DETAILED ACTION
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 .
Priority
The current application is a Continuation of US Patent Application 17/392,569, filed August 3, 2021; which is a Continuation of US Patent Application 14/888,972, filed November 4, 2015, now abandoned; which is a 371 national stage application of application No. PCT/US2014/038602 filed on May 19, 2014, now expired, which application claims the benefit of U.S. Provisional Application No. 61/825,177, filed May 20, 2013, now expired.
Information Disclosure Statement
The Information Disclosure Statement(s) filed 5/20/2013 has/have been considered by the Examiner. The submission(s) is/are in compliance with the provisions of 37 CFR §§ 1.97 and 1.98. Enclosed with this Office Action is a return-copy of the Forms PTO-1449 with the Examiner’s signature and indication of those references that have been considered.
Claim Objections
Claims 3 and 12 are objected to because of the following informalities:
Claim 3, line 1: the term “in” should be deleted.
Claim 3, lines 3 and 4: each recitation of the term “dipropyleneglycol” should be “dipropylene glycol”.
Claim 12, line 2: the term “isoxazoline” should be deleted to keep consistency with Claim 1.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
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 applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 3 depends indirectly from Claim 1. Claim 1 recites “a glycol ether selected from the group consisting of” the listed glycol ethers. Claim 1 is without a limitation for their mixture. Claim 3 however recites that “the glycol ether is” each of five different glycol ethers joined by “and”. It is unclear whether the claim requires the composition to comprise all five recited glycol ethers or, alternatively, whether the glycol ether is intended to be selected from the five recited glycol ethers. Because Claim 1 is directed to “a glycol ether selected from the group consisting of” the listed glycol ethers, Claim 3 will be construed to encompass embodiments that comprise one glycol ether.
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, 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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-4, 8, 9, 11-13 and 15 are rejected under 35 U.S.C. 103 as being unpatentable over Curtis et al. (US PG-PUB 2012/0232026) in view of Pfizer (WO 00/30449 A1). References cited in 02/07/2024 IDS.
Claimed invention
Claim 1 is drawn to a long-acting topical composition comprising:
a spiro-azetidine isoxazoline compound that is 1-(5'-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-yl)-2-(methylsulfonyl)ethenone - “Compound 1” - or a stereoisomer;
a glycol ether such as diethylene glycol monomethyl ether (i.e., DEGMME), diethylene glycol monobutyl ether (i.e., butyl digol), and
at least one veterinarily acceptable solvent such as isopropyl myristate, oleic acid, eucalyptol, benzyl alcohol, benzyl benzoate, ethanol, or isopropanol (“IPA”).
Claim 11 is drawn to a method of treating an animal with a parasitic infestation comprising administering long-acting topical composition of Claim 1.
Prior art
Curtis et al. teaches use of a spirocyclic isoxazoline derivatives, including (S)-1-(5'-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-yl)-2-(methylsulfonyl)ethanone, i.e., Compound 1, as antiparasitic compounds. See title; abstract; [0137],[0294]; see also Claims 12, 13 and 14. They are used for the treatment of a parasitic infection or infestation in an animal. See 0354,0376; see also Claim 20. The compounds are preferably administered topically to the skin or mucosa. Typical formulations for this purpose include pour-on, spot-on, multi-spot-on, stripe-on, comb-on, roll-on, dip, spray, lotion, etc. Typical carriers include glycol monomethyl ethers, propylene glycol, and the like. See [0417]. Pour-on or spot-on veterinary formulations may be prepared by dissolving the compound in solvents such as butyl digol, i.e., diethylene glycol monobutyl ether a.k.a. DEGMBE, liquid paraffin or a non-volatile ester, optionally with the addition of a volatile component. See [0351],[0417].
While the Curtis reference teaches the treatment of parasitic infection in an animal by applying a topical pour-on formulation containing a spirocyclic isoxazoline derivative such as Compound 1 and lists of carriers (such as glycol monomethyl ethers) and solvents (such as butyl digol, liquid paraffin, or combinations thereof), the reference does not teach or exemplify, with enough specificity to anticipate, a single composition containing all of the required claimed components together: a) Compound 1, b) glycol ether such as DEGMME or butyl glycol and c) solvent (e.g., isopropanol – “IPA”).
