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
This application is a Continuation of PCT/JP2021/046869 which claims the benefit of JP 2020-210289 with an effective filing date of 18 December 2020 as reflected in the filing receipt mailed on 07 July 2023.
Status of the Claims
Claims 1, 3, and 6-13 are pending.
Claims 1, 6, 7, and 13 are amended.
Claims 2 and 5 are currently cancelled.
Claim 4 was previously cancelled.
Response to Amendments
Applicant’s amendments filed 16 March 2026 are acknowledged.
Claim Rejections - 35 USC § 103
Applicant’s amendments to claims 1 and 13 limiting the fluorine sources in (A) and specifying chlorine as the source (B) are taught by Higashi and are not sufficient to overcome the rejection of claims 1-3 and 5-13 under 35 U.S.C. 103 as being unpatentable over Higashi et al. (US20180111898, hereinafter Higashi). The rejection is maintained; however due to the amendments to claims 1 and 13 and the cancellation of claims, modified ground(s) of rejection is/are provided below.
Response to Arguments
Applicant’s arguments filed 16 March 2026 have been fully considered but they are not persuasive.
Applicant’s argue that Higashi does not disclose the limitations as recited in amended claims 1 and 13. These arguments have been considered but are not persuasive for the reasons set forth in the modified grounds of rejection below and the response to arguments below.
In response to applications arguments on pages 6-7 of the remarks filed on 16 March 2026 that in Higashi “iodine would not be introduced to the unsaturated bond if IF5 is not used as an iodine source”, “Applicant's claims do not require the IF5-pyridine-HF complex. Applicant's invention can achieve the introduction of fluorine and chlorine to an unsaturated bond by using the specific combination of the fluorine source (A) and the chlorine source (B)”, and “Higashi fails to disclose or suggest a fluorination and halogenation other than iodination, especially chlorination reaction without using the IF5-pyridine-HF complex.” “The use of patents as references is not limited to what the patentees describe as their own inventions or to the problems with which they are concerned. They are part of the literature of the art, relevant for all they contain”, see In re Heck, 699 F.2d 1331, 1332-33, 216 USPQ 1038, 1039 (Fed. Cir. 1983) (quoting In re Lemelson, 397 F.2d 1006, 1009, 158 USPQ 275, 277 (CCPA 1968)) and MPEP 2123.
In this case, Higashi teaches “fluorine or iodine is added to a carbon-carbon double bond or carbon-carbon triple bond” [emphasis added], where “R8a, R8a′R8b, and R8b′ may be the same or different, and each represents a … halogen atom”, see Paras. [0186]-[0187], as stated on page 4 of the previous office action dated 15 December 2025 “Higashi Formula 1 is contacted with a fluorinating/halogenating composition comprising IF5, HF, IF5-pyridine-HF, acids, bases, salts, and/or additives, see Paras. [0017]-[0032];[0072]”, “IF5 may be complexed with an acid and a base” [emphasis added], see Para. [0110], and the “halogens include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom”, see Paras. [0093];[0193]. Therefore, Higashi teaches iodine may not be added to a carbon-carbon double bond or carbon-carbon triple bond, IF5 may not be used, and HF, chlorine, fluorine, salts, and/or additives are added to Formula I. Higashi teaches the addition salts include “sodium fluoride, potassium fluoride, cesium fluoride, ammonium fluoride, tetraethylammonium fluoride, tetrabutylammonium fluoride, polyarylammonium fluoride, sodium chloride, ammonium chloride, sodium hypochlorite, sodium chlorite, sodium chlorate, sodium perchlorate”, “NaBF4, KBF4, LiBF4, NaSbF6, NaAsF6, NaPF6, NH4BF4, NH4SbF6, NH4PF6, and like metal salts or amine salts formed of Lewis acids and hydrogen halide”, where “[t]hese salts may be used alone or in a combination of two or more”, and “[t]he composition of the present invention particularly preferably contains HF as an acid and pyridine as a base”, see Paras. [0099]-[0100];[0103];[0106]-[0109]. In addition, Higashi teaches “the composition of the present invention may contain IF5, pyridine, HF, or a combination thereof, which do not constitute IF5-pyridine-HF. The amount thereof is preferably 45 mass % or less in total” [emphasis added], see Para. [0121]. Therefore, Higashi also does not require iodine or the IF5-pyridine-HF complex and Higashi adds halogens, such as chlorine to the double or triple bond.
