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 .
Election/Restrictions
Applicant’s election without traverse of Group I, drawn to a compound of formula (I) or a pharmaceutically acceptable salt thereof; and a pharmaceutical composition comprising the compound of formula (I) or pharmaceutically acceptable salt thereof and a therapeutically inert carrier; and (3R)-N-[2,4-difluoro-3-[8-methyl-7-oxo-2-(2-phenylethylamino)pyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-fluoropyrrolidinel-sulfonamide, which is the compound having the structure of:
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as the elected compound species of formula (I) are maintained.
Claims 16 and 18-20 remain withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Expansion of Election of Species Requirement
A reasonable and comprehensive search of the elected compound species of formula (I) conducted by the Examiner determined that the prior art at the time of the present invention was such that it did not anticipate or render obvious the elected compound species:
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. In light of this discovery, the search was expanded to the subject matter of the subgenus of the elected compound species, i.e.,
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, and (3R)-N-[3-[2-( cyclopropylmethylamino)-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2,4-difluorophenyl]-3-fluoropyrrolidine-1-sulfonamide having the structure of:
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(see page 62, compound 10 of the instant specification).
Status of Claims
Acknowledgement is made of the receipt and entry of the amendment to the claims filed on June 26, 2026, wherein claims 1-15 and 17-20 are unchanged; and claim 16 is amended.
Claims 1-20 are pending.
Claims 16 and 18-20 are withdrawn.
Claims 1-15 and 17 are under examination in accordance with the elected species along with the expanded species set forth in the Expansion of Election of Species Requirement section above.
Priority
The instant application 18/210,991 filed on June 16, 2023 is a continuation of PCT/EP2021/086050 filed on December 16, 2021, which claims priority to, and the benefits of Foreign Application No. EP20215299.7 filed on December 18, 2020.
Action Summary
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Acknowledgement is made of the receipt and entry of the amendment to title of the invention and the specification filed on June 26, 2026. Specifically, the specification has been amended the redrawn the double bonds within the sulfur dioxide group for clarity. Applicant’s amendment to the specification overcomes each and every objection previously set forth in the Non-Final Office Action mailed on January 26, 2026.
Claims 1-15 and 17 rejected under 35 U.S.C. 103 as being unpatentable over Ren et al. (Bioorg Med Chem Lett. 2012;22(10):3387-3391; cited in the IDS filed on August 14, 2024), in view of Ding et al. (WO 2005/034869 A2) are maintained.
Claim Rejections - 35 USC § 103
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 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 1-15 and 17 remain rejected under 35 U.S.C. 103 as being unpatentable over Ren et al. (Bioorg Med Chem Lett. 2012;22(10):3387-3391; cited in the IDS filed on August 14, 2024), in view of Ding et al. (WO 2005/034869 A2).
Ren et al. teaches B-Raf inhibitor compound 17 having the structure of (see shaded):
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is a potent, selective and orally available agent with excellent pharmacokinetic properties and robust tumor growth inhibition in xenograft studies (see e.g., Table 4; abstract).
Ren et al. does not teach a compound of formula (I).
Ding et al. teaches a compound of Example 2 having the structure of:
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is an exemplary compound of Formula I (see e.g., p. 24, Example 2). Ding et al. further teaches compounds of Formula I:
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useful for modulating the activity of protein tyrosine kinases (see e.g., [0019]), wherein Y is selected from -C(H)= and -N=; R1 is selected from, inter alia, hydrogen and R4; R4 is selected from -XNR5S(O)0-2R6 ; wherein X is a bond; R5 is, inter alia, hydrogen; R6 is selected from, inter alia, C1-6 alkyl and C3-8heterocycloalkyl-C0-4alkyl; wherein any heterocycloalkyl of R4 is optionally substituted by 1 to 3 radicals independently selected from, inter alia, halo (see e.g., [0005]). Ding et al. further teaches the term “halogen” (or halo) preferably represents chloro or fluoro (see e.g., [0013]). Ding et al. further teaches examples of “heterocycloalkyl” includes, inter alia, pyrrolidinyl (see e.g., [0012]). Ding et al. further teaches the compounds of the present invention also inhibit cellular processes involving b-Raf kinase, providing a new therapeutic opportunity for treatment of human cancers, especially for melanoma (see e.g., [0031]). Ding et al. further teaches compounds of the invention can be prepared as their individual stereoisomers by reacting a racemic mixture of the compound with an optically active resolving agent to form a pair of diastereoisomeric compounds, separating the diastereomers and recovering the optically pure enantiomers (see e.g., [0063]). Ding et al. further teaches a pharmaceutical composition comprising the compound in free form or in a pharmaceutically acceptable salt form in association with at least one pharmaceutically acceptable carrier or diluent can be manufactured in a conventional manner by mixing, granulating or coating methods (see e.g., [0043]).
