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 .
Information Disclosure Statement
The information disclosure statement (IDS) submitted is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement has been considered by the examiner.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1-3 and 7 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Qinglin et al. (CN106748843, published 31 May 2017, see Original and Machine Translation, hereinafter Qinglin).
Qinglin is in the known prior art field of “a preparation method of levocarnitine” aka l-carnitine, by “taking epoxy chloropropane as a starting material, then carrying out amination, cyaniding and carrying out ester exchange under the action of lipase CALB to obtain corresponding chiral ester, then carrying out alkaline hydrolysis and acidification, and then removing chlorine ions under the action of strongly alkaline resin, so that the levocarnitine finished product is obtained”, see Abstract.
Regarding the limitations of instant application claims 1-3 and 7, Qinglin discloses a “method for preparing levocarnitine, characterized by comprising the following steps: S1. Trimethylamine is added to methanol, cooled to 0-5℃, and the internal temperature is controlled not to exceed 10℃. Concentrated hydrochloric acid is added dropwise to adjust the pH to 6-7. The temperature is raised to 40-50℃, and a certain proportion of epichlorohydrin is added dropwise. The reaction is kept at this temperature for 4-5 hours. The reaction solution is concentrated under reduced pressure, and the residue is recrystallized using a recrystallization reagent to obtain intermediate I”, i.e., L-3-chloro-2-hydroxypropyl trimethylammonium chloride, see Machine Translation Claim 1; Original Para. [0029]
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, meeting:
Step (a) in instant application claim 1;
The specific solvent methanol in instant application claim 2 and in instant application claim 3;
Then in step “S2. Intermediate I was added to a methanol solution, heated to 50°C, and after complete dissolution, NaCN was added. The reaction was maintained at this temperature for 4–5 hours. The filter cake was then recrystallized using a recrystallization reagent to obtain intermediate II”, i.e., L-carnitinenitrile chloride, see Machine Translation Claim 1; Original Para. [0033]
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, meeting:
Step (b) in instant application claim 1;
The specific cyanide sodium cyanide in instant application claim 7;
Then in steps S4.-S5. the L-carnitinenitrile chloride is converted to levocarnitine aka l-carnitine, see Machine Translation Claim 1; Original Paras. [0040]-[0045]
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, meeting the production of L-carnitine and step (c) in instant application claim 1.
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 1-7 are rejected under 35 U.S.C. 103 as being obvious over Hu et al. (US20240217920, filed 28 December 2022, published 04 July 2024, hereinafter Hu ‘920).
The applied reference has common applicants and inventors with the instant application. Based upon the earlier effectively filed date of the reference, it constitutes prior art under 35 U.S.C. 102(a)(2).
The below rejection under 35 U.S.C. 103 might be overcome by: (1) a showing under 37 CFR 1.130(a) that the subject matter disclosed in the reference was obtained directly or indirectly from the inventor or a joint inventor of this application and is thus not prior art in accordance with 35 U.S.C.102(b)(2)(A); (2) a showing under 37 CFR 1.130(b) of a prior public disclosure under 35 U.S.C. 102(b)(2)(B); or (3) a statement pursuant to 35 U.S.C. 102(b)(2)(C) establishing that, not later than the effective filing date of the claimed invention, the subject matter disclosed and the claimed invention were either owned by the same person or subject to an obligation of assignment to the same person or subject to a joint research agreement, see generally MPEP § 717.02.
Regarding the limitations of instant application claims 1-7, Hu ‘920 teaches the production of L-carnitine by first producing L-carnitinenitrile chloride by the “reaction of trimethylamine hydrochloride, (S)-epichlorohydrin” “in the presence of an organic solvent”, such as “methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol” to obtain “L-3-chloro-2-hydroxylpropyl trimethylammonium chloride” that is reacted with “a source of cyanide”, such as “alkali cyanide, alkaline earth metal cyanide, zinc cyanide, and a cyanohydrin; wherein the alkali is lithium, sodium, or potassium” to obtain L-carnitinenitrile chloride, see Paras. [0003]-[0006];[0019]-[0021];[0023];[0029]; Claims 1, 5 & 6, meeting:
The reacting steps (a) and (b) in instant application claim 1;
The specific organic solvents in instant application claim 2, in instant application claim 3, in instant application claim 4, in instant application claim 5, and in instant application claim 6;
The specific cyanide in instant application claim 7; and,
Then the L-carnitinenitrile chloride is “converted to L-carnitine by one of the known methods, for example, by using hydrochloric acid to hydrolyze the nitrile group in L-carnitinenitrile chloride”, see Para. [0030]; Claim 1, meeting the production of L-carnitine and step (c) in instant application claim 1.
