Dibenzoylmethane compounds as photochemical precursors of ultraviolet absorbers.

Description

1 / 27 “DIBENZOYLMETHANE COMPOUNDS AS PHOTOCHEMICAL PRECURSORS OF ULTRAVIOLET ABSORBERS

[0001] This request claims the benefit of European Patent Application EP23382293 filed on March 28, 2023. Technical field

[0002] This invention relates to photochemical precursors of ultraviolet absorbers, especially to some dibenzoylmethane compounds, as well as to the process of preparation and uses thereof. Background

[0003] The invisible ultraviolet A rays (UVA, Light (320-400 nm) and ultraviolet B (UVB, 290-320 nm) rays emitted by the sun can cause both immediate and long-term skin damage. Examples include sunburn, rashes, cell and tissue damage, and skin cancer. Growing awareness of these risks has led to a shift in tanning habits. This includes clothing, hats, sunglasses, sunscreens, and other forms of sun protection.

[0004] Sunscreen is any substance or material that protects the skin from ultraviolet rays. Sunscreens are generally sold in the form of sprays, creams, topical lotions, ointments, and gels.

[0005] Several benzoic acid esters have been described as photochemical precursors of ultraviolet absorbers. Their photoprotective activity is due to the fact that they are susceptible to being photochemically converted into Petition 870250087335, dated 09 / 26 / 2025, page 16 / 57 2 / 27 situ in a sunscreen compound with UV protection capability.

[0006] The paper by Adaya Gallardo and colleagues, “Dose-dependent progressive sunscreens. A new strategy for photoprotection?”, Photochemical & Photobiological Sciences, 2010, vol. 9, pp. 530-534 reveals that benzophenones absorb UV-B and UVA-II radiation, while dibenzoylmethanes absorb UV-A radiation, thus preventing its penetration into the skin.

[0007] Benzophenones and dibenzoylmethanes play a prominent role in UV filters currently approved for use in cosmetics. These families share an aromatic beta-hydrocarbonyl group in their structure, which is an essential component for their sun protection action.

[0008] Avobenzone, dioxybenzone, oxybenzone, sulisobenzone are some widely used sunscreen compounds.

[0009] When radiation is absorbed, a phototautomerization is triggered, forming an unstable enol that releases the absorbed radiation as heat. Each molecule participates in several cycles before being degraded.

[00010] Photostability can be defined as the response of a molecule to exposure to sunlight, UV light, and visible light. This can vary depending on the solvent or vehicle used.

[00011] Avobenzone is one of the most widely used filters. It offers protection across a broad range of the UV-A spectrum, including UVA-I. Unfortunately, concerns have arisen regarding its photostability and its ability to degrade other sunscreen ingredients. Petition 870250087335, dated 09 / 26 / 2025, page 17 / 57 3 / 27

[00012] The precursor of avobenzone, preavobenzone, is one of the most commonly used molecules. However, preavobenzone needs more than 20 minutes to achieve complete photoconversion. Therefore, it is desirable to discover new sunscreen compounds that achieve complete photoconversion more quickly. Summary of the Invention

[00013] The inventors discovered that dibenzoylmethane compounds with an amide group on one of the rings exhibit enhanced photoconversion compared to 1-(4-methoxyphenyl)vinyl 4-(tert-butyl)benzoate (preavobenzone).

[00014] One aspect of the present invention relates to a compound of formula (I), a pharmaceutically or cosmetically acceptable salt thereof, or a stereoisomer of either or mixtures thereof. or alternatively, Petition 870250087335, dated 09 / 26 / 2025, p. 18 / 57 4 / 27 where in compound (I), R' is selected from the group consisting of H; (alkyl (C1-C1e), and cycloalkyl (C1-C1e); R1, R2, R4, Rs, Re, Rs, Rs, and R1o are radicals independently selected from the group consisting of H, hydroxy, amino, (alkyl (C1-C1e), alkoxy (C1-C1e), alkylamino (C1-C1e), and alkylamino (C1-C1e); Rs is (alkyl (C1-C1e); and Rs is selected from the group consisting of (alkyl (C1-C1e), alkoxy (C1-C1e), hydroxy, amino, alkylamino (C1-C1e), and alkylamino (C1-C1e); and in compound (!'), R1 and R2 are radicals independently selected from the group consisting of H, amino, (alkyl (C1-C1e), alkoxy (C1-C1e), alkylamino (Ci-Ce), and alkylamino (Ci-Ce); R', R2, R4, Rs, Rs, Rg, Rio, Rs, and Rs are as defined in compound (I).

[00015] Another aspect of the present invention relates to a compound (I) or a compound (I') as defined above, for use in protecting a living human or animal body, or a material, against ultraviolet radiation.

[00016] Another aspect of the present invention relates to a method for protecting a material from ultraviolet radiation comprising treating the material with a compound (I) or a compound (I') as defined above.

[00017] Another aspect of the present invention relates to a composition selected from a cosmetic composition, a pharmaceutical composition and a composition for Petition 870250087335, dated 09 / 26 / 2025, page 19 / 57 5 / 27 personal care, comprising an amount effective for the protection of a human or animal body against ultraviolet radiation, of a compound as defined above, together with one or more pharmaceutically or cosmetically acceptable excipients or vehicles; or, alternatively, a composition comprising at least an amount effective for the protection of a material against ultraviolet radiation, of a compound as defined above, together with appropriate vehicles.

