Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
DETAILED ACTION
This Office action is based on the 19/115488 application originally filed March 26, 2025.
Amended claims 1-12, filed March 26, 2025, are pending and have been fully considered.
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim(s) 1-12 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Chava et al. (WO 2015/097717 A2) hereinafter “Chava”.
Regarding Claim 1
Chava discloses on page 2 lines 35-40 and page 3 lines 1-11, an improved process for preparation of β-carotene having pharmaceutically acceptable level of residual organic solvents, which comprise of reacting a symmetrical dialdehyde and two equivalents of a Wittig salt in a suitable organic solvent in presence of a base to provide β-carotene of formula (I). In one embodiment, the present invention provides a process for the preparation of β-carotene of formula (I),
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comprises of reacting the symmetrical dialdehyde compound of formula (II) and Wittig salt compound of formula (III)
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wherein Ri, R2 and R3 are same or different and are selected from an alkyl, cycloalkyl, aryl or arylalkyl and X is an anion of strong acid; in the presence of an appropriate base in a suitable solvent selected from esters, ethers, hydrocarbons selected from the group consisting of aromatic hydrocarbons, C5-8 linear, branched or cyclic hydrocarbons, halogenated hydrocarbons and the like, to obtain β-carotene of formula (I).
Chava discloses on page 5 lines 15-36, examples of the lower alkyl group in the Wittig salt compound of formula (III) include a (C1-C5) straight or branched chain alkyl group such as a methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl group, n-pentyl group, i-pentyl group, neo-pentyl group and the like. Specific examples of the group of formula: PR1R2R3 in the Wittig salt compound of formula (III) includes triethylphosphine, tripropylphosphine, tributylphosphine, tripentylphosphine, trihexylphosphine, triphenylphosphine, tri-(o-tolyl)phosphine and the like, preferably triphenylphosphine. Examples of the anions are those of acids selected from the group consisting of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, sulfonic acids, formic acid and acetic acid; particularly chloro. bromo, iodo, methane sulfonyl, ethane sulfonyl, trifluoromethane sulfonyl, benzene sulfonyl, fluoroacetyloxy, trifluoroacetyloxy, more preferably bromo.
Chava discloses on page 7 lines 39-40 and page 8 lines 1-2, examples of suitable organic solvents used for the removal of triphenylphosphine oxide and other inorganic salts include but are not limited to methanol, ethanol, n-propanol. isopropanol, n-butanol, tert-butanol, acetone, tetrahydrofuran, dimethylformamide and dimethylsulfoxide; preferably methanol.
The claimed invention is anticipated by the reference because the reference teaches a composition which comprises all of the claimed components. In the alternative, no patentable distinction is seen to exist between the reference and the claimed invention absent evidence to the contrary.
Regarding Claims 2 and 3
Chava discloses on page 5 lines 15-36, examples of the lower alkyl group in the Wittig salt compound of formula (III) include a (C1-C5) straight or branched chain alkyl group such as a methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl group, n-pentyl group, i-pentyl group, neo-pentyl group and the like. Specific examples of the group of formula: PR1R2R3 in the Wittig salt compound of formula (III) includes triethylphosphine, tripropylphosphine, tributylphosphine, tripentylphosphine, trihexylphosphine, triphenylphosphine, tri-(o-tolyl)phosphine and the like, preferably triphenylphosphine. Examples of the anions are those of acids selected from the group consisting of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, sulfonic acids, formic acid and acetic acid; particularly chloro. bromo, iodo, methane sulfonyl, ethane sulfonyl, trifluoromethane sulfonyl, benzene sulfonyl, fluoroacetyloxy, trifluoroacetyloxy, more preferably bromo.
Regarding Claims 4-6
Chava discloses on page 7 lines 39-40 and page 8 lines 1-2, examples of suitable organic solvents used for the removal of triphenylphosphine oxide and other inorganic salts include but are not limited to methanol, ethanol, n-propanol. isopropanol, n-butanol, tert-butanol, acetone, tetrahydrofuran, dimethylformamide and dimethylsulfoxide; preferably methanol.
Regarding Claims 7-9
Chava discloses on page 6 lines 22-30, the base used herein is selected from alkali metal alkoxide such as potassium methoxide, potassium ethoxide, potassium n-butoxide, potassium t-butoxide, sodium methoxide, sodium ethoxide, sodium n-butoxide, sodium t-butoxide and the like; an alkali metal hydroxide such as lithium hydroxide, potassium hydroxide, sodium hydroxide and the like; alkali metal hydrides such as sodium hydride, potassium hydride and the like. An epoxide such as an ethylene oxide or 1 ,2-butene oxide may be used instead of the base. Preferably the base is alkali metal alkoxide; more preferably sodium methoxide.
Regarding Claims 10 and 11
Chava discloses on page 6 lines 31-33, further the base can be used in an amount of about 0.5 to about 3 equivalents of the starting dialdehyde compound of formula (II), preferably about 2.5 equivalents.
Regarding Claim 12
Chava discloses on page 6 lines 39-40 and page 7 lines 1-2, the reaction may be advantageously carried out at a suitable temperature at about 20°C to about reflux temperature. Preferably, the reaction is carried out at about 20°C to about 40°C. The reaction is allowed to stir for a period of time from about 30 min to until completion of the reaction, preferably for 1 hr to 4 hr.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Li et al. (CN 108752251 A) discloses in the abstract, a preparation method of all-trans β-carotene. The method provides a strong alkaline environment through the alkaline ionic liquid, so that 2,4-pentadiene pentadecyl phosphonate and 2,7-dimethyl-2,4,6-octatriene-1,8- The dialdehyde reacts under the action of a weak base to directly obtain all-trans β-carotene. The invention adopts strong alkaline ionic liquid as the alkaline auxiliary agent, the selectivity and yield of β-carotene both reach more than 94%, and the purity of trans-β-carotene in the product is >96%. The method has the advantages of simple reaction operation, rapid separation of products, environmental friendliness and suitability for industrial production.
Koo et al. (US 2002/0026082) discloses in abstract, intermediates useful in the synthesis of a compound having polyene chain structure, processes for preparing the same, and a process for preparing β-carotene utilizing the same are disclosed. Also disclosed is a novel compound, retinyl sulfide, which was synthesized by the coupling of a diallylic sulfide of the present invention with the corresponding Wittig salt.
Ernst et al. (US 2006/0106257) discloses in the abstract, a process for preparing carotenoids, in which the process includes reacting a dialkoxy dialdehyde in a double Wittig condensation with a phosphonium salt of or in a double Wittig-Horner condensation with a phosphonate. The carotenoids include, for example, β-carotene, zeaxanthin, canthaxanthin, astaxathin, lycopene and croceptin, which are useful as nutraceuticals, food colorants, and feed additives.
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/Latosha Hines/Primary Examiner, Art Unit 1771
