ingredients. This carrier can be a liquid or a solid.

[0039] As examples of liquid carriers, one can cite, but not limitingly, a Petition 870220074448, dated 08 / 18 / 2022, p. 21 / 85 13 / 71 emulsifier system, that is, a solvent and a surfactant system or a solvent commonly used in perfumery. A detailed description of the nature and type of solvent commonly used in perfumery cannot be exhaustive. However, examples may include, but are not limited to, solvents such as butylene or propylene glycol, glycerol, dipropylene glycol and its monoether, 1,2,3-propanetriyl triacetate, dimethyl glutarate, dimethyl adipate, 1,3-diacetyloxypropan-2-yl acetate, diethyl phthalate, isopropyl myristate, benzyl benzoate, benzyl alcohol, 2-(2-ethoxyethoxy)-1-ethane, triethyl citrate, or mixtures thereof, which are the most commonly used.For compositions comprising both a fragrance carrier and a fragrance base, other suitable fragrance carriers besides those specified above may also be ethanol, water / ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar® (origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark Dowanol® (origin: Dow Chemical Company) or hydrogenated castor oils such as those known under the trademark Cremophor® RH 40 (origin: BASF).

[0040] A solid carrier indicates a material to which the fragrance composition or some element of the fragrance composition can be chemically or physically bound. Generally, such solid carriers are employed either to stabilize the composition or to control the evaporation rate of the compositions or of some ingredients. The use of a solid carrier is currently used in the art, and a person skilled in the art knows how to achieve the desired effect. However, by way of non-limiting examples of solid carriers, one may mention absorbent gums or polymers or inorganic material, such as porous polymers, cyclodextrins, wood-based materials, organic or inorganic gels, clays, gypsum talc or zeolites.

[0041] As other non-limiting examples of solid carriers, encapsulation materials may be mentioned. Examples of such materials may include wall-forming materials and plasticizers, such as mono-, di- or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, acetates of Petition 870220074448, dated 08 / 18 / 2022, page 22 / 85 14 / 71 polyvinyl, polyvinyl alcohols, proteins or pectins, or even the materials cited in reference texts such as H. Scherz, Hydrokolloide: Stabilisatoren, Dickungs- und Geliermittel in Lebensmitteln, Band 2 der Schriftenreihe Lebensmittelchemie, Lebensmittelqualitat, Behr's Verlag GmbH & Co., Hamburg, 1996. Encapsulation is a process well known to a person skilled in the art and can be carried out, for example, using techniques such as spray drying, agglomeration or even extrusion, or it consists of encapsulation by coating, including coacervation and complex coacervation techniques.

[0042] As non-limiting examples of solid carriers, one may cite, in particular, core-shell capsules with aminoplastic, polyamide, polyester, polyurea or polyurethane type resins or a mixture thereof (all said resins are well known to those skilled in the art) using techniques such as a polymerization-induced phase separation process, interfacial polymerization, coacervation or in combination (all said techniques were described in the prior art), optionally in the presence of a polymeric stabilizer or a cationic copolymer.

[0043] Resins can be produced by the polycondensation of an aldehyde (e.g., formaldehyde, 2,2-dimethoxyethanal, glyoxal, glyoxylic acid or glycoaldehyde and mixtures thereof) with an amine such as urea, benzoguanamine, glycoluryl, melamine, methylol melamine, guanazole and the like, as well as mixtures thereof. Alternatively, pre-formed alkylated polyamine resins can be used, such as those commercially available under the trademarks Urac® (origin: Cytec Technology Corp.), Cymel® (origin: Cytec Technology Corp.), Urecoll® or Luracoll® (origin: BASF).

[0044] Other resins are those produced by polycondensation of a polyol, such as glycerol, and a polyisocyanate, such as a hexamethylene diisocyanate trimer, an isophorone diisocyanate trimer or xylylene diisocyanate or hexamethylene diisocyanate biuret or a xylylene diisocyanate trimer with trimethylolpropane (known by the trade name Takenate®, origin: Mitsui Chemicals), among which are a xylylene diisocyanate trimer with Petition 870220074448, dated 08 / 18 / 2022, page 23 / 85 15 / 71 trimethylolpropane and a hexamethylene diisocyanate biuret.

[0045] Part of the seminal literature related to the encapsulation of perfumes by polycondensation of amine resins, namely, melamine-based resins with aldehydes, is represented by articles such as those published by K. Dietrich et al. Acta Polymerica, 1989, volume 40, pages 243, 325 and 683, as well as 1990, volume 41, page 91. These articles already describe the various parameters that affect the preparation of such core-shell microcapsules following prior art methods that are also more detailed and exemplified in the patent literature. US patent no. 4,396,670, from Wiggins Teape Group Limited, is a pertinent early example of the latter. Since then, many other authors have enriched the literature in this field and it is impossible to cover all the developments published in this document, however the general knowledge in encapsulation technology is very significant.More recent publications of relevance that reveal appropriate uses of such microcapsules are represented, for example, by the article by K. Bruyninckx and M. Dusselier, ACS Sustainable Chemistry & Engineering, 2019, volume 7, pages 804-8054.

[0046] In the present context, “perfume base” means a composition comprising at least one fragrant co-ingredient.

[0047] The said perfuming co-ingredient is not of formula (I). Furthermore, in the present context, perfuming co-ingredient means a compound that is used in a perfuming preparation or in a composition in addition to the perfuming ingredient of formula (I) and that imparts to such perfuming ingredient of formula (I) a hedonic effect. In other words, such a co-ingredient, to be considered perfuming, must be recognized by a person skilled in the art as having the capacity to impart or modify, in a positive or pleasant manner, the odor of a composition and not merely as having an odor.

[0048] In particular, one can cite the fragrant co-ingredients that are commonly used in perfume formulations, such as: - Aldehydic ingredients: decanal, dodecanal, 2-methyl-undecanal, 10-undecenal, octanal, nonanal and / or nonanal; Petition 870220074448, dated 08 / 18 / 2022, p. 24 / 85 16 / 71 - Aromatic herb ingredients: eucalyptus oil, camphor, eucalyptol, 5-methyltricyclo[6.2.1.0~2,7~]undecan-4-one, 1-methoxy-3-hexanethiol, 2-ethyl-4,4-dimethyl1,3-oxathione, 2,2,7 / 8,9 / 10-Tetramethylspiro[5,5]undec-8-en-1-one, menthol and / or alpha-pinene; - Balsamic ingredients: coumarin, ethyl vanillin and / or vanillin; - Citrus ingredients: dihydromyrcenol, citral, orange oil, linalyl acetate, citronellyl nitrile, orange terpenes, limonene, 1-p-menten-8-yl acetate and / or 1,4(8)-p-mentadiene; - Floral ingredients: methyl dihydrojasmonate, linalool, citronalol, phenylethanol, 3-(4-terc-butylphenyl)-2-methylpropanal, hexylcinaldeído, benzyl acetate, benzyl salicylate, tetra-hydro-2-isobutyl-4-methyl-4(2H)-pyranol, beta ionone, 2-(methylamino)benzoate de methyl, (E)-3-methyl-4-(2,6,6-trimethyl-2-cyclo-hexen-1-yl)-3buten-2-ona, (1 E)-1 -(2,6,6-trimethyl-2-cyclo-hexen-1-yl)-1-penten-3-ona, 1 -(2,6,6trimethyl-1,3-cyclo-hexadien-1-yl)-2-buten-1-one, (2E)-1-(2,6,6-trimethyl-2-cyclo-hexen-1yl)-2-buten-1-one, (2E)-1-[2,6,6-trimethyl-3-cyclo-hexen-1 -yl]-2-buten-1 -one, (2E)-1 (2,6,6-trimethyl-1-cyclo-hexen-1-yl)-2-buten-1-one, 2,5-dimethyl-2-indanmethanol, 2,6,6trimethyl-3-cyclo-hexeno-1-carboxylate, 3-(4,4-dimethyl-1-cyclo-hexen-1-yl)propanal, hexyl salicylate, 3,7-dimethyl-1,6-nonadien-3-ol, 3-(4-isopropylphenyl)-2-methylpropanal, verdila acetate, geraniol, p-ment-1-en-8-ol acetate, 4-(1,1-dimethylethyl)-1-cyclohexyla, 1,1-dimethyl-2-phenylethyl acetate,4-cyclohexyl-2-methyl-2-butanol, amyl salicylate, cis dihydrojasmonate, 3-methyl-5-phenyl-1-pentanol, verdyl propionate, geranyl acetate, tetrahydrolinalool, cis-7-p-menthol, propyl (S)-2-(1,1-dimethylpropoxy)propanoate, 2-methoxynaphthalene, 2,2,2-trichloro-1-phenylethyl acetate, 4 / 3-(4-hydroxy-4-methylpetyl)-3-cyclohexene-1-carbaldehyde, amylcinnamaldehyde, 8-decen-5-olide, 4-phenyl-2-butanone, isononyl acetate, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, verdyl isobutyrate and / or a mixture of methylionone isomers; - Fruity ingredients: gamma-undecalactone, 2,2,5-trimethyl-5-petylcyclopentanone, 2-methyl-4-propyl-1,3-oxathione, 4-decanolide, ethyl 2-methylpentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma-nonalactone, heptanoate Petition 870220074448, dated 08 / 18 / 2022, page 25 / 85 Allyl 17 / 71, 2-phenoxyethyl isobutyrate, 2-methyl-1,3-dioxolane-2-ethyl acetate, 3(3,3 / 1,1-dimethyl-5-indanyl)propanal, 1,4-cyclo-hexanedicarboxylate-diethyl-1-methyl,3-acetyl [3-ethyl-2-oxyranyl]1-[3,3-dimethylcyclo-hexyl]ethyl acetate and / or 1,4-cyclo-hexane diethyl dicarboxylate; - Green ingredients: 2-methyl-3-hexanone (E)-oxime, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 2-tert-butyl-1-cyclo-hexyl acetate, styralyl acetate, (2methylbutoxy)-3-acetyl-alylylic acid diphenyl, (Z)-3-hexen-1-ol and / or 1 -(5,5-dimethyl-1 -cyclo-hexen-1-yl)-4-penten-1 -one; - Musk ingredients: 1,4-dioxa-5,17-cycloheptadecanedione, (Z)-4-cyclopentadecen-1-one, 3-methylcyclopentadecanone, 1-oxa-12-cyclohexadecen-2-one, 1-oxa-13-cyclohexadecen-2-one, (9Z)-9-cycloheptadecen-1-one, 2{1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxoethyl propionate, 3-methyl-5-cyclopentadecen-1-one, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-γ-2-benzopyran, (1S,1'R)-2-[1-(3',3'-dimethyl-1 '-cyclohexyl)ethoxy]-2-methylpropyl, oxacyclohexadecan2-one and / or (1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methyl propanoate; - Lengh ingredients: 1-[(1RS,6SR)-2,2,6-trimethylcyclo-hexyl]-3-hexanol, 3,3-dimethyl-5-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 3,4'- dimethylspiro[oxirano-2,9'-tricyclo[6.2.1.02'7]undec[4]eno, (1-ethoxietoxi)cyclododecane, 2,2,9,11-tetramethylspiro[5.5]undec-8-en-1-yl acetate, 1-(octa-hydro-2,3,8,8tetramethyl-2-naphthalenyl)-1-etanona, patchouli oil, terpene fractions óleo Patchouli, clearwood®, (1 'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-2-buten-1 ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, methyl cedril cetone, 5-(2,2,3trimethyl-3-cyclopentenyl)-3-methylpentan-2-ol, 1 -(2,3,8,8-tetramethyl-1,2,3,4,6,7,8,8a-octahidronaphthalene-2-yl)ethan-1-ona and / or isobornyl acetate; - Other ingredients (e.g., amber, chili powder or watered): dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,1-b]furan and any of its stereoisomers, heliotropin, anisic aldehyde, eugenol, cinnamaldehyde, clove oil, 3-(1,3-benzodioxol-5-yl)-2-methylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)one, 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydro-2-naphthalenol, 1-phenylvinyl acetate, 6-methyl-7-oxa-1-thia-4-azaespiro[4.4]nonane and / or 3-(3-isopropyl-1-phenyl)butanal. Petition 870220074448, dated 08 / 18 / 2022, p. 26 / 85 18 / 71

[0049] A perfumery base, according to the invention, cannot be limited to the perfumery co-ingredients mentioned above, and many other such co-ingredients are, in any case, listed in reference texts, such as S. Arctander's book, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery. Furthermore, it is understood that said co-ingredients may also be compounds known to controllably release various types of perfume compounds also known as pro-perfumes or pro-fragrances. Non-limiting examples of suitable pro-perfumes or pro-fragrances may include 4-(dodecylthio)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone, 3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone, 2-(dodecylthio)octan-4-one,2-phenylethyl oxo(phenyl)acetate, 3,7-dimethyloctate-2,6-diene-1-yl oxo(phenyl)acetate, (Z)-hex-3-en-1-yl oxo(phenyl)acetate, 3,7-dimethyl-2,6-octadiene hexadecanoate bis(3,7-dimethyloct-2,6-diene-1 -yl)succinate, (2-((2-methylundec-1 -en-1 il)oxy)ethyl)benzene, 1 -methoxy-4-(3-methyl-4-phenotoxibut-3-en-1 -phenoto1-benzene-3, (4 -yl)benzene, 1 -(((Z)-hex-3-en-1-yl)oxy)-2-methylundec-1-ene, (2-((2methylundec-1 -en-1 -yl)oxy)ethoxy)benzene, 2-methyl-ene -(octan-3-c-1yloxy)uene methoxy-4-(1-phenothoxyprop-1-en-2-yl)benzene, 1-methyl-4-(1-phenothoxyprop-1-en-2yl)benzene, 2-(1-phenothoxyprop-1-en-2-yl)naphthalene, (2-phenothoxyvinyl)benzene, 2-(1-((3,7dimethyloct-6-en-1-yl)oxy)prop-1-en-2-yl)naphthalene, (2-((2petylcyclopethylidene)methoxy)ethyl)benzene or a mixture of both.,

[0050] The term perfume adjuvant is understood as an ingredient capable of conferring an additional benefit, such as color, specific lightfastness, chemical stability, etc. A detailed description of the nature and type of adjuvant commonly used in perfume bases cannot be exhaustive, however it should be mentioned that the ingredients are well known to a person skilled in the art. However, the following may be cited as specific, non-limiting examples: viscosity agents (e.g., surfactants, thickeners, gelling agents and / or rheology modifiers), stabilizing agents (e.g., surfactants, thickeners, gelling agents and / or rheology modifiers), stabilizing agents (e.g., Petition 870220074448, dated 08 / 18 / 2022, page 27 / 85 19 / 71 example, preservatives, antioxidants, heat / light and / or buffers or chelating agents, such as BHT), coloring agents (e.g., dyes and / or pigments), preservatives (e.g., antibacterial or antimicrobial or antifungal or anti-irritant agents), abrasives, skin cooling agents, fixatives, insect repellents, ointments, vitamins and mixtures thereof.

[0051] It is understood that a person skilled in the art has full ability to design ideal formulations for the desired effect by mixing by addition the components of a perfume composition mentioned above, simply by applying standard knowledge of the art, as well as by trial and error methodologies.

[0052] A composition of the invention consisting of at least one compound of formula (I) and at least one perfumery carrier represents a specific embodiment of the invention, as does a perfumery composition comprising at least one compound of formula (I), at least one perfumery carrier, at least one perfumery base and optionally at least one perfumery adjuvant.