Hu ‘920 does not specifically teach the limitations of the above instant application claims in one single express embodiment or Example.
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 Hu ‘920 to choose the desired organic solvent, cyanide, and sequence of reactions to produce the desired products with a reasonable predictability of success for the purpose of efficiently producing optically pure L-carnitine in a mixed aqueous organic solvent solution with minimal byproducts and residual alkali cyanide, see Hu ‘920, Paras. [0007]-[0008];[0011];[0017]-[0021].
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 Hu ‘920 to select the desired organic solvent, cyanide, and sequence of reactions to produce the desired products as taught by Hu ‘920 with a reasonable predictability of success for the purpose of efficiently producing optically pure L-carnitine in a mixed aqueous organic solvent solution with minimal byproducts and residual alkali cyanide, see Hu ‘920, Paras. [0007]-[0008];[0011];[0017]-[0021]; 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 material, such as any of the organic solvents and cyanides taught by Hu ‘920, based on its suitability for its 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.
“Where applicant claims a composition in terms of a function, property or characteristic and the composition of the prior art is the same as that of the claim but the function is not explicitly disclosed by the reference, the examiner may make a rejection under both 35 U.S.C. 102 and 103.”, see MPEP 2112 III. In this case, the Hu ‘920 teaching of a reaction of trimethylamine hydrochloride and (S)-epichlorohydrin in an organic solvent will inherently lead to the production of L-3-chloro-2-hydroxylpropyl trimethylammonium chloride, see Para. [0019]; Claim 6.
In addition, merely discovering and claiming a new benefit of an old process cannot render the process again patentable, for example reversing the order of the prior art process steps, selection of any order of performing process steps, and selection of any order of mixing ingredients are all prima facie obvious in the absence of new or unexpected results, see MPEP 2144.04 IV.C. and In re Woodruff, 919 F.2d 1575, 1578 (Fed. Cir. 1990).
Claims 1-9 are rejected under 35 U.S.C. 103 as being obvious over Hu et al. (US20240228429, filed 04 January 2023, published 11 July 2024, hereinafter Hu ‘429).
The applied reference has common applicants and inventors with the instant application. Based upon the earlier effectively filed date of the reference, it constitutes prior art under 35 U.S.C. 102(a)(2).
The below rejection under 35 U.S.C. 103 might be overcome by: (1) a showing under 37 CFR 1.130(a) that the subject matter disclosed in the reference was obtained directly or indirectly from the inventor or a joint inventor of this application and is thus not prior art in accordance with 35 U.S.C.102(b)(2)(A); (2) a showing under 37 CFR 1.130(b) of a prior public disclosure under 35 U.S.C. 102(b)(2)(B); or (3) a statement pursuant to 35 U.S.C. 102(b)(2)(C) establishing that, not later than the effective filing date of the claimed invention, the subject matter disclosed and the claimed invention were either owned by the same person or subject to an obligation of assignment to the same person or subject to a joint research agreement, see generally MPEP § 717.02.
Regarding the limitations of instant application claims 1-7 and 9, Hu ‘429 teaches the production of L-carnitine, see Abstract, by first reacting “(S)-epichlorohydrin with trimethylamine hydrochloride in an organic solvent”, such as “methanol, ethanol, n-propanol, isopropanol, butanol, isobutanol, tert-butanol, 2-butanol”, to obtain “L-3-chloro-2-hydroxylpropyl trimethylammonium chloride”, then the “L-3-chloro-2-hydroxylpropyl trimethylammonium chloride” is reacted with “a source of cyanide to form L-carnitinenitrile chloride”, such as “alkali cyanide, alkaline earth metal cyanide, zinc cyanide, and a cyanohydrin; wherein the alkali is lithium, sodium, or potassium”, see Paras. [0026]-[0028], meeting:
The reacting steps (a) and (b) in instant application claim 1;
The specific organic solvents in instant application claim 2, in instant application claim 3, in instant application claim 4, in instant application claim 5, in instant application claim 6, and in instant application claim 9;
The specific cyanide in instant application claim 7; and,
Then the L-carnitinenitrile chloride is “converted to L-carnitine”, see Para. [0057], meeting the production of L-carnitine and step (c) in instant application claim 1.
