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 provisional election without traverse of the following species:
1) (pyrrole):
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(2) (solvent): ether;
(3) (salt): sodium chloride;
(4) (aliphatic or aromatic aldehyde):
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(5) (catalyst): boron trifluoride etherate; and
(6) (oxidizing agent): peroxide,
in the reply filed on March 5, 2026 is acknowledged.
In view of Applicant’s arguments with regard to the lack of unity, the previous restriction requirement is withdrawn.
Claims 1, 2, 4-9, 11, 14, 16, 17, 18, 20, 21, and 23-27 are under examination and are the subject of this office action.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on September 27, 2023, is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement has been considered by the examiner, please refer to the initialed and signed copy of Applicant’s PTO-1449 form, attached herewith.
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 1, 2, 4-9, 11, 14, 16, 17, 18, 20, 21, and 23-27 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.
8. Claim 1 is unclear in the following aspects:
(a) Claim 1 recites the step “oxidizing the formed porphyrinogen” in step (c), however there is insufficient antecedent basis for this recitation in in the claim, because the limitation “formed porphyrinogen” has not been previously recited. While step (b) recites “to form a porphyrinogen,” this is not consistent with the term “formed porphyrinogen.”
(b) Claim 1 recites: “wherein the porphyrin comprises a residue of the pyrrole or substituted pyrrole having an aliphatic group or an aromatic groups derived from the aliphatic or the aromatic aldehyde that are pendant from a heterocycle,” which is redundant and also confusing because it is unclear if the aliphatic group or aromatic group(s) are attached to the pyrrole itself or are contained elsewhere in the porphyrin, because it is also unclear if the term heterocycle refers to the pyrrole or an additional, as-yet unrecited heterocycle.
(c) In claim 1, the limitation “having an aliphatic group or an aromatic groups” [emphasis added] is confusing regarding the recitation of plural “groups.”
Clarification is requested.
9. In view of a broadest reasonable interpretation, for purposes of applying prior art, the recitation in claim 1 of: “wherein the porphyrin comprises a residue of the pyrrole or substituted pyrrole having an aliphatic group or an aromatic groups derived from the aliphatic or the aromatic aldehyde that are pendant from a heterocycle,” is not given patentable weight.
10. Claims 2, 4-9, 11, 14, 16, 17, 18, 20, 21, and 23-27 are rejected as being dependent upon and including all of the limitations of claim 1.
11. Claim 5 is confusing because it recites the catalyst “boron trifluoride etherate,” however the previous recitations of the same catalyst in claims 2 and 4 refer to the catalyst as “BF3-etherate.” It is recommended that Applicant employ the same nomenclature throughout the claims for consistency.
12. Claim 18 depends from claim 1 and recites the limitation: “wherein the pyrrole or substituted pyrrole, the aliphatic or aromatic aldehyde, the salt, and solvent are mixed before the catalyst is added and the porphyrinogen is mixed with the catalyst.” However, there is insufficient antecedent basis for this limitation in the claim, because in the method recited in claim 1, step (b), the vessel is charged with a catalyst to form a porphyrinogen, i.e., the porphyrinogen is a result of adding the catalyst. Therefore the resulting porphyrinogen cannot then be mixed with the catalyst, as claim 18 alleges.
In view of a broadest reasonable interpretation, for purposes of applying prior art, claim 18 is construed to mean:
“wherein the pyrrole or substituted pyrrole, the aliphatic or aromatic aldehyde, the salt, and solvent are mixed before the catalyst is added.”
13. Claim 20 is rejected as being dependent upon and including the limitations of claim 18.
14. Claim 17 is confusing because it recites the oxidizing agent “hydrogen peroxide” in lines 1-2, however the previous recitation of the same oxidizing agent in claim 16 refers to the oxidizing agent as “hydroperoxide,” and in claim 17, line 2, the term “tert-butyl hydroperoxide” is used. It is recommended that Applicant employ the same nomenclature throughout the claims for consistency.
15. Claim 20 is rejected for reciting that the porphyrinogen is mixed “about 5 minutes or more and about 15 minutes or less,” which is confusing because it is not clear if the claim intends to embrace a first mixing period of 5 minutes or more and a second mixing period of about 15 minutes or less, or if the claim intends one period that is from at least about 5 minutes up to about 15 minutes.