As stated on pages 4-5 of the POA, Higashi teaches additional “examples of salts include sodium hypochlorite, sodium chlorite, sodium chlorate, sodium perchlorate, sodium perbromate, sodium periodate, etc., including a plurality of instantly claimed R3(OX)m compounds, for example sodium hypochlorite NaClO, where R3 is sodium, X is chlorine, and m is 1, see Paras. [0098]-[0099];[0103]”. Higashi also teaches “additives include halogens, interhalogen compounds, polyhalides, and the like” containing a chlorine source, see Paras. [0092]-[0096];[0193], where these halogens are “added to a carbon-carbon double bond or carbon-carbon triple bond”, see Paras. [0186]-[0187]. Therefore, Higashi teaches adding halogens, such a fluorine atom, a chlorine atom, a bromine atom, and/or an iodine atom “to a carbon-carbon double bond or carbon-carbon triple bond”, see Paras. [0092]-[0095];[0186]-[0187];[0193].
A rationale to support a conclusion that the claim would have been obvious is that a particular known technique was recognized as part of the ordinary capabilities of one skilled in the art. Another rationale to support a conclusion that the claim would have been obvious is that the substitution of one known element for another yields predictable results to one of ordinary skill in the art. One of ordinary skill in the art would have been capable of modifying Higashi to select the appropriate halogen source for adding to a carbon-carbon double bond or a carbon-carbon triple bond as taught by Higashi with a reasonable predictability of success for the purpose of efficiently adding halogens to compounds having a carbon-carbon double bond or a carbon-carbon triple bond at high yield without using toxic, corrosive, and explosive chemical reactants, see Higashi, Paras. [0002]-[0005];[0011];[0098]-[0099];[0103];[0186]-[0212]; and MPEP 2143 I. B-D.
Furthermore, instant claim 1 states “the method comprising reacting the compound represented by formula (1) with …” [emphasis added]. Instant claim 13 states “A halogenating agent comprising (A) and (B) below: …” [emphasis added]. MPEP 2111.03 I. states “[t]he transitional term “comprising”, which is synonymous with “including,” “containing,” or “characterized by,” is inclusive or open-ended and does not exclude additional, unrecited elements or method steps.” Therefore, instant claims 1 and 13 do not exclude the addition of IF5, pyridine and/or the IF5-pyridine-HF complex along with the claimed fluorine sources and the claimed chlorine source.
For the reasons indicated above, applicant’s above arguments are not persuasive.
Maintained and Modified Rejections Based on Amendments to the Claims in the reply filed on 16 March 2026
In the Spirit of Compact Prosecution
Throughout prosecution the examiner has attempted to identify all objections and clarity issues amongst the claims, applicant is advised that some objections and clarity issues may still remain. Going forward, the examiner respectfully requests applicant to perform a detailed review of the claims regarding clarity, grammar, antecedent basis, word spacing, and spelling issues.
For clarity between the modified and maintained rejections, the specific modified rejections below are in italics.
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, 3, and 6-13 stand rejected in modified form under 35 U.S.C. 103 as being unpatentable over Higashi et al. (US20180111898, published 26 April 2018, hereinafter Higashi).