[0053] It is worth mentioning in this document that it is important to have the possibility, in the compositions mentioned above, of using, in addition to a compound of formula (I), other compounds of a similar or different nature, which may generate other fragrances, as this allows the perfumer to prepare accords, perfumes that have the olfactory tone of several compounds of the invention, thus creating new building blocks for the purpose of creation.

[0054] For the sake of clarity, it is also understood that any mixture directly resulting from a chemical synthesis, for example, a reaction medium without adequate purification, in which the compound of the invention is involved as an initial, intermediate or final product, cannot be considered a perfumery composition according to the invention if the mixture does not provide the compound of the invention in a form suitable for perfumery. Thus, unpurified reaction mixtures are generally excluded from the present invention, unless otherwise specified. Petition 870220074448, dated 08 / 18 / 2022, page 28 / 85 20 / 71

[0055] Furthermore, the compound of formula (I) of the invention can also be used advantageously in all fields of modern perfumery, i.e., fine or functional perfumery, to positively impart a lasting or consistent fruity and / or floral scent to a consumer product to which said compound (I) is added.

[0056] Consequently, another aspect of the present invention relates to a perfumed consumer product comprising as a perfumed ingredient at least one compound of formula (I) or a perfumed composition, as defined above.

[0057] The compound of the invention can be added as such or as part of a fragrance composition of the invention.

[0058] For clarity, it should be mentioned that a perfumed consumer product means a consumer product that provides at least a pleasant perfume effect to the surface to which it is applied (e.g., skin, hair, textile or hard surface). In other words, a perfumed consumer product according to the invention is a perfumed consumer product comprising the functional formulation as well as, optionally, additional beneficial agents corresponding to the desired consumer product, for example, a conditioner, a detergent or an air freshener, and an effective olfactory quantity of at least one compound of the invention. For clarity, the perfumed consumer product is a non-edible product.

[0059] The nature and type of constituents of the perfumed consumer product do not justify a more detailed description here, which is by no means exhaustive, and a person skilled in the art may select them based on their general knowledge and in accordance with the nature and desired effect of the product.

[0060] As used in this document, “consumer product” means baby care, personal care, textiles and household care, family care, feminine care, health care, beauty care and similar products generally intended to be used or consumed in the form in which they are sold.

[0061] Non-limiting examples of fragrant consumer products may be Petition 870220074448, dated 08 / 18 / 2022, page 29 / 85 21 / 71 one, such as fine perfume, cologne or aftershave lotion; a fabric care product, such as a liquid or solid detergent or a single-dose detergent (such as a powder tablet, a liquid single-dose detergent or a multi-chamber single-dose detergent), a fabric softener, a fabric freshener, laundry water, paper, bleach, carpet cleaner, or curtain care products;a body care product, such as a hair care product (for example, shampoo, a hair coloring preparation or hairspray, a color care product or a hair styling product, a dental care product, a disinfectant, an intimate care product), a cosmetic preparation (for example, a skin cream or lotion, a bleaching cream or a deodorant or antiperspirant (for example, a spray or roll-on), a hair remover, a tanning lotion, sunscreen or after-sun protection products, a nail product, a nail cleaner or makeup), a penis care product (for example, a perfumed soap, shower or bath mousse, oil or gel, a hygiene product or a foot / hand care product);an air freshener product, such as a ready-to-use powder air purifier or air freshener that can be used in a domestic space (rooms, refrigerators, closets, shoe closets or car) and / or in a public space (hallways, hotels, shopping malls, etc.); or a home care product, such as a mildew remover, a furniture care product, a paper towel, a dishwashing detergent or detergent for hard surfaces (e.g., a floor, bathtub, toilet or windows), a leather care product; a car care product, such as a polish, waxes or plastic cleaner.

[0062] The preferred perfuming compositions or perfuming articles are perfumes, detergents for fabrics or hard surfaces, skin or hair products and fabric softeners or purifiers.

[0063] Typical examples of fabric detergents or softening compositions in which the compounds of the invention may be incorporated are described in document no. WO 97 / 34986 or in patents no. US 4,137,180 and 5,236,615 or in document no. EP 799 885. Other typical detergents and softening compositions that Petition 870220074448, dated 08 / 18 / 2022, page 30 / 85 22 / 71 can be used and are described in works such as Ullmann's Encyclopedia of Industrial Chemistry, volume 20, Wiley-VCH, Weinheim, pages 355-540 (2012); Flick, Advanced Cleaning Product Formulations, Noye Publication, Park Ridge, New Jersey (1989); Showell, in Surfactant Science Series, volume 71: Powdered Detergents, Marcel Dekker, New York (1988); Proceedings of the World Conference on Detergents (4th edition, 1998, Montreux, Switzerland), AOCS imprint.

[0064] Some of the consumer product bases mentioned above may represent an aggressive environment for the compound of the invention, so it may be necessary to protect it from premature decomposition, for example, by encapsulation.

[0065] The proportions in which the compounds according to the invention can be incorporated into the various articles or compositions mentioned above vary within a wide range of values. These values ​​depend on the nature of the article to be perfumed and the desired organoleptic effect, as well as on the nature of the co-ingredients on a given basis when the compounds according to the invention are mixed with perfume co-ingredients, solvents, or additives commonly used in the art.

[0066] For example, in the case of fragrance compositions, typical concentrations are in the order of 0.001% to 10% by weight, or more, of the compounds of the invention based on the weight of the composition in which they are incorporated. In the case of perfumed consumer products, typical concentrations are in the order of 0.0001% to 5% by weight, or more, of the compounds of the invention based on the weight of the consumer product in which they are incorporated.

[0067] As mentioned above, the invention relates to a method for imparting a long-lasting or consistent odor, imparted by cyclopentanone-derived perfumery ingredients, such as fruity and / or floral scents, to surfaces such as hard surfaces, fabrics, skin, or hair. Perfume ingredients that impart a fruity and / or floral scent to the environment by evaporation from a surface are typically not long-lasting or consistent. As described above, one reason for this is their relatively high volatility, which ensures efficient evaporation after the Petition 870220074448, dated 08 / 18 / 2022, page 31 / 85 23 / 71 Surface deposition. Another reason for this is that often only small amounts of these compounds are efficiently deposited on the surface. This is specifically the case when these compounds are applied to a surface through scented compositions or scented articles, which are rinsed off after application. This rinsing step also removes a large amount of perfume that should remain on the target surface. Examples of this are washing and cleaning agents such as hard surface cleaners, detergents, shower gels, shampoos, and the like, which are rinsed off after application. Furthermore, perfuming a surface by placing it in contact with scented compositions or scented articles, from which the perfume is deposited on the surface by a partitioning equilibrium between the scented compositions or articles and the corresponding surface, may be inefficient for perfume deposition.Examples of this case are surface conditioners or purifiers, such as fragrance softeners, which are placed in contact with the target and then removed or left to dry. The compounds of formula (I) according to the present invention are suitable for increasing perfume deposition and consequently imparting a long-lasting odor conferred by cyclopentanone-derived perfumery ingredients to surfaces such as hard surfaces, fabrics, skin or hair.

[0068] Therefore, another aspect of the present invention relates to a method of imparting a lasting or consistent odor imparted by cyclopentanone-derived perfumery ingredients to the environment or surfaces, such as hard surfaces, fabrics, skin or hair, by adding at least one compound of formula (I) to perfume compositions or perfumed articles and applying them to the corresponding target environment or surface.

[0069] The present invention also relates to a microcapsule comprising at least one compound of formula (I). In one embodiment, the at least one compound of formula (I) is encapsulated in a core-shell microcapsule wherein the at least one compound of formula (I) is contained within the core enclosed by the shell. In one embodiment, the microcapsule shell protects Petition 870220074448, dated 08 / 18 / 2022, page 32 / 85 24 / 71 the compound of formula (I) from the environment. The shell is produced from a material that has the capacity to release at least one compound of formula (I). In one embodiment, the shell is produced from a material that has the capacity to release the compound of formula (I) after rupture of the shell and / or by diffusion through the shell. A person skilled in the art is well acquainted with the processes for preparing said microcapsules.

[0070] According to a particular embodiment, the microcapsule shell comprises a material selected from the group consisting of polyurea, polyurethane, polyamide, polyester, poly(meth)acrylate (i.e., polyacrylate and / or polymethacrylate), polysiloxane, polycarbonate, polysulfonamide, urea-formaldehyde polymers, melamine and formaldehyde, melamine and urea, or melamine and glyoxal, and mixtures thereof. The shell may also be hybrid, namely, organic-inorganic, such as a hybrid shell composed of at least two types of cross-linked inorganic particles, or a shell resulting from the hydrolysis and condensation reaction of a polyalkoxysilane macromonomeric composition.

[0071] According to a specific embodiment, the core-shell microcapsule (or core-shell microcapsules) may also be derived using different methods or using more than one encapsulation method.

[0072] In a preferred embodiment, the microcapsule shells can be selected, each independently, from the group of aminoplastic, polyamide, polyester, polyurea and polyurethane shells and mixtures thereof.

[0073] In one specific embodiment, the microcapsule shell comprises an aminoplastic copolymer, such as melamine-formaldehyde or urea-formaldehyde or crosslinked melamine-formaldehyde or melamine glyoxal.

[0074] In a specific embodiment, the microcapsule shell is polyurea-based, produced, for example, but not limited to, from isocyanate-based monomers and amine-containing crosslinkers such as guanidine carbonate and / or guanazole. Certain polyurea microcapsules comprise a polyurea wall that is the product of the polymerization reaction between at least one polyisocyanate comprising at least two isocyanate functional groups. Petition 870220074448, dated 08 / 18 / 2022, p. 33 / 85 25 / 71 and at least one reagent selected from the group consisting of an amine (for example, a water-soluble guanidine salt and guanidine); a colloidal stabilizer or emulsifier and an encapsulated perfume. However, the use of an amine may be omitted.

[0075] In a specific embodiment, the colloidal stabilizer includes an aqueous solution of between 0.1% and 0.4% polyvinyl alcohol, between 0.6% and 1% of a cationic copolymer of vinylpyrrolidone and a quaternized vinylimidazole (wherein all percentages are defined by weight relative to the total weight of the colloidal stabilizer). In a specific embodiment, the emulsifier is an anionic or amphiphilic biopolymer that may be chosen, for example, from the group consisting of gum arabic, soy protein, gelatin, sodium caseinate and mixtures thereof.

[0076] In a specific embodiment, the microcapsule shell is based on polyurethane produced, for example, but without limitation, from polyisocyanate and polyols, polyamide, polyester, etc.

[0077] In one specific embodiment, the microcapsules have a polymeric shell resulting from complex coacervation in which the shell is possibly crosslinked.

[0078] In a specific embodiment of core-shell microcapsules, the core-shell microcapsules comprise an oil-based core comprising a hydrophobic active, preferably at least one compound of formula (I) and a composite shell comprising a first material and a second material, wherein the first material and the second material are different, the first material is a coacervate, the second material is a polymeric material.

[0079] In a specific embodiment, the weight ratio between the first material and the second material is between 50:50 and 99.9:0.1.

[0080] In a specific embodiment, the coacervate comprises a first polyelectrolyte selected, preferably, from proteins (such as gelatin), polypeptides or polysaccharides (such as chitosan), more preferably gelatin, and a second polyelectrolyte, preferably alginate salts, cellulose derivatives, guar gum, pectinate salts, carrageenan, polyacrylic and methacrylic acid or gum Petition 870220074448, dated 08 / 18 / 2022, page 34 / 85 26 / 71 xanthan gum or, alternatively, vegetable gums such as acacia gum (gum arabic), with gum arabic being more preferred.

[0081] The first coacervate material can be chemically hardened using a suitable crosslinking agent such as glutaraldehyde, glyoxal, formaldehyde, tannic acid or genipin, or it can be enzymatically hardened using an enzyme such as transglutaminase.

[0082] The second polymeric material may be selected from the group consisting of polyurea, polyurethane, polyamide, polyester, polyacrylate, polysiloxane, polycarbonate, polysulfonamide, urea-formaldehyde polymers, melamine-formaldehyde, melamine-urea, or melamine-glyoxal and mixtures thereof, preferably polyurea and / or polyurethane. The second material is preferably present in an amount less than 3% by weight, preferably less than 1% by weight based on the total weight of the microcapsule flow paste.

[0083] The preparation of a fluid dispersion / paste of core-shell microcapsules is well known to a person skilled in the art. In a particular embodiment, the microcapsule wall material may comprise any suitable resin and especially including melamine, glyoxal, polyurea, polyurethane, polyamide, polyester, etc. Suitable resins include the reaction product of an aldehyde and an amine; suitable aldehydes include formaldehyde and glyoxal. Suitable amines include melamine, urea, benzoguanamine, glycoluryl and mixtures thereof. Suitable melamines include methylol melamine, methylated methylol melamine, imino melamine and mixtures thereof. Suitable urea includes dimethylol urea, methylated dimethylol urea, urea-resorcinol and mixtures thereof. Suitable materials for manufacturing can be obtained from one or more of the following companies: Solutia Inc. (St. Louis, Missouri, USA), Cytec Industries (West Paterson, New Jersey, USA), Sigma-Aldrich (St. Louis, Missouri, USA).Louis, Missouri (USA).

[0084] In a particular embodiment of core-shell microcapsules, the core-shell microcapsules comprise - an oil-based core comprising a hydrophobic active ingredient comprising, preferably, at least one compound of formula (I), Petition 870220074448, dated 08 / 18 / 2022, page 35 / 85 27 / 71 - optionally an inner casing produced from a polymerized polyfunctional monomer; - a biopolymer envelope comprising a protein, in which at least one protein is cross-linked.

[0085] According to a specific embodiment, the protein is chosen from the group consisting of milk proteins, caseinate salts, such as sodium caseinate or calcium caseinate, casein, whey protein, hydrolyzed proteins, gelatins, gluten, pea protein, soy protein, silk protein and mixtures thereof, preferably sodium caseinate, more preferably sodium caseinate.

[0086] According to a specific embodiment, the protein comprises sodium caseinate and a globular protein, preferably chosen from the group consisting of whey protein, beta-lactoglobulin, ovalbumin, bovine serum albumin, vegetable proteins and mixtures thereof.

[0087] Preferably, the protein is a mixture of sodium caseinate and whey protein.

[0088] According to a specific embodiment, the biopolymer shell comprises a cross-linked protein selected from the group consisting of sodium caseinate and / or whey protein.

[0089] According to a specific embodiment, the microcapsule paste comprises at least one microcapsule produced from: - an oil-based core comprising the hydrophobic active ingredient comprising, preferably, at least one compound of formula (I), - an inner casing produced from a polymerized polyfunctional monomer, preferably a polyisocyanate having at least two isocyanate functional groups; - a biopolymer envelope comprising a protein, wherein at least one protein is cross-linked; wherein the protein preferably contains a mixture comprising sodium caseinate and a globular protein, preferably whey protein; Petition 870220074448, dated 08 / 18 / 2022, page 36 / 85 28 / 71 - optionally, at least one outer mineral layer.

[0090] According to one embodiment, sodium caseinate and / or whey protein are cross-linked proteins.

[0091] The weight ratio between sodium caseinate and whey protein is preferably between 0.01 and 100, preferably between 0.1 and 10, most preferably between 0.2 and 5.

[0092] In a specific embodiment, the microcapsule is a single-shell aminoplastic core-shell microcapsule that can be obtained by a process comprising the steps of: 1) Mixing by addition a perfumed oil with at least one polyisocyanate that has at least two isocyanate functional groups to form an oil phase; 2) Disperse or dissolve an aminoplastic resin in water and, optionally, with a stabilizer to form an aqueous phase; 3) Prepare an oil-in-water dispersion, in which the average droplet size is between 1 and 100 microns, by mixing the oil phase with the aqueous phase by addition; 4) perform a curing step to form the wall of said microcapsule; and 5) Optionally, dry the final dispersion to obtain the dry core-shell microcapsule.