In view of a broadest reasonable interpretation of claim 20 for purposes of applying prior art, the limitation of “about 5 minutes or more and about 15 minutes or less,” is construed to mean “for a period of time of about 5 minutes to about 15 minutes.”
16. Claim 21 is rejected for reciting that the porphyrinogen is mixed with the oxidizing agent for “8 hours or more and 24 hours or less,” which is confusing because it is not clear if the claim intends to embrace a first mixing period of 8 hours or more and a second mixing period of about 24 hours or less, or if the claim intends one period that is from at least about 8 hours up to about 24 hours.
In view of a broadest reasonable interpretation of claim 21 for purposes of applying prior art, the limitation of “8 hours or more and 24 hours or less,” is construed to mean “for a period of time of from 8 hours to 24 hours.”
17. Claim 23 depends from claim 1 and recites: “further comprising extracting the oxidizing agent with a polar aprotic solvent before being mixed with the porphyrinogen,” which is confusing because it is not clear what the oxidizing agent is being extracted from, or what is being extracted from the oxidizing agent. It is also not clear from the claim if the oxidizing agent or the polar aprotic solvent is mixed with the porphyrinogen.
18. Claim 24 depends from claim 1 and recites: “further comprising extracting an aqueous hydrogen peroxide solution with a polar aprotic solvent to remove water and form an anhydrous peroxide solution,” which is confusing because it is not clear during/before/after which step the aqueous hydrogen peroxide solution is extracted.
18. Therefore, claims 23 and 24 have not been further treated on the merits. In re Steele, 305 F.2d 859,134 USPQ 292 (CCPA 1962) (it is improper to rely on speculative assumptions regarding the meaning of a claim and then base a rejection under 35 U.S.C. 103 on these assumptions).
Claim Rejections - 35 USC § 112(a)
19. Claims 2, 4-9, 11, 14, 16, 17, 18, 20, 21, and 23-27 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, because the specification, while being enabling for a method of preparing the tetraphenylporphyrin disclosed in Example 1, comprising combining dichloromethane, sodium chloride, 1H-pyrrole, and benzaldehyde in a vessel, charging the vessel with the catalyst boron trifluoride etherate to form a porphyrinogen, followed by oxidizing the porphyrinogen with hydrogen peroxide (see paragraph [0102]), is not considered enabled for a method of preparing any porphyrin compound comprising the combination of any solvent, any salt, any pyrrole, any aldehyde, and any peroxide oxidizing agent, wherein the porphyrin is free of hydroquinone byproducts, as presently recited. The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to use the invention commensurate in scope with these claims.
20. The standard for determining whether the Specification meets the enablement requirement was cast in the Supreme Court decision of Mineral Separation v. Hyde, 242 U.S. 261 (1916) which postured the question: is the experimentation needed to practice the invention undue or unreasonable? As recognized by the court in In re Wands, 858 F.2d 731 (Fed. Cir. 1988), that is still the standard to be applied, determined by consideration of the Wands factors (MPEP 2164.01(A)); namely, nature of the invention, breadth of the claims, guidance of the specification, the existence of working examples, state of the art, predictability of the art and the amount of experimentation necessary. All of the Wands factors have been considered, with the most relevant factors discussed below:
1) the quantity of experimentation necessary,
2) the amount of direction or guidance provided,
3) the presence or absence of working examples,
4) the nature of the invention,
5) the state of the prior art,
6) the relative skill of those in the art,
7) the predictability of the art, and
8) the breadth of the claims.
21. These factors are always applied against the background understanding that scope of enablement varies inversely with the degree of unpredictability involved. In re Fisher, 57 CCPA 1099, 1108, 427 F.2d 833, 839, 166 USPQ 18, 24 (1970). Keeping that in mind, the Wands factors are relevant to the instant fact situation for the following reasons.
22. Nature of the Invention: As stated in MPEP 2164.05(a), “[t]he initial inquiry” for determining whether the Specification is enabling “is into the nature of the invention, i.e., the subject matter to which the claimed invention pertains.”