Higashi teaches the claims 1, 3, and 6-13 limitations of a method for producing a fluorinated organic compound with a high yield, see Abstract, where “a fluorine atom, a chlorine atom, a bromine atom, and[/or] an iodine atom” are added to a carbon-carbon double bond or carbon-carbon triple bond, such as the formula R8aR8a’=CR8bR8b’, hereinafter Higashi Formula 1, to yield FR8aC-CR8bI,
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102
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, where R8a is C2 alkyl, and R8a’, R8b, R8b’ are each independently hydrogen or a halogen atom, such as a chlorine atom, see Paras. [0186]-[0212], meeting formula (1) and formula 1(a), where n is 2, one R1 is R1a which is C1 alkyl, one R1 is hydrogen, and each R2 is independently a hydrogen atom or a halogen atom in instant application claim 1, in instant application claim 8, and in instant application claim 10,
Instant application claim 9 depends from instant application claim 8 where R1 and R2 are as indicated above; therefore, instant application claim 9 is optional and is met as is instant application claim 8. In addition, R8a or R1/R1a may be “an alkyl group that may have at least one substituent” such as “C1-6 alkyl groups, halogen atoms, C1-6 alkoxy groups, C1-6alkylthio, cyano, nitro, an amino group, a hydroxyl group, and the like”, see Paras. [0186]-[0187];[0210], meeting the limitations in instant application claim 9;
The addition of fluorine and an additional chlorine halide to Higashi Formula 1 in instant application claim 1 and in instant application claim 13;
Higashi Formula 1 is contacted with a fluorinating/halogenating composition comprising HF, acids, bases, salts, and/or additives, see Paras. [0017]-[0032];[0072];[0193], where one or more addition acids include “hydrogen fluoride, fluoric acid, hydrochloric acid” “hypochlorous acid, chlorous acid, chloric acid, perchloric acid”, see Paras. [0073]-[0077], where one or more addition salts include “sodium fluoride, potassium fluoride, cesium fluoride, ammonium fluoride, tetraethylammonium fluoride, tetrabutylammonium fluoride, polyarylammonium fluoride, sodium chloride, ammonium chloride, sodium hypochlorite, sodium chlorite, sodium chlorate, sodium perchlorate”, “NaBF4, KBF4, LiBF4, NaSbF6, NaAsF6, NaPF6, NH4BF4, NH4SbF6, NH4PF6, and like metal salts or amine salts formed of Lewis acids and hydrogen halide”, where “[t]hese salts may be used alone or in a combination of two or more”, see Paras. [0098]-[0100];[0103];[0106]-[0108], and “R8a, R8a′R8b, and R8b′ may be the same or different, and each represents a … halogen atom” of “a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom”, see Paras. [0186]-[0187];[0193], meeting the specific (A) fluorine source in instant application claim 1 and instant application claim 13;
The acid and the base may exist as a salt in the composition, see Para. [0098], examples of salts include sodium hypochlorite, sodium chlorite, sodium chlorate, sodium perchlorate, sodium perbromate, sodium periodate, etc., including a plurality of instantly claimed R3(OX)m compounds, for example sodium hypochlorite NaClO, where R3 is sodium, X is chlorine, and m is 1, see Paras. [0098]-[0099];[0103], meeting the specific chlorine halogen source (B) formula in instant application claim 1, in instant application claim 6, and instant application claim 13;
The reaction takes place in an organic solvent, such as methylene chloride, see Paras. [0012]-[0015];[0217]-[0220], meeting the specific solvent in instant application claim 11 and in instant application claim 12;
The acid and the base contain fluorine and chlorine, see Paras. [0098]-[0100];[0103];[0106]-[0109]. The amount of acid “is preferably within a range of 0.5 to 20 mol, more preferably within a range of 0.8 to 10 mol, and even more preferably within a range of 0.9 to 5 mol, per mol of IF5”, see Para. [0080], the amount of base “is preferably within a range of 0.5 to 20 mol, more preferably within a range of 0.8 to 10 mol, and still more preferably within a range of 0.9 to 5 mol, per mol of IF5”, see Para. [0091], “IF5 may be complexed with an acid and a base”, see Para. [0110], and “the amount of the IF5 is within a range of 0.2 to 10 mol per mol of the moiety subjected to fluorination of the organic compound”, which is a starting compound, see Para. [0213], for example, as calculated by the examiner based on about 1 mol of IF5 per mole of the Higashi Formula 1 compound equates to a chlorine or fluorine containing acid of about 1 x 0.5 to 1 x 20 or 0.5 to 20 mol of a chlorine or fluorine containing acid per mole of Higashi Formula 1 compound and equates to a chlorine or fluorine containing base of about 1 x 0.5 to 1 x 20 or 0.5 to 20 mol of a chlorine or fluorine containing base per mole of Higashi Formula 1 compound, meeting and within the range of the fluorine source in instant application claim 3 and the chlorine source in instant application claim 7;
The amount of the IF5 is within a range of 0.2 to 10 mol per mol of the moiety subjected to fluorination of the organic compound, such as the Higashi Formula 1 compound, see Para. [0213], the acid and the base may exist as a salt in the composition, see Paras. [0098]-[0099];[0103], the amount of acid is preferably within a range of 0.5 to 20 mol, more preferably within a range of 0.8 to 10 mol, and even more preferably within a range of 0.9 to 5 mol, per mol of IF5, see Para. [0080], and the amount of base is preferably within a range of 0.5 to 20 mol, more preferably within a range of 0.8 to 10 mol, and still more preferably within a range of 0.9 to 5 mol, per mol of IF5, see Para. [0091], as calculated by the examiner the halogen chlorine source salt (B) is within a range of (half of 0.2 mol IF5) = 0.1 to (20 x 10 mol IF5) = 200 mol of the moiety subjected to chlorination and fluorination of the organic compound, such as the Higashi Formula 1, meeting within the range of the chlorine source in instant application claim 7.