In the present case, Ren et al. teaches compound 17 is a B-Raf inhibitor. The difference between the compound 17 of Ren et al. and the claimed compound of formula (I) is that the prior art compound has propyl (-CH2-CH2-CH3) substituted on the sulfur dioxide moiety rather than a pyrrolidine ring shown below (see shaded):
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. It would have been prima facie obvious to one of ordinary skill in the art at the time the application was filed to select the compound 17 of Ren et al., and then modify said compound by substituting the propyl with a pyrrolidine ring in view of the Formula (I) taught by Ding et al. to arrive at the claimed invention. One would have been motivated to do so, because Ding et al. teaches compounds of Formula (I) are also useful for inhibiting cellular processes involving b-Raf kinase; and further teaches a list of R6, including C1-6 alkyl and heterocycloalkyl such as pyrrolidinyl, that can be interchanged to give the -XNR5S(O)0-2R6 moiety at the R4 position of Formula I. One would have a reasonable expectation of success to arrive at the claimed invention, because one would have reasonably expected that the compound 17 of Ren et al. is structurally similar to compound of Formula (I) taught by Ding et al. with similar utilities (B-Raf inhibitor), and therefore, said compound 17 modified in view of the Formula (I) of Ding et al. by substituting the propyl with a pyrrolidine ring as the heterocycloalkyl would have successfully arrive at a compound that is similarity useful for inhibiting cellular processes involving b-Raf kinase; and one would have reasonably expected that said modified compound can successfully be combined with a pharmaceutically acceptable carrier to arrive at a pharmaceutical composition. Please note the pharmaceutically acceptable carrier taught by Ding et al. is a therapeutically inert carrier. Please note the modified compound 17 of Ren et al. in view of Ding et al. sets forth above is a compound of formula (I)
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instantly claimed, wherein R1 is
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; R2 and R3 are fluorine; R4 is methyl; n is 1; R5 is
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.
Regarding the limitations recites in claims 4-5 and 14-15, the difference between the modified compound 17 of Ren et al. and Ding et al. sets forth above and the claimed compound, (3R)-N-[2,4-difluoro-3-[8-methyl-7-oxo-2-(2-phenylethylamino)pyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-fluoropyrrolidinel-sulfonamide, is that the claimed compound has a fluorine atom substituted on the pyrrolidine ring shown below (see shaded):
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.
It would have been prima facie obvious to one of ordinary skill in the art at the time the application was filed to modify the modified compound 17 of Ren et al. and Ding et al. sets forth above by substituting the heterocycloalkyl, in this case, the pyrrolidinyl ring with a fluorine atom as the halogen as taught by Ding et al. One would have been motivated to do so, because Ding et al. further teaches the any heterocycloalkyl of R4 can be optionally substituted by 1 to 3 radicals, including halo that is preferably chloro or fluoro, to arrive at the compound of Formula I useful for inhibiting cellular processes involving b-Raf kinase; and further teaches the compound can be prepared as their individual stereoisomers from the racemic mixture of the compound. One would have a reasonable expectation of success to arrive at the claimed invention, because one would have reasonably expected that the modified compound 17 of Ren et al. and Ding et al. substituted with a fluorine atom on the pyrrolidinyl ring would have successfully arrive at a compound useful for inhibiting cellular processes involving b-Raf kinase. Please note the fact that Ding et al. teaches individual stereoisomers of the compound separate from the racemic mixture of the compound renders obvious the limitation of
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instantly claimed.
Therefore, the claimed invention is prima facie obvious to one of ordinary skill in the art at the time the application was filed, absent factual evidence to the contrary.