[0093] In one specific embodiment, the core-shell microcapsule is a formaldehyde-free capsule. A typical process for preparing a formaldehyde-free aminoplastic microcapsule paste comprises the steps of 1) Prepare an oligomeric composition comprising the following reaction product, which is obtainable by reacting the following: a. a polyamine component in the form of melamine or a mixture of melamine and at least one C1-C4 compound comprising two NH2 functional groups; b. an aldehyde component in the form of a mixture of glyoxal, a C4-6 2,2-dialkoxyethanol and, optionally, a glyoxalate, wherein said mixture has a ratio Petition 870220074448, dated 08 / 18 / 2022, page 37 / 85 29 / 71 molar ratio between glyoxal / C4-6 2,2-dialkoxyethanol ranging from 1 / 1 to 10 / 1; and c. a protic acid catalyst; 2) Prepare an oil-in-water dispersion, in which the droplet size is between 1 and 600 microns and comprises: a. an oil; b. a medium with water; c. at least one oligomeric composition, as obtained in step 1; d. at least one crosslinking agent selected from: i. C4-C12 aromatic or aliphatic di- or tri-isocyanates and their biurets, triurets, trimers, trimethylolpropane adducts and mixtures thereof; and / or ii. a di- or tri-oxirane compound of the formula: Q-(oxiran-2-ylmethyl)m where m is 2 or 3 and Q represents a C2-C6 group comprising, optionally, 2 to 6 nitrogen and / or oxygen atoms; and optionally, a C1-C4 compound comprising two functional NH2 groups; 3) heat the dispersion; and 4) Cool the dispersion.

[0094] The above process is described in more detail in document no. WO 2013 / 068255.

[0095] In a specific embodiment of core-shell microcapsules, a core-shell microcapsule is a polyamide core-shell microcapsule comprising: - an oil-based core comprising a hydrophobic active ingredient, preferably comprising at least one compound of formula (I), and - a polyamide casing comprising or obtainable from: • an acyl chloride, • a first amino compound, and • a second amino compound. Petition 870220074448, dated 08 / 18 / 2022, page 38 / 85 30 / 71

[0096] According to a particular embodiment, the polyamide core-shell microcapsule comprises: an oil-based core comprising a hydrophobic active ingredient, preferably comprising at least one compound of formula (I), and a polyamide shell comprising or obtained from: • an acyl chloride, preferably in an amount between 5 and 98%, preferably between 20 and 98%, more preferably between 30 and 85% w / w; • a first amino compound comprising, preferably, an amount between 1% and 50% by w / w, preferably between 7% and 40% by w / w; • a second amino compound, preferably in an amount between 1% and 50% by w / w, preferably between 2% and 25% by w / w; • a stabilizer, preferably a biopolymer, preferably in an amount between 0 and 90%, preferably between 0.1 and 75%, more preferably between 1 and 70%.

[0097] According to a particular embodiment, the polyamide core-shell microcapsule comprises: - an oil-based core comprising a hydrophobic active ingredient preferably comprising at least one compound of formula (I), and - a polyamide casing comprising or obtainable from: • an acyl chloride, • a first amino compound which is an amino acid, preferably chosen from the group consisting of L-Lysine, L-Arginine, L-Histidine, L-Tryptophan and / or a mixture thereof. • a second amino compound chosen from the group consisting of ethylenediamine, diethylenetriamine, cystamine and / or a mixture thereof, and • a biopolymer chosen from the group consisting of casein, sodium caseinate, bovine serum albumin, whey protein and / or a mixture thereof. Petition 870220074448, dated 08 / 18 / 2022, page 39 / 85 31 / 71

[0098] The first amino compound may be different from the second amino compound.

[0099] Typically, a process for preparing a polyamide-based microcapsule includes the following steps: a) Dissolve at least one acyl chloride in a hydrophobic material, preferably a perfume, to form an oily phase; b) disperse the oily phase obtained in step a) in an aqueous phase comprising a first amino compound to form an oil-in-water emulsion; c) perform a curing step to form polyamide microcapsules in the form of a fluid paste; wherein a stabilizer is added to the oil phase and / or the aqueous phase, and wherein at least one second amino compound is added to the aqueous phase before the formation of the oil-in-water emulsion and / or to the oil-in-water emulsion obtained after step b).

[00100] In one specific embodiment, the microcapsule shell is based on polyurea or polyurethane. Examples of processes for preparing polyurea- and polyurethane-based microcapsule pastes are described, for example, in documents no. WO 2007 / 004166, EP 2300146 and EP 2579976. Typically, a process for preparing fluid polyurea- or polyurethane-based microcapsule pastes includes the following steps: a) Dissolve at least one polyisocyanate with at least two isocyanate groups in an oil to form an oil phase; b) prepare an aqueous solution of an emulsifier or colloidal stabilizer to form an aqueous phase; c) add the oil phase to the aqueous phase to form an oil-in-water dispersion, in which the average droplet size is between 1 and 500 μm, preferably between 5 and 50 μm; and d) Apply sufficient conditions to induce interfacial polymerization and form microcapsules in the form of a fluid paste. Petition 870220074448, dated 08 / 18 / 2022, p. 40 / 85 32 / 71

[00101] In a specific embodiment, the microcapsule may be in the form of a powder that can be obtained, specifically, by subjecting the fluid microcapsule paste to a drying step, such as spray drying, to provide the microcapsules in this way, that is, in a powder form. It is understood that any standard method known to a person skilled in the art for carrying out such drying is also applicable. Specifically, the paste may be spray-dried, preferably in the presence of a polymeric carrier material such as polyvinyl acetate, polyvinyl alcohol, dextrins, natural or modified starch, gum arabic, vegetable gums, pectins, xanthan gums, alginates, carrageenans, or cellulose derivatives to provide microcapsules in powder form.

[00102] However, other drying methods can also be mentioned, such as extrusion, galvanizing, spray granulation or fluidized bed processes or even drying at room temperature using materials (carrier, desiccant) that meet specific criteria as revealed in document no. WO 2017 / 134179.

[00103] The compounds of formula (I) of the invention can be prepared according to standard methods known in the art, as described below. EXAMPLES

[00104] The invention will be described in more detail below by means of the following examples, wherein the abbreviations have the common meaning in the art, temperatures are indicated in degrees Celsius (°C). NMR spectral data were recorded on a Bruker Avance III 500 or 600 spectrometer. Unless otherwise indicated, the spectra were recorded in CDCl3 at 500 MHz for 1H and at 125.8 MHz for 13C. Chemical shifts δ are indicated in ppm relative to Si(CH3)4 as the standard, coupling constants J are expressed in Hz (br. = broad peak). The reactions were carried out in standard glassware under N2. Commercially available reagents and solvents were used without further purification, unless otherwise indicated.

[00105] Although specific conformations or configurations are indicated for some of the compounds, this does not limit the use of these compounds to isomers. Petition 870220074448, dated 08 / 18 / 2022, page 41 / 85 33 / 71 described. EXAMPLE 1 PREPARATION OF COMPOUNDS ACCORDING TO FORMULA (I) (A) SYNTHESIS OF (±)-6-(5-HEXENYL)-1,4-DIAZAESPIRO[4,4]NONAN-2-ONE (COMPOUND 1)

[00106] In a Soxhlet extractor with molecular sieves (4 A), a mixture of 2(5-hexenyl)cyclopentan-1-one (1.73 g, 10 mmol), triethylamine (TEA, 1.5 ml, 11 mmol) and glycinamide hydrochloride (1.13 g, 10 mmol) in methanol (125 ml) was heated under reflux for several days. After cooling to room temperature, the solvent was evaporated under reduced pressure, and the mixture absorbed in ethyl acetate (50 ml) and water (25 ml). After separation, the aqueous phase was extracted again with ethyl acetate (50 ml) and the organic phases were washed with a saturated aqueous solution of NaCl (25 ml). The combined organic phases were dried (Na2SO4), filtered and concentrated under reduced pressure. Column chromatography (SiO2, ethyl acetate) yielded 0.15 g of the first diastereoisomer (Compound 1a) of the target product; further elution (ethyl acetate / ethanol) yielded 0.24 g of a mixture of isomers and 0.19 g of the second diastereoisomer (Compound 1b).The compound can be used in the form of its individual separate diastereoisomers or as a mixture of non-separate isomers.

[00107] 1H NMR (Compound 1a): 6.89 (br, s, 1 H), 5.85-5.74 (m, 1 H), 5.03-4.91 (m, 2 H), 3.50 (d, J = 16.4, 1 H), 3.41 (d, J = 16.4, 1 H), 2.09-2.00 (m, 2 H), 1.97-1.84 (m, 3 H), 1.83-1.58 (m, 4 H), 1.56-1.46 (m, 1 H), 1.45-1.33 (m, 4 H), 1.31-1.17 (m, 2 H).

[00108] 13C NMR (Compound 1a): 176.76, 138.86, 114.41, 85.22, 49.72, 48.72, 39.34, 33.65, 29.17, 28.39, 28.08, 27.86, 19.79.

[00109] 1H NMR (Compound 1b): 7.43 (br, s, 1 H), 5.85-5.74 (m, 1 H), 5.03-4.91 (m, 2 H), 3.49 (m, 2 H), 2.09-1.94 (m, 4 H), 1.91-1.79 (m, 2 H), 1.78-1.64 (m, 3 H), 1.53-1.19 (m, 6 H), 1.18-1.09 (m, 1 H).

[00110] 13C NMR (Compound 1b): 176.73, 138.82, 114.43, 86.18, 49.29, 48.98, 39.59, 33.67, 29.53, 29.43, 29.09, 27.76, 20.51. Petition 870220074448, dated 08 / 18 / 2022, page 42 / 85 34 / 71 (B) SYNTHESIS OF (±)-(7A'S)-2-(5-HEXENYL)TETRA- HYDROSPIRO[CYCLOPENTANE-1,3'-PYRROLO[1,2-C]IMIDAZOLE]-T(2H)-ONE (COMPOUND 2)

[00111] As described for Compound 1 with 2-(5-hexenyl)cyclopentan-1-one (1.73 g, 10 mmol), TEA (2.25 ml, 16 mmol), L-prolinamide hydrochloride (2.26 g, 15 mmol) in methanol (125 ml). Column chromatography (SiO2, ethyl acetate, then ethyl acetate / ethanol 9:1) yielded several product fractions which were purified again (SiO2, ethyl acetate) to yield 0.22 g of the first diastereoisomer (Compound 2a) and 0.48 g of the second diastereoisomer of the target product (Compound 2b). The compound can be used in the form of its individual separated diastereoisomers or the mixture of non-separated isomers.

[00112] RMN de1H (Composto 2a, 600 MHz): 6,85 (br, s, 1 H), 5,84-5,74 (m, 1 H), 5,03-4,89 (m, 2 H), 3,78 (dd, J = 9,6, 5,8, 1 H), 2,95-2,88 (m, 1 H), 2,75-2,67 (m, 1 H), 2,18-1,95 (m, 4 H), 1,94-1,86 (m, 1 H), 1,86-1,62 (m, 7 H), 1,62-1,54 (m, 1 H), 1,51-1,43 (m, 1 H), 1,43-1,30 (m, 3 H), 1,24-1,14 (m, 2 H).

[00113] RMN de13C (Composto 2a, 151,0 MHz): 178,94, 139,01, 114,26, 87,00, 65,01,51,76, 50,35, 33,75, 32,16, 29,45, 29,22, 27,80, 27,59, 27,05, 25,61, 19,84.

[00114] RMN de1H (Composto 2b, 600 MHz): 7,32 (br, s, 1 H), 5,82-5,73 (m, 1 H), 5,01-4,89 (m, 2 H), 3,92 (dd, J = 9,2, 5,8, 1 H), 3,06-2,99 (m, 1 H), 2,77-2,69 (m, 1 H), 2,18-2,10 (m, 1 H), 2,10-1,99 (m, 3 H), 1,99-1,88 (m, 3 H), 1,86-1,66 (m, 5 H), 1,59-1,50 (m, 1 H), 1,43-1,30 (m, 3 H), 1,30-1,18 (m, 2 H), 1,14-1,05 (m, 1 H).

[00115] 13C NMR (Compound 2b, 151.0 MHz): 179.09, 138.90, 114.32, 87.58, 64.73, 50.83, 50.61,33.76, 33.22, 29.72, 29.24, 27.71,27.63, 27.17, 25.54, 20.11. (C) SYNTHESIS OF (±)-(6-(HEX-5-ENIL)-3-METHYL-1-OXA-4-AZASPYRO[4.4]NONAN3-YL)METHHANOL (COMpound 3)

[00116] 2-Amino-2-methylpropane-1,3-diol (1.06 g, 10 mmol) and ptoluenesulfonic acid monohydrate (0.10 g) were added to a shaken solution of 2-(5-hexenyl)cyclopentan-1-one (3.82 g, 22 mmol) in toluene (25 ml). The mixture was heated under reflux overnight and, after cooling to room temperature, filtered through NaHCO3 and concentrated. Column chromatography (SiO2, n Petition 870220074448, dated 08 / 18 / 2022, page 43 / 85 35 / 71 heptane / ethyl acetate 7:3) yielded 1.21 g (48%) of a mixture of two pairs of diastereomers in a ratio of approximately 2:1.

[00117] 1H NMR (main isomers): 5.86-5.75 (m, 1H), 5.03-4.90 (m, 2H), 3.70 and 3.69 (d, J = 8.7, 1H), 3.53 and 3.43 (d, J = 8.3, 1H), 3.44 and 3.31 (d, J = 10.6, 1H), 3.41 (d, J = 8.6, 1H), 2.34-0.98 (m, 15H), 1.27 and 1.24 (s, 3H), signs for OH and NH are not assigned.

[00118] 13C NMR (main isomers): 139,13 and 138,96, 114,36 and 114,20, 105,35 and 105,14, 73,56 and 72,92, 66,71 and 66,43, 62,53 and 61,72, 47,97 and 47,81, 39,98 and 39,21,33,79 and 33,75, 29,63, 29,28, 29,22, 29,16, 28,12, 28,00, 27,97, 27,90, 23,30 and 22,59, 21,33 and 20,81.

[00119] 1H NMR (secondary isomers): 5.86-5.75 (m, 1H), 5.03-4.90 (m, 2H), 3.70 and 3.66 (d, J = 8.7, 1H), 3.49 and 3.47 (d, J = 8.3, 1H), 3.46 and 3.34 (d, J = 10.6, 1H), 3.39 and 3.33 (d, J = 8.6, 1H), 2.34-0.98 (m, 15H), 1.26 (2s, 3H), the signs for OH and NH are not assigned.