[00018] Another aspect of the present invention relates to a process for preparing a compound (I) or a compound (I') as defined above, wherein: when the compound is the compound of formula (I), the process comprises a reaction step of a compound of formula (Ia), or an appropriate salt thereof, with an acyl halide (Ci-Ce), in the presence of an appropriate solvent and an appropriate base; wherein in compound (Ia), R', R1-R10 are as defined in compound (I), and Rsa' is NH2; and wherein when the compound is the compound of formula (I'), the process comprises irradiating the compound of formula (I) with UV light to produce the compound of formula (I'). R' Rs 1 O R-| r7JL JL á. r2 XX0XX 8 ] ^10 ^5 |K3a R& (There is)

[00019] Finally, another aspect of the present invention relates to a compound of formula (II), a salt Petition 870250087335, dated 09 / 26 / 2025, p. 20 / 57 6 / 27 pharmaceutically or cosmetically acceptable thereof, or a stereoisomer of any of them or mixtures thereof, wherein: in compound (II), R' is selected from the group consisting of H; alkyl (C1-Ce) and cycloalkyl (C1-Ce); Ri, Rg, R4, Rs, Re, Ri, Rg, and Rio are a radical independently selected from the group consisting of H, hydroxy, amino, (alkyl (C1-Ce), alkoxy (C1-Ce), alkylamino (C1-Ce), and alkylamino (C1-Ce); Rs' is amino or nitro; and Rs is selected from the group consisting of (alkyl (C1-Ce), alkoxy (C1-Ce), hydroxy, amino, alkylamino (C1-Ce), and dialkylamino (C1-Ce), Brief Description of the Drawings

[00020] Figures a) and b) are UV-Vis spectra showing the absorption changes of a Preavobenzone (PvB 360) (a) and 1-(4-methoxyphenyl)vinyl 4-acetamidobenzoate (PVB-1) (b) when a 3x10⁻⁵M solution in MeOH is irradiated at 312 nm.

[00021] Figure 2 shows the SPF and UVA-FP of PvB 360 (Preavobenzone, comparative compound) and PVB-1 (compound of the present invention) at different irradiation times. (PVB-1) corresponds to compound (I) where, R' is H, Ri, Rg, R4, Rs, Re, R7, Rg, and Rio are H; Rg is methyl; and Rs is methoxyl. Petition 870250087335, dated 09 / 26 / 2025, p. 21 / 57 7 / 27

[00022] For the purposes of the invention, any ranges provided include the lower and upper endpoints of the range. Ranges provided, such as temperatures, times, sizes and the like, should be considered approximate unless specifically stated.

[00023] The term “ambient temperature”, as disclosed in this document, refers to ambient temperature, without heating or cooling, and generally comprises 20 to 25°C.

[00024] The terms “alkyl (Ci-Co)”, “alkoxy (Ci-Co)”, “alkylamino (Ci-Co)” and “dialkylamino (Ci-Co)” should be interpreted as linear or branched chains.

[00025] The term “pharmaceutically or cosmetically acceptable salts” used in this document covers any salt formed from non-toxic, pharmaceutically or cosmetically acceptable acids, including inorganic or organic acids. There is no limitation as to the salts, except that if used for therapeutic purposes, they must be pharmaceutically or cosmetically acceptable.

[00026] Since some of the compounds in formula (I) are basic compounds, salts can be prepared from pharmaceutically acceptable non-toxic acids, including inorganic and organic acids. Such acids include, for example, acetic, benzenesulfonic, benzoic, camphorsulfonic, citric, ethanesulfonic, fumaric, gluconic, glutamic, hydrobromic, hydrochloric, lactic, maleic, malic, malonic, mandelic, methanesulfonic, phosphoric, succinic, sulfuric, nitric, adipic, aspartic, Petition 870250087335, dated 09 / 26 / 2025, page 22 / 57 8 / 27 1,5-naphthalenesulfonic, oxalic, pivalic, propionic, tartaric, p-toluenesulfonic acid and similar acids.

[00027] The preparation of pharmaceutically acceptable salts of compounds of formula (I), formula (I') or formula (II), including compounds of formula (IIa) or (IIb), can be carried out by methods known in the art. For example, they can be prepared from the original compound, which contains a basic fraction, by conventional chemical methods. Generally, such salts are, for example, prepared by reacting the basic form of these compounds with a stoichiometric amount of the appropriate pharmaceutically acceptable acid in water or in an organic solvent or in a mixture thereof.

[00028] The compounds of the invention may be in crystalline form, as free-solvating compounds or as solvates (e.g., hydrates), and it is intended that both forms are within the scope of the present invention. Solvation methods are generally known in the art.

[00029] The term solvate refers to a molecular complex comprising any of the compounds of formula (I), formula (I') or formula (II), including compounds of formula (IIa) or (IIb) or any of their salts, and a stoichiometric or non-stoichiometric amount of one or more solvent molecules linked by non-covalent intermolecular forces. When one or more solvent molecules that are part of the molecular complex are water, the solvate is a hydrate.

[00030] The expression "effective quantity for the protection of a living human or animal body, or of a material, against ultraviolet radiation," as used herein. Petition 870250087335, dated 09 / 26 / 2025, p. 23 / 57 9 / 27 document, refers to the amount of a compound that, when administered, is sufficient to protect against UV radiation. In the case of human or animal bodies, this means preventing skin damage. Therefore, the effective amount, as used in this document, refers to a therapeutically effective amount.

[00031] The term pharmaceutically or cosmetically acceptable excipients or vehicles refers to materials, compositions or vehicles that are pharmaceutically acceptable. Each component must be pharmaceutically or cosmetically acceptable in the sense that it is compatible with the other ingredients of the pharmaceutical or cosmetic composition. It must also be suitable for use in contact with the skin of humans and animals, without excessive toxicity, irritation, allergic response, immunogenicity or other problems or complications consistent with a reasonable benefit / risk ratio.

