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 .
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.
This office action is a response to applicant’s communication submitted June 21, 2024, wherein claims 3-12 were preliminarily amended.
Claims 1-12 are pending in this application.
Priority
This application is a 371 of PCT/EP2022/086874 filed 12/20/2022 and claims foreign priority to EP 21306866.1 filed 12/21/2021.
Specification
Applicant is reminded of the proper content of an abstract of the disclosure.
A patent abstract is a concise statement of the technical disclosure of the patent and should include that which is new in the art to which the invention pertains. The abstract should not refer to purported merits or speculative applications of the invention and should not compare the invention with the prior art.
If the patent is of a basic nature, the entire technical disclosure may be new in the art, and the abstract should be directed to the entire disclosure. If the patent is in the nature of an improvement in an old apparatus, process, product, or composition, the abstract should include the technical disclosure of the improvement. The abstract should also mention by way of example any preferred modifications or alternatives.
Where applicable, the abstract should include the following: (1) if a machine or apparatus, its organization and operation; (2) if an article, its method of making; (3) if a chemical compound, its identity and use; (4) if a mixture, its ingredients; (5) if a process, the steps.
Extensive mechanical and design details of an apparatus should not be included in the abstract. The abstract should be in narrative form and generally limited to a single paragraph within the range of 50 to 150 words in length.
See MPEP § 608.01(b) for guidelines for the preparation of patent abstracts.
Applicant is reminded of the proper language and format for an abstract of the disclosure.
The abstract should be in narrative form and generally limited to a single paragraph on a separate sheet within the range of 50 to 150 words in length. The abstract should describe the disclosure sufficiently to assist readers in deciding whether there is a need for consulting the full patent text for details.
The language should be clear and concise and should not repeat information given in the title. It should avoid using phrases which can be implied, such as, “The disclosure concerns,” “The disclosure defined by this invention,” “The disclosure describes,” etc. In addition, the form and legal phraseology often used in patent claims, such as “means” and “said,” should be avoided.
The abstract of the disclosure is objected to because it uses legal phraseology. A corrected abstract of the disclosure is required and must be presented on a separate sheet, apart from any other text. See MPEP § 608.01(b).
The disclosure is objected to because of the following informalities:
The use of the term Chromatorex® (See USPTO trademark registry), which is a trade name or a mark used in commerce, has been noted in this application (pg. 10 of instant specification, top of page). The term should be accompanied by the generic terminology; furthermore the term should be capitalized wherever it appears or, where appropriate, include a proper symbol indicating use in commerce such as ™, SM , or ® following the term.
Although the use of trade names and marks used in commerce (i.e., trademarks, service marks, certification marks, and collective marks) are permissible in patent applications, the proprietary nature of the marks should be respected and every effort made to prevent their use in any manner which might adversely affect their validity as commercial marks.
Appropriate correction is required.
Claim Objections
Claim 12 objected to because of the following informalities: Claim 12 should recite “The process for purifying” to be consistent with claim 1 of which it depends.
Appropriate correction is required.
Claim Rejections - 35 USC § 112 (b)
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.
Claims 7 and 11 are 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 7 recites the limitation "said compound of formula (IV)". There is insufficient antecedent basis for this limitation in the claim.
Claim 11 is drawn to a manufacturing process for preparing a compound of formula (I) as defined in claim 1. However, claim 1 is not drawn to a compound but rather a purification process. It is unclear whether the claim is attempting to merely utilize the definition from claim 1, which is improper, or is meant to be dependent on claim 1 which is improper under 112(d) as described below. It is unclear whether infringement would occur only if the purification process were included or only following the steps recited by instant claim 11. The metes and bounds of the invention cannot be determined and the claim is rendered indefinite.
Claim Rejections - 35 USC § 112 (d)
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 11 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Claim 11 is drawn to a manufacturing process for preparing a compound of formula (I) as defined in claim 1. However, claim 1 is not drawn to a compound but rather a purification process. Thus claim 11 does not include all the limitations recited in claim 1 as the purification process is not explicitly required by instant claim 11.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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.
Claim 11 is rejected under 35 U.S.C. 103 as being unpatentable over Scherrer (WO 2016/135052, IDS filed June 21, 2024) in view of Hoffmann (Drug Metabolism and Disposition, 2007, cited on PTO-892) and Conrow (J. Organic Chemistry, 1971, cited on PTO-892).
Regarding claim 11: Scherrer teaches the
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(pg. 36, claim 1). Scherrer teaches the
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(pgs. 36-37, claim 6). Scherrer teaches the following synthesis
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(pg. 6, scheme 1). Scherrer teaches The reaction between compounds (2) and (3) may be performed according to a Koenigs-Knorr synthesis, which is well known to the man skilled in the art, suitably in a solvent such as nitromethane, typically at the reflux temperature of the solvent (pg. 7, lines 20-22) . Scherrer teaches compound (4) may be thereafter treated by using hydro-peroxide salts, for example by addition of hydrogen peroxide to a lithium hydroxide mono hydrate in water to obtain a solution of lithium hydroperoxide (pg. 7, lines 25-30). Compound (4) may thus be placed in a solvent such as tetrahydrofurane or dioxan in presence of the previous obtained solution, and be stirred for example during 0.5 to 1.5 hours (pg. 7, lines 25-30).