In the instant case, the claims as presently written embrace a method of preparing any porphyrin compound comprising the combination of any solvent, any salt, any pyrrole, any aliphatic or aromatic aldehyde, and any peroxide oxidizing agent, wherein the porphyrin is free of hydroquinone byproducts.
23. The state of the prior art, level of predictability and relative skill level: As stated in MPEP 2164.05(a), “[t]he state of the prior art is what one skilled in the art would have known, at the time the application was filed, about the subject matter to which the claimed invention pertains” and, as stated in MPEP 2164.05(b), “[t]he relative skill of those in the art refers to the skill of those in the art in relation to the subject matter to which the claimed invention pertains at the time the application was filed.”
As discussed above, the instantly claimed invention embraces a method of preparing any porphyrin compound comprising the combination of any solvent, any salt, any pyrrole, any aliphatic or aromatic aldehyde, and any peroxide oxidizing agent, wherein the porphyrin is free of hydroquinone byproducts.
24. The relative skill of those in the art is high, that of an MD or PhD.
25. The state of the art regarding porphyrins is that they are large, ring-shaped macrocyclic compounds that are compose of four modified pyrrole rings that are connected via methine links. Regarding porphyrin synthesis, their yield is unpredictable and can be influenced by several reaction parameters, including acidity of the medium, nature of the catalyst, and the substituents on the aldehyde component, i.e. “[i]t was found that the acidity (pKa) of the medium and the nature of acid catalyst (organic acid, Lewis acid) are crucial for the efficient cyclotetramerization of pyrrole with aldehyde [102]…. In almost any of these methods, the yield of meso-tetraarylporphyrins strongly depends on the substituent in the benzaldehyde component, including its elec-tronic effect and steric factor (Table 2). Numerous studies have shown that there is virtually no effect of steric factor in reactions with para- and meta-substi-tuted benzaldehydes; therefore, only electronic effects of substituents can be taken into account. In the case of tetraarylporphyrins with ortho substituents at the phenyl rings, the steric factor prevails over the elec-tronic one [107]. However, the rate of the condensation of pyrrole with aromatic aldehydes does not always correlate with the yield of porphyrin. Linear polymers or stable condensation products of pyrrole and alde-hyde can be formed as by-products which do not undergo cyclotetramerization with the formation of tetrapyrrole macroheterocycle. For example, the con-densations of p-nitro and p-aminobenzaldehydes with pyrrole gave tetrakis(4-nitrophenyl)porphyrin and tetra-kis(4-aminophenyl)porphyrin in as low yields as 7 and 1%, respectively [107]. (Koifman et al., Russian Journal of Organic Chemistry 2022, page 450, right column, second and third paragraphs).
26. The amount of direction or guidance provided and the presence or absence of working examples: The amount of direction provided by the Applicant is considered to be determined by the Specification and the working examples. In the instant case, the Specification provides no direction or guidance for the use of the full scope of the aforementioned reactants/solvents/catalysts etc, for preparing any porphyrin. The Specification discloses only one working example of the preparation of any porphyrin: Example 1 discloses the preparation of a tetraphenylporphyrin comprising combining the solvent dichloromethane, the salt sodium chloride, 1H-pyrrole, and the aromatic aldehyde benzaldehyde in a vessel, charging the vessel with the catalyst boron trifluoride etherate to form a porphyrinogen, followed by oxidizing the porphyrinogen with hydrogen peroxide (see paragraphs [0101]- [0102] at page 31).
No reasonably specific guidance is provided concerning methods of preparing any porphyrin comprising mixing any other solvent(s), salt(s), pyrrole(s), aldehyde(s), catalyt(s), or oxidizing agent(s).
27. The breadth of the claims: For purposes of enablement, the relevant concern is whether the scope of enablement provided to one skilled in the art by the disclosure is commensurate in scope with the protection sought by the claims. Thus, while “a patent application is entitled to claim his invention generically” it is necessary that “he provide a disclosure sufficient to enable one skilled in the art to carry out the invention commensurate with the scope of his claims." Amgen, Inc., v. Chugai Pharmaceutical Co., Ltd. (Fed. Cir. 1991). As noted by the court in In re Fisher, 427 F.2d 833 (CCPA 1970), the scope of enablement must bear a “reasonable correlation” to the scope of the claims. See also Ak Steel Corp. v. Sollac, 344 F.3d 1234 (Fed. Cir. 2003) and In re Moore, 439 F.2d 1232 (CCPA 1971). As stated in MPEP 2164.08, resolution of this concern requires two stages of inquiry: “[t]he first is to determine how broad the claim is with respect to the disclosure. The entire claim must be considered. The second inquiry is to determine if one skilled in the art is enabled to make and use the entire scope of the claim without undue experimentation”.
