DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claims 1-10 are pending in the instant application. Claims 1, 2, 4-10 has been withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention.
Claim 3 is under consideration in this Office Action.
The previous objection to the title has been withdrawn in view of the amendment to the title filed 11/07/2025.
In view of the claim amendment and arguments filed 11/07/2025, the previous rejections of the claims have been withdrawn in favor of the instant rejections of the claims stated below.
Claim Rejections - 35 USC § 112(b) or 35 U.S.C. 112 (pre-AIA ) 2nd Paragraph
The following is a quotation of 35 U.S.C. 112(b):
(B) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 3 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor, or for pre-AIA the applicant regards as the invention.
Claim 3 recites the phrase “the carboxylic ester hydrolase comprises Pseudomonas stutzeri lipase, Pseudomonas cepacia lipase, Alcaligenes sp. lipase E, Alcaligenes sp. lipase C, Pseudomonas fluorencens lipase, Burkholderia cepacia lipase A or Burkholderia cepacia lipase B” which renders the claim vague and indefinite since it is unclear how the carboxylic ester hydrolase comprises another enzyme. Amending the claim to recite that the carboxylic ester hydrolase is Pseudomonas stutzeri lipase, Pseudomonas cepacia lipase, Alcaligenes sp. lipase E, Alcaligenes sp. lipase C, Pseudomonas fluorencens lipase, Burkholderia cepacia lipase A or Burkholderia cepacia lipase B would aid in overcoming the rejection.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102 of this title, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
Claim 3 is rejected under 35 U.S.C. 103 as being unpatentable over WO2018071320 (04/19/2018; IDS filed 10/11/2024) in view of US20030003552 (01/02/2003; reference of record), US20060003428 (01/05/2006; reference of record), US20230193163 (06/22/2023; PTO 892).
WO2018071320 teaches process for the preparation of (1r,3r)- and (1s,3s)-2,2-dihalo-3-(substituted phenyl)cyclopropanecarboxylic acids where the process involves chemical resolution of a racemic mixture of a trans-2,2-dichloro-3-(substituted phenyl)cyclopropanecarboxylic acid with an enantiomeric amine, isolation of a diastereomeric amine salt and finally treatment of the salt with an acid. WO2018071320 teaches in Examples 1-4 representative compounds encompassed by S2a and S3a recited in the instant claim. See entire publication and claims especially pages 6-10 and claims 1-10. The teachings of the reference differ from the claims in that the reference does not teach the claimed process comprising hydrolyzing S2a to S3a using one or more carboxylic ester hydrolases.
US20030003552 teaches method of kinetic resolution of racemates of alcohols or carboxylic acid esters, where fluorine phase marking of the quicker or more slowly reacting enantiomer is obtained by lipase-catalysed reaction of racemic alcohols with fluorinated carboxylic acid esters of racemic alcohols with water, and the enantiomers are then extractively separated by division between an organic and a fluorine phase (see entire publication and claims especially paragraphs [0007]-[0051], Examples 1-7, and claims 1-12).
US20060003428 teaches process for enzymatically resolving a mixture of R- and S-enantiomers of an α-substituted carboxylic acid or an ester or thioester thereof, in which a Carica papaya lipase is used as a biocatalyst to effect the resolution as desired (see entire publication and claims especially paragraphs [0016]-[0029]. US20060003428 teaches the following in the claims:
1. A process for enzymatically resolving a mixture of R- and S-enantiomers of an α-substituted carboxylic acid or an ester or thioester thereof of formula (I):
wherein
X represents —O— or —S—;
Y is a halogen or a methyl group;
R1 represents: a straight-chain or branched saturated or unsaturated C1-C20 aliphatic group optionally substituted with one to three substituents selected from the group consisting of halo, amino, cyano, hydroxy, —SH, —COOH, —CF3, —OCF3, —SCF3, —CONH2, a C1-C6 alkoxy group and an aryl group; an aryl group, an aryloxy group or a C3-C12 heterocyclic group containing one to three heteroatoms selected from O, S and N, each group being optionally substituted with one to three substituents selected from the group consisting of halo, amino, cyano, hydroxy, —SH, —COOH, —CF3, —OCF3, —SCF3, —CONH2, a C1-C6 alkoxy group, an aryl group and a C3-C12 heterocyclic group containing one to three heteroatoms selected from O, S and N; and
R2 represents: H; a straight-chain or branched saturated or unsaturated C1-C12 aliphatic group optionally substituted with one to three substituents selected from the group consisting of halo, amino, cyano, hydroxy, —CF3, —OCF3, —SCF3, —Si(CH3)3, a C1-C4 alkyloxy group, a C1-C4 alkylthio group, an aryl group, vinyl and a 2-alkenyl group having 3 to 12 carbon atoms; an aryl group or a C3-C12 heterocyclic group containing one to three heteroatoms selected from O, S and N, each group being optionally substituted with one to three substituents selected from the group consisting of halo, amino, cyano, hydroxy, —SH, —COOH, —CF3, —OCF3, —SCF3, —CONH2, a C1-C6 alkoxy group, an aryl group and a C3-C12 heterocyclic group containing one to three heteroatoms selected from O, S and N;
with the proviso that Y and R1 cannot be methyl at the same time; the process comprising subjecting the mixture of R- and S-enantiomers of the α-substituted carboxylic acid or ester or thioaster thereof of formula (I) to an enzymatic resolution catalyzed by a Carica papaya lipase in a liquid phase.
2. The process of claim 1, wherein the liquid phase comprises a solvent system selected from an aqueous solution, an anhydrous organic solvent, an organic solvent saturated with water, and combinations thereof forming a biphasic solution.