Regarding the limitations of instant application claim 8, Hu ‘429 teaches “a cyclic process, wherein the mother liquor solution can be further concentrated to yield additional product or combined with a fresh solution of L-carnitinenitrile chloride and alkali chloride”, see Para. [0037], where the process includes first reacting “(S)-epichlorohydrin with trimethylamine hydrochloride in an organic solvent”, such as “methanol, ethanol, n-propanol, isopropanol, butanol, isobutanol, tert-butanol, 2-butanol”, to obtain “L-3-chloro-2-hydroxylpropyl trimethylammonium chloride”, then the “L-3-chloro-2-hydroxylpropyl trimethylammonium chloride” is reacted with “a source of cyanide to form L-carnitinenitrile chloride”, see Paras. [0026]-[0028], and the “L-3-chloro-2-hydroxylpropyl trimethylammonium chloride of formula (II)” is “used as an isolated intermediate”, see Paras. [0027];[0041], meeting steps (1), (2), and (3) in instant application claim 8.
Hu ‘429 does not specifically teach the limitations of the above instant application claims in one single express embodiment or Example.
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 Hu ‘429 to choose the desired organic solvent, cyanide, sequence of reactions to produce the desired products, recovery of reactants, and recycle of reactants with a reasonable predictability of success for the purpose of efficiently producing optically pure L-carnitine in a mixed aqueous organic solvent solution with a reduction in “the formation of inorganic salts” and with minimal byproducts and residual alkali cyanide, see Hu ‘429, Paras. [0007]-[0008];[0011];[0017]-[0021];[0030];[0037].
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 Hu ‘429 to select the desired organic solvent, cyanide, sequence of reactions to produce the desired products, recovery of reactants, and recycle of reactants as taught by Hu ‘429 with a reasonable predictability of success for the purpose of efficiently producing optically pure L-carnitine in a mixed aqueous organic solvent solution with a reduction in “the formation of inorganic salts” and with minimal byproducts and residual alkali cyanide, see Hu ‘429, Paras. [0007]-[0008];[0011];[0017]-[0021];[0030];[0037]; 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 material, such as any of the organic solvents and cyanides taught by Hu ‘429, based on its suitability for its 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, merely discovering and claiming a new benefit of an old process cannot render the process again patentable, for example reversing the order of the prior art process steps, selection of any order of performing process steps, and selection of any order of mixing ingredients are all prima facie obvious in the absence of new or unexpected results, see MPEP 2144.04 IV.C. and In re Woodruff, 919 F.2d 1575, 1578 (Fed. Cir. 1990).
Claims 1-7 are rejected under 35 U.S.C. 103 as being unpatentable over Qinglin et al. (CN106748843, published 31 May 2017, see Original and Machine Translation, hereinafter Qinglin) in view of Wiegand (US4070394, patented 24 January 1978).