Response to Arguments
Applicant's arguments filed on August 27, 2026 with respect to the rejection of claims 1-15 and 17 under 35 U.S.C. 103 as being unpatentable over Ren et al. (Bioorg Med Chem Lett. 2012;22(10):3387-3391; cited in the IDS filed on August 14, 2024), in view of Ding et al. (WO 2005/034869 A2) have been fully considered but they are not persuasive.
In Summary, Applicant argues the claimed compounds of Formula (I) are BRAF inhibitors that show “considerably less paradoxical activation of the MAPK signaling pathway” by directing attention to page 3, line 18-20 of the specification:
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, and noted that it is supported by the data represented in Table 1 on page 85-88 of the specification. Specifically, Applicant argues the sixth column of Table 1 disclosed compound 1-50 demonstrate desirable selectively for inhibiting P-ERK formation. Applicant further argues Ren et al. is completely silent that the BRAF inhibitors have the properties of “paradox breaking” and provides no motivation to develop “paradox breaking” BRAF inhibitors. Applicant further argues that the examiner’s conclusion of obvious is based upon improper hindsight reasoning, because only one out of 139 compounds contain -NHS(O2)- moiety, and none of the exemplified compounds contain the moieties of
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or
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.
Ding et al. also fails to disclose any “paradox breaking” BRAF inhibitors and only disclose the kinase inhibitory activity data of one compound, i.e., example 8, and said compound was highly unselective with activity against over a dozen kinases; and therefore, one would not have reasonably modify the compounds of Ren et al. based on the teachings of Ding et al. Applicant further argues the compound of Example 8 of Ding et al. is structurally distinct, and provides no reason for one of ordinary skill in the art to select such compound for modification.
In response, applicant’s arguments are not found persuasive for the reasons set forth below:
First, the mere fact that Ren et al. and Ding et al. are silent regarding the “paradox breaking” property or silent about having “considerably less paradoxical activation of the MAPK signaling pathway”, it does not undermine the motivation to modify the B-Raf inhibitor compound 17 of Ren et al. According to MPEP 2144, IV, “[t]he reason or motivation to modify the reference may often suggest what the inventor has done, but for a different purpose or to solve a different problem. It is not necessary that the prior art suggest the combination to achieve the same advantage or result discovered by applicant. See, e.g., In re Kahn, 441 F.3d 977, 987, 78 USPQ2d 1329, 1336 (Fed. Cir. 2006)”. While Ren et al. and Ding et al. are both silent about the property of “paradox breaking”, the reason or motivation to modify the compound 17 of Ren et al. set forth in the rejection of record is based on the fact that said compound 17 and the compound of Formula (I) of Ding et al. shares very close structural similarities and are both taught to have B-Raf inhibiting effect, and would expected that the compound 17 of Ren et al. modified in view of the Formula (I) of Ding et al. by substituting the propyl with a pyrrolidine ring as the heterocycloalkyl would have successfully arrive at a compound that is similarity useful for inhibiting cellular processes involving b-Raf kinase; rather than achieving “less paradoxical activation of the MAPK signaling pathway" specifically challenged by the applicant.
Additionally, Applicant’s assertion that the “less paradoxical activation of the MAPK signaling pathway”, also referred to therein as “paradox breaking”, is an unexpected property of the claimed invention appears to be mere argument without factual support. Applicant fails to provide any comparative evidence showing that the claimed invention actually exhibits an unexpected reduction in paradoxical MAPK activation relative to the closest prior art compound(s). Merely asserting that the claimed compounds have reduced paradoxical activation of the MAPK signaling pathway or pointing out that the prior art does not discuss that property, does not establish that the property of paradox breaking is unexpected. One cannot take prior arts’ silence regarding the property of “paradox breaking” in their BRAF inhibitors as an admission that the property was absent, because a chemical compound and its properties are inseparable. Therefore, without any side-by-side comparison or other persuasive evidence establishing the magnitude and unexpectedness of paradoxical MAPK activation, such arguments presented by the applicant cannot take the place of evidence in the record. In re Schulze, 346 F.2d 600, 602, 145 USPQ 716, 718 (CCPA 1965) and In re De Blauwe, 736 F.2d 699, 705, 222 USPQ 191, 196 (Fed. Cir. 1984). Examples of statements which are not evidence and which must be supported by an appropriate affidavit or declaration include statements regarding unexpected results, commercial success, solution of a long-felt need, inoperability of the prior art, invention before the date of the reference, and allegations that the author(s) of the prior art derived the disclosed subject matter from the inventor or at least one joint inventor.