[00120] 13C NMR (secondary isomers): 139.06 and 138.96, 114.41 and 114.26, 106.30 and 105.80, 72.92 and 72.49, 66.97 and 66.68, 62.97 and 62.38, 47.13 and 47.07, 38.19 and 37.79, 33.78 and 33.70, 30.64 and 29.93, 29.12 and 29.11, 28.99 and 28.96, 27.73 and 27.56, 23.30 and 22.93, 20.71 and 20.39. (D) SYNTHESIS OF (±)-6-PETYL-1,4-DIAZAESPIRO[4.4]NONAN-2-ONE (COMPOUND 4)

[00121] A mixture of 2-petylcyclopentan-1-one (13.90 g, 90 mmol), TEA (15 ml, 108 mmol) and glycinamide hydrochloride (10.15 g, 90 mmol) in methanol (250 ml) was heated under reflux for 16 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. Water (50 ml) was added, and the mixture was extracted with ethyl acetate (2 x 100 ml). The combined organic phases were washed with a saturated aqueous solution of NaCl (50 ml), dried (Na2SO4), filtered and concentrated under reduced pressure. Column chromatography (SiO2, heptane / ethyl acetate 7:3, then ethyl acetate / ethanol 1:1) yielded 6.75 g (36%) of a mixture of two diastereomers in a ratio of approximately 1:1. Petition 870220074448, dated 08 / 18 / 2022, page 44 / 85 36 / 71

[00122] 1H NMR: 7.89 and 7.43 (br, s, 1 H), 3.51 and 3.50 (d, J = 16.4, 1 H), 3.47 and 3.41 (d, J = 16.4, 1 H), 2.55-2.36 (m, 1.6.6 H), (m, 6 H), 1.53–1.08 (m, 9 H), 0.88 (t, J = 6.8, 3 H).

[00123] NMR of13C: 177.08 and 176.94, 86.39 and 85.40, 49.83 and 49.36, 49.04 and 48.65, 39.61 and 39.29, 32.17 and 32.10 and 29.62 and 29.6 29.41 and 28.42, 28.07 and 28.00, 22.62 and 22.59, 20.53 and 19.81, 14.06. (E) SYNTHESIS OF (±)-(3S)-3-METHYL-6-PETHYL-1,4-DIAZASPYRO[4.4]NONAN-2-ONE (COMPOUND 5)

[00124] TEA (15.3 ml, 110 mmol) and 2-petylcyclopentan-1-one (7.71 g, 50 mmol) were added to a solution of L-alaninamide hydrochloride (12.45 g, 100 mmol) in methanol (250 ml). The reaction mixture was heated under reflux for 24 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. Water (100 ml) was added, and the mixture was extracted with ethyl acetate (100 ml). After phase separation, the aqueous phase was extracted again with ethyl acetate (150 ml). The combined organic phases were washed with water (100 ml), with a saturated aqueous solution of NaCl (100 ml), dried (Na2SO4), filtered and concentrated under reduced pressure to yield 8.23 ​​g of a mixture of four diastereoisomers in a ratio of approximately 1.9:1.0:1.4:1.8 (Compound 5).Column chromatography of 6.18 g (SO2, ethyl acetate / n-heptane 4:1, then ethyl acetate) yielded 0.52 g of compound 5a, 3.40 g of a mixture of compounds 5a-5d, and 0.13 g of compound 5d. The compound can be used in the form of its individual separated diastereomers or the mixture of non-separated isomers.

[00125] 1H NMR (Compound 5a): 7.16 (br, s, 1 H), 3.54 (q, J = 6.9 Hz, 1 H), 2.121.99 (m, 2 H), 1.93-1.83 (m, 1 H), 1.79-1.53 ​​(m, 4 H), 1.52-1.15 (m, 9 H), 1.35 (d, J = 7.1 Hz, 3 H), 0.87 (t, J = 7.1 Hz, 3 H).

[00126] 13C NMR (Compound 5a): 178.86, 83.13, 55.86, 49.83, 40.96, 32.21, 28.47, 28.41, 28.10, 22.59, 19.76, 18.52, 14.06.

[00127] 1H NMR (Compound 5b, 600 MHz): 7.18 (br, s, 1 H), 3.61 (q, J = 6.8 Hz, 1 H), 2.08-1.92 (m, 3 H), 1.92-1.61 (m, 4 H), 1.49-1.18 (m, 8 H), 1.34 (d, J = 6.9 Hz, Petition 870220074448, dated 08 / 18 / 2022, page 45 / 85 37 / 71 H), 1,15-1,05 (m, 1 H), 0,89 (t, J = 6,9 Hz, 3 H).

[00128] RMN de13C (Composto 5b, 151,0 MHz): 178,83, 82,96, 54,24, 46,13, 38,51, 32,11,28,47, 28,24, 27,93, 22,57, 19,73, 17,06, 14,05.

[00129] RMN de1H (Composto 5c, 600 MHz): 7,61 (br, s, 1 H); 3,64 (q, J = 6,9 Hz, 1 H), 2,08-1,92 (m, 2 H), 1,92-1,61 (m, 5 H), 1,49-1,18 (m, 8 H), 1,34 (d, J = 6,9 Hz, 3 H), 1,15-1,05 (m, 1 H), 0,87 (t, J = 7,1 Hz, 3 H).

[00130] RMN de13C (Composto 5c, 151,0 MHz): 178,79, 84,06, 55,02, 49,42, 40,67, 32,14, 29,55, 28,00, 22,62, 20,29, 18,65, 14,05.

[00131] RMN de1H (Composto 5d): 7,28 (br, s, 1 H), 3,59 (q, J = 6,8 Hz, 1 H), 2,011,96 (m, 1 H), 1,94-1,83 (m, 2 H), 1,83-1,75 (m, 1 H), 1,75-1,59 (m, 3 H), 1,49-1,18 (m, 8 H), 1,34 (d, J = 7,1 Hz, 3 H), 1,14-1,03 (m, 1 H), 0,89 (t, J = 6,9 Hz, 3 H).

[00132] RMN de13C (Composto 5d): 178,53, 83,71, 54,27, 48,29, 39,93, 32,11, 29,71,29,66, 27,97, 22,61,20,93, 17,48, 14,05. (F) SYNTHESIS OF (±)-(3S)-3-BENZYL-6-PETYL-1,4-DIAZAESPIRO[4,4]NONAN-2-ONE (COMPOUND 6)

[00133] A mixture of 2-petylcyclopentan-1-one (3.87 g, 25 mmol), TEA (3.9 ml, 28 mmol) and L-phenylalaninamide hydrochloride (5.14 g, 25 mmol) in methanol (150 ml) was heated under reflux over the weekend. After cooling to room temperature, the solvent was evaporated under reduced pressure. Water (50 ml) was added, and the mixture was extracted with ethyl acetate (2 x 100 ml). The combined organic phases were washed with a saturated aqueous solution of NaCl (2 x 50 ml), dried (Na2SÜ4), filtered, and concentrated under reduced pressure. Column chromatography (SiO2, n-heptane / ethyl acetate 7:3, ethyl acetate and ethyl acetate / ethanol 1:1) yielded 1.01 g of a mixture of two diastereomers at a ratio of approximately 2.9:1 (Compound 6a) and 2.02 g of another mixture of two diastereomers at a ratio of approximately 1.2:1 (Compound 6b).

[00134] NMR of1H (Compound 6a, major isomer): 7.34-7.19 (m, 5 H), 7.04 (br, s, 1 H), 3.80 (t, J = 5.4 Hz, 1 H), 3.07 (t, J = 5.1.2 Hz, 1 H), 3.07 (t, J = 5.1.2 Hz, 1 H), ( , 1.2 H 1.88–1.72 (m, 2 H), 1.72–1.50 (m, 3 H), 1.50–1.38 (m, 1 H), 1.38–1.03 (m, 9 H), 0.87 (t, J = 7.0 Hz, 3 H). Petition 870220074448, of 18 / 08 / 2022, p. 46 / 85 38 / 71

[00135] NMR of13C (Compound 6a, major isomer): 177.15, 136.87, 129.65, 128.63, 126.85, 83.22, 60.84, 49.75, 40.47, 37.23, 28.6 28.26, 28.06, 22.61, 19.64, 14.06.

[00136] NMR of1H (Compound 6a, secondary isomer): 7.47 (br, s 1 H), 7.34-7.19 (m, 5 H), 3.88 (dd, J = 7.1, 4.2 Hz, 1 H), 3.07 (dd, J = 5.1 Hz, 5.1 Hz), 2.95 (dd, J = 14.1, 7.1 Hz, 1 H), 2.08 (br, s, 1 H), 2.00-1.89 (m, 1 H), 1.88-1.72 (m, 1 H), 1.72-1.50 (m, 4 H), 1.50-1.38 (m, 2 H), 1.38–1.03 (m, 7 H), 0.86 (t, J = 6.9 Hz, 3 H).

[00137] 13C NMR (Compound 6a, secondary isomer): 176.96, 137.34, 129.64, 128.57, 126.76, 84.28, 60.38, 49.66, 40.54, 38.27, 32.14, 29.30, 28.93, 28.06, 22.64, 20.03, 14.04.

[00138] 1H-NMR (Compound 6b, main isomer): 7.34-7.21 (m, 5 H), 3.82 (q, J = 5.3 Hz, 1 H), 3.12 (dd, J = 14.1, 5.4 Hz, 1 H), 3.06 (dd, J = 13.3, 4.6 Hz, 1 H), 2.20 (br, s, 1 H), 1.99-1.74 (m, 3 H), 1.74-1.51 (m, 2 H), 1.50-1.40 (m, 1 H), 1.37-0.96 (m, 7 H), 0.91-0.70 (m, 2 H), 0.87 (t, J = 7.2 Hz, 3 H), a signal for NH was not assigned.

[00139] 13C NMR (Compound 6b, major isomer): 177.06, 136.74, 129.79, 128.67, 126.96, 83.72, 59.33, 47.90, 40.39, 36.35, 31.86, 29.63, 28.98, 27.78, 22.50, 20.84, 14.06.

[00140] 1H NMR (Compound 6b, secondary isomer): 7.34-7.21 (m, 5 H), 6.80 (br, s, 1 H), 3.82 (q, J = 5.3 Hz, 1 H), 3.20 (dd, J = 13.8, 5.2 Hz, 1 H), 3.04 (dd, J = 12.5, 4.8 Hz, 1 H), 2.20 (br, s, 1 H), 1.99-1.82 (m, 2 H), 1.74-1.51 (m, 4 H), 1.37-0.96 (m, 7 H), 0.91-0.70 (m, 1 H), 086 (t, J = 7.3 Hz, 3 H), 0.64-0.53 (m, 1 H).

[00141] 13C NMR (Compound 6b, secondary isomer): 177.23, 136.67, 129.94, 128.70, 126.99, 82.85, 59.04, 46.43, 38.68, 35.78, 32.04, 28.41, 27.91, 27.37, 22.45, 19.67, 14.04. (G) SYNTHESIS OF (±)-(7A,S)-2-PETHYLTETRAHYDROSPIRO[CYCLOPENTANE-1)3,PYRROLO[1,2-C]IMIDAZOLE]-1,(2,H)-ONE (COMPOUND 7)

[00142] A mixture of 2-petylcyclopentan-1-one (23.14 g, 150 mmol), TEA (46 ml, 330 mmol) and L-prolinamide hydrochloride (47.56 g, 300 mmol, 2 eq.) in methanol (500 ml) was heated under reflux for 22 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure. Water (150 ml) and pentane Petition 870220074448, dated 08 / 18 / 2022, page 47 / 85 39 / 71 (150 ml) were added, and the mixture was shaken for 15 minutes. After phase separation, the aqueous layer was extracted again with pentane (2 x 150 ml), and the combined organic layers were washed with water (100 ml), dried (Na2SO4), filtered, and concentrated. The residue was absorbed on ethyl acetate, filtered through Celite® and activated charcoal, concentrated, and dried under vacuum to yield 21.85 g (58%) of a mixture of three diastereomers in a ratio of approximately 9:6:1 (Compound 7). Column chromatography (SO2, ethyl acetate / n-heptane 2:1) allowed the separation of the different isomers. The compound can be used in the form of its individual separated diastereomers or the mixture of unseparated isomers.

[00143] RMN de1H (Composto 7a): 7,41 (br, s, 1 H), 3,93 (dd, J = 9,3, 5,8 Hz, 1 H), 3,07-2,99 (m, 1 H), 2,77-2,72 (m, 1 H), 2,19-2,01 (m, 2 H), 2,01-1,87 (m, 3 H), 1,871,61 (m, 5 H), 1,59-1,48 (m, 1 H), 1,39-1,14 (m, 7 H), 1,13-1,03 (m, 1 H), 0,86 (t, J = 7,1 Hz, 3 H).

[00144] RMN de13C (Composto 7a): 179,15, 87,64, 64,73, 50,86, 50,60, 33,24, 32,24, 29,83, 27,91,27,65, 27,14, 25,52, 22,68, 20,12, 14,07.

[00145] RMN de1H (Composto 7b): 6,96 (br, s, 1 H), 3,79 (dd, J = 9,3, 5,4 Hz, 1 H), 2,95-2,88 (m, 1 H), 2,76-2,67 (m, 1 H), 2,15-2,03 (m, 2 H), 1,95-1,62 (m, 8 H), 1,611,52 (m, 1 H), 1,52-1,42 (m, 1 H), 1,39-1,12 (m, 7 H), 0,87 (t, J = 6,9 Hz, 3 H).

[00146] RMN de13C (Composto 7b): 179,03, 87,03, 65,05, 51,81, 50,36, 32,23, 32,18, 29,55, 27,99, 27,59, 27,06, 25,61,22,67, 19,84, 14,09.

[00147] 1H NMR (Compound 7c): 6.74 (br, s, 1 H), 3.85 (dd, J = 9.6, 4.8 Hz, 1 H), 3.04-2.95 (m, 1 H), 2.64-2.55 (m, 1 H), 2.19-2.04 (m, 3 H), 2.04-1.94 (m, 2 H), 1,911.53 (m, 5 H), 1.51-1.05 (m, 9 H), 0.89 (t, J = 6.7 Hz, 3 H).

[00148] 13C NMR (Compound 7c): 179.21, 86.64, 63.68, 48.17, 42.77, 40.27, 31.87, 31.50, 30.76, 27.87, 25.69, 25.30, 22.60, 21.68, 14.06. (H) SYNTHESIS OF (±)-2-PETYLTETRA-HYDRO-2Ή-SPIRO[CYCLOPENTA-1,3,IMIDAZO[1,5-A]PYRIDIN]-1'(5'H)-ONE (COMPOUND 8)

[00149] TEA (0.85 ml, 6 mmol) and 2-petylcyclopentan-1-one (4.63 g, 30 mmol) were added to a solution of 2-piperidinecarboxamide (8.09 g, 60 mmol) in methanol. Petition 870220074448, dated 08 / 18 / 2022, p. 48 / 85 40 / 71 (50 ml). The reaction mixture was heated under reflux for 45 h, and after cooling to room temperature, it was concentrated. The residue was absorbed in ethyl acetate (150 ml) and treated with water (50 ml). The aqueous phase was extracted with ethyl acetate (150 ml), and the combined organic phases were washed with water (50 ml) and a saturated aqueous solution of NaCl (50 ml), dried (Na2SO4), filtered, and concentrated. Bulb-to-bulb distillation (130 °C, 0.4 mbar) to remove the remaining 2-petylcyclopentan-1-one yielded 3.14 g (40%) of a mixture of three diastereomers in a ratio of approximately 7:1:2 (Compound 8). Column chromatography (SO2, toluene / ethyl acetate 4:1, then 3:1) allowed the (partial) separation of the different isomers, generating Compound 8a, a mixture of Compounds 8a and 8b in a ratio of approximately 1:1.3, and Compound 8c.The compound can be used in the form of its individual separate diastereoisomers or a mixture of unseparated isomers.

[00150] de1H NMR (Compound 8a, 600 MHz): 6.93 (br, s, 1 H), 2.88-2.81 (m, 2 H), 2.27 (dt, J = 11.0, 2.3 Hz, 1 H), 2.02-1.82 m, (1.47 H), (m, 7 H), 1.39–1.11 (m, 9 H), 1.03–0.94 (m, 1 H), 0.88 (t, J = 6.9 Hz, 3 H).