Regarding the limitations of instant application claims 1-3 and 7, Qinglin discloses a “method for preparing levocarnitine, characterized by comprising the following steps: S1. Trimethylamine is added to methanol, cooled to 0-5℃, and the internal temperature is controlled not to exceed 10℃. Concentrated hydrochloric acid is added dropwise to adjust the pH to 6-7. The temperature is raised to 40-50℃, and a certain proportion of epichlorohydrin is added dropwise. The reaction is kept at this temperature for 4-5 hours. The reaction solution is concentrated under reduced pressure, and the residue is recrystallized using a recrystallization reagent to obtain intermediate I”, i.e., L-3-chloro-2-hydroxypropyl trimethylammonium chloride, see Machine Translation Claim 1; Original Para. [0029]
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, meeting:
Step (a) in instant application claim 1;
The specific solvent methanol in instant application claim 2 and in instant application claim 3;
Then in step “S2. Intermediate I was added to a methanol solution, heated to 50°C, and after complete dissolution, NaCN was added. The reaction was maintained at this temperature for 4–5 hours. The filter cake was then recrystallized using a recrystallization reagent to obtain intermediate II”, i.e., L-carnitinenitrile chloride, see Machine Translation Claim 1; Original Para. [0033]
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, meeting:
Step (b) in instant application claim 1;
The specific cyanide sodium cyanide in instant application claim 7;
Then in steps S4.-S5. the L-carnitinenitrile chloride is converted to levocarnitine aka l-carnitine, see Machine Translation Claim 1; Original Paras. [0040]-[0045]
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, meeting the production of L-carnitine and step (c) in instant application claim 1.
Qinglin does not teach the limitations of instant application claims 4-6.
Wiegand is in the known prior art field of a “process for the production of carnitine nitrile halide” by “contacting a 2,3-epoxypropyl halide with trimethylamine in an organic solvent to produce a 2,3-epoxypropyl trimethyl ammonium halide” then “contacting at a temperature from 0° to about 30° C, said 2,3-epoxypropyl trimethyl ammonium halide with a cyano compound selected from the group consisting of a metal cyanide, ammonium cyanide and hydrocyanic acid whereby carnitine nitrile halide is produced”, see Abstract; Claim 1; Col. 2, Lns. 16-45, “wherein said (2,3-epoxypropyl)-trimethylammonium halide is (2,3-epoxypropyl)trimethylammonium chloride, said cyano compound is a metal cyanide and said metal cyanide is sodium cyanide”, see Claims 2-9, and the produced carnitine nitrile halide is converted to carnitine, see Col. 5, Lns. 24-43.
Regarding the limitations of instant application claims 4-6, Wiegand teaches the “preparation of (2,3-epoxypropyl)trialkylammonium halide is carried out in an organic solvent”, that is inert to the reactants, such as “methanol, ethanol, propanol, isopropanol, butanol, sec-butanol and the like” and “acetone, tetrahydrofuran, dimethoxyethane, ether, ethyl acetate and the like”, see Col. 3, Lns. 27-51; Col. 4, Lns. 35-64, meeting the specific organic solvent in instant application claim 4, in instant application claim 5, and in instant application claim 6.
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 the organic solvent of Qinglin to choose the desired inert organic solvents as taught by Wiegand with a reasonable predictability of success for the purpose of efficiently producing carnitine nitrile halides “in high yield and purity from epichlorohydrin and trimethylamine by reacting in an organic solvent” that helps to suppress “the formation of alkali metal halide”, see Wiegand, Col. 2, Lns. 16-45; Col. 3, Lns. 27-51; Col. 4, Lns. 35-64.
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 the organic solvent of Qinglin to select the desired inert organic solvent as taught by Wiegand with a reasonable predictability of success for the purpose of efficiently producing carnitine nitrile halides “in high yield and purity from epichlorohydrin and trimethylamine by reacting in an organic solvent” that helps to suppress “the formation of alkali metal halide”, see Wiegand, Col. 2, Lns. 16-45; Col. 3, Lns. 27-51; Col. 4, Lns. 35-64; and MPEP 2143 I. B-D.
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 Qinglin and Wiegand both teach reacting epichlorohydrin and trimethylamine in an organic solvent to produce a trialkylammonium halide, a person of ordinary skill in the art has good reason to modify Qinglin by relying upon Wiegand before the effective filing date of the claimed invention for knowledge generally available within the trialkylammonium halide production art regarding the desired organic solvent, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing carnitine nitrile halides “in high yield and purity from epichlorohydrin and trimethylamine by reacting in an organic solvent” that helps to suppress “the formation of alkali metal halide”, see Wiegand, Col. 2, Lns. 16-45; Col. 3, Lns. 27-51; Col. 4, Lns. 35-64; and, MPEP 2141 and 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 material, such as organic solvents, based on its suitability for its 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.
