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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on August 11, 2026 has been entered.
Claims 1-2,12-13,15,18-19,22-23,25-26,30,31,33 and 179-183 are pending. Claims 3-11,14,16,17,20,21,24,27-29,32 and 34-178 have been cancelled. Claims 1,15 and 182 have been amended.
The rejection of Claim 182 under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, is withdrawn in view of applicant’s amendments to the claim.
Claims 1,2,12,13,15,18,19,23,25 stand rejected under 35 U.S.C. 103 as being unpatentable over Bartholomew (US 2020/0048469) for the reasons set forth below.
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.
Claims 1,2,12,13,15,18,19,22,23,25 and 179-183 are rejected under 35 U.S.C. 103 as being unpatentable over Bartholomew (US 2020/0048469).
Bartholomew teaches tandem dyes which are water soluble (paragraph 0099) and have absorbance maximums of 550nm to 600 nm (paragraph 0154). Bartholomew teaches the dyes of formula (I) paragraph 0032, wherein
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Y1 and Y2 can be the species attached to the B paragraph 0092 where q is 6-20, also see the figures on the right column of page 10, with q=11 or 16, in particular the last formula on the right column of page 10. q can be 11 or 16 as any value between 6-20 is taught. R2 and R7 can be substituted or unsubstituted aryl (phenyl, paragraph 0035) wherein the substituent is 2-20 polyethylene glycol units and polyethers of (CH2CH2O)pR (paragraph 0129-0131). R2 can be a WSG which can be halogen (chlorine is one of the 4 halogens; paragraph 0129) or Z1 can be carboxylic acid, paragraph 0074, paragraph 0068, formula (VIIa). R2 can be arylene substituted with aryl or aryl substituted with cyano (paragraphs 0035, 0360). R1 can be alkyl substituted with carboxyl (paragraph 0035, 0360). R3 and R4 can make a 5- or 6-membered fused heterocycle (paragraph 0036). Substituents can be substituted aryls (paragraph 0360), allowing for alkylene with a substituted aryl group.
Bartholomew teaches compounds of paragraph 0092
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In which q is 6-20 (entirely in applicant’s 6-24 range of claim 12, wherein the R5 group can be selected from aryl, substituted aryl which embody 2 of 15 choices of R5 in paragraph 0035. Further R2 can be a halogen water solubilizing group and R3-R4 can be the claimed aryl or heteroaryl groups particularly a fused 6 membered aryl ring (paragraphs 0036, 0129).
Bartholomew also teaches compounds of paragraph 0092,
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in which the phenyl group attaches to the alkenyl group may be substituted since substituents can be substituted aryls (paragraph 0360), allowing for alkylene with a substituted aryl group and Bartholomew teaches the functional equivalence of q values of 6-20. This structure only requires only a single methyl substitution and a change from 16 to 11 OPEG groups to meet claim 18 dye the last formula in the first row. The alkenyl group substituted by phenyl and the adjacent R3 group can be substituted for a R2-R3 5-memebered ring alkyl substituted carbocycle with (paragraph 0036).
Bartholomew does not teach al the claimed embodiments in a single compound but selection from the claimed substituents allows one of ordinary skill in the art to arrive at the claimed compounds.
It would have been obvious to one of ordinary skill in the art at the time the invention was made to select the instantly claimed dyes as Bartholomew teaches these dyes with the same base structure and selection of the claimed substituents allows for the production of water soluble dyes with the absorbance maximums in the 550 to 600 nm range for the benefit of use in a variety of biological applications particularly diagnostic kits with parameters of interest of the dyes such as excitation and emission wavelengths , stokes shifts and fluorescence quantum yield being selected by selection of the claimed substituents. These tandem dyes have the benefit of narrow emission fluorophores. Substitution of the functionally equivalent substituents listed to arrive at the claimed structures and desired water solubility and absorbance maximum can be done through routine experimentation. The dyes of Bartholomew broadly teach the claimed compounds and only require small substitutions of the exemplified structures to arrive at the claimed compounds.
Bartholomew clearly teaches that applicant's claimed R5 can be substituted alkenyl or the equivalent species aryl, substituted aryl or water solubilizing groups of halogen. Bartholomew is not limited to only the species it shows the exact structures for as these examples are not limiting. Rather the entire disclosure of Bartholomew must be considered and equivalent substituents taught as useful for substituents at applicant's R5 position are also appropriate for the compounds. In many cases a simple single or double
substitution of the exemplified compounds is needed to arrive at applicant's claimed dyes. Selecting the alternate embodiments of substituents for applicant's R5 group from the teaching of Bartholomew permits a compound with the R5 which does not have R5 substituted alkenyl. Applicant teaches several possibilities for R5 in the claims and in particular claim 1 allows for the many of the same possibilities as listed in applicant's claim 1. The examiner only needs to find one compound matching the claimed structures and is not required to find every potential disclosed species of applicant's claims. Further the substitution in Bartholomew is permitted to exemplified structures as the broader teachings allow for many different substituents in applicant's R5 position. Similarly applicant's own claims teach many possibilities of dyes and are not limited to only the specific structures exemplified as a complete compound. A reference is not limited to the working examples, see In re Fracalossi, 215 USPQ 569 (CCPA 1982) All disclosures of the prior art, including non-preferred embodiment, must be considered. See In re Lamberti and Konort, 192 USPQ 278 (CCPA 1967); In re Snow 176 USPQ, 328, 329 (CCPA 1973). Non-preferred embodiments can be indicative of obviousness, see Merck & Co. V. Biocraft Laboratories Inc. 10 USPQ 2d 1843 (Fed. Cir. 1989); In re Lamberti, 192 USPQ 278(CCPA 1976); In re Kohler, 177 USPQ 399. Regarding the R5 para isomer, meta, para and ortho isomers suggest one another and are expected to behave similarly absent a showing of unexpected results. Note that structurally similar compounds are generally expected to have similar properties. In re Gvurik, 596 F. 2d 1012,201 USPQ 552. Closely related homologues, analogs and isomers in chemistry may create a prima facie case of obviousness. In re Dillon USPQ 2d 1 1904 (Fed. Cir. 1990); In re Payne 203 USPQ 245 (CCPA 1979); In re Mills 126 USPQ 5 13 (CCPA 1960); In re Henze 85 USPQ 261 (CCPA 1950); In re Hass 60 USPQ 544 (CCPA 1944). Bartholomew allows for substitution in ortho, para and meta positions of a phenyl ring with a R9 group and these location are considered equivalent unless data of unexpected results demonstrates otherwise. Bartholomew clearly teaches applicant's claimed R5 and R6 substituents can be fused into a 5 or 6 member ring. It is the examiner's central position that Bartholomew teaches the same base structure and possible selection of substituents to prepare the same dyes with the same yellow-green absorption range of 561 nm. In the absence of data demonstrating unexpected superiority of a particular selection of the substituents, the selection of the claimed substituents to produce the claimed compounds is obvious.