3. The process of claim 1, wherein the liquid phase comprises an organic solvent selected from isooctane, heptane, hexane, cyclohexane, pentane, decane, toluene, benzene, carbon tetrachloride, t-butanol, t-pentanol, isopropyl ether, methyl t-butyl ether, methyl isobutyl ether, and combinations thereof.
4. The process of claim 1, wherein the mixture is a racemic mixture of the α-substituted carboxylic acid or ester or thioester thereof of formula (I).
5. The process of claim 1, wherein the Carica papaya lipase is prepared from a latex exudate of a plant of Carica papaya.
6. The process of claim 1, wherein the enzymatic resolution of the mixture by the Carica papaya lipase is conducted in a liquid phase comprising an organic solvent in combination with an organic base.
7. The process of claim 6, wherein the organic solvent is selected from isooctane, heptane, hexane, cyclohexane, pentane, decane, toluene, benzene, carbon tetrachloride, t-butanol, t-pentanol, isopropyl ether, methyl t-butyl ether, methyl isobutyl ether, and combinations thereof.
8. The process of claim 6, wherein the organic base is selected from the group consisting of tertiary amines, amidines, guanidines, phosphazene bases, and combinations thereof.
9. The process of claim 8, wherein the organic base is selected from the group consisting of triethylamine, tributylamine, trioctylamine, 7-methyl-1,5,7-triazabicyclo[4,4,0]dec-5-ene, 1,8-diazabicyclo [5,4,0] undec-7-ene, 1,4-diazabicyclo [2.2.2] octane, t-butylimino-tris(pyrrolidino)phosphorane, t-butylimino-tris(dimethylamino)phosphorane, 1-t-butyl-4,4,4-tris(dimethylamino)-2,2-bis[tris(dimethylamino)-phosphoranylidenamino]-2λ54λ5-catenadi(phosphazene), diethylaminomethyl-polystyrene, and combinations thereof.
10. The process of claim 8, wherein the organic base is carried on a support selected from an organic support and an inorganic support.
11. The process of claim 8, wherein the organic base is carried on an anion-exchange resin.
12. The process of claim 1, wherein the enzymatic resolution of the mixture by the Carica papaya lipase is conducted at a temperature ranging from 20° C. to 90° C.
13. The process of claim 1, wherein the mixture comprises R- and S-enantiomers of an α-substituted carboxylic acid ester or thioester of formula (I), and wherein the enzymatic resolution of the mixture by the Carica papaya lipase is conducted in a liquid phase comprising a solvent system selected from an aqueous solution, a water-saturated organic solvent and combinations thereof forming a biphasic solution, such that either R-form or S-form of the α-substituted carboxylic acid ester or thioester of formula (I) is enantioselectively hydrolyzed by the Carica papaya lipase.
14. The process of claim 13, wherein the α-substituted carboxylic acid ester or thioester of formula (I) is at least any one of the following compounds: an ethyl, propyl, butyl, hexyl, phenyl or tritluoroethyl ester of naproxen, fenoprofen, ibuprofen, ketoprofen, suprofen, flurbiprofen, 2-phenyl propionic acid, 2-(4-chlorophenoxy)propionic acid or 2-chloro-2-phenylacetic acid; an ethyl, propyl, butyl, hexyl, phenyl or trifluoroethyl thioester of naproxen, fenoprofen, ibuprofen, ketoprofen, suprofen, flurbiprofen, 2-phenyl propionic acid, 2-(4-chlorophenoxy)propionic acid or 2-chloro-2-phenylacetic acid; and diclofog methyl ester.
15. The process of claim 13, wherein the liquid phase further comprises an organic base selected from the group consisting of tertiary amines, amidines, guanidines, phosphazene bases, and combinations thereof.
16. The process of claim 15, wherein the organic base is selected from the group consisting of triethylamine, tributylamine, trioctylamine, 7-methyl-1,5,7-triazabicyclo[4,4,0]dec-5-ene, 1,8-diazabicyclo [5,4,0] undec-7-ene, 1,4-diazabicyclo [2.2.2]octane, t-butylimino-tris(pyrrolidino)phosphorane, t-butylimino-tris(dimethylamino)phosphorane, 1-t-butyl-4,4,4-tris(dimethylamino)-2,2-bis [tris(dimethylamino)-phosphoranylidenamino]-2λ5,4λ5-catenadi(phosphazene), diethylaminomethyl-polystyrene, and combinations thereof.
17. The process of claim 1, wherein the mixture comprises R- and S-enantiomers of an α-substituted carboxylic acid ester or thioester of formula (I), and wherein the enzymatic resolution of the mixture by the Carica papaya lipase is conducted in a liquid phase comprising an anhydrous organic solvent in combination with an alcohol, such that either R-form or S-form of the α-substituted carboxylic acid ester or thioester of formula (I) is enantioselectively transesterified by the Carica papaya lipase using said alcohol.
US20230193163 teaches Pseudomonas stutzeri lipase and use in washing agents or cleaning agents (see entire publication and claims especially claims 1-5)
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify and/or combine the reference teachings to make the claimed invention by contacting any of the compounds taught by WO2018071320 with the Pseudomonas stutzeri lipase of US20230193163 to make the claimed products. One of ordinary skill in the art before the effective filing date of the claimed invention would have been motivated to do this in order to obtain simple method to obtain the recited products by enzymatic activity of lipase. One of ordinary skill in the art before the effective filing date of the claimed invention would have a reasonable expectation of success in view of the reference teachings showing the use of lipases. Hence, the claimed invention as a whole is prima facie obvious.
Conclusion
No claim is allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any extension fee pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Christian L Fronda whose telephone number is (571)272 0929. The examiner can normally be reached Monday-Thursday and alternate Fridays between 9:00AM-5:00PM.
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/CHRISTIAN L FRONDA/Primary Examiner, Art Unit 1652