Scherrer does not teach wherein compound III is fractionally introduced into solution or wherein compound 4 is deprotected with lithium hydroxide in the absence of hydrogen peroxide.
However, Hoffmann teaches tigecycline glucuronide conjugates were synthesized using modified Koenigs-Knorr reaction conditions (Ag2CO3/MeCN in the presence of EDTA and molecule sieves) with an acyl-protected 1-bromo-sugar as the donor to generate protected tigecycline glucuronides followed by de-protection in the presence of 0.1 N lithium hydroxide (in methanol/water 1:1) (pg. 1545, col. 2, para. 6). Additionally Conrow teaches steroid glucuronide conjugates prepared from a Koenigs-Knorr reaction (abstract). Conrow teaches that the bromo sugar 1 decomposes during the reaction (pg. 864, col. 1, scheme, col. 1, bottom half of page). Conrow teaches a limited investigation of other reaction variables determined that complete reaction of the estrone was achieved when 2 equiv of bromo sugar were added dropwise, over 1 hr, to a mixture of the steroid and CdC03 in distilling toluene followed by an additional 0.5-hr reaction time (i.e. fractional introduction (pg. 864, col. 2, para. 1).
Taken together, it would have been prima facie obvious to modify the method of Scherrer such that compound III is fractionally introduced into solution as taught by Conrow and wherein compound 4 is deprotected with lithium hydroxide instead of in the presence of hydrogen peroxide as taught by Hoffmann. A person of ordinary skill in the art would have had the motivation to do so with a reasonable expectation of success in order to improve yield by avoiding decomposition of compound 3, and the art recognizes lithium hydroxide is a reagent that can deprotect acyl groups of glucuronide conjugates. Wherein lithium hydroxide is an established reagent for this purpose, it is prima facie obvious to substitute equivalents known for the same purpose (See MPEP 2144.06 (II)).
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 filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual 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/apply/applying-online/eterminal-disclaimer.
Claims 11 is rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 4 of U.S. Patent No. 10,329,317 (cited on PTO-892) in view of Hoffmann (Drug Metabolism and Disposition, 2007, cited on PTO-892) and Conrow (J. Organic Chemistry, 1971, cited on PTO-892).
The patented claims teach
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(claim 1). The patented claims teach
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(claim 4).
The patented claims do not teach wherein compound III is fractionally introduced into solution or wherein compound 4 is deprotected with lithium hydroxide in the absence of hydrogen peroxide.
However, Hoffmann teaches tigecycline glucuronide conjugates were synthesized using modified Koenigs-Knorr reaction conditions (Ag2CO3/MeCN in the presence of EDTA and molecule sieves) with an acyl-protected 1-bromo-sugar as the donor to generate protected tigecycline glucuronides followed by de-protection in the presence of 0.1 N lithium hydroxide (in methanol/water 1:1) (pg. 1545, col. 2, para. 6). Additionally Conrow teaches steroid glucuronide conjugates prepared from a Koenigs-Knorr reaction (abstract). Conrow teaches that the bromo sugar 1 decomposes during the reaction (pg. 864, col. 1, scheme, col. 1, bottom half of page). Conrow teaches a limited investigation of other reaction variables determined that complete reaction of the estrone was achieved when 2 equiv of bromo sugar were added dropwise, over 1 hr, to a mixture of the steroid and CdC03 in distilling toluene followed by an additional 0.5-hr reaction time (i.e. fractional introduction (pg. 864, col. 2, para. 1).
Taken together, it would have been prima facie obvious to modify the method of the patented claims such that compound III is fractionally introduced into solution as taught by Conrow and wherein compound 4 is deprotected with lithium hydroxide instead of in the presence of hydrogen peroxide as taught by Hoffmann. A person of ordinary skill in the art would have had the motivation to do so with a reasonable expectation of success in order to improve yield by avoiding decomposition of compound 3, and the art recognizes lithium hydroxide is a reagent that can deprotect acyl groups of glucuronide conjugates. Wherein lithium hydroxide is an established reagent for this purpose, it is prima facie obvious to substitute equivalents known for the same purpose (See MPEP 2144.06 (II)).
Allowable Subject Matter
Claims 1-6, 8-10, and 12 are objected to as having rejected dependent claims, but would be allowable if rewritten or amended to overcome the rejection(s) under 35 U.S.C. 112(b) and the 35 U.S.C. 112(d) as well as the claim objections set forth in this Office action.
The following is a statement of reasons for the indication of allowable subject matter: The closest prior art is Scherrer (WO 2016/135052, IDS filed June 21, 2024). Scherrer teaches the method as described above in the 103 rejections above. Scherrer teaches the purification includes extracting with ethyl acetate and chromatographing (pg. 25, lines 16-28). Scherrer does not teach purification via solubilizing with methanol and precipitating with water.
While precipitation is a general technique in the art of purifying compounds, it would be improper hindsight to suggest it would have been obvious to specifically use a methanol/water system to do so with a reasonable expectation of success as there is nothing in the prior art that suggests such a combination would result in improved purity of the claimed compounds.
Conclusion
No claims are allowed in this action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SAMUEL L GALSTER whose telephone number is (571)270-0933. The examiner can normally be reached Monday - Friday 8:00 AM - 5:00 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Y Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/SAMUEL L GALSTER/Examiner, Art Unit 1693