[00032] The term “cosmetically acceptable”, used interchangeably herein, refers to excipients or vehicles suitable for use in contact with the skin or with humans and animals, without undue toxicity, incompatibility, instability, allergic response, among others.

[00033] As mentioned above, one aspect of the present invention relates to a compound of formula (I) or formula (I'), its pharmaceutically or cosmetically acceptable salts, or its stereoisomers of either or mixtures thereof, as defined above.

[00034] In a particular embodiment, the compound of the present invention is the compound of formula (I), or a salt Petition 870250087335, dated 09 / 26 / 2025, page 24 / 57 10 / 27 pharmaceutically or cosmetically acceptable thereof, or a stereoisomer of either thereof or mixtures thereof.

[00035] In a particular embodiment, compounds of formula (I) are those in which Ri and R6 are a radical selected independently from the group consisting of H, amino, alkyl (C1-Ce), alkoxy (C1-Ce), alkylamino (C1Ce) and dialkylamino (C1-Co).

[00036] In another particular embodiment, the compounds of the present invention of formula (I) or, alternatively, of formula (I') are those in which R1, R2, R4, R5, R1, R7, R9, and R10 are H and R8 is an alkoxy (C1-C3), and R' is H. In another particular embodiment, the compounds are those in which R3 is an alkyl (C1-C3). In another particular embodiment, the compounds of the present invention are those in which in formula (I) and in formula (I'), R', R1, R2, R4, R5, R1, R7, R9, and R10 are H; R3 is methyl; and R8 is methoxy.

[00037] Also part of the invention is a compound as defined above, for use in protecting human or animal bodies against ultraviolet radiation. This aspect of the present invention can also be formulated as the use of compound (I) or (I') as defined above for the manufacture of a cosmetic composition, a pharmaceutical composition or a personal care composition for the protection of a human or live animal body against ultraviolet radiation. The present invention also relates to a method for protecting a human or animal body against ultraviolet radiation, comprising administering an amount effective for the protection of a human or animal body against ultraviolet radiation, of a compound as defined above, together with one or more Petition 870250087335, dated 09 / 26 / 2025, page 25 / 57 11 / 27 excipients or vehicles that are pharmaceutically or cosmetically acceptable. In one specific embodiment, the living body of the animal is a mammal.

[00038] The use of a compound as defined above for the protection of a human or living animal body against ultraviolet radiation is considered part of the invention. In particular, the use as defined above, wherein it comprises the photochemical conversion of the compound of formula (I) in situ into a sunscreen compound.

[00039] Also part of the invention is a method for protecting a material from ultraviolet radiation comprising treating the material with a compound (I) or a compound (I') as defined above. Generally, the method for protecting the material comprises applying an effective amount of the compound (I) or the compound (I') as defined above to protect a material from ultraviolet radiation.

[00040] The material may be selected from the group consisting of organic compounds, oils, fats, waxes, gelatins, sunscreens, polymers such as polyolefins, polyketones, polystyrene, polyvinyl chloride (PVC), polyacrylates, polymethacrylates, polyacrylamides, polyacrylonitriles, polyvinyl alcohol derivatives, polyvinyl acetate derivatives, polyurethanes, polyamides, polyesters, polyureas, polycarbonates, polysiloxanes, polyethylenes, radiation-curable compositions, resins such as hydrocarbon resins, phenol / formaldehyde resins, urea / formaldehyde resins, melamine / formaldehyde resins, unsaturated polyester resins, crosslinkable acrylic resins, crosslinked epoxy resins, Petition 870250087335, dated 09 / 26 / 2025, page 26 / 57 12 / 27 epoxy / melamine resins, varnishes, cellulose, cellulose-based paper formulations, photographic materials, photographic film paper, metal products, ceramic products, biocides, fibers, textile fabrics, dyes, printing inks, coatings, adhesives, leathers, woods, lenses, composites, mixtures or similar blends.

[00041] The term “effective amount of compound (I) or compound (I') to protect a material from ultraviolet radiation”, as used in this document, refers to the amount of a compound that, when applied to a material, is sufficient to protect it from UV radiation, i.e., an effective amount that prevents or minimizes the degradation of the material.

[00042] In a particular embodiment of the method, compound (I) or compound (I') as defined above is applied in the form of a composition further comprising suitable components selected from at least one polymer, one solvent, one additive and a mixture thereof. Examples of additives are antioxidants, preservatives, thickeners, colorants or opacifiers. In a particular embodiment of the method, the composition used in the method is an industrial composition.

[00043] In another particular embodiment, the compound of the present invention is a compound of formula (I) as defined above, wherein said compound of formula (I) is capable of being photochemically converted in situ into a sunscreen compound.

[00044] In another specific embodiment, the compound of the present invention of formula (I) or formula (I') Petition 870250087335, dated 09 / 26 / 2025, page 27 / 57 13 / 27, for use as defined above, are those whose protection is against UV-A and UV-B.

[00045] In another specific embodiment, the compound for use as defined above, are those whose protection is against UV radiation emitted by the sun.

[00046] In another particular embodiment, the compounds for use as defined above are those characterized by progressive UV protection depending on the time of sun exposure and the degree of solar radiation.