28. As to the first inquiry, as discussed above, it is evident that the claims are very broad insofar as they are directed to the preparation of any porphyrin compound, comprising: combining any solvent, any salt, any pyrrole, any aliphatic or aromatic aldehyde, with the oxidizing agent peroxide, wherein the resulting porphyrin is free of hydroquinone byproducts. Considering that the possible combinations of all of the recited reactants/ ingredients encompasses hundreds of thousands of possible syntheses, it is evident that the claims are broad. It is also noted that the claims presently embrace the preparation of any porphyrin within the class of porphyrins, including any future porphyrin. Yet, as discussed above, the instant Specification discloses only one working example (Example 1). As such, the claim is extremely broad with respect to the disclosure. The second inquiry is discussed in detail below.
29. The amount of experimentation necessary: In view of all of the foregoing, at the time the invention was made, it would have required undue experimentation to practice the entire scope of the invention as claimed. As discussed above, the claims presently embrace the preparation of any porphyrin compound, comprising the combination of any solvent, any salt, any pyrrole, any aliphatic or aromatic aldehyde, with an oxidizing agent that is a peroxide, wherein the resulting porphyrin is free of hydroquinone byproducts.
30. In the instant case, the claimed synthesis is complex and is exacerbated by the broadness of the recited any porphyrin compound, comprising the combination of any solvent, any salt, any pyrrole, any aliphatic or aromatic aldehyde, with respect to the disclosure since the possible combinations of said reactants/ingredients/ catalysts encompasses hundreds of thousands of alternatives, whereas the instant Specification discloses only one working example. Although the relative skill of those in the art to which the invention pertains is high, the state of the art and unpredictability within the art is such that even the most talented artisan could not reasonably predict which of the reactants/ ingredients/ catalysts etc that are encompassed by the claims could be combined to prepare the desired porphyrin product. Although the skilled artisan would have known that certain chemical modifications to the disclosed compounds may predictably provide structurally related compounds having similarly activity, the skilled artisan would have also known that even minor changes in reaction conditions can and frequently will drastically alter the yield of said reaction, as evidenced by Koifman et al., above. That is, the only way one skilled in the art is enabled to use the entire scope of the claim based on the instant disclosure entails undue experimentation.
To overcome this rejection, Applicant should narrow the scope of the claims such that they bear a reasonable correlation with the disclosure, i.e., limit the genus of porphyrins and reactants, ingredients, etc embraced by the claims.
Claim Rejections - 35 USC § 103
31. 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.
32. 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.
33. Claims 1, 2, 4-9, 11, 14, 16, 17, 18, 20, 21, and 26 are rejected under 35 U.S.C. 103 as being unpatentable over Arja et al., Chemistry Open, Supplement: Supporting Information (2018), in view of Serra et al., Journal of Photochemistry and Photobiology B (2008, cited on Applicant’s IDS of September 27, 2023).
Claim 1 is drawn to a method comprising:
(a) combining a solvent (more specifically, dichloromethane (claim 14)), a salt (more specifically, NaCl (claims 6-9 and 11), pyrrole or substituted pyrrole, and an aliphatic or aromatic aldehyde in a vessel;
(b) charging the vessel with a catalyst (more specifically, boron trifluoride etherate (BF3-etherate)(claims 2, 4 and 5) to form a porphyrinogen of the pyrrole or substituted pyrrole; and
(c) oxidizing the formed porphyrinogen of the pyrrole or substituted pyrrole with an oxidizing agent to form a porphyrin, wherein the oxidizing agent is peroxide (more specifically, hydrogen peroxide (claims 16 and 17);
wherein the porphyrin comprises a residue of the pyrrole or substituted pyrrole having an aliphatic group or an aromatic groups derived from the aliphatic or the aromatic aldehyde that are pendant from a heterocycle (more specifically, wherein the porphyrin comprises tetraphenylporphyrin (claim 26)); and
wherein the porphyrin is free of hydroquinone byproducts, and
wherein the pyrrole or substituted pyrrole, the aliphatic or aromatic aldehyde, the salt, and solvent are mixed before the catalyst is added (claim 18), wherein the porphyrin is mixed for a period of time of from about 5 minutes to about 15 minutes (claim 20).