Claims 1-3 and 7-9 are rejected under 35 U.S.C. 103 as being unpatentable over Qinglin et al. (CN106748843, published 31 May 2017, see Original and Machine Translation, hereinafter Qinglin) in view of Kimbrell et al. (US5077435, patented 31 December 1991, hereinafter Kimbrell).
Regarding the limitations of instant application claims 1-3 and 7, Qinglin discloses a “method for preparing levocarnitine, characterized by comprising the following steps: S1. Trimethylamine is added to methanol, cooled to 0-5℃, and the internal temperature is controlled not to exceed 10℃. Concentrated hydrochloric acid is added dropwise to adjust the pH to 6-7. The temperature is raised to 40-50℃, and a certain proportion of epichlorohydrin is added dropwise. The reaction is kept at this temperature for 4-5 hours. The reaction solution is concentrated under reduced pressure, and the residue is recrystallized using a recrystallization reagent to obtain intermediate I”, i.e., L-3-chloro-2-hydroxypropyl trimethylammonium chloride, see Machine Translation Claim 1; Original Para. [0029]
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, meeting:
Step (a) in instant application claim 1;
The specific solvent methanol in instant application claim 2 and in instant application claim 3;
Then in step “S2. Intermediate I was added to a methanol solution, heated to 50°C, and after complete dissolution, NaCN was added. The reaction was maintained at this temperature for 4–5 hours. The filter cake was then recrystallized using a recrystallization reagent to obtain intermediate II”, i.e., L-carnitinenitrile chloride, see Machine Translation Claim 1; Original Para. [0033]
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, meeting:
Step (b) in instant application claim 1;
The specific cyanide sodium cyanide in instant application claim 7;
Then in steps S4.-S5. the L-carnitinenitrile chloride is converted to levocarnitine aka l-carnitine, see Machine Translation Claim 1; Original Paras. [0040]-[0045]
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, meeting the production of L-carnitine and step (c) in instant application claim 1.
Regarding the limitations of instant application claims 8-9, Qinglin teaches preparing L-3-chloro-2-hydroxypropyl trimethylammonium chloride by mixing trimethylamine hydrochloride, methanol, and epichlorohydrin to obtain L-3-chloro-2-hydroxypropyl trimethylammonium chloride that is then separated from solution and crystallized, see Machine Translation Claim 1; Original Para. [0029], meeting:
Step (1) in instant application claim 8;
Most of step (2) in instant application claim 8;
The production of L-3-chloro-2-hydroxypropyl trimethylammonium chloride in instant application claim 8; and,
The specific solvent methanol in instant application claim 9.
Qinglin does not teach the instant application claim 8 limitations of production of L-3-chloro-2-hydroxypropyl trimethylammonium chloride in a cyclic process and the step (3) recycle of the mother liquor as a solvent.
Kimbrell is in the known prior art field of “a process for producing halohydroxypropyltrialkylammonium halides by reacting a trialkylamine salt with an epihalohydrin, the improvement comprising using 1,3-dihalo-2-propanol as a cosolvent”, where the “cosolvent is preferably separated from the reaction mixture and recycled for use with additional trialkylamine salt and epihalohydrin” and the “process is particularly useful in preparing chlorohydroxypropyltrimethylammonium chloride”, see Abstract.
Regarding the limitations of instant application claim 8, Kimbrell teaches the production of 3-chloro-2-hydroxypropyl trimethylammonium chloride by reacting aqueous trimethylamine hydrochloride with epichlorohydrin and 1,3-dichloro-2-propanol as the cosolvent, where after the reaction the “overhead vapors are condensed and allowed to separate into 1,3-dichloro-2-propanol and aqueous phases in a reflux tank/phase separator” and “the 1,3-dihalo-2-propanol, preferably with any unreacted epihalohydrin, is recycled” “for use with additional trialkylamine hydrochloride and epichlorohydrin”, see Col. 4, Lns. 45-54; Col. 6, Ln. 45-Col. 7, Ln. 56; Claims 1, 2, 10 & 12, meeting:
The production of L-3-chloro-2-hydroxypropyl trimethylammonium chloride in a cyclic process in instant application claim 8; and,
The step (3) recycle of the mother liquor as a solvent in instant application claim 8.