[00047] The compounds of formula (I) or formula (I') of the present invention may be in the form of a composition selected from a cosmetic composition, a pharmaceutical composition and a personal care composition, comprising an amount effective for the protection of a living human or animal body, or a material, from ultraviolet radiation, of such compounds, together with one or more pharmaceutically or cosmetically acceptable excipients or carriers.

[00048] The particular embodiments of the first aspect of the invention mentioned above are also considered embodiments of the composition of the present invention.

[00049] In one specific embodiment, the cosmetic composition, pharmaceutical composition, or personal care composition, as defined above, is one in which the effective amount of the compound of formula (I) or (I') ranges from 0.1 to 10% by weight, based on the total weight of the composition. In another specific embodiment, the cosmetic composition, pharmaceutical composition, or personal care composition, as defined above, is one in which the effective amount of the compound of Petition 870250087335, dated 09 / 26 / 2025, page 28 / 57 14 / 27 formula (I) or (I') varies from 0.5 to 8% by weight, based on the total weight of the composition. In another specific embodiment, the cosmetic composition, the pharmaceutical composition or the personal care composition are those in which the effective amount of the compound of formula (I) or (I') varies from 1 to 6% by weight based on the total weight of the composition.

[00050] In another specific embodiment, the compositions of the present invention are those comprising an effective amount of a dibenzoylmethane compound of formula (I), a pharmaceutically or cosmetically acceptable salt thereof, or a stereoisomer of either or mixtures thereof, wherein the composition has enhanced photoconversion.

[00051] In another specific embodiment, the compounds of the present invention can also be used to form a photostable composition. Such photostable compositions may further include a variety of other components known in the art, including triazines, benzotriazoles, hindered amine light stabilizers, radical scavengers, antioxidants and the like.

[00052] The composition of the present invention is intended for topical administration. In a specific embodiment, the cosmetic composition, the pharmaceutical composition or the personal care composition, as defined above, are those in which the composition is selected from the group consisting of creams, ointments, oils, lotions, gels, sticks, foams, milks, suspensions, powders, emulsions, dispersions, sprays, aerosols, lipsticks, foundations, makeup, loose or pressed powders, eye blushes, eye shadows, mascara, nail polishes, lacquers Petition 870250087335, dated 09 / 26 / 2025, page 29 / 57 15 / 27 for nails and non-permanent hair dye composition.

[00053] In another specific embodiment, the compositions of the present invention may contain one or more additional organic sunscreens in order to filter UV-A or UV-B.

[00054] In another specific embodiment, the composition is a sunscreen composition. In another specific embodiment, the sunscreen composition may have a sun protection factor (SPF) equal to or greater than 6, preferably equal to or greater than 30, more preferably equal to or greater than 50. Preferably, the sunscreen composition comprises physical filters, chemical filters, or combinations thereof.

[00055] Excipients or vehicles suitable for the composition of the present invention are, for example, dispersing agents, preservatives, antifoaming agents, perfumes, fragrances, oils, waxes, propellants, dyes, pigments, emulsifiers, surfactants, thickeners, humectants, exfoliants and emollients.

[00056] The topical compositions of the present invention can be produced by conventional processes known in the art, such as by mixing the different components of the composition in any order. The appropriate excipients and / or carriers, and their quantities, can be easily determined by those skilled in the art according to the type of composition being prepared.

[00057] Part of the invention is a composition comprising at least an amount effective for protection. Petition 870250087335, dated 09 / 26 / 2025, page 30 / 57 16 / 27 of a material that protects against ultraviolet radiation, of a compound as defined above, together with appropriate components selected from at least one polymer, one solvent, one additive and a mixture thereof. Examples of additives are antioxidants, preservatives, thickeners, colorants or opacifiers. The composition may be an industrial composition comprising the compound as defined above.

[00058] In one specific embodiment, the composition for protecting a material against ultraviolet radiation, as defined above, is one in which the effective amount of the compound of formula (I) or (I') varies from 0.1 to 10% by weight based on the total weight of the composition. In another specific embodiment, the composition as defined above is one in which the effective amount of the compound of formula (I) or (I') varies from 0.5 to 8% by weight based on the total weight of the composition. In yet another specific embodiment, the composition is one in which the effective amount of the compound of formula (I) or (I') varies from 1 to 6% by weight based on the total weight of the composition.

[00059] The compounds of formula (I) of the present invention can be prepared by a process comprising a reaction step of a compound of formula (IIa) or an appropriate salt thereof; with an acyl halide (C1-C12), such as acetyl chloride, or an acid anhydride (C2-C12), such as acetic anhydride, in the presence of an appropriate solvent and an appropriate base; wherein in the compound of formula (IIa), R', R1-R10 are as defined in compound (I) and R3a' is NH2; Petition 870250087335, dated 09 / 26 / 2025, p. 31 / 57 17 / 27

[00060] In a particular embodiment of the process, the appropriate solvent for the preceding step is selected from the group consisting of aromatic hydrocarbons (Ce-Cs), such as toluene or xylene, or chlorine-containing solvents (CiC3), such as dichloromethane or dichloroethane. In another particular embodiment of the process, the appropriate base is a tertiary amine, such as triethylamine alone or with 4-dimethylaminopyridine, or N,N-diisopropylethylamine. This step of the process is generally carried out at a temperature in the range of -20°C to 0°C.