[00151] NMR of13C (Compound 8a, 151.0 MHz): 174.97, 86.01,61.94, 44.48, 43.09, 32.09, 29.26, 29.00, 28.67, 28.15, 26.7, 26.7 24.46, 22.63, 20.52, 14.10.

[00152] de1H NMR (Compound 8b, 600 MHz): 6.45 (br, s, 1 H), 2.89-2.81 (m, 1 H), 2.81-2.75 (m, 1 H), 2.38 (dt, J = 10.9, 2.7 Hz, 2.14-Hz), (m, 1 H), 2.03-1.82 (m, 3 H), 1.82-1.10 (m, 17 H), 0.88 (t, J = 6.9 Hz, 3 H).

[00153] NMR of13C (Compound 8b, 151.0 MHz): 174.91,85.04, 62.21,48.20, 47.35, 32.29, 30.90, 30.28, 29.27, 28.22, 26.2,26.6 24.15, 22.67, 21.46, 14.13.

[00154] de1H NMR (Compound 8c, 600 MHz): 6.94 (br, s, 1 H), 3.31-3.24 (m, 1 H), 3.00-2.93 (m, 1 H), 2.52 (dt, J = 11.6, 2.7 Hz, 1.31 Hz), (m, 5 H), 1.77–1.11 (m, 16 H), 0.88 (t, J = 6.9 Hz, 3 H).

[00155] NMR of13C (Compound 8c, 151.0 MHz): 175.51,86.05, 61.71,43,61,43.33, 37.17, 32.13, 30.36, 29.03, 28.01, 27.52,25.6 24.24, 22.66, 19.94, 14.06. SYNTHESIS OF (±)-(3-METHYL-6-PETHYL-1-OXA-4-AZASPYRO[4.4]NONAN-3YL)METANOL (COMPOUND 9) Petition 870220074448, of 18 / 08 / 2022, p. 49 / 85 41 / 71

[00156] 2-Amino-2-methylpropane-1,3-diol (5.31 g, 50 mmol) and ptoluenesulfonic acid monohydrate (0.20 g) were added to a shaken solution of 2-petylcyclopentan-1-one (8.48 g, 55 mmol) in toluene (100 ml). The mixture was heated under reflux for 22 hours. After cooling to room temperature, ethyl acetate (100 ml) was added, and the mixture was washed with a saturated aqueous solution of NaHCO3 (100 ml). The aqueous layer was extracted again with ethyl acetate (100 ml), and the combined organic phases were washed with a saturated aqueous solution of NaCl (100 ml), dried (Na2SO4), filtered, and concentrated. Column chromatography (SiU2, ethyl acetate) yielded 7.07 g of the crude compound. Furthermore, column chromatography of 2.00 g (SiÜ2, n-heptane / ethyl acetate 1:1) yielded 0.6 g (18%) of Compound 9 as a mixture of four diastereoisomers in a ratio of approximately 2.0:1.2:1:1.The compound can be used in the form of its individual separate diastereoisomers or as a mixture of non-separate isomers.

[00157] 1H NMR (Compound 9, main isomer): 3.73-3.64 (m, 1 H), 3.51-3.37 (m, 2 H), 3.36-3.28 (m, 1 H), 2.50-2.15 (br, m, 1 H), 2.15-1.15 (m, 19 H), 0.94-0.84 (m, 3 H).

[00158] 13C NMR (Compound 9, major isomer): 105.39, 73.56, 66.43, 62.55, 47.83, 39.98, 32.28, 29.62, 28.20*, 28.18*, 22.57, 22.67*, 21.33, 14.09 (* = provisional assignment).

[00159] 1H NMR (Compound 9, second most abundant isomer): 3.73-3.64 (m, 1H), 3.55-3.37 (m, 3H), 2.50-2.15 (br, m, 1H), 2.15-1.15 (m, 19H), 0.94-0.84 (m, 3H).

[00160] 13C NMR (Compound 9, second most abundant isomer): 105,19, 72,92, 66,69, 61,76, 48,00, 39,21, 32,22, 29,17, 28,20*, 28,01, 23,29, 22,69*, 20,83, 14,10 (* = provisional assignment).

[00161] 1H NMR (Compound 9, secondary isomers): 3.73-3.64 (m, 1 H), 3.513.37 (m, 2 H), 3.36-3.28 (m, 1 H), 2.50-2.15 (br, m, 1 H), 2.15-1.15 (m, 18 H), 1,130.95 (m, 1 H), 0.94-0.84 (m, 3 H).

[00162] 13C NMR (Compound 9, secondary isomers): 106.34 and 105.82, 72.92 Petition 870220074448, dated 08 / 18 / 2022, p. 50 / 85 42 / 71 and 72.49, 66.97 and 66.67, 62.97 and 62.38, 47.18 and 47.12, 38.23 and 37.81, 32.13 and 32.11, 30.76 and 30.04, 29.00 and 28.98, 27.95 and 27.78, 23.28 and 22.95, 22.69 and 22.63, 20.74 and 20.42, 14.07 and 14.04. SYNTHESIS OF (±)-6-HEXYL-1,4-DIAZAESPIRO[4.4]NONAN-2-ONE (COMPOSITE 10)

[00163] A mixture of 2-hexylcyclopentan-1-one (5.31 g, 30 mmol), TEA (9.3 ml = 9.75 g, 66 mmol, 2.2 eq.) and glycinamide hydrochloride (6.77 g, 60 mmol, 2 eq.) in methanol (50 ml) was heated under reflux for 24 hours. After cooling to room temperature, the reaction mixture was filtered, and the solvent was evaporated under reduced pressure. Water (50 ml) was added, and the mixture was extracted with ethyl acetate (2 x 100 ml). The combined organic phases were washed with water (50 ml) and with a saturated aqueous solution of NaCl (50 ml), dried (Na2SO4), filtered, and concentrated under reduced pressure. Column chromatography (SiO2, heptane / ethyl acetate 7:3, then ethyl acetate / ethanol 1:1) yielded 3.48 g (52%) of a mixture of diastereomers in an approximately 1:1 ratio. The compound can be used in the form of its individual separated diastereomers or the mixture of non-separated isomers.

[00164] RMN de1H (600 MHz): 7,76 e 7,28 (br, s, 1 H), 3,51 e 3,49 (d, J = 16,6 e 16,2, 1 H), 3,47 e 3,41 (d, J = 16,6 e 16,2, 1 H), 2,05-1,60 (m, 7 H), 1,54-1,08 (m, 11 H), 0,88 (t, J = 6,7, 3 H).

[00165] RMN de13C (150,9 MHz): 176,99 e 176,87, 86,32 e 85,33, 49,83 e 49,37, 49,03 e 48,68, 39,62 e 39,32, 31,83 e 31,80, 29,67, 29,58 e 29,42, 28,41 e 28,39, 28,31 e 28,27, 22,64 e 22,63, 20,53 e 19,81, 14,09. SYNTHESIS OF (±)-6-HEPTYL-1,4-DIAZAESPIRO[4.4]NONAN-2-ONE (COMPOSITE 11)

[00166] A mixture of glycinamide hydrochloride (6.77 g, 60 mmol, 2 eq.), TEA (9.3 ml, 66 mmol, 2.2 eq.) and 2-heptylcyclopentan-1-one (5.47 g, 30 mmol) in methanol (50 ml) was heated under reflux for 24 hours. After cooling to room temperature, the reaction mixture was filtered and the solvent was evaporated under reduced pressure. Water (50 ml) was added, and the mixture was extracted with ethyl acetate (2 x 100 ml). The combined organic phases were washed with water (50 ml) and with a saturated aqueous solution of NaCl (50 ml), dried (Na2SO4), filtered and Petition 870220074448, dated 08 / 18 / 2022, page 51 / 85 43 / 71 concentrated under reduced pressure. Column chromatography (SiO2, heptane / ethyl acetate 7:3, then ethyl acetate and ethyl acetate / ethanol 1:1) yielded 4.35 g (61%) of a mixture of diastereomers in an approximately 1:1 ratio (Compound 11). Further column chromatography (SiO2, heptane / ethyl acetate 7:3, then ethyl acetate and ethyl acetate / ethanol 1:1) yielded several product fractions. The first fraction was filtered through cotton wool, washed with acetone, partially concentrated, and placed in a freezer to generate white crystals. Removal of the liquid by pipette and washing with a minimum of cold acetone yielded 0.11 g of white crystals of one of the diastereomers (Compound 11a). The second (main) fraction was crystallized again with acetone. After filtration, the mother liquor was again subjected to chromatography (SiO2, ethyl acetate) to generate the other diastereoisomer (Compound 11b) and some mixed fractions.The compound can be used in the form of its individual separated diastereomers or the mixture of non-separated isomers.

[00167] 1H NMR (Compound 11a): 7.23 (br, s, 1H), 3.49 (d, J = 16.3, 1H), 3.41 (d, J = 16.3, 1H), 1.96-1.85 (m, 3H), 1.83-1.60 (m, 4H), 1.55-1.45 (m, 1H), 1.45-1.33 (m, 2H), 1.33-1.14 (m, 10H), 0.89 (t, J = 6.7, 3H).

[00168] 13C NMR (Compound 11a): 176.95, 85.32, 49.81, 48.69, 39.33, 31.86, 29.97, 29.27, 28.44, 28.42, 28.28, 22.66, 19.81, 14.11.

[00169] 1H NMR (Compound 11b): 7.27 (br, s, 1 H), 3.51 (d, J = 16.7, 1 H), 3.47 (d, J = 16.7, 1 H), 2.07-1.95 (m, 1 H), 1.94-1.88 (m, 2 H), 1.88-1.62 (m, 3 H), 1.521.41 (m, 1 H), 1.41-1.17 (m, 12 H), 1.17-1.06 (m, 1 H), 0.88 (t, J = 6.7, 3 H).

[00170] 13C NMR (Compound 11b): 176.59, 86.18, 49.21, 48.97, 39.56, 31.84, 29.87, 29.73, 29.45, 29.29, 28.33, 22.66, 20.54, 14.11. SYNTHESIS OF (±)-2-(2-OXO-6-PETYL-1,4-DIAZASPYRO[4.4]NONAN-7-YL)METHYL ACETATE (COMPOUND 12)

[00171] A mixture of methyl 2-(3-oxo-2-petylcyclopetyl)acetate (Hedione®, 6.79 g, 30 mmol), TEA (9.3 ml = 9.75 g, 66 mmol) and glycinamide hydrochloride (6.77 g, 60 mmol) in methanol (50 ml) was heated under reflux for 70 hours. After cooling to room temperature, the reaction mixture was concentrated under Petition 870220074448, dated 08 / 18 / 2022, page 52 / 85 44 / 71 reduced pressure. Ethyl acetate (100 ml) was added, and the mixture was washed with an aqueous solution of NaCl (50%, 50 ml). The aqueous phase was extracted again with ethyl acetate (100 ml), and the combined organic phases were washed with saturated aqueous NaCl solution (50 ml), dried (Na2SO4), filtered, and concentrated under reduced pressure. Column chromatography (SiO2, n-heptane / ethyl acetate 7:3, then ethyl acetate / ethanol 1:1) and bulb-to-bulb distillation of the main fraction to remove remaining volatiles yielded 3.90 g (46%) of a mixture of diastereomers in a ratio of approximately 1:1. The compound can be used in the form of its individual separated diastereomers or the mixture of non-separated isomers.

[00172] 1H NMR (600 MHz): 7.63 and 7.44 (br, s, 1 H), 3.67 (s, 3 H), 3.53, 3.43 (d, J = 16.2) and 3.45 (d, J = 1.9) (2 H), 2.58-2.52 (m, 1 H), 2.37-2.21 (m, 1 H), 2.20-1.84 (m, 2 H), 1.83-1.71 (m, 1 H), 1.63-1.18 (m, 12 H), 0.88 and 0.87 (t, J = 6.7, 3 H).

[00173] 13C NMR (150.9 MHz): 176.93 and 176.47, 173.20 and 173.09, 86.34 and 85.41, 53.61 and 52.67, 51.55, 49.63 and 48.82, 40.35 and 39.71, 40.24 and 39.03, 38.82 and 38.57, 32.43 and 32.27, 30.30 and 28.33, 28.23 and 28.10, 27.94 and 27.22, 22.51 and 22.48, 14.06. EXAMPLE 2 PERFORMANCE OF A FABRIC SOFTENER BASE COMPRISING A COMPOUND OF FORMULA (I) OF THE INVENTION

[00174] The performance of the compounds of formula (I) of the present invention was tested in a fabric softening surfactant emulsion with the following final composition: Stepantex® VL90 A (origin: Stepan) 12.21% by weight Calcium chloride (10% aqueous solution) 0.40% by weight Proxel® GXL (origin: Avecia) 0.04% by weight Water 87.35% by weight (A) DYNAMIC VOID SPACE MEASUREMENTS

[00175] The compound of formula (I) of the invention (0.1 mmol) was dissolved in ethanol (0.2 ml) and added to 7.0 g of the fabric softener formulation described above. After homogenization, an aliquot of the sample (0.07 g) was diluted with water. Petition 870220074448, dated 08 / 18 / 2022, page 53 / 85 45 / 71 cold demineralized stream (23.0 g). Then, a cotton sheet (EMPA cotton test no. 221, origin: Eidgenossische Materialprüfanstalt), pre-washed with an unscented detergent powder and cut into sheets of approximately 15 x 15 cm, approximately 5.2 g) was added and manually agitated for 3 minutes, left to stand for 2 minutes, then hand-wrung and weighed (approximately 10.0 g) to obtain a constant amount of residual water. A reference sample consisting of an equal molarity amount of the corresponding unmodified formula compound (VI) instead of the formula compound (I) was prepared and analyzed in the same manner. The cotton sheets were line-dried for 1 or 3 days before analysis.For the measurements, the leaves were placed in an empty-space sampling cell (approximately 160 ml internal volume), which was thermostated at 25 °C and exposed to a constant airflow of approximately 200 ml / min. The air was filtered with activated carbon and aspirated through a saturated NaCl solution (to ensure a constant air humidity of approximately 75%). The system was equilibrated for 15 minutes during the absorption of volatiles onto a Tenax® waste cartridge. Then, seven times consecutively, the volatiles were adsorbed for 15 minutes onto a clean Tenax® cartridge and for 45 minutes onto a Tenax® waste cartridge. The waste cartridges were discarded, while the other cartridges were desorbed in a Perkin Elmer TurboMatrix ATD desorber coupled to an Agilent Technologies 7890A gas chromatograph equipped with an HP-1 capillary column (30 m, 0.32 μm inner diameter, 0.25 μm film) and an FID detector.Volatiles were analyzed using a temperature gradient from 80 °C to 260 °C at 15 °C / min. Void space concentrations (in ng / l of air) were obtained by standard external calibrations using different concentrations of the fragrance to be released in ethanol. Each calibration solution (0.2 μl) was injected into a clean Tenax® cartridge which was desorbed and analyzed under the same conditions. Table 1 summarizes the results obtained for the release of the respective compounds of formula (VI) compared to an amount of equal molarity of the fragrance-free modified compounds of the formula. Petition 870220074448, dated 08 / 18 / 2022, pp. 54 / 85 46 / 71 (VI) after a total sampling time of 270 min above dry cotton after drying on a clothesline for 1 and 3 days. All data are average values ​​of at least two measurements. TABLE 1: AVERAGE VOID SPACE CONCENTRATIONS OF FORMULA (VI) COMPOUNDS MEASURED AFTER LINE DRYING FOR 1 DAY AND 3 DAYS AND SAMPLING FOR 270 MINUTES ON DRY COTTON IN A FABRIC SOFTENER APPLICATION. THE INCREASE FACTOR WITH RESPECT TO THE REFERENCE IS INDICATED IN PARENTHESES. Compound Concentration of 2-(5-hexenyl)cyclopentan-1-one [ng / l] measured after drying on a clothesline for 1 day Concentration of 2-(5-hexenyl)cyclopentan-1-one [ng / l] measured after drying on a clothesline for 3 days Reference 1.0 0.8 Compound 1a 7.5 (x 8) 12.4 (x 16) Compound 1b 7.5 (x 8) 11.3 (x 14) Compound 2a 86.7 (x 87) 15.7 (x 20) Compound 2b 44.0 (x 44) 48.9 (x 61) Compound 3 84.2 (x 84) 42.1 (x 53) Compound Concentration of 2-petyl-1cyclopentanone [ng / l] measured after drying on a clothesline for 1 day Concentration 2-petyl-1cyclopentanone [ng / l] measured after drying on a clothesline for 3 days Reference 0.7 0.7 Compound 4 7.2 (x 10) 9.1 (x 13) Compound 5 5.0 (x 7) 4.0 (x 6) Compound 6a 3.5 (x 5) 7.8 (x 11) Petition 870220074448, dated 08 / 18 / 2022, pp. 55 / 85 47 / 71 Compound 6b 1.9 (x 3) 2.7 (x 4) Compound 7 75.1 (x 107) 49.8 (x 71) Compound 7a 53.1 (x 76) 58.5 (x 84) Compound 7b 78.6 (x 112) 33.2 (x 46) Compound 7c 57.8 (x 83) 28.5 (x 41) Compound 8 2.5 (x 4) 1.3 (x 2) Compound 9 32.8 (x 47) 7.5 (x 11) Concentration of 2-hexyl-1-cyclopentanone [ng / l] measured after drying on a clothesline for 1 day Concentration of 2-hexyl-1-cyclopentanone [ng / l] measured after drying on a clothesline for 3 days Reference 1.1 1.3 Compound 10 13.6 (x 12) 12.3 (x 9)