However, the combination of glycol ethers and solvents with antiparasitic actives was already known to provide benefits to topical antiparasitic formulations. For example, Pfizer teaches antiparasitic formulations suitable for topical application, including pour-on formulations (see p. 8, line 20), containing a) an active (specifically drawn to avermectin or milbemycin), b) a di(C2-4 glycol)mono(C1-4 alkyl) ether (i.e., glycol ether), c) optionally a volatile solvent and d) optionally an antioxidant. See p. 2, lines 2-8. The volatile solvent is acceptable for the skin and preferably isopropanol (“IPA”). See p. 3, lines 13-15. The compositions have good cosmetic profile and are applied topically to a cat or dog, spreads well giving good skin contact across a wide range of temperatures and are effective enough to enable long periods between treatments. See p. 2, lines 13-20. A preferred di(C2-4 glycol)mono(C1-4 alkyl) ether is DEGMME. See p. 2, lines 31-32; see also Claim 6.
One of ordinary skill in the art would have found it obvious to combine Compound 1 with DEGMME and a volatile solvent such as IPA to make a topical antiparasitic composition for administration to an animal because Curtis teaches that Compound 1 (as the active) is useful in topical antiparasitic veterinary compositions that further comprise suitable carriers such as glycol monomethyl ethers and volatile solvents while Pfizer teaches that a di(C2-4 glycol)mono(C1-4 alkyl) ether such as DEGMME and a volatile solvents like IPA can be combined with an antiparasitic active to provide compositions that can be applied topically to an animal, have good cosmetic profile, spread well giving good skin contact across a wide range of temperatures and are effective enough to enable long periods between treatments. The artisan would have reasonably expected that the DEGMME and volatile solvent (e.g., IPA) would be suitable to provide their intended purposes as carriers and solvent for antiparasitic active ingredients for topical application to animals. Additionally, the artisan would have also found it obvious to combined butyl digol (instead of DEGMME) as the di(C2-4 glycol)mono(C1-4 alkyl) ether with the volatile solvent and antiparasitic active because butyl digol is a species of di(C2-4 glycol)mono(C1-4 alkyl) ether that is mentioned by Curtis as a suitable carrier amongst a list of carriers and solvents. Similar to DEGMME, the artisan would have reasonably expected that the butyl digol and volatile solvent would be suitable to provide their intended purposes as carriers and solvent for active antiparasitic ingredients for topical application to animals.
Regarding Claim 2, which is drawn to a specific S-isomer of Compound 1, Curtis teaches the same S-isomer claimed, specifically (S)-1-(5'-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-yl)-2-(methylsulfonyl)ethenone. See Curtis, 0102. This also meets the limitations of Claim 12.
Regarding Claim 3, wherein the glycol ether is a diethylene glycol monomethyl ether (i.e., DEGMME), as described above, the artisan would have reasonably expected that the DEGMME would be suitable to provide its intended purpose as a carrier or solvent for antiparasitic active agents for topical application to animals.
Regarding Claim 4, Pfizer teaches antioxidants may be added to the compositions including propylgallate, BHA (2-t-butyl-4-methoxyphenol), and BHT (2,6-di- t-butyl-4-methylphenol). See Pfizer, p. 3, last para.; see also Claims 17 and 18. This also meets the limitations of Claim 13.
Regarding Claim 8, isopropanol (IPA) is taught by Pfizer and is suggested as suitably combined with an antiparasitic active and a glycol ether for topical application as outlined above.
Regarding Claim 9, Curtis teaches the composition can further comprise at least one additional veterinary agent, e.g., endoparasiticides, endectocides, ectoparasiticides, insecticides, and anthelmintic. See Curtis 0431-0434;see also Claims 17-18.
Regarding Claim 15, Curtis teaches the animal is a companion animal or livestock. See 0431, Claim 22.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/process/file/efs/guidance/eTD-info-I.jsp.
A. Claims 1-4, 8, 9, 11-13 and 15 are rejected on the ground of nonstatutory double patenting as being unpatentable over Claims 1-36 of U.S. Patent No. 8,466,115 (patented claims or reference) in view of Curtis et al. (US PG-PUB 2012/0232026) and Pfizer (WO 00/30449 A1). References cited in 02/07/2024 IDS.