[00061] In another specific embodiment, the process, as defined above, further comprises a prior step comprising subjecting a compound of formula (IIb) to a reduction reaction to produce a compound of formula (IIa) as defined above, wherein, in the compound of formula (IIb), R', Ri-RlO are as defined in compound (I) and Rab' is NO2. Petition 870250087335, dated 09 / 26 / 2025, page 32 / 57 18 / 27

[00062] The reduction reaction can be carried out with a reducing agent, such as an oxidized metal, in the presence of an acid. Examples of suitable metals are, for example, Fe, Sn, or Zn. Examples of suitable acids are, for example, hydrochloric acid or acetic acid. In one particular embodiment, the metal is zinc. In another particular embodiment of the process, this step is carried out in the presence of a suitable solvent, which may be a chlorine-containing (C1-C3) solvent, such as chloroform or dichloromethane. In another particular embodiment, the preferred ratio of solvent to chlorine-containing (C1-C3) acid is 11:1.5 or 7:0.5, respectively. This step of the process is generally carried out at a temperature in the range of -20°C to 0°C.

[00063] In another specific embodiment, the process of the present invention, as defined above, further comprises a prior step comprising subjecting a compound of formula (III) to an elimination reaction to produce a compound of formula (Ilb), wherein, in compound (III), X is a halide, R1-R10 are as defined in compound (I) and Rsb' is NO2, Petition 870250087335, dated 09 / 26 / 2025, page 33 / 57 19 / 27

[00064] In a particular embodiment, X is a halogen selected from the group consisting of Br, Cl and I. In a particular embodiment of the process, the compound of formula (III) is that in which X is bromine.

[00065] The compound of formula (III) can be prepared from 2-halo-l-(4-methoxyphenyl)ethan-l-one. The term halo means any of the following: Cl, Br, and I. The compound can be subjected to a reduction reaction with a reducing agent, such as NaBH4, in the presence of a suitable solvent. Generally, the reaction is carried out at low temperatures, such as (-20 °C)-10 °C. The solvent can be a (C1-C4) alcohol, such as methanol, to produce 2-halo-l-(4-methoxyphenyl)ethan-l-ol. The compound thus obtained can react with a p-nitrobenzoyl halide, such as p-nitrobenzoyl chloride, in the presence of a suitable solvent and a suitable base. An example of a suitable solvent is tetrahydrofuran. Examples of suitable bases are tertiary amines, such as triethylamine, alone or with 4-dimethylaminopyridine. Petition 870250087335, dated 09 / 26 / 2025, page 34 / 57 20 / 27

[00066] In compounds of formula (III), formula (IV) and formula (V), Ri-Rio are as defined in compound (I), X is a halogen selected from the group consisting of Br, Cl and I, and Rab' is NO2.

[00067] The compounds of formula (I') of the present invention can be prepared by a process comprising irradiating the compound of formula (I) with UV light to produce the compound of formula (I') of the present invention. Compounds of formula (IIa) and (IIb) are also part of the invention. They may also be in the form of a pharmaceutically or cosmetically acceptable salt, or a stereoisomer, or any one of them or mixtures thereof.

[00068] The salts of the compound of formula (IIa) or (IIb) refer to non-toxic salts. As some of the compounds of formula (IIa) or (IIb) are basic compounds, the salts can be prepared with pharmaceutically or cosmetically acceptable non-toxic acids.

[00069] Throughout the description and claims, the word includes and variations of the word are not intended to exclude other characteristics. Petition 870250087335, dated 09 / 26 / 2025, page 35 / 57 21 / 27 techniques, additives, components or steps. Furthermore, the word "comprise" includes the case of "consist of". Additional objects, advantages and features of the invention will become apparent to those skilled in the art by examining the description or can be learned by practicing the invention. The following examples and drawings are provided for illustrative purposes only and are not intended to be limiting of the present invention. Furthermore, the present invention encompasses all possible combinations of particular and preferred embodiments described herein. Examples Example 1: Preparation of 2-bromo-1-(4-methoxyphenyl)ethan-1-ol

[00070] In a 100 mL round-bottom flask, 3 g of BMAP (13.2 mmol, 1 eq.) were dissolved in 60 mL of MeOH. Then, 1 g of NaBH4 (26.4 mmol, 8 eq.) was added in portions at -10°C (ice-salt bath). The solution was stirred at this temperature for 1 h (until completion by TLC). Then, 100 mL of DCM and 150 mL of 1 M aqueous HCl were added. The resulting mixture was stirred at 0°C for 30 min. The organic phase was decanted and the aqueous phase was extracted twice with DCM. The organic phases were combined, washed with brine, and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to yield the product as a colorless oil (2.86 g, 94% yield). Example 2: Preparation of 2-bromo-1-(4-methoxyphenyl)ethyl 4-nitrobenzoate Petition 870250087335, dated 09 / 26 / 2025, page 36 / 57 22 / 27

[00071] 2-bromo-1-(4-methoxyphenyl)ethan-1-ol (2.5 g, 10.82 mmol, 1 eq.) was dissolved in 50 mL of dry THF under an inert N2 atmosphere. The mixture was then cooled to 0°C (ice bath) and 2.26 mL of NEt3 (16.23 mmol, 1.5 eq.) was added. Finally, using an addition funnel, a solution of 4 g of p-NBCl (21.64 mmol, 2.0 eq.) in 7 mL of dry THF was added dropwise. After stirring at 0°C for 10 min., the mixture was stirred at room temperature for 7 h, after which complete conversion of the starting material was observed by 1H NMR. Next, the volatiles were partially evaporated under reduced pressure and the crude mixture was washed with a saturated aqueous solution of NaHCO2. The resulting organic phase was dried over anhydrous Na2SO4 and the solvent evaporated under reduced pressure. The product was purified by silica gel column chromatography using hexanes / DCM (7:3 to 6:4) as the mobile phase to yield the product as a yellowish oil (3.709 g, 90% yield).1H-NMR (300 MHz; Chloroform-d) δ ppm. 8.35 - 8.21 (m, 4H), 7.42 - 7.33 (m, 2H), 6.98 - 6.88 (m, 2H), 6.18 (dd, J1 = 8.5 Hz, J2 = 4.4 Hz, 1H), 3.83 (dd, J1 = 10.9 Hz, J2 = 8.5 Hz, 1H) 3.71 (dd, J1 = 10.9 Hz, J2 = 4.4 Hz, 1H).13C-NMR (75 MHz; Chloroform-d) δ ppm 163.53(1C), 160.08 (1C), 150.54 (1C), 135.12 (1C), 130.80 (2C), 129.06 (1C), 127.96 (2C), 123.51 (2C), 114.17 (2C), 76.16(1C), 55.20 (1C), 34.14(1C). Example 3: Preparation of 1-(4-methoxyphenyl)vinyl 4-nitrobenzoate