34. Arja et al. teach the preparation of the porphyrin of Compound 8:
methyl-mono-(p-carboxy)-tetraphenylporphyrin (Me-pcTPP):
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, wherein an aldehyde (benzaldehyde), pyrrole, and a salt (sodium chloride) were added to a solvent (dichloromethane (DCM)), degassed and stirred at room temperature for 10 minutes. The catalyst boron trifluoride etherate was then added and the reaction mixture and stirred for another 30 minutes. The oxidizing agent DDQ was added and the reaction was let continue for an hour. Triethylamine was added to the reaction mixture and the solvent was reduced in vacuo. The crude mixture was filtered, followed by purification to isolate the resulting tetraphenyl porphyrin, Compound 8 aka methyl mono-(p-carboxy)-tetraphenylporphyrin (Me-pcTPP) (see pages 4-5).
35. As such, Arja et al. teach a process of preparing a porphyrin comprising mixing the same solvent, salt, pyrrole, aldehyde and catalyst that are instantly recited, but do not teach that the oxidizing agent is a peroxide.
36. However, Serra et al. specifically teach the replacement of DDQ with hydrogen peroxide in the oxidative step of the preparation of porphyrins (page 61, right column, last paragraph, and Scheme 1). Serra et al. disclose Porphyrin Syntheses 2.3.2 and 2.3.3, wherein a benzaldehyde and pyrrole are added to dichloromethane solvent, followed by addition of the catalyst boron trifluoroboroetherate (aka boron trifluoride etherate), and the reaction is allowed to continue overnight. The reaction is stopped with triethylamine followed by addition of the oxidizing agent hydrogen peroxide, resulting in tetraphenylporphyrins PS1 and PS2, (page 60, left column). Neither PS1 nor PS2 contain hydroquinone byproducts.
37. Therefore it would have been obvious to one of skill in the art before the effective filing date of the claimed invention to modify the tetraphenylporphyrin synthesis taught by Arja et al. by substituting DDQ with hydrogen peroxide, as explicitly guided by Serra et al., with a reasonable expectation of success.
As such, claims 1, 2, 4-9, 11, 14, 16, 17, 18, 20 and 26 are prima facie obvious.
Claim 21 is drawn to claim 1 and limits wherein the porphyrinogen is mixed with the oxidizing agent for a period of time of from 8 hours to 24 hours.”
38. Serra et al. teach that the porphyrinogen is mixed with hydrogen peroxide and stirred until complete oxidation for 1 to 3 hours (page 60, left column, under 2.3.2.). And, discovery of an optimum value of a result effective variable in a known process is ordinarily within the skill of the art. See In re Boesch, 617 F.2d 272, 205 USPQ 215 (CCPA 1980). Therefore one of skill in the art before the effective filing date of the claimed invention would have been motivated to optimize the time period for mixing the oxidizing agent, starting from 3 hours as guided by Serra et al., in order to achieve full oxidation, with a reasonable expectation of success.
As such, claim 21 is prima facie obvious.
39. Claim 25 is rejected under 35 U.S.C. 103 as being unpatentable over Arja et al., Chemistry Open, Supplement: Supporting Information (2018), in view of Serra et al., Journal of Photochemistry and Photobiology B (2008), as applied to claims 1, 2, 4-9, 11, 14, 16, 17, 18, 20, 21, and 26, above, and further in view of Mamardashvili and Golubchikov, Russian Chemical Reviews (2000).
Claim 1 is addressed in detail, above.
Claim 25 is drawn to claim 1 and limits the solvent to ether or diethyl ether.