Claimed invention
Claim 1 is drawn to a long-acting topical composition comprising:
a spiro-azetidine isoxazoline compound that is 1-(5'-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-yl)-2-(methylsulfonyl)ethenone - “Compound 1” - or a stereoisomer;
a glycol ether such as diethylene glycol monomethyl ether (i.e., DEGMME), diethylene glycol monobutyl ether (i.e., butyl digol), and
at least one veterinarily acceptable solvent such as isopropyl myristate, oleic acid, eucalyptol, benzyl alcohol, benzyl benzoate, ethanol, or isopropanol (“IPA”).
Claim 11 is drawn to a method of treating an animal with a parasitic infestation comprising administering long-acting topical composition of Claim 1.
Reference
The patented claims are directed to compounds of formula (V.1) or (V.2) including (S)-1-(5'-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-yl)-2-(methylsulfonyl)ethanone), i.e., Compound 1. See Claim 14. The compounds are used in veterinary compositions further containing diluents, carriers, and excipients. See Claim 16. The compounds are used in therapeutic amounts as antiparasitic agents. See Claim 19. They are administered topically. See Claim 20.
The patented claims do not teach the claimed glycol ethers and solvents.
However, the combination of glycol ethers and solvents with compounds of these antiparasitic actives was already known as well as benefits provided by the solvents and glycol ethers to topical antiparasitic formulations. Similar to the reference claims, Curtis teaches Compound 1 as an antiparasitic active. See Curtis, Claim 14 and 20. Curtis also teaches that the antiparasitic compounds can be formulated in topical compositions with solvent including butyl digol and volatile solvents among other listed solvents. See Curtis, 0417. Pfizer also teaches antiparasitic formulations suitable for topical application, including pour-on formulations (see p. 8, line 20), containing a) an active (specifically drawn to avermectin or milbemycin), b) a di(C2-4 glycol)mono(C1-4 alkyl) ether (i.e., glycol ether), c) optionally a volatile solvent and d) optionally an antioxidant. See p. 2, lines 2-8. The compositions have good cosmetic profile and are applied topically to a cat or dog, spreads well giving good skin contact across a wide range of temperatures and are effective enough to enable long periods between treatments. See p. 2, lines 13-20. A preferred di(C2-4 glycol)mono(C1-4 alkyl) ether is DEGMME, i.e., a glycol ether. See p. 2, lines 31-32; see also Claim 6.
One of ordinary skill in the art would have found it obvious to combine Compound 1 with DEGMME and a volatile solvent for a topical antiparasitic composition for administration to an animal because the patented claims teach that Compound 1 is useful in topical antiparasitic veterinary compositions that further comprise suitable excipients, diluents, or carriers while Curtis teaches compounds of the reference claim can be formulated with solvents like butyl digol and volatile solvents and Pfizer teaches that a di(C2-4 glycol)mono(C1-4 alkyl) ether such as DEGMME and a volatile solvent can be combined with an antiparasitic active to provide compositions that can be applied topically to an animal, have good cosmetic profile, spread well giving good skin contact across a wide range of temperatures and are effective enough to enable long periods between treatments. The artisan would have reasonably expected that the DEGMME and volatile solvent would be suitable to provide their intended purposes as carriers and solvent of active antiparasitic ingredients for topical application to animals. Additionally, the artisan would have also found it obvious to combined butyl digol (instead of DEGMME) as the di(C2-4 glycol)mono(C1-4 alkyl) ether with the volatile solvent and antiparasitic active because butyl digol is a species of di(C2-4 glycol)mono(C1-4 alkyl) ether that is mentioned by Curtis as a suitable carrier amongst a list of carriers and solvents. Similar to DEGMME, the artisan would have reasonably expected that the butyl digol and volatile solvent would be suitable to provide their intended purposes as carriers and solvent for active antiparasitic ingredients for topical application to animals as well as provide similar benefits as a di(C2-4 glycol)mono(C1-4 alkyl) ether.
Regarding Claim 2, the S-isomer of Compound 1 is disclosed by the reference claims and Curtis. This also meets the limitations of Claim 12.