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 the process of Qinglin to recover and recycle the organic solvent as taught by Kimbrell with a reasonable predictability of success for the purpose of efficiently and economically “producing halohydroxypropyltrialkylammonium halides” with “a simplified purification” and a “reduced production of dihalopropanol, epoxy and diquaternary by-products”, see Kimbrell, Abstract; Col. 2, Lns. 10-29; Col. 4, Lns. 15-54.
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 the process of Qinglin to recover and recycle the organic solvent as taught by Kimbrell with a reasonable predictability of success for the purpose of efficiently and economically “producing halohydroxypropyltrialkylammonium halides” with “a simplified purification” and a “reduced production of dihalopropanol, epoxy and diquaternary by-products”, see Kimbrell, Abstract; Col. 2, Lns. 10-29; Col. 4, Lns. 15-54; and MPEP 2143 I. B-D.
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 Qinglin and Kimbrell both teach reacting epichlorohydrin and trimethylamine in an organic solvent to produce 3-chloro-2-hydroxypropyl trimethylammonium chloride, a person of ordinary skill in the art has good reason to modify Qinglin by relying upon Kimbrell before the effective filing date of the claimed invention for knowledge generally available within the 3-chloro-2-hydroxypropyl trimethylammonium chloride production art regarding the process recycle and recovery, see MPEP 2143 B & G and 2141, for the benefit of efficiently and economically “producing halohydroxypropyltrialkylammonium halides” with “a simplified purification” and a “reduced production of dihalopropanol, epoxy and diquaternary by-products”, see Kimbrell, Abstract; Col. 2, Lns. 10-29; Col. 4, Lns. 15-54; and, MPEP 2141 and 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.
In addition, merely discovering and claiming a new benefit of an old process cannot render the process again patentable, for example reversing the order of the prior art process steps, selection of any order of performing process steps, and selection of any order of mixing ingredients are all prima facie obvious in the absence of new or unexpected results, see MPEP 2144.04 IV.C. and In re Woodruff, 919 F.2d 1575, 1578 (Fed. Cir. 1990).
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-7 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 5, and 6 of copending Application No. 18090005 to Hu et al. (hereinafter Hu ‘005) in view of Wiegand (US4070394, patented 24 January 1978).
This is a provisional nonstatutory double patenting rejection.
Regarding the limitations of instant application claim 1, the claims of Hu ‘005 recite a process for the production of L-carnitine, see Claim 1, comprising: (a) reacting (S)-epichlorohydrin with trimethylamine hydrochloride to obtain L-3-chloro-2-hydroxypropyl trimethylammonium chloride, see Claims 5 & 6; (b) reacting the L-3-chloro-2-hydroxypropyl trimethylammonium chloride of step (a) with a source of cyanide to yield L-carnitinenitrile chloride, see Claims 5 & 6; and (c) converting the L-carnitinenitrile chloride of step (b) to L-carnitine, see Claim 1, meeting most of the limitations in instant application claim 1.
Regarding the limitations of instant application claim 7, the claims of Hu ‘005 recite wherein the source of cyanide is selected from the group consisting of alkali cyanide, alkaline earth metal cyanide, zinc cyanide, and cyanohydrin; wherein alkali is lithium, sodium, potassium or a mixture thereof, see Claims 5 & 6; and wherein alkaline earth metal is magnesium, calcium, barium, or a mixture thereof, meeting the specific cyanide in instant application claim 7.
The claims of Hu ‘005 do not recite:
The instant application claim 1 limitations of reacting (S)-epichlorohydrin with trimethylamine hydrochloride in an organic solvent; and,
The limitations of instant application claims 2-6.