[00176] The compounds according to formula (I) released higher amounts of compounds of formula (VI) onto dry cotton in the empty space above than the reference sample consisting of an amount of equal molarity of the corresponding unmodified compound of formula (VI). Therefore, the compounds of formula (I) according to the present invention have the ability to increase the durability for the perception of cyclopentanone-derived perfumery ingredients. (B) SENSORY PANEL EVALUATIONS

[00177] The performance of the compounds of formula (I) of the present invention was tested in a fabric softening surfactant emulsion with the following composition: Methyl sulfate of methyl bis[ethyl(seboat)]-2-hydroxyethyl ammonium(1)8,88 10% calcium chloride solution 0.36 Petition 870220074448, dated 08 / 18 / 2022, pp. 56 / 85 48 / 71 1,2-benzisothiazolin-3-one2)0.04 Water 90.72 1) Stepantex® VL 90A - Stepan 2) Proxel® GXL - Arch

[00178] The softener was prepared by weighing methyl bis[ethyl (seboat)]-2-hydroxyethyl ammonium sulfate which was heated to 65 °C. Then, water and 1,2-benzisothiazolin-3-one were placed in the reactor and heated to 65 °C under shaking. Methyl bis[ethyl (seboat)]-2-hydroxyethyl ammonium sulfate was added to the above mixture. The mixture was shaken for 15 minutes, and CaCb was added. Then, 0.1 g of Compound 7 or 0.0616 g of 2-petylcyclopentanone was added. The mixture was shaken for 15 minutes and cooled to room temperature under stirring (viscosity measurement: result 35 + / - 5 mPas. (shear rate 106 s-1)).

[00179] Cotton terry towels (36 pieces, 18 cm * 18 cm, approximately 30 g each) were washed with 55 g of unscented detergent in a European washing machine (Miele Novotronic W300-33CH) at 40 °C using the cycle program. The wash was followed by a rinse at 900 rpm with 23 g of concentrated fabric softener. The terry towels were then line-dried for 24 hours before being evaluated by a panel of 20 trained participants. Participants were asked to rate the odor intensity of the towels after gently hand-rubbing the fabrics on a scale of 1 to 7, where 1 corresponds to odorless and 7 corresponds to a very strong odor. The results obtained are summarized in Table 2. TABLE 2: EVALUATION OF THE PANEL IN AN APPLICATION OF FABRIC SOFTENER. Overall Perfume Intensity Line Drying 1 day 3 days 7 days Fabric Softener + 0.1% of Compound 7 2.19 3.29 3.28 Fabric Softener + 0.0616% of 2-petylcyclopentanone 2.23 2.50 2.04 Petition 870220074448, dated 08 / 18 / 2022, page 57 / 85 49 / 71

[00180] The olfactory performance on dry fabrics due to the presence of Compound 7 pro-perfume performed relatively close to the 2-petylcyclopentanone control on Day 1 and was perceived as significantly more intense than the 2-petylcyclopentanone control on Day 3 and Day 7. Based on the results, Compound 7 pro-perfume at 0.1% performed significantly better than the 2-petylcyclopentanone control at 0.0616%, at least from 3 dry days up to 7 dry days. EXAMPLE 3 PERFORMANCE OF A GENERAL PURPOSE CLEANING FORMULATION FOR HARD SURFACES COMPRISING A COMPOUND OF FORMULA (I) OF THE INVENTION

[00181] The release of compounds of formula (VI) from compounds of formula (I) of the present invention was tested in a general purpose surface cleaner (APC). An APC formulation with the following composition was prepared: Neodol® 91-8 (origin: Shell Chemicals) 5.0% by weight; Marlon® A 375 (origin: Hüls AG) 4.0% by weight; Sodium cumolsulfonate 2.0% by weight; Kathon® CG (origin: Rohm and Haas) 0.2% by weight; Deionized water 88.8% by weight

[00182] In a flask, one of the compounds of the invention of formula (I) (0.0369 mmol) was dissolved in ethanol (100 μl). Then, the APC formulation (3.0 ml) was added, and the sample was gently shaken. An aliquot of these samples (1 ml) was removed by pipette with demineralized tap water (9 ml). A film of this solution (0.75 ml) was pipetted onto a porous ceramic plate (approximately 5 x 10 cm) and left to stand at room temperature. Similarly, a reference sample consisting of an equal molarity amount of the corresponding unmodified compound of formula (VI) (0.0369 mmol) instead of one of the compounds of the invention of formula (I) in ethanol (100 μl) was prepared and processed in the same manner.

[00183] After one day, each of the ceramic plates was placed inside Petition 870220074448, dated 08 / 18 / 2022, page 58 / 85 A 50 / 71 vacuum sampling cell (approximately 625 ml) was exposed to a constant airflow of approximately 200 ml / min. The air was filtered with activated carbon and aspirated through a saturated aqueous NaCl solution (to ensure a constant air humidity of approximately 75%). The system was equilibrated for 15 min by adsorbing the volatiles onto a Tenax® waste cartridge. Then, the volatiles were alternately adsorbed for 10 minutes onto a clean Tenax® cartridge and for 20 minutes onto a Tenax® waste cartridge (6x). The waste cartridges were discarded; the clean cartridges were desorbed and analyzed as described in Example 2. All measurements were performed at least twice.The average void space concentrations of compounds of formula (VI) released from compounds of formula (I), as prepared in Example 1, or from the reference sample after 55 minutes of sampling above the porous ceramic plates are listed in Table 3. Table 3 also indicates the increase factors of compounds of formula (VI) released from compounds of the invention of formula (I) relative to the reference sample. TABLE 3: AVERAGE CONCENTRATIONS OF FORMULA (VI) COMPOUNDS MEASURED IN THE VOID SPACE AFTER DRYING FOR 1 DAY AND 55 MINUTES OF SAMPLING OF THE ABOVE SAMPLING CERAMIC PLATES IN AN APC APPLICATION. THE INCREASE FACTOR WITH RESPECT TO THE REFERENCE IS INDICATED IN PARENTHESES. Compound Concentration of 2-(5-hexenyl)cyclopentan-1-one [ng / l] after drying for 1 day Reference 15.5 Compound 2 70.7 (x 5) Concentration of 2-petyl-1-cyclopentanone [ng / l] after drying for 1 day Reference 5.5 Compound 9 186.4 (x 34) Petition 870220074448, dated 08 / 18 / 2022, page 59 / 85 51 / 71 Concentration of 2-heptyl-1-cyclopentanone [ng / l] after drying for 1 day Reference 17.3 Compound 11 35.3 (x 2)

[00184] After 1 day, the compounds of the invention of formula (I), as prepared in Example 1, release more compound of formula (VI) into the void space than in the reference sample. Thus, the compounds of formula (I) of the invention have the capacity to provide a lasting and consistent release of the compounds of formula (VI) to a hard surface of an APC application. EXAMPLE 4 PERFORMANCE OF A HAIR CONDITIONER FORMULATION COMPRISING A COMPOUND OF FORMULA (I) OF THE INVENTION

[00185] The generation of compounds of formula (VI) from compounds of formula (I) of the present invention was tested in a hair conditioning application. A hair conditioner formulation with the following final composition was prepared: Dehyquart® C 4046 (origin: BASF) 5.00% by weight Glycerin (85%) (source: Brenntag) 2.00% by weight Liquid Paraffin (source: Acros) 2.00% by weight Genamin® CTAC (source: Clariant) 1.00% by weight Xiameter MEM-949 Cationic Emulsion (source: Xiameter) 1.00% by weight Jaguar® C14 S (source: Lubrizol) 0.30% by weight Kathon® CG (source: Rohm and Haas) 0.08% by weight EDTA Powder B (source: BASF) 0.05% by weight Deionized water 88.57% by weight

[00186] A solution of one of the compounds of formula (I) of the present invention in ethanol was prepared by precisely weighing 0.3 mmol of the compound into a volumetric flask (5 ml) and filling it with ethanol. Similarly, a Petition 870220074448, dated 08 / 18 / 2022, pp. 60 / 85 52 / 71 reference solution containing an equal amount of the compound of formula (VI) to be released was prepared

[00187] The hair conditioner formulation described above (920 mg) was weighed into a sample tube (3 ml), then the ethanol solution (100 μl) containing one of the compounds of the invention of formula (I) or (VI, reference) was added. The tube was closed, shaken (50x) and centrifuged with a manual centrifuge (approximately 3500 rpm) for 30 s.

[00188] A tuft of Caucasian hair (origin: Kerling International Haarfabrik GmbH, approximately 10 cm long, about 0.5 g) was rinsed and rubbed under running water at 37 °C with a flow of approximately 2 l / min for 30 s, and excess water was removed by squeezing the tuft with the fingertips. An unscented shampoo formulation (0.1 g) was spread on the tuft of hair, which was washed for 30 seconds. Then, the shampoo was removed by rinsing with running water at 37 °C for 30 seconds, and excess water was removed by squeezing the tuft with the fingertips. Then, the hair conditioner formulation (0.1 g) containing either of the compounds of the invention, according to formula (I) or the compound of reference formula (VI), was spread on the tuft of hair. The tuft of hair was gently rubbed between the ends of the dice for 1 minute, combed, and dried on a clothesline.

[00189] After 6 hours, the tuft of hair was combed (10x) and fixed with adhesive tape inside a thermostatically controlled (25 °C) void sampling cell with an internal volume of approximately 165 ml. A constant airflow (200 ml / min) was pumped into the sample. The incoming air was filtered through activated carbon and through a saturated aqueous NaCl solution. The system was equilibrated for 10 min by absorbing the volatiles onto a Tenax® waste cartridge. Then, the volatiles were adsorbed for 10 minutes onto a first clean Tenax® cartridge and for another 10 minutes onto a second clean Tenax® cartridge. The pump was then stopped. The tuft of hair was left inside the void sampling cell without connecting a cartridge. After 24 h, a Tenax® waste cartridge was connected, the pump was turned on, and the system was equilibrated for 10 minutes. In Petition 870220074448, dated 08 / 18 / 2022, pp. 61 / 85 53 / 71 Subsequently, the volatiles were consecutively adsorbed for 10 minutes onto two Tenax® cleaning cartridges. The waste cartridges were discarded; the clean cartridges were desorbed and analyzed as described in Example 2. All measurements were performed at least twice.

[00190] The average concentrations of 2-petyl-1-cyclopentanone (compound of formula (VI)) released from compound 9 (compound of formula (I), as prepared in Example 1) or from the reference sample (desorbed from the first cartridge) after 6 hours and after 24 hours are listed in Table 4. Table 4 also indicates the factors of increase in fragrance released from the compounds of the invention of formula (I) relative to the reference sample. TABLE 4: AVERAGE VOID SPACE CONCENTRATIONS OF 2-PETYL-1CYCLOPENTANONE MEASURED AFTER 6 HOUR AND 24 HOUR DRYING ON HAIR IN A HAIR CONDITIONER APPLICATION. THE INCREASE FACTOR RELATIVE TO THE REFERENCE IS INDICATED IN PARENTHESES. Concentration of 2-petyl-1-cyclopentanone [ng / l] measured after drying for 6 hours. Concentration of 2-petyl-1-cyclopentanone [ng / l] measured after drying for 24 hours. Reference 1.9 4.2 Compound 9 40.3 (x 21) 152.7 (x 36)

[00191] The compounds of formula (I) of the invention, as prepared in Example 1, release larger amounts of fragrance into the void space than the reference sample, especially after longer periods of time (24 hours). Thus, the compounds of formula (I) of the invention have the ability to provide a long-lasting and consistent perfume scent to the hair from a hair conditioner application. EXAMPLE 5 PREPARATION OF A PERFUMED OIL

[00192] A non-limiting example of a typical perfumed oil is prepared Petition 870220074448, dated 08 / 18 / 2022, pp. 62 / 85 54 / 71 mixing by addition the following fragrance co-ingredients: % in Ingredients weight Ethyl 2-Methylbutanoate 0.16 Hexyl acetate 0.37 Limonene 1.67 2,6-Dimethyl-7-octen-2-ol 0.94 2-Phenylethanol2,15 Linalool0.73 (2RS,4SR / 4RS)-4-Methyl-2-(2-methyl-1-propen-1-yl)tetrahydro-2H-pyran 0.30 2-Methyl-1,3-dioxolane-2-ethyl acetate0.32 Benzyl acetate2,46 Allyl Heptanoate0.38 alpha-Terpineol0.88 3,7-Dimethyl-6-octen-1-ol 0.55 4-Methoxybenzaldehyde1.00 (E)-4-Methyl-3-decen-5-ol0.37 [cis / trans-4-(2-propanyl)cyclohexyl]methanol0.47 -Methoxy-4-[(1 E)-1-propen-1-yl]benzene0.15 (1RS,2RS / 2SR)-2-(2-Methyl-2-propanyl)cyclohexyl acetate1.95 1,1-dimethyl-2-phenylethyl acetate0.95 Tricyclo acetate[5.2.1.02'~]dec-3 / 4-en-8-ila3,34 3-Cyclo-hexylpropanoate0.26 3-(4-Isopropylphenyl)-2-methylpropanal8,18 Petition 870220074448, 18 / 08 / 2022, pág. 63 / 85 55 / 71 (3E)-3-Methyl-4-(2,6,6-trimethyl-2-cyclo-hexen-1-yl)-3-buten-2-ona and (1E)-1(2,6,6-trimethyl-2-cyclo-hexen-1 -yl)-1 -penten-3-ona1,13 2-Methylpropanoate de 2-phenoxiethyla5,38 Propanoato de triciclo[5.2.1.0(2,6)]dec-3 / 4-en-8-ila2,32 5-heptyldi-hidro-2(3H)-furanona2,30 2 / 3-Methylbutyl salicylate1,42 Salicylate de (3Z)-3-Hexen-1-ila0,31 -(2,3,8,8-Tetramethyl-1,3,4,5,6,7-hexa-hidronaphthalen-2-yl)ethanone16.03 2-Hidroxybenzoato de hexila5,04 (2E)-2-benzylideno-octanal21,22 (-)-(3aR,5aS,9aS,9bR)-3a,6,6,9a-Tetramethyldodeca-hidronaphtho[2,1b]furan0,27 -Oxa-12 / 13-ciclo-hexadecen-2-ona4,78 Oxacyclo-hexadecan-2-ona3,82 Benzyl 2-Hydroxybenzoate3.01 Dipropylene glycol5,39 Total: 100 EXAMPLE 6 PREPARATION OF TRANSPARENT ISOTROPIC FORMULATIONS FOR SHAMPOO COMPRISING A COMPOUND OF FORMULA (I) OF THE INVENTION