Regarding Claim 3, wherein the glycol ether is a diethylene glycol monomethyl ether (i.e., DEGMME), as described above, the artisan would have reasonably expected that the DEGMME would be suitable to provide its intended purpose as a carrier or solvent for antiparasitic active agents for topical application to animals.
Regarding Claim 4, Pfizer teaches antioxidants may be added to the compositions including propylgallate, BHA (2-t-butyl-4-methoxyphenol), and BHT (2,6-di- t-butyl-4-methylphenol). See Pfizer, p. 3, last para.; see also Claims 17 and 18. A POSA would have found it obvious to incorporate an antioxidant to impart its antioxidative effects to predictably provide protection against oxidation. This also meets the limitations of Claim 13.
Regarding Claim 8, isopropanol (IPA) is taught by Pfizer and is suggested as suitably combined with an antiparasitic active and a glycol ether for topical application as outlined above.
Regarding Claim 9, Curtis teaches the composition can further comprise at least one additional veterinary agent, e.g., endoparasiticides, endectocides, ectoparasiticides, insecticides, and anthelmintic. See Curtis 0431-0434;see also Claims 17-18.
Regarding Claim 15, Curtis teaches the animal is a companion animal or livestock. See 0431, Claim 22.
B. Claims 1-4, 8, 9, 11-13, and 15 are rejected on the ground of nonstatutory double patenting as being unpatentable over Claims 1-20 of U.S. Patent No. 9,226,928 in view of Curtis et al. (US PG-PUB 2012/0232026) and Pfizer (WO 00/30449 A1). References cited in 02/07/2024 IDS.
Claimed invention
Claim 1 is drawn to a long-acting topical composition comprising:
a spiro-azetidine isoxazoline compound that is 1-(5'-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-yl)-2-(methylsulfonyl)ethenone - “Compound 1” - or a stereoisomer;
a glycol ether such as diethylene glycol monomethyl ether (i.e., DEGMME), diethylene glycol monobutyl ether (i.e., butyl digol), and
at least one veterinarily acceptable solvent such as isopropyl myristate, oleic acid, eucalyptol, benzyl alcohol, benzyl benzoate, ethanol, or isopropanol (“IPA”).
Claim 11 is drawn to a method of treating an animal with a parasitic infestation comprising administering long-acting topical composition of Claim 1.
Reference
The patented claims are directed to compounds of formula 1 including the S-isomer of
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which is (S)-1-(5'-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-yl)-2-(methylsulfonyl)ethanone), i.e., Compound 1, that are useful for treating parasitic infection in an animal (i.e., cat or dog). See Claims 1, 2, 7 and 19. The compounds are used in veterinary compositions further containing carrier. See Claim 6. They are administered topically. See Claim 11.
The patented claims do not teach the claimed glycol ethers and solvents.
However, the combination of glycol ethers and solvents with antiparasitic actives was already known to provide benefits to topical antiparasitic formulations. Similar to the reference claims, Curtis teaches Compound 1 as an antiparasitic active. See Curtis, Claim 14 and 20. Curtis also teaches that the antiparasitic compounds can be formulated in topical compositions with solvent including butyl digol and volatile solvents among other listed solvents. See Curtis, 0417. Pfizer also teaches antiparasitic formulations suitable for topical application, including pour-on formulations (see p. 8, line 20), containing a) an active (specifically drawn to avermectin or milbemycin), b) a di(C2-4 glycol)mono(C1-4 alkyl) ether (i.e., glycol ether), c) optionally a volatile solvent and d) optionally an antioxidant. See p. 2, lines 2-8. The compositions have good cosmetic profile and are applied topically to a cat or dog, spreads well giving good skin contact across a wide range of temperatures and are effective enough to enable long periods between treatments. See p. 2, lines 13-20. A preferred di(C2-4 glycol)mono(C1-4 alkyl) ether is DEGMME. See p. 2, lines 31-32; see also Claim 6.