Higashi does not disclose the above limitations in one single express embodiment.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified Higashi to select various specific acids, bases, combined acid base salts, and additives with a reasonable predictability of success for the purpose of adding halogens to compounds having a carbon-carbon double bond or a carbon-carbon triple bond at high yield without using toxic, corrosive, and explosive chemical reactants, see Paras. [0002]-[0005];[0011];[0098]-[0099];[0103];[0186]-[0212].
By applying “routine optimization” and “predictable results” to select the optimal salt reactants for halogenation of an organic compound, one of ordinary skill in the art would have been motivated to make these modifications because Higashi provides a finite number of identified, predictable solutions. A person of ordinary skill in the art has good reason to add halogens to compounds having a carbon-carbon double bond or a carbon-carbon triple bond at high yield without using toxic, corrosive, and explosive chemical reactants, see Paras. [0002]-[0005];[0011];[0098]-[0099];[0103];[0186]-[0212] and MPEP 2141 and 2145 X.B
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Higashi teaches halogenation of organic compounds, a person of ordinary skill in the art has good reason to add fluorine and iodine to an organic compound, by pursuing the known options within their technical grasp before the effective filing date of the claimed invention for the benefit of adding halogens to compounds having a carbon-carbon double bond or a carbon-carbon triple bond at high yield without using toxic, corrosive, and explosive chemical reactants, see Paras. [0002]-[0005];[0011];[0098]-[0099];[0103];[0186]-[0212] and MPEP 2141.
A rationale to support a conclusion that the claim would have been obvious is that a particular known technique was recognized as part of the ordinary capabilities of one skilled in the art. Another rationale to support a conclusion that the claim would have been obvious is that the substitution of one known element for another yields predictable results to one of ordinary skill in the art. One of ordinary skill in the art would have been capable of modifying Higashi to select the appropriate halogen source for adding to a carbon-carbon double bond or a carbon-carbon triple bond as taught by Higashi with a reasonable predictability of success for the purpose of efficiently adding halogens to compounds having a carbon-carbon double bond or a carbon-carbon triple bond at high yield without using toxic, corrosive, and explosive chemical reactants, see Paras. [0002]-[0005];[0011];[0098]-[0099];[0103];[0186]-[0212]; and MPEP 2143 I. B-D.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §
103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”, see MPEP 2141.
Selection of a known materials, various specific combined acid base salts, based on their suitability for their intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945), see MPEP 2144.07.
In addition, “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions,” such as the moles of reactants in the reaction, “or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions. In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929)”, see MPEP 2144.05.
Conclusion
No claims are 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 nonprovisional extension fee (37 CFR 1.17(a)) 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 mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Y. Lynnette Kelly-O'Neill whose telephone number is (571) 270-3456. The examiner can normally be reached Tuesday-Friday, 8:30 a.m. - 6:30 p.m., EST, with Flex Time.
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/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699
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