[00072] 2-bromo-1-(4-methoxyphenyl)ethyl-4-nitrobenzoate (2.14 g, 5.64 mmol, 1.0 eq.) was introduced into a three-necked round-bottom flask and dissolved. Petition 870250087335, dated 09 / 26 / 2025, p. 37 / 57 23 / 27 in 50 mL of anhydrous toluene. The mixture was then heated to reflux and 1.7 mL of DBU (11.28 mmol, 2.0 eq.) was added slowly. The mixture was stirred at reflux temperature for 1 h. The mixture was then cooled to room temperature and the reaction was stopped with 60 mL of 0.5 M aqueous HCl. The phases were separated and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with brine, and dried over anhydrous Na2SO4. The product was obtained as an orange solid (1.501 g, 90% yield) after evaporation of the solvent under reduced pressure. 1H-NMR (300 MHz; Chloroform-d) δ ppm 8.36 (s, 4H), 7.48 - 7.39 (m, 2H), 6.93 - 6.84 (m, 2H), 5.49 (d, J = 2.5 Hz, 1H), 5.09 (d, J = 2.5 Hz, 1H), 3.81 (s, 3H).13C-NMR (75 MHz; Chloroform-d) δ ppm 163.02 (1C), 160.43 (1C),152.83 (1C), 150.90 (1C), 134.92 (1C), 131.25 (2C), 126.36 (2C), 126.33 (1C), 123.79 (2C), 114.09 (2C), 100.83 (1C), 55.35 (1C). Example 4: Preparation of 1-(4-methoxyphenyl)vinyl 4-aminobenzoate

[00073] 1-(4-methoxyphenyl)vinyl 4-nitrobenzoate (507.6 mg, 1.65 mmol, 1.0 eq.) was dissolved in 50 mL of CHCl3 / acetic acid 9:1 in a 100 mL round-bottom flask. The mixture was cooled to < 0°C (ice-salt bath) and then 2.15 g of zinc (33 mmol, 20 eq.) were added in portions. The solution was stirred at < 0°C and after 20 min, TLC analysis (Hexanes / DCM, 4:6) showed that no starting material remained in the reactant mixture. Subsequently, the excess zinc was removed by filtration with Celite®. Saturated aqueous NaHCO3 (50 mL) was added to the resulting filtrate and the mixture was stirred for 15 min. Then, Petition 870250087335, dated 09 / 26 / 2025, page 38 / 57 24 / 27 The organic layer was separated and washed with more saturated aqueous NaHCO3. The aqueous phases were extracted with CHCl3. The organic phases were combined, dried over anhydrous Na2SO4, and the solvent evaporated under reduced pressure to produce the product as a brownish-yellow solid (410 mg, 92% yield). 1H-NMR (300 MHz; Chloroform-d) δ ppm 8.05 — 7.94 (m, 2H), 7.51 — 7.41 (m, 2H), 6.91 — 6.79(m, 2H), 6.74 — 6.63 (m, 2H), 5.43 (d, J = 2.0 Hz, 1H), 5.01(d, J = 2.0 Hz, 1H), 4.14 (broad s, 2H), 3.80 (s, 3H).13C-NMR (75 MHz; Chloroform-d) δ ppm 165.05 (1C), 160.19(1C), 153.17 (1C), 151.58 (1C), 132.42 (2C), 127.45 (1C), 126.47 (2C), 118.85 (1C), 114.00 (4C), 100.29 (1C), 55.42(1C). Example 5: Preparation of 1-(4-methoxyphenyl)vinyl 4-acetamidobenzoate

[00074] In a 100 mL Schlenk flask, 303.0 mg (1.13 mmol, 1.0 eq.) of 1-(4-methoxyphenyl)vinyl 4-aminobenzoate were dissolved in 30 mL of dry DCM under an inert N2 atmosphere. Then, 0.24 mL of Net3 (1.688 mmol, 1.5 eq.) were added. Following this, 0.104 mL of CH3COCl (1.46 mmol, 1.3 eq.) were added dropwise to the mixture at < 0°C (ice-salt bath). The mixture was stirred at < 0°C for 1 h, after which complete conversion of the material was observed by TLC. Then, 30 mL of saturated aqueous NH4Cl solution were added to neutralize the excess acid chloride. The organic layer was separated and washed with a more saturated aqueous NH4Cl solution. The aqueous phase was extracted with DCM and the organic layers were combined, washed with brine, dried over anhydrous Na2SO4, and the solvent evaporated under reduced pressure. 1H-NMR (300 MHz; Chloroform-d) δ ppm 8.20-8.15 (m, 2H), 7.73-7.63 (m, 2H), 7.53 — 7.42 (m, 1H), Petition 870250087335, dated 09 / 26 / 2025, p. 39 / 57 25 / 27 7.39 (s, 1H), 6.94 - 6.83 (m, 2H), 5.48 (d, J = 2.2 Hz, 1H), 5.06 (d, J = 2.2 Hz, 1H), 3.82 (s, 3H), 2.25 (s, 3H).13CNMR (75 MHz; Chloroform-d) δ ppm 169.01 (1C), 164.74(1C), 160.33 (1C), 153.08 (1C), 143.06 (1C), 131.49 (2C), 126.94 (2C), 126.41 (2C), 124.68 (1C), 119.09 (1C), 114.08(2C), 100.51 (1C), 55.42 (1C), 24.80(1C). Example 6: Photoactivation of 1-(4-methoxyphenyl)vinyl-4-acetamidobenzoate