One of ordinary skill in the art would have found it obvious to combine Compound 1 with DEGMME and a volatile solvent for a topical antiparasitic composition for administration to an animal because the patented claims teach that Compound 1 is useful in topical antiparasitic veterinary compositions that further comprise suitable carrier while Pfizer teaches that a di(C2-4 glycol)mono(C1-4 alkyl) ether such as DEGMME and a volatile solvent can be combined with an antiparasitic active to provide compositions that can be applied topically to an animal, have good cosmetic profile, spread well giving good skin contact across a wide range of temperatures and are effective enough to enable long periods between treatments. The artisan would have reasonably expected that the DEGMME and volatile solvent would be suitable to provide their intended purposes as carriers and solvent of active antiparasitic ingredients for topical application to animals. Additionally, the artisan would have also found it obvious to combined butyl digol (instead of DEGMME) as the di(C2-4 glycol)mono(C1-4 alkyl) ether with the volatile solvent and antiparasitic active because butyl digol is a species of di(C2-4 glycol)mono(C1-4 alkyl) ether that is mentioned by Curtis as a suitable carrier amongst a list of carriers and solvents. Similar to DEGMME, the artisan would have reasonably expected that the butyl digol and volatile solvent would be suitable to provide their intended purposes as carriers and solvent for active antiparasitic ingredients for topical application to animals as well as provide similar benefits as a di(C2-4 glycol)mono(C1-4 alkyl) ether.
Regarding Claim 2, the S-isomer of Compound 1 is disclosed by the reference claims and Curtis. This also meets the limitations of Claim 12.
Regarding Claim 3, wherein the glycol ether is a diethylene glycol monomethyl ether (i.e., DEGMME), as described above, the artisan would have reasonably expected that the DEGMME would be suitable to provide its intended purpose as a carrier or solvent for antiparasitic active agents for topical application to animals.
Regarding Claim 4, Pfizer teaches antioxidants may be added to the compositions including propylgallate, BHA (2-t-butyl-4-methoxyphenol), and BHT (2,6-di- t-butyl-4-methylphenol). See Pfizer, p. 3, last para.; see also Claims 17 and 18. A POSA would have found it obvious to incorporate an antioxidant to impart its antioxidative effects to predictably provide protection against oxidation. This also meets the limitations of Claim 13.
Regarding Claim 8, isopropanol (IPA) is taught by Pfizer and is suggested as suitably combined with an antiparasitic active and a glycol ether for topical application as outlined above.
Regarding Claim 9, Curtis teaches the composition can further comprise at least one additional veterinary agent, e.g., endoparasiticides, endectocides, ectoparasiticides, insecticides, and anthelmintic. See Curtis 0431-0434;see also Claims 17-18.
Regarding Claim 15, Curtis teaches the animal is a companion animal or livestock. See 0431, Claim 22.
C. Claims 1-4, 8, 9, 11-13 and 15 are rejected on the ground of nonstatutory double patenting as being unpatentable over Claims 1-20 of U.S. Patent No. 9,200,003 in view of Curtis et al. (US PG-PUB 2012/0232026) and Pfizer (WO 00/30449 A1). References cited in 02/07/2024 IDS.
Claimed invention
Claim 1 is drawn to a long-acting topical composition comprising:
a spiro-azetidine isoxazoline compound that is 1-(5'-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-yl)-2-(methylsulfonyl)ethenone - “Compound 1” - or a stereoisomer;
a glycol ether such as diethylene glycol monomethyl ether (i.e., DEGMME), diethylene glycol monobutyl ether (i.e., butyl digol), and
at least one veterinarily acceptable solvent such as isopropyl myristate, oleic acid, eucalyptol, benzyl alcohol, benzyl benzoate, ethanol, or isopropanol (“IPA”).
Claim 11 is drawn to a method of treating an animal with a parasitic infestation comprising administering long-acting topical composition of Claim 1.
Reference
The patented claims are directed to a crystalline form of (S)-1-(5'-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-yl)-2-(methylsulfonyl)ethanone), i.e., Compound 1, that are useful for treating parasitic infection in an animal (i.e., cat or dog). See Claims 1 and 11. The compounds are used in veterinary compositions further containing carrier, carrier excipient or mixtures thereof. See Claim 9. They are administered topically. See Claim 13.
The patented claims do not teach the claimed glycol ethers and solvents.