Furthermore, Applicant’s assertion of unexpected results is not commensurate in scope with the claimed invention. According to MPEP 716.02(d), “whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the ‘objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support.’ In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range. In re Clemens, 622 F.2d 1029, 1036, 206 USPQ 289, 296 (CCPA 1980)”. In this case, Applicant argues unexpected results are demonstrated in Table 1 of the specification, specifically, column 6 of Table 1 that disclosed the “Fold Selectivity HCT-116 EC50-50/A375” of compound ex. 1 to 50. In contrast, claim 1 broadly recites a compound of formula (I) composed of wide variety of substituents, including R1-R5 and n.
It is respectfully noted that Applicant only exemplified the unexpected result using compound ex. 1 to 50, in which compound ex 39 is reported therein to have 1.0 fold selectivity (see e.g., Table 1). According to Example 39 on page 78 of the specification, said compound ex 39 has the chemical name of (3R)-N-[3-[8-[2-[2-(2-aminoethoxy)ethoxy]ethyl ]-2-(cyclopropylmethylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2,4-difluorophenyl]-3-fluoropyrrolidine-1-sulfonamide hydrochloride and is encompassed by the instant claims. In other words, the 1 fold ratio reports therein represent no change between two measured values; therefore, the disclosure does not provide adequate basis for concluding that similar unexpected results would be obtained for other species of compound of Formula (I) given that the compound ex 39 encompassed by instant claims clearly does not have the desired fold change. Accordingly, these findings demonstrate that applicant’s assertion of unexpected results is not commensurate in scope with the claimed invention and are not found persuasive.
Second, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986). In this case, applicant improperly evaluate each reference individually rather than considering the combined teachings of the reference as a whole. It is respectfully noted that applicant presents arguments specifically against Ren et al. and Ding et al., respectively, rather than considering all the cited prior arts together. It is respectfully noted that the obviousness-type rejection under 35 U.S.C. 103 does not require that each and every claimed limitation be disclosed within a single reference. Rather, the issue is whether the collective teachings of the prior art(s) would have suggested the claimed invention to one of ordinary skill in the art with a reasonable expectation of success. For instance, applicant argues Ding et al. fails to teach
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when the rejection of record relies on Ren et al. to teach a B-Raf inhibitor compound 17, which already contain such moiety. Additionally, applicant argues Ren et al. fails to teach the modification of propyl sulfonamide when the rejection of record further relies on Ding et al. to teach a list of R6, including C1-6alkyl and C3-8 heterocycloalkyl-C0-4alkyl, suitable to form the -XNR5(SO)0-2R6 moiety at R4 of Formula I to arrive at compounds useful for inhibiting cellular processes involving b-Raf kinase; and expressly demonstrates the compound of Example 2 having the structure of:
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(see e.g., p. 24, Example 2), which contains -NH(SO)2R6- at R4, is one of the exemplary compounds of Formula I that are tested for their ability to inhibit the activity of b-Raf (see e.g., [0067]; [00166]; [00168]). In other words, while Ren et al. does not expressly modify the propyl sulfonamide, the disclosure of Ding et al. provides teachings, suggestions or motivations to do so.
Third, applicant appears to mischaracterize the rejection of record. Specifically, applicant argues the compound of Example 8 of Ding et al. is structurally distinct and one would not have a reasonable expectation of success to modify said compound to arrive at the claimed invention; However, the obviousness-type rejection of record is not form on the basis that Ding et al. teaches a compound of Example 8. Instead, the rejection relies on Ren et al. to teach a compound 17 with B-Raf inhibiting properties, and Ding et al. to teach a list of R6, including C1-6alkyl and C3-8 heterocycloalkyl-C0-4alkyl, suitable to form the -XNR5(SO)0-2R6 moiety at R4 of Formula I to arrive at compounds useful for inhibiting cellular processes involving b-Raf kinase; and that does not rely on compound of Example 8 of Ding et al.