Allowable Subject Matter
Claims 22,26,30,31 and 33 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims. The prior art would require too much picking and choosing from substituents to arrive at these structures.
Response to Arguments
Applicant's arguments filed regarding Bartholomew have been fully considered but they are not persuasive. The examiner argues that the broad disclosure of Bartholomew allows for one of ordinary skill in the art to arrive at applicant’s claimed water-soluble dipyrromethene based dyes which absorb in the green range at 561 nm. Selecting from the disclosed substituents to arrive at the claimed dyes is obvious absent a showing of unexpected results for any particular substituent or dye species. Applicant has not provided any unexpected results in the form of experimental data commensurate in scope with the claims and in comparison to the prior art of Bartholomew, therefore the claimed substituent selection is obvious. The R2 group of Bartholomew (applicant’s R5 group) can be selected from aryl, substituted aryl, halogen, and water solubilizing groups which can be halogens (paragraph 0032-0035). These structures have no requirement for group to be a substituted alkenyl as this is an alternate embodiment. The selection of the aryl or substitutes aryl only requires selection from 15 species listed in paragraph 0035. The examiner highlighted the formula in Bartholomew of paragraph 92 as a possible embodiment in which alternate species can be used in place of the substituents. The broader scope of the structures taught by Bartholomew do not require the exact substituents of this exemplified structure. The substituents exemplified in the examples of Bartholomew are just preferred embodiments and the examiner highlights them to show significant similarities to the claimed structures but also looks to the broader disclosure to demonstrate Bartholomew allows for substitutions of other substituents for those present on the example. No prior art is limited only to the exemplified structures and when Bartholomew teaches several different species can be used in each substituent location, selecting from any species listed is permitted to arrive at the claimed dyes. The structure of Bartholomew paragraphs 0032-0035 has no requirement for a substituted alkenyl and from the substituents disclosed in paragraphs 0032-0040 of Bartholomew, applicant’s claimed dyes can be created. If the substituted alkenyl was deemed essential, the dyes of Bartholomew would not teach it as an alternate embodiment. Exemplifying a preferred structure is not the same as prohibiting substitution of art taught functional equivalents. A reference is not limited to the working examples, see In re Fracalossi, 215 USPQ 569 (CCPA 1982) All disclosures of the prior art, including non-preferred embodiment, must be considered. See In re Lamberti and Konort, 192 USPQ 278 (CCPA 1967); In re Snow 176 USPQ, 328, 329 (CCPA 1973). Non-preferred embodiments can be indicative of obviousness, see Merck & Co. V. Biocraft Laboratories Inc. 10 USPQ 2d 1843 (Fed. Cir. 1989); In re Lamberti, 192 USPQ 278(CCPA 1976); In re Kohler, 177 USPQ 399.
Regarding the R5 para isomer, meta, para and ortho isomers suggest one another and are expected to behave similarly absent a showing of unexpected results. Note that structurally similar compounds are generally expected to have similar properties. In re Gvurik, 596 F. 2d 1012,201 USPQ 552. Closely related homologues, analogs and isomers in chemistry may create a prima facie case of obviousness. In re Dillon USPQ 2d 1 1904 (Fed. Cir. 1990); In re Payne 203 USPQ 245 (CCPA 1979); In re Mills 126 USPQ 5 13 (CCPA 1960); In re Henze 85 USPQ 261 (CCPA 1950); In re Hass 60 USPQ 544 (CCPA 1944). Bartholomew allows for substitution in ortho, para and meta positions of a phenyl ring with a R9 group and these location are considered equivalent unless data of unexpected results demonstrates otherwise. Bartholomew clearly teaches applicant's claimed R5 and R6 substituents can be fused into a 5 or 6 member ring. It is the examiner's central position that Bartholomew teaches the same base structure and possible selection of substituents to prepare the same dyes with the same yellow-green absorption range of 561 nm. In the absence of data demonstrating unexpected superiority of a particular selection of the substituents, the selection of the claimed substituents to produce the claimed compounds is obvious. The examiner reiterates the broad structures of paragraph 0032 of Bartholomew allow for para, meta or ortho substitutions and the prior art is again not limited to the examples.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMINA S KHAN whose telephone number is (571)272-5573. The examiner can normally be reached Monday-Friday, 9am-5:30pm EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Angela Brown-Pettigrew can be reached on 571-272-2817. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/AMINA S KHAN/Primary Examiner, Art Unit 1761
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