[00193] A typical fragrance-free transparent isotropic formulation for shampoo is listed in Table 5. The fragrance-free shampoo formulation is prepared by dispersing Polyquaternium-10 in water. The remaining ingredients of Phase A are mixed separately by adding one after the other, while mixing well after each addition. This premix is ​​added to the Polyquaternium-10 dispersion and Petition 870220074448, dated 08 / 18 / 2022, pp. 64 / 85 56 / 71 mixed for another 5 minutes. Then, the premixed Phase B and the premixed Phase C are added (Monomels® 90L-12 is heated to melt in Texapon® NSO IS) while stirring. Phase D and Phase E are added while stirring. The pH is adjusted with a citric acid solution to 5.5-6.0. TABLE 5: COMPOSITION OF A TYPICAL UNSCENTED, TRANSPARENT ISOTROPIC FORMULATION FOR SHAMPOO. Phase Ingredients Quantity [% by weight] A Deionized water 44.4 Polyquaternium-10 (1) 0.3 Glycerin 85% (2) 1.0 DMDM ​​Hydantoin (3) 0.2 B Sodium laureth sulfate (4) 28.0 Cocamidopropyl betaine (5) 3.2 Disodium cocoamphodiacetate (6) 4.0 Stearyl alcohol ethoxylate (20)(7) 1.0 C Sodium laureth sulfate (4) 3.0 Glyceryl laureate (8) 0.2 D Deionized water 1.0 Sodium methylparaben (9) 0.1 E Sodium chloride (10% aqueous solution) 15.0 Citric acid (10% aqueous solution with pH 5.5-6.0) as needed (1) JR-400 Ucare® polymer; origin: Noveon (2) origin: Brenntag Schweizerhall AG (3) Glydant®; origin: Lonza Petition 870220074448, dated 08 / 18 / 2022, pages 65 / 85 57 / 71 (4) Texapon® NSO IS; origin: Cognis (5) Tego® Betain F 50; origin: Evonik (6) Amphotensid GB 2009; origin: Zschimmer & Schwarz (7) Brij® S20; origin: Croda (8) Monomuls® 90 L-12; origin: Gruenau GmbH (9) Nipagin Monosodium; origin: NIPA

[00194] Next, the perfumed shampoo formulation is obtained by adding, under gentle stirring, a perfumed oil (such as, for example, those described in Example 5, 0.1 to 0.8% by weight relative to the total weight of the unscented shampoo formulation) and at least one of the compounds of formula (I) (0.05 to 0.50% by weight relative to the total weight of the unscented shampoo formulation) to the unscented shampoo formulation listed in Table 5. EXAMPLE 7 PREPARATION OF PEARLIZED SHAMPOO FORMULATIONS COMPRISING A COMPOUND OF FORMULA (I) OF THE INVENTION

[00195] A typical unscented pearlescent shampoo formulation is listed in Table 6. The unscented shampoo formulation is prepared by dispersing Tetrasodium EDTA, Guar Hydroxypropyltrimonium Chloride, and Polyquaternium-10 in water. NaOH (10% aqueous solution, Phase B) is added after Phase A becomes homogeneous. Then, the premixed Phase C is added, and the mixture is heated to 75 °C. The ingredients of Phase D are added and mixed until the mixture becomes homogeneous. The mixture is cooled. At 45 °C, the ingredients of Phase E are added during mixing. The final viscosity is adjusted with NaCl (25% aqueous solution) and a pH of 5.5–6.0 is adjusted with NaOH (10% aqueous solution). TABLE 6: COMPOSITION OF A TYPICAL PEARLIZED SHAMPOO FORMULATION. Phase Ingredients Quantity [% by weight] Deionized water 45.97 Petition 870220074448, dated 08 / 18 / 2022, pp. 66 / 85 58 / 71 Tetrasodium EDTA (1) 0.05 Hydroxypropyltrimonium Guar Chloride (2) 0.05 Polyquaternium-10 (3) 0.075 B NaOH (10% aqueous solution) 0.30 C Ammonium Lauryl Sulfate (4) 34.00 Ammonium Laureth Sulfate (5) 9.25 Cocamidopropyl Betaine (6) 2.00 Dimethicone (and) C12-13 Pareth-4 (and) C12-13 Pareth-23 (and) Salicylic Acid (7) 2.50 D Cetyl Alcohol (8) 1.20 Cocamide MEA (9) 1.50 Glycol Distearate (10) 2.00 E Methylchloroisothiazolinone and Methylisothiazolinone (11) 0.10 D-Panthenol 75% (12) 0.10 Deionized water 0.30 F Sodium chloride (25% aqueous solution) 0.60 (1) EDETA® Powder; origin: BASF (2) Jaguar® C14 S; origin: Rhodia (3) Ucare® JR-400 Polymer; origin: Noveon (4) Sulfetal® LA BE; origin: Zschimmer & Schwarz (5) Zetesol® LA; origin: Zschimmer & Schwarz (6) Tego® Betain F 50; origin: Evonik (7) Xiameter® MEM-1691; origin: Dow Corning (8) Lanette®16; origin: BASF (9) Comperlan® 100; origin: Cognis (10) Cutina® AGS; origin: Cognis Petition 870220074448, dated 08 / 18 / 2022, pp. 67 / 85 59 / 71 (11) Kathon® CG; origin: Rohm & Haas (12) D-Panthenol; origin: Roche

[00196] Next, the pearly scented shampoo formulation is obtained by adding, under gentle stirring, a scented oil (such as, for example, those described in Example 5, 0.1 to 0.8% by weight relative to the total weight of the unscented shampoo formulation) and at least one of the compounds of formula (I) (0.05 to 0.50% by weight relative to the total weight of the unscented shampoo formulation) to the unscented shampoo formulation listed in Table 6. EXAMPLE 8 PREPARATION OF RINSE-OFF HAIR CONDITIONER FORMULATIONS COMPRISING A COMPOUND OF FORMULA (I) OF THE INVENTION

[00197] A typical fragrance-free rinse-out hair conditioner formulation is listed in Table 7. The fragrance-free rinse-out hair conditioner formulation is prepared by mixing the ingredients of Phase A until a uniform mixture is obtained. Tylose® is allowed to dissolve completely. The mixture is then heated to 70-75 °C. The ingredients of Phase B are combined and melted at 70-75 °C. Then, the ingredients of Phase B are added to Phase A with good stirring, and mixing is continued until the mixture reaches a temperature of 60 °C. Then, the ingredients of Phase C are added while stirring and maintaining the mixture until it cools to 40 °C. The pH is adjusted with a citric acid solution to 3.5-4.0. TABLE 7: COMPOSITION OF A TYPICAL RINSE-OFF HAIR CONDITIONER FORMULATION. Phase Ingredients Quantity [% by weight] A Deionized water 81.8 Behentrimonium chloride (1) 2.5 Hydroxyethylcellulose (2) 1.5 Petition 870220074448, dated 08 / 18 / 2022, pages 68 / 85 60 / 71 B Cetearyl Alcohol (3) 4.0 Glyceryl Stearate (and) PEG-100 Stearate (4) 2.0 Behentrimonium Methosulfate (and) Cetyl Alcohol (and) Butylene Glycol (5) 4.0 Ethoxylated Stearyl Alcohol (20)(6) 1.0 C Amodimethicone (and) Trideceth-12 (and) Cetrimonium Chloride (7) 3.0 Chlorhexidine Digluconate (20% aqueous solution)(8) 0.2 D Citric Acid (10% aqueous solution with pH 3.5-4.0) as needed (1) Genamin® KDMP; origin: Clariant (2) Tylose® H10 Y G4; origin: Shin Etsu (3) Lanette® O; origin: BASF (4) Arlacel® 165; origin: Croda (5) Incroquat® Behenyl TMS-50-PA- (MH); origin: Croda (6) Brij® S20; origin: Croda (7) Xiameter® MEM-949; origin: Dow Corning (8) origin: Alfa-Aesar

[00198] Next, a perfumed rinse-out hair conditioner formulation is obtained by adding, under gentle stirring, a perfumed oil (as described, for example, in Example 5, 0.2 to 1.0 % by weight relative to the total weight of the unscented conditioner formulation) and at least one of the compounds of formula (I) (0.05 to 0.5 % by weight relative to the total weight of the unscented conditioner formulation) to the unscented rinse-out hair conditioner formulation listed in Table 7. EXAMPLE 9 PREPARATION OF STRUCTURED FORMULATIONS FOR SHOWER GEL COMPRISING A COMPOUND OF FORMULA (I) OF THE INVENTION Petition 870220074448, dated 08 / 18 / 2022, pp. 69 / 85 61 / 71

[00199] A formulation for a typical unscented structured shower gel is listed in Table 8. A scented structured shower gel is prepared by adding, under gentle stirring, a scented oil (as described, for example, in Example 5, 0.1 to 1.5% by weight relative to the total weight of the structured shower gel) and at least one of the compounds of formula (I) of the invention (0.05 to 0.50% by weight relative to the total weight of the structured shower gel) to the unscented structured shower gel formulation of Table 8. TABLE 8: COMPOSITION OF A FORMULATION FOR A STRUCTURED SHOWER GEL WITHOUT TYPICAL PERFUME. Ingredients Quantity [% by weight] Deionized water 49.35 Tetrasodium EDTA (1) 0.05 Acrylates copolymer (2) 6.00 C12-15 Sodium pareth sulfate (3) 35.00 Sodium hydroxide (20% aqueous solution) 1.00 Cocamidopropyl betaine (4) 8.00 Methylchloroisothiazolinone and methylisothiazolinone (5) 0.10 Citric acid (40% aqueous solution) 0.50 (1) EDETA Powder B; origin: BASF (2) Carbopol Aqua SF-1 Polymer; origin: Noveon (3) Zetesol AO 328 U; origin: Zschimmer & Schwarz (4) Tego Betain F 50; origin: Goldschmidt (5) Kathon® CG; origin: Rohm & Haas EXAMPLE 10 PREPARATION OF TRANSPARENT SHOWER GEL FORMULATIONS THAT INCLUDES A COMPOUND OF FORMULA (I) OF THE INVENTION

[00200] A typical fragrance-free transparent shower gel formulation is listed Petition 870220074448, dated 08 / 18 / 2022, pp. 70 / 85 62 / 71 in Table 9. A transparent, unscented shower gel is prepared by adding, under gentle stirring, a perfumed oil (as described, for example, in Example 5, 0.5 to 1.5% by weight relative to the total weight of the transparent shower gel) and at least one of the compounds of formula (I) of the invention (0.05 to 0.50% by weight relative to the total weight of the transparent shower gel) to the transparent, unscented shower gel formulation of Table 9. TABLE 9: COMPOSITION OF A FORMULATION OF A TRANSPARENT SHOWER GEL WITHOUT TYPICAL FRAGRANCE Ingredients Quantity [% by weight] Deionized water 52.40 Tetrasodium EDTA (1) 0.10 Sodium benzoate 0.50 Propylene glycol 2.00 C12-15 Sodium pareth sulfate (2) 35.00 Cocamidopropyl betaine (3) 8.00 Polyquaternium-7 (4) 0.20 Citric acid (40% aqueous solution) 1.00 Sodium chloride 0.80 (1) EDETA Powder B; origin: BASF (2) Zetesol AO 328 U; origin: Zschimmer & Schwarz (3) Tego Betain F 50; origin: Goldschmidt (4) Merquat® 550; origin: Lubrizol EXAMPLE 11 Preparation of milky bath gel formulations that INCLUDES A COMPOUND OF FORMULA (I) OF THE INVENTION

[00201] A typical fragrance-free milky shower gel formulation is listed in Petition 870220074448, dated 08 / 18 / 2022, pp. 71 / 85 63 / 71 Table 10. A perfumed milky shower gel is prepared by adding, under gentle stirring, a perfumed oil (as described, for example, in Example 5, 0.1 to 1.5% by weight relative to the total weight of the milky shower gel) and at least one of the compounds of formula (I) of the invention (0.05 to 0.50% by weight relative to the total weight of the milky shower gel) to the unscented milky shower gel formulation of Table 10. TABLE 10: COMPOSITION OF A TYPICAL UNSCENTED FORMULATION OF MILKY SHOWER GEL. Ingredients Quantity [% by weight] Deionized water 50.95 Tetrasodium EDTA (1) 0.05 Sodium benzoate 0.50 Glycerin (86% aqueous solution) 3.50 Sodium laureth sulfate (2) 27.00 Polyquaternium-7 (3) 1.00 Coco-betaine (4) 6.00 PEG-120 Methylglucose Triolate (5) 1.00 Citric acid (40% aqueous solution) 1.00 Glycol distearate and laureth-4 and cocamidopropyl betaine (6) 3.00 Sodium chloride (20% aqueous solution) 5.00 PEG-40 hydrogenated castor oil (7) 1.00 (1) EDETA® Powder; origin: BASF (2) Texapon® NSO IS; origin: Cognis (3) Merquat® 550; origin: Lubrizol (4) Dehyton® AB-30; origin: Cognis Petition 870220074448, dated 08 / 18 / 2022, pp. 72 / 85 64 / 71 (5) Glucamate® LT; origin: Lubrizol (6) Euperlan® PK 3000 AM; origin: Cognis (7) Cremophor® RH 40; origin: BASF EXAMPLE 12 PREPARATION OF ANHYDROUS ANTIPERSPIRANT SPRAY FORMULATIONS COMPRISING A COMPOUND OF FORMULA (I) OF THE INVENTION

[00202] A typical formulation of an unscented anhydrous antiperspirant spray is listed in Table 11. The anhydrous antiperspirant spray formulation is prepared using a high-speed shaker. Silica and Quaternium-18hectorite are added to the mixture of isopropyl myristate and cyclomethicone. After complete expansion, aluminum chlorohydrate is added in portions while shaking until the mixture becomes homogeneous and free of lumps. TABLE 11: COMPOSITION OF A TYPICAL UNSCENTED ANHYDROUS ANTIPERSPIRANT SPRAY. Ingredients Quantity [% by weight] Cyclomethicone(1) 53.51 Isopropyl myristate 9.04 Silica (2) 1.03 Quaternium-18-hectorite (3) 3.36 Aluminum chlorohydrate (4) 33.06 (1) Dow Corning® Fluid 345; origin: Dow Corning (2) Aerosil® 200; origin: Evonik (3) Bentone® 38; origin: Elementis Specialities (4) Micro Dry Ultrafine; origin: Reheis