In response to applicant's argument that the examiner's conclusion of obviousness is based upon improper hindsight reasoning, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971). According to MPEP 2123, II, “[d]isclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments. In re Susi, 440 F.2d 442, 169 USPQ 423 (CCPA 1971)”. In other words, the mere fact that Ding et al. teaches compound of Example 8, N-{3-[7-(6-Methoxy-pyridin-3-ylamino)-1-methyl-2-oxo-1,2-dihydro-[1,6]naphthyridin-3-yl]-4-methyl-phenyl}-3-trifluoromethyl-benzamide, has an IC50 of 500 nM for b-Raf enzyme assays (see e.g., [00170]), such disclosure does not constitute a teachings away from a broader disclosure. In other words, such disclosure does not mean the compounds of Formula I taught by Ding et al., including the compound of Example 2, would not exhibit b-Raf inhibiting effect. While Ding et al. does not expressly disclose the b-Raf inhibitory assay of compound of Example 2, Ding et al. clearly teaches compounds of the invention are tested for their ability to inhibit the activity of b-Raf (se e.g., [00166]); and inhibit cellular process involving b-Raf kinase, providing a new therapeutic opportunity for treatment of human cancers, especially for melanoma (see e.g., [0031]). According to MPEP 2121, I, “[w]hen the reference relied on expressly anticipates or makes obvious all of the elements of the claimed invention, the reference is presumed to be operable. Once such a reference is found, the burden is on applicant to rebut the presumption of operability. In re Sasse, 629 F.2d 675, 207 USPQ 107 (CCPA 1980). See also MPEP § 716.07. See also In re Antor Media Corp., 689 F.3d 1282, 103 USPQ2d 1555 (Fed. Cir. 2012)”. Same logic is applicable to instant case, if applicant contends the compounds of Formula I taught by Ding et al., including compound of Example 2 and compounds of Formula (I) with the -XNR5S(O)0-2R6 at R4, is incapable of exhibiting b-Raf inhibiting effect, said objective evidence is respectfully requested.
Moreover, according to MPEP 2141.02, VI, “[a] prior art reference must be considered in its entirety, i.e., as a whole, including portions that would lead away from the claimed invention. W.L. Gore & Assoc., Inc. v. Garlock, Inc., 721 F.2d 1540, 220 USPQ 303 (Fed. Cir. 1983), cert. denied, 469 U.S. 851 (1984)”; and “’the prior art’s mere disclosure of more than one alternative does not constitute a teaching away from any of these alternatives because such disclosure does not criticize, discredit, or otherwise discourage the solution claimed….’ In re Fulton, 391 F.3d 1195, 1201, 73 USPQ2d 1141, 1146 (Fed. Cir. 2004). See also MPEP § 2123”. In this case, the mere fact that Ding et al. also teaches other compounds of formula (I) that is not a compound of example 2, and other alternatives suitable at R4, it does not mean Ding et al. is criticizing, discrediting or otherwise discourage the incorporate of C3-8heterocycloalkyl-C0-4alkyl, including pyrrolidinyl as the pyrrolidinyl (see e.g., [0012], as the R6 alternative taught by Ding et al. to form -NHS(O)2R6 at R4, because Ding et al. clearly demonstrates a compound of Example 2:
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, which contains the -NHS(O)2R6 moiety at R4, as an exemplary compound of Formula I (see e.g., p. 24, Example 2); and expressly teaches a list of R6, including C1-6 alkyl and C3-8heterocycloalkyl-C0-4alkyl (see e.g., [0005]), such as pyrrolidinyl as the exemplary heterocycloalkyl (see e.g., [0012]), that are contemplated for use to arrive at compounds with similar activity.
In view of the foregoing, applicant’s argument is not found persuasive; and therefore, the rejection of record has been maintained for the same reason of record and for the reasons set forth herein.
Conclusion
No claims are allowed.
THIS ACTION IS MADE FINAL. 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 Chihyi Lee whose telephone number is (571)270-0663. The examiner can normally be reached Monday - Friday 8:30 am - 5:00 pm EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Amy L. Clark can be reached at (571) 272-1310. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/CHIHYI LEE/Examiner, Art Unit 1628 /JEAN P CORNET/Primary Examiner, Art Unit 1628
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