[00075] 1-(4-methoxyphenyl)vinyl-4-acetamidobenzoate (102.9 mg, 0.33 mmol) was dissolved in 50 mL of degassed MeOH in a photochemical reactor. The solution was then irradiated with a high-pressure mercury lamp (HPK125W) for 2 hours (cooling temperature = -15°C) under an inert atmosphere. The solvent was then evaporated and the product purified by silica gel column chromatography using hexanes / ethyl acetate (7:3) as the mobile phase. The photoconverted product was obtained as a slightly yellow solid (42.6 mg, 42% yield). Example 7: Comparison of the photochemical properties of 1-(4-methoxyphenyl)vinyl 4-acetamidobenzoate and preavobenzone

[00076] UV-Vis spectra of (a) preabovenzone, PvB-360, (comparative example) and (b) 1-(4-methoxyphenyl)vinyl 4-acetamidobenzoate, PVB-1, (compound according to the invention) were obtained when a 3x10-5M solution in MeOH is irradiated at 312 nm. These UV-Vis spectra show the absorption changes of both compounds.

[00077] The main difference is that 1-(4-methoxyphenyl)vinyl 4-acetamidobenzoate is photoconverted into the subsequent photoproduct more rapidly than avobenzone. Petition 870250087335, dated 09 / 26 / 2025, pp. 40 / 57 26 / 27 After 10 minutes of irradiation, 1-(4-methoxyphenyl)vinyl 4-acetamidobenzoate is completely converted into the photoproduct, however avobenzone needs more than 20 minutes to achieve complete photoconversion.

[00078] Furthermore, 1-(4-methoxyphenyl)vinyl 4-acetamidobenzoate has maximum absorption at 270 nm and can absorb more UV-B radiation than avobenzone (see Figures 1(a) and (b)). Example 8: Irradiation activation study using a PvB-360 solar simulator (comparative example) and PVB-1 (example of the invention)

[00079] An activation study was performed by irradiation, using a solar simulator, a thin layer of the filter on top of a PMMA plate dissolved in a suitable solvent. In this case, dibutyl adipate (2% w / w filter) was used as the solvent. It was possible to measure the SPF and UVA-PF of (Preavobenzone) and PVB-1 at different irradiation times (measured in MEDs) using a Labsphere® instrument (See Figure 2 SPF and UVA-PF of PvB-360 (Preavobenzone) and PVB-1 at different irradiation times).

[00080] It was observed that SPF values ​​are higher for PVB-1 compared to PvB360. Regarding UVA-PF values, it was observed that PVB-1 reaches higher values ​​at the same irradiation dose. In fact, PVB-1 reached slightly more than 3 UVA-PF units when irradiated by 2.5 MEDs. Meanwhile, the maximum value for PvB-360 was reached after irradiating 5 MEDs, with a value around 2.5 units. List of Citations Patent Literature Petition 870250087335, dated 09 / 26 / 2025, pp. 41 / 57 27 / 27 WO2006100225 Non-Patented Literature Adaya Gallardo and collaborators, "Dose-dependent progressive sunscreens. A new strategy for photoprotection?", Photochemical & Photobiological Sciences, 2010, vol. 9, pp. 530-534 Petition 870250087335, dated 09 / 26 / 2025, pp. 42 / 57

Claims

1 / CLAIM 1. A compound according to formula (I), a pharmaceutically or cosmetically acceptable salt thereof, or (I) or alternatively, (D characterized in that: in compound (I), R' is selected from the group consisting of H; alkyl (C1-Ce) and cycloalkyl Cs-Ce); Ri, Ra, R4, Rs, Re, Rs, Rg, and Rio are a radical independently selected from the group consisting of H, hydroxy, amino, alkyl (C1-Ce), alkoxy (C1-Ce), alkylamino (C1-Ce), and dialkylamino (C1-Ce); Rs is alkyl (C1-Ce); and Petition 870250087335, dated 26 / 09 / 2025, p. 9 / 57 2 / 7 R8 is selected from the group consisting of alkyl (C1-C6), alkoxy (C1-C6), hydroxy, amino, alkylamino (C1-C6) and dialkylamino (C1-C6); and in compound (I'), Ri and R8 are a radical independently selected from the group consisting of H, amino, alkyl (C1-C6), alkoxy (C1-C6), alkylamino (C1-C6) and dialkylamino (C1-C6); R', R2, R4, R5, R7, R9, R10, R3 and R8 are as defined in compound (I).

2. Compound according to claim 1, characterized in that it is the compound of formula (I), or a pharmaceutically or cosmetically acceptable salt thereof, or a stereoisomer of any of them or mixtures thereof.