[00203] Next, the perfumed formulation is obtained by adding a perfumed oil (as described, for example, in Example 5, 0.85% by weight relative to the total weight of the antiperspirant spray formulation) and at least one Petition 870220074448, dated 08 / 18 / 2022, pp. 73 / 85 65 / 71 of the compounds in formula (I) of the invention (0.15% by weight relative to the total weight of the antiperspirant spray formulation) in the fragrance-free antiperspirant spray formulation of Table 11. EXAMPLE 13 PREPARATION OF DEODORANT SPRAY EMULSION FORMULATIONS COMPRISING A COMPOUND OF FORMULA (I) OF THE INVENTION

[00204] A typical deodorant spray emulsion formulation is prepared by mixing and dissolving all the ingredients according to the sequence in Table 12. Then, a perfumed oil (as described, for example, in Example 5, 1.35% by weight relative to the total weight of the deodorant spray formulation) and at least one of the compounds of formula (I) of the invention (0.10 to 0.20% by weight relative to the total weight of the deodorant spray formulation) are added under gentle stirring. Then, the aerosol cans can be loaded, and the propellant is pressure-closed and added. Aerosol loading: 40% active solution, 60% propane / butane (2.5 bar). TABLE 12: COMPOSITION OF A TYPICAL FORMULATION OF UNSCENTED DEODORANT SPRAY. Ingredients Quantity [% by weight] Ethanol (95%) 90.65 Triclosan (1) 0.26 Isopropyl myristate 9.09 (1) Irgasan® DP 300; origin: BASF EXAMPLE 14 PREPARATION OF STICKY DEODORANT FORMULATIONS COMPRISING A COMPOUND OF FORMULA (I) OF THE INVENTION

[00205] A typical sticky, unscented deodorant formulation is listed in Table 13. The sticky deodorant formulation is obtained by weighing all the components of Part A and heating to 70-75 °C. Ceteareth-25 is added after the Petition 870220074448, dated 08 / 18 / 2022, pp. 74 / 85 66 / 71 other ingredients of Part A to be mixed and heated. After the Ceteareth-25 is dissolved, stearic acid is added. Part B is prepared by dissolving Triclosan in 1,2-propylene glycol. The evaporated water is compensated for. Then, Part B is slowly poured and mixed into Part A. TABLE 13: COMPOSITION OF A TYPICAL STICKY UNSCENTED DEODORANT FORMULATION. Phase Ingredients Quantity [% by weight] A Stearic acid 5.05 1,2-Propylene glycol 41.87 Sodium hydroxide (20% aqueous solution) 4.24 Water 30.30 Tetrasodium EDTA (1) 0.10 Ceteareth-25 (2) 1.52 PPG-3 myristyl ether (3) 1.52 B 1,2-Propylene glycol 15.14 Triclosan (4) 0.25 (1) Edeta® B Power; origin: BASF (2) Cremophor® A25; origin: BASF (3) Tegosoft® APM; origin: Evonik (4) Irgasan® DP 300; origin: BASF

[00206] Next, the sticky scented deodorant formulation is obtained by adding perfumed oil (as described, for example, in Example 5, 0.85% by weight relative to the total weight of the sticky deodorant formulation) and at least one of the compounds of formula (I) of the invention (0.10 to 0.20% by weight relative to the total weight of the sticky deodorant formulation) under gentle stirring. For storage, a plastic bag is placed in the bucket to be Petition 870220074448, dated 08 / 18 / 2022, pages 75 / 85 67 / 71 sealed after cooling. The molds were loaded at approximately 70 °C. EXAMPLE 15 PREPARATION OF FORMULATIONS FOR ROLL-ON TYPE DEODORANT COMPRISING A COMPOUND OF FORMULA (I) OF THE INVENTION

[00207] A typical formulation for unscented roll-on deodorant is listed in Table 14. Part A is prepared by gradually sprinkling hydroxyethylcellulose into water while rapidly shaking with a turbine until the hydroxyethylcellulose has fully expanded, yielding a clear gel. Part B is slowly poured into Part A while continuing to shake until the entire mixture becomes homogeneous. Then, Part C is added. TABLE 14: THE COMPOSITION OF A TYPICAL FORMULATION FOR UNSCENTED ROLL-ON DEODORANT. Phase Ingredients Quantity [% by weight] A Water 50.51 Hydroxyethylcellulose (1) 0.71 B Ethanol (95%) 40.40 1,2-Propylene glycol 5.05 Triclosan (2) 0.30 C PEG-40 hydrogenated castor oil (3) 3.03 (1) Natrosol® 250 H; origin: Ashland (2) Irgasan® DP 300; origin: BASF (3) Cremophor® RH 40; origin: BASF

[00208] Next, a roll-on deodorant formulation is obtained by adding perfumed oil (as described, for example, in Example 5, 0.85% by weight relative to the total weight of the sticky deodorant formulation) and at least one of the compounds of formula (I) of the invention (0.10-0.20% by weight in Petition 870220074448, dated 08 / 18 / 2022, pp. 76 / 85 68 / 71 in relation to the total weight of the sticky deodorant formulation) under gentle agitation. EXAMPLE 16 PREPARATION OF O / W EMULSIONS BASED ON DAY CREAM COMPRISING A COMPOUND OF FORMULA (I) OF THE INVENTION

[00209] A typical O / W emulsion formulation based on day cream comprising a compound of formula (I) of the invention is listed in Table 15. Phases A and B are heated separately to 70-75 °C, then Phase A is added to Phase B, and vacuum is applied. The mixture is shaken and rapidly cooled to 55 °C for 15 minutes. After cooling to room temperature, phenoxyethanol (and) piroctone olamine (Part C) are added when a temperature of 45 °C is reached. The mixture is shaken for 5 minutes before sodium carbomer (Part D), a perfumed oil (as described, for example, in Example 5) and at least one of the compounds of formula (I) of the invention (Part E) are added. The mixture is shaken for 3 minutes, then stirring is stopped for 15 minutes. When the mixture reaches 30°C, stirring is resumed for another 15 minutes until the cream is smooth, glossy, and free of lumps.If necessary, the pH is adjusted to 6.70-7.20 with Glydant®, Phenoni® or Nipaguard® PO5 or to 6.30-7.00 with Nikkoguard®. TABLE 15: COMPOSITION OF A TYPICAL DAY CREAM-BASED O / W EMULSION. Phase Ingredients Quantity [% by weight] Steareth-2 (and) PEG-8 distearate (1) 5.0 Cetyl alcohol 0.5 Ceteth-20 (and) Glyceryl stearate (and) PEG6 stearate (and) Steareth-20 (2) 4.0 Squalane (3) 1.0 Paraffin oil (4) 2.0 Petition 870220074448, dated 08 / 18 / 2022, pp. 77 / 85 69 / 71 Petrolatum (5) 5.5 B Deionized water 75.9 Propylene glycol 5.0 C Phenoxyethanol (e) Piroctone olamine (6) 0.6 D Sodium carbomer (7) 0.2 E Perfume oil (as in Example 5) 0.15 Compound of formula (I) 0.15 (1) Arlacel® 985; origin: Croda (2) Tefose® 2561; origin: Gattefossé (3) Biolip P 90; origin: Gattefossé (4) Mineral oil 30-40 CPS (5) Vaseline (6) Nipaguard® PO 5; origin: Clariant (7) PNC 400 EXAMPLE 17 PREPARATION OF LIQUID DETERGENT FORMULATIONS COMPRISING A COMPOUND OF FORMULA (I) OF THE INVENTION

[00210] A typical liquid detergent formulation is prepared by mixing the ingredients listed in Table 16. Then, a perfumed oil (as described, for example, in Example 5, 0.3 to 0.8% by weight relative to the total weight of the liquid detergent) and at least one of the compounds of formula (I) of the invention (0.05 to 1.0% by weight relative to the total weight of the liquid detergent) are added under gentle stirring to the unscented liquid detergent formulation of Table 16. TABLE 16: COMPOSITION OF A TYPICAL UNSCENTED LIQUID DETERGENT FORMULATION. Ingredients Quantity [%) Petition 870220074448, dated 08 / 18 / 2022, pp. 78 / 85 70 / 71 [by weight] Sodium sulfonate C14-17 alkyl sec.(1) 7.0 Fatty acids, C12-18 and C18 unsaturated (2) 7.5 Polyglycol ether of C12 / 14 fatty alcohol with EO at 7 mol (3) 17.0 Triethanolamine 7.5 Propylene glycol 11.0 Citric acid 6.5 Potassium hydroxide 9.5 Properase® L (4) 0.2 Puradax® EG L(4) 0.2 Purastar® ST L(4) 0.2 Methacrylate structuring crosspolymer Acrylates / Steareth- 20 (5) 6.0 Deionized water 27.4 (1) Hostapur® SAS 60; origin: Clariant (2) Edenor® K 12-18; origin: Cognis (3) Genapol® LA 070; origin: Clariant (4) Origin: Genencor International (5) Aculyn® 88; origin: Dow Chemicals EXAMPLE 18 PREPARATION OF HANDMADE DISHWASHING FORMULATIONS COMPRISING THE COMPOUND OF FORMULA (I) OF THE INVENTION

[00211] A typical fragrance-free hand dishwashing formulation is listed in Table 17. Fragrance-free hand dishwashing is prepared by mixing water with sodium hydroxide and diethanolamide. Then, linear alkylbenzene sulfonic acid is added. After neutralization, the ingredients Petition 870220074448, dated 08 / 18 / 2022, pp. 79 / 85 The remaining 71 / 71 are added, and the pH is adjusted to 7-8 if necessary. TABLE 17: COMPOSITION OF A TYPICAL UNSCENTED HAND DISHWASH FORMULATION. Ingredients Quantity [% by weight] Linear alkylbenzenesulfonic acid(1) 20.0 Diethanolamide (2) 3.5 Sodium hydroxide (50%)(3) 3.4 Secondary alcohol ethoxate (4) 2.5 Sodium xylene sulfonate 6.3 Deionized water 64.3 (1) Biosoft® S-118; origin: Stepan (2) Ninol® 40-CO; origin: Stepan (3) Stepanate® SXS; origin: Stepan (4) Tergitol® 15-S-9; origin: Dow Chemicals

[00212] Thus, the perfumed hand dishwashing formulation is obtained by adding perfumed oil (as described, for example, in Example 5, 0.85% by weight relative to the total weight of the hand dishwashing formulation) and at least one of the compounds of formula (I) of the invention (0.10 to 0.20% by weight relative to the total weight of the dishwashing formulation) under gentle stirring to the unscented hand dishwashing formulation of Table 17.

Claims

1. A compound of formula in the form of any one of its stereoisomers or a mixture thereof, characterized in that n is 1, 2, 3 or 4; the dashed line represents a single or double bond, X is an oxygen atom or an NR group wherein R is a hydrogen atom, a C1 to C4 alkyl group, a phenyl group or a benzyl group, R1 is a hydrogen atom or a C1 to C4 hydrocarbon group comprising optionally 1 to 5 oxygen atoms and / or a sulfur atom and / or one, two or three nitrogen atoms; R2 and R2' are, independently of each other, a hydrogen atom, a C1 to C4 alkyl group or a CHR1XH group or R2 and R2' form, when taken together, a carbonyl group; R3 is a hydrogen atom, a C1 to C4 alkyl group, a phenyl group or a benzyl group; R4 being a hydrogen atom, a COOR' group, or a C1-3 alkyl group optionally substituted by a COOR' group wherein R' is a C1-3 alkyl group;R5 being, independently of each other, a hydrogen atom or a methyl group; or R and R1 forming, when taken together, a C4-6 azocycloalkyl group; or R1 and R2 forming, when taken together, a C5-6 cycloalkyl group; or, R2 and R3 forming, when taken together, a group of formula Petition 870220074448, dated 08 / 18 / 2022, p. 81 / 85 2 / 4 in which the bold line is connected to the carbon atom of R2 and the dashed line is connected to the nitrogen atom of R3; provided that 1,3-dibenzyl-2'-petylocta-hydrospiro[benzo[d]imidazol-2,1'-cyclopentane] is excluded.

2. Compound according to claim 1, characterized in that R3 is a hydrogen atom, a methyl group or an ethyl group; preferably, R3 is a hydrogen atom.

3. Compound according to claim 1 or 2, characterized in that n is 2, 3 or 4 and wherein R4 and R5 are hydrogen atoms.

4. Compound according to any one of claims 1 to 3, characterized in that X is an NR group wherein R is a hydrogen atom, a methyl group or an ethyl group, or R and R1 are obtained together to form a C4-6 azocycloalkyl group.

5. A compound according to any one of claims 1 and 4, characterized in that n is 3, and the dashed line is a double bond.

6. A compound according to any one of claims 1 to 5, characterized in that R2 is a methyl group or an ethyl group, and R2' is a hydroxymethyl group, or R2 and R2' are taken together and form a carbonyl group.

7. Compound, according to any one of claims 1 to 6, characterized in that R1 is a hydrogen atom or a residue derived from an amino acid of the formula R1CH(NH2)COOH and, specifically, from a natural α-amino acid, such as S-alanine, S-arginine, S-asparagine, R-cysteine, S-glutamine, glycine, shistidine, S-isoleucine, S-leucine, S-lysine, S-methionine, S-phenylalanine, S-serine, streonine, S-tryptophan, S-tyrosine, S-valine, S-aspartic acid and S-glutamic acid or Petition 870220074448, dated 08 / 18 / 2022, p. 82 / 85 3 / 4 of an artificial α-amino acid selected from the group of norleucine, norvaline, 2-phenylglycine, ornithine, homoalanine, homocysteine ​​and homoserine.

8. Compound according to any one of claims 1 to 6, characterized in that R and R1 are taken together and form a C4-5 azocycloalkyl group.

9. Use of a compound of formula (I), of the type defined in any one of claims 1 to 8, characterized in that it is used as a fragrance ingredient to provide a long-lasting odor imparted by cyclopentanone-derived fragrance ingredients to the environment.

10. Method for imparting, intensifying, enhancing or modifying the odor properties of a perfume composition or perfumed article, the method characterized by comprising adding to said composition or article an effective amount of at least one compound of formula (I), of the type defined in any one of claims 1 to 8.

11. Perfume composition characterized by comprising: i) as a perfume ingredient, at least one compound of formula (I), of the type defined in any one of claims 1 to 8; ii) at least one ingredient selected from the group consisting of a perfume carrier and a perfume base; and iii) optionally at least one perfume adjuvant.

12. Perfumed consumer product characterized by comprising, as a perfume ingredient, at least one compound of formula (I), of the type defined in any of claims 1 to 8, or a perfume composition, of the type defined in claim 11.

13. Perfumed consumer product, according to claim 12, characterized in that the perfumed consumer product is a perfume, a fabric care product, a body care product, an air care product or a household care product.

14. Perfumed consumer product, according to claim 13, characterized in that the perfumed consumer product is a fine perfume, a liquid or solid detergent, a fabric softener, a fabric deodorizer, ironing water, a shampoo, a coloring preparation, a hairspray, a deodorant or antiperspirant, a perfumed soap, a bath mousse for use in a bath or tub, an oil or gel, a hygiene product, an air freshener, a ready-to-use powdered air freshener, or a hard surface detergent.

15. Method for imparting a lasting or consistent odor imparted by cyclopentanone-derived perfumery ingredients to the environment or to surfaces, such as hard surfaces, fabrics, skin or hair, characterized by adding at least one compound of formula (I), of the type defined in any of claims 1 to 8, to the perfumery composition or perfumed articles and applying the same to the corresponding desired environment or surface.