However, the combination of glycol ethers and solvents with antiparasitic actives was already known to provide benefits to topical antiparasitic formulations. Similar to the reference claims, Curtis teaches Compound 1 as an antiparasitic active. See Curtis, Claim 14 and 20. Curtis also teaches that the antiparasitic compounds can be formulated in topical compositions with solvent including butyl digol and volatile solvents among other listed solvents. See Curtis, 0417. Pfizer also teaches antiparasitic formulations suitable for topical application, including pour-on formulations (see p. 8, line 20), containing a) an active (specifically drawn to avermectin or milbemycin), b) a di(C2-4 glycol)mono(C1-4 alkyl) ether (i.e., glycol ether), c) optionally a volatile solvent and d) optionally an antioxidant. See p. 2, lines 2-8. The compositions have good cosmetic profile and are applied topically to a cat or dog, spreads well giving good skin contact across a wide range of temperatures and are effective enough to enable long periods between treatments. See p. 2, lines 13-20. A preferred di(C2-4 glycol)mono(C1-4 alkyl) ether is DEGMME. See p. 2, lines 31-32; see also Claim 6.
One of ordinary skill in the art would have found it obvious to combine Compound 1 with DEGMME and a volatile solvent for a topical antiparasitic composition for administration to an animal because the patented claims teach that Compound 1 is useful in topical antiparasitic veterinary compositions that further comprise suitable carrier while Pfizer teaches that a di(C2-4 glycol)mono(C1-4 alkyl) ether such as DEGMME and a volatile solvent can be combined with an antiparasitic active to provide compositions that can be applied topically to an animal, have good cosmetic profile, spread well giving good skin contact across a wide range of temperatures and are effective enough to enable long periods between treatments. The artisan would have reasonably expected that the DEGMME and volatile solvent would be suitable to provide their intended purposes as carriers and solvent of active antiparasitic ingredients for topical application to animals. Additionally, the artisan would have also found it obvious to combined butyl digol (instead of DEGMME) as the di(C2-4 glycol)mono(C1-4 alkyl) ether with the volatile solvent and antiparasitic active because butyl digol is a species of di(C2-4 glycol)mono(C1-4 alkyl) ether that is mentioned by Curtis as a suitable carrier amongst a list of carriers and solvents. Similar to DEGMME, the artisan would have reasonably expected that the butyl digol and volatile solvent would be suitable to provide their intended purposes as carriers and solvent for active antiparasitic ingredients for topical application to animals as well as provide similar benefits as a di(C2-4 glycol)mono(C1-4 alkyl) ether.
Regarding Claim 2, the S-isomer of Compound 1 is disclosed by the reference claims and Curtis. This also meets the limitations of Claim 12.
Regarding Claim 3, wherein the glycol ether is a diethylene glycol monomethyl ether (i.e., DEGMME), as described above, the artisan would have reasonably expected that the DEGMME would be suitable to provide its intended purpose as a carrier or solvent for antiparasitic active agents for topical application to animals.
Regarding Claim 4, Pfizer teaches antioxidants may be added to the compositions including propylgallate, BHA (2-t-butyl-4-methoxyphenol), and BHT (2,6-di- t-butyl-4-methylphenol). See Pfizer, p. 3, last para.; see also Claims 17 and 18. A POSA would have found it obvious to incorporate an antioxidant to impart its antioxidative effects to predictably provide protection against oxidation. This also meets the limitations of Claim 13.
Regarding Claim 8, isopropanol (IPA) is taught by Pfizer and is suggested as suitably combined with an antiparasitic active and a glycol ether for topical application as outlined above.
Regarding Claim 9, Curtis teaches the composition can further comprise at least one additional veterinary agent, e.g., endoparasiticides, endectocides, ectoparasiticides, insecticides, and anthelmintic. See Curtis 0431-0434;see also Claims 17-18.
Regarding Claim 15, Curtis teaches the animal is a companion animal or livestock. See 0431, Claim 22.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to CHRIS E SIMMONS whose telephone number is (571)272-9065. The examiner can normally be reached M-F: 8-4:30 PM.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, James H. Alstrum-Acevedo can be reached on (571)272-5548. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/CHRIS E SIMMONS/Examiner, Art Unit 1622
/JAMES H ALSTRUM-ACEVEDO/
Supervisory Patent Examiner, Art Unit 1622
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