3. Compound according to claim 1, characterized in that R1, R2, R4, R5, R6, R7, R9 and R10 are H and R8 is an alkoxy (C1-C0), and R' is H.

4. Compound according to claim 1, characterized in that R3 is (C1-C3) alkyl.

5. Compound according to claim 1, characterized in that in formula (I) and formula (I') R', R1, R2, R4, R5, R6, R7, R9 and R10 are H; R3 is methyl; and R8 is methoxyl.

6. Use of a compound (I) or (I') as defined in claim 1, characterized in that it is intended for the manufacture of a cosmetic composition, a pharmaceutical composition or a personal care composition for the protection of a human or animal organism against ultraviolet radiation. Petition 870250087335, dated 09 / 26 / 2025, page 10 / 57 3 / 7 7. Method for protecting a material from ultraviolet radiation characterized in that it comprises treating the material with a composition comprising an effective amount of a compound as defined in claim 1.

8. Use according to claim 6, characterized in that the use comprises the photochemical conversion of the compound of formula (I) in situ into a sunscreen compound.

9. A selected composition from the group consisting of a cosmetic composition, a pharmaceutical composition and a personal care composition, characterized in that it comprises at least an amount effective for protecting a human or animal organism from ultraviolet radiation, from a compound as defined in claim 1, together with one or more pharmaceutically or cosmetically acceptable excipients or vehicles or alternatively, a composition comprising at least an amount effective for protecting a material from ultraviolet radiation, of a compound as defined in claim 1, together with appropriate components selected from at least one polymer, a solvent, an additive and a mixture thereof.

10. Cosmetic or pharmaceutical composition, or personal care composition, according to claim 9, characterized in that the effective amount varies from 0.1 to 10% by weight, based on the total weight of the composition.

11. Composition for protecting a material against ultraviolet radiation according to claim 9, Petition 870250087335, dated 09 / 26 / 2025, page 11 / 57, characterized in that the effective amount varies from 0.1 to 10% by weight, based on the total weight of the composition.

12. A cosmetic or pharmaceutical composition, or a personal care composition, according to claim 9, characterized in that the composition is selected from the group consisting of creams, ointments, oils, lotions, gels, sticks, foams, milks, suspensions, powders, emulsions, dispersions, sprays, aerosols, lipsticks, foundations, makeup, loose or pressed powders, eye blushes, eye shadows, mascara, nail polishes, nail lacquers, and non-permanent hair styling compositions.

13. Process for preparing a compound as defined in claim 1, characterized in that: when the compound is a compound of formula (I), the process comprises a reaction step of a compound of formula (IIa) or an appropriate salt thereof; with an acyl halide (Ci-Ce) in the presence of an appropriate solvent and an appropriate base; wherein R', Ri-Rio are as defined in compound (I) and Rsa' is NH2; and wherein when the compound is the compound of formula (I'), the process comprises irradiating the compound of formula (I) with UV light to produce the compound of formula (I'). Petition 870250087335, dated 09 / 26 / 2025, page 12 / 57 5 / Ί 14. Process according to claim 13, characterized in that it further comprises a prior step comprising subjecting a compound of formula (Ilb) to a reduction reaction to produce a compound of formula (Ha), (Ilb) wherein in the compound of formula (lib), R', R1-R10 are as defined in compound (I) and Rab' is NO2.

15. Compound of formula (II), a pharmaceutically or cosmetically acceptable salt thereof, or a stereoisomer of either or mixtures thereof, characterized in that: in compound (II), Petition 870250087335, dated 26 / 09 / 2025, page 13 / 57 6 / 7 R' is selected from the group consisting of H; alkyl (C1-C0) and cycloalkyl C3-C0); R1, R2, R4, R5, R0, R7, R9, and R10 are a radical independently selected from the group consisting of H, hydroxy, amino, alkyl (C1-C0), alkoxy (C1-C0), alkylamino (C1-C0) and dialkylamino (C1-C0); R3' is amino or nitro; and R8 is selected from the group consisting of alkyl (Ci-Có), alkoxy (Ci-Có), hydroxy, amino, alkylamino (Ci-Có) and dialkylamino (Ci-Có).

16. Compound according to claim 2, characterized in that R1, R2, R4, R5, R6, R7, R9 and R10 are H and R8 is an alkoxyl (C1-C6), and R' is H.

17. Compound according to claim 3, characterized in that R3 is (C1-C3) alkyl.

18. A selected composition from the group consisting of a cosmetic composition, a pharmaceutical composition, and a personal care composition, characterized in that it comprises at least an amount effective for the protection of a human or animal body against ultraviolet radiation of a compound as defined in claim 5, together with one or more pharmaceutically or cosmetically acceptable excipients or vehicles; or alternatively, a composition comprising at least an amount effective for the protection of a material against ultraviolet radiation of a compound as defined in claim 5, together with appropriate components selected from at least one polymer, one solvent, one additive, and a mixture thereof. Petition 870250087335, dated 09 / 26 / 2025, page 14 / 57 7 / 7 19. A selected composition from the group consisting of a cosmetic composition, a pharmaceutical composition, and a personal care composition, characterized in that it comprises at least an amount effective for the protection of a human or animal organism against ultraviolet radiation of a compound as defined in claim 5, together with one or more pharmaceutically or cosmetically acceptable excipients or vehicles; or alternatively, a composition comprising at least an amount effective for the protection of a material against ultraviolet radiation of a compound as defined in claim 5, together with appropriate components selected from at least one polymer, one solvent, one additive, and a mixture thereof. Petition 870250087335, dated 09 / 26 / 2025, page 15 / 57

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