40. Arja et al. in view of Serra et al. teach the synthesis of tetraphenylporphyrin wherein a benzaldehyde and pyrrole are added to dichloromethane solvent, followed by addition of the catalyst boron trifluoride etherate, and then oxidizing the resulting porphyrinogen with the oxidizing agent hydrogen peroxide, wherein said tetraphenylporphyrin is free of hydroquinone byproducts, but do not teach an ether or diethyl ether solvent.
41. However, Mamardashvili teaches the synthesis of porphyrin compounds, comprising a first step of mixing a substituted pyrrole with an aldehyde in the presence of diethyl ether, dichloromethane or glacial acetic acid solvents (see page 308, left column, sixth paragraph). As the subgenus of organic solvents taught by Mamardashvili is comprised of only three solvents, one skilled in the art would have immediately envisaged selecting diethyl ether to employ as the solvent, with a reasonable expectation of success.
42. As such, one of skill in the art before the effective filing date of the claimed invention would have reasonably considered substituting a diethyl ether solvent for the dichloromethane solvent taught in the porphyrin syntheses of both Arja et al. and Serra et al., with a reasonable expectation of success.
Thus, claim 25 is prima facie obvious.
43. Claim 27 is rejected under 35 U.S.C. 103 as being unpatentable over Arja et al., Chemistry Open, Supplement: Supporting Information (2018), in view of Serra et al., Journal of Photochemistry and Photobiology B (2008), as applied to claims 1, 2, 4-9, 11, 14, 16, 17, 18, 20, 21, and 26, above, and further in view of Zhuo et al., Chinese J Polym Sci (2018).
Claim 1 is addressed in detail, above.
Claim 27 is drawn to claim 1, and further comprises the step of contacting the porphyrin with a metalating agent that includes an aluminum compound or a chromium compound.
44. Arja et al. in view of Serra et al. teach the synthesis of tetraphenylporphyrin wherein a benzaldehyde and pyrrole are added to dichloromethane solvent, followed by addition of the catalyst boron trifluoride etherate, and then oxidizing the resulting porphyrinogen with the oxidizing agent hydrogen peroxide, wherein said tetraphenylporphyrin is free of hydroquinone byproducts, but do not teach the step of contacting the porphyrin with a metalating agent that includes an aluminum compound or a chromium compound.
45. Yet, Zhuo et al. teach the advantages of Aluminum porphyrin complexes, i.e., they are environmentally friendly, heavy-metal-free and soil-tolerant green catalysts for the copolymerization of CO2 and propylene oxide (PO) (see abstract). Zhou et al. teach the preparation of Aluminum tetraphenylporphyrin compounds in Schemes 2 and 3, comprising mixing pyrrole with benzaldehyde in a dichloromethane solvent at room temperature and adding the catalyst BF3etherate, followed by an oxidizing agent and further comprising adding the metalating agent diethylaluminum chloride (Et2AlCl) (see page 254 and page 255, left column, under “Synthesis of 5,10,15,20-Tetra(1,2,3,4,5,6,7,8-octahydro- 1,4:5,8-dimethanoanthracen-9-yl)porphyrin (e)” and under “General Procedure for Aluminum Porphyrin Complex”).
46. As such, one of skill in the art before the effective filing date of the claimed invention would have been motivated to modify the synthesis suggested by Arja et al. in view of Serra et al. by introducing an aluminum metalating agent, in order to prepare an improved tetraphenylporphyrin complex comprising aluminum, with a reasonable expectation of success.
Thus claim 27 is prima facie obvious.
Claim Objections
47. Claim 26 depends from claim 1 and recites “the porphyrin comprises tetraphenyl-porphyrin” but appears to omit the term “wherein” after the recitation of “claim 1.”
Conclusion
48. Claims 1, 2, 4-9, 11, 14, 16, 17, 18, 20, 21, and 23-27 are pending in the application, and all claims are rejected. No claim is presently allowed.
49. Any inquiry concerning this communication or earlier communications from the examiner should be directed to JANET L COPPINS whose telephone number is (571)272-0680. The examiner can normally be reached Monday-Friday 8:30AM-5PM EST.
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/JANET L COPPINS/Examiner, Art Unit 1628
/Rayna Rodriguez/Primary Examiner, Art Unit 1628
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