Regarding the limitations of instant application claims 1-6, Wiegand teaches a “process for the production of carnitine nitrile halide” by “contacting a 2,3-epoxypropyl halide with trimethylamine in an organic solvent to produce a 2,3-epoxypropyl trimethyl ammonium halide” then “contacting at a temperature from 0° to about 30° C, said 2,3-epoxypropyl trimethyl ammonium halide with a cyano compound selected from the group consisting of a metal cyanide, ammonium cyanide and hydrocyanic acid whereby carnitine nitrile halide is produced”, see Abstract; Claim 1; Col. 2, Lns. 16-45. The “preparation of (2,3-epoxypropyl)trialkylammonium halide is carried out in an organic solvent”, that is inert to the reactants, such as “methanol, ethanol, propanol, isopropanol, butanol, sec-butanol and the like” and “acetone, tetrahydrofuran, dimethoxyethane, ether, ethyl acetate and the like”, see Col. 3, Lns. 27-51; Col. 4, Lns. 35-64, meeting the specific organic solvent in instant application claim 1, in instant application claim 2, in instant application claim 3, in instant application claim 4, in instant application claim 5, and in instant application claim 6.
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 the claims of Hu ‘005 to add an organic solvent as taught by Wiegand with a reasonable predictability of success for the purpose of efficiently producing carnitine nitrile halides “in high yield and purity from epichlorohydrin and trimethylamine by reacting in an organic solvent” that helps to suppress “the formation of alkali metal halide”, see Wiegand, Col. 2, Lns. 16-45; Col. 3, Lns. 27-51; Col. 4, Lns. 35-64.
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 the claims of Hu ‘005 to add the desired inert organic solvent as taught by Wiegand with a reasonable predictability of success for the purpose of efficiently producing carnitine nitrile halides “in high yield and purity from epichlorohydrin and trimethylamine by reacting in an organic solvent” that helps to suppress “the formation of alkali metal halide”, see Wiegand, Col. 2, Lns. 16-45; Col. 3, Lns. 27-51; Col. 4, Lns. 35-64; and MPEP 2143 I. B-D.
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 the claims of Hu ‘005 and Wiegand both teach reacting epichlorohydrin and trimethylamine to produce a trialkylammonium halide, a person of ordinary skill in the art has good reason to modify the claims of Hu ‘005 by relying upon Wiegand before the effective filing date of the claimed invention for knowledge generally available within the trialkylammonium halide production art regarding the desired organic solvent, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing carnitine nitrile halides “in high yield and purity from epichlorohydrin and trimethylamine by reacting in an organic solvent” that helps to suppress “the formation of alkali metal halide”, see Wiegand, Col. 2, Lns. 16-45; Col. 3, Lns. 27-51; Col. 4, Lns. 35-64; and, MPEP 2141 and 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 material, such as organic solvents, based on its suitability for its 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.
Claims 1, 8, and 9 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 5, and 6 of copending Application No. 18090005 to Hu et al. (hereinafter Hu ‘005) in view of Kimbrell et al. (US5077435, patented 31 December 1991, hereinafter Kimbrell).
This is a provisional nonstatutory double patenting rejection.
Regarding the limitations of instant application claim 1, the claims of Hu ‘005 recite a process for the production of L-carnitine, see Claim 1, comprising: (a) reacting (S)-epichlorohydrin with trimethylamine hydrochloride to obtain L-3-chloro-2-hydroxypropyl trimethylammonium chloride, see Claims 5 & 6; (b) reacting the L-3-chloro-2-hydroxypropyl trimethylammonium chloride of step (a) with a source of cyanide to yield L-carnitinenitrile chloride, see Claims 5 & 6; and (c) converting the L-carnitinenitrile chloride of step (b) to L-carnitine, see Claim 1, meeting most of the limitations in instant application claim 1.
Regarding the limitations of instant application claim 8, the claims of Hu ‘005 recite comprising the steps of: (1) mixing (S)-epichlorohydrin and trimethylammonium hydrochloride, see claim 6, meeting most of step (1) in instant application claim 8.
The claims of Hu ‘005 do not recite:
The instant application claim 1 limitations of reacting (S)-epichlorohydrin with trimethylamine hydrochloride in an organic solvent;
The instant application claim 8 limitations of wherein the L-3-chloro-2-hydroxypropyl trimethylammonium chloride is produced in a cyclic process, (1) mixing (S)-epichlorohydrin and trimethylammonium hydrochloride in an organic solvent to form L-3-chloro-2-hydroxypropyl trimethylammonium chloride, (2) isolating the L-3 -chloro-2-hydroxypropyl trimethylammonium chloride of step (1) to yield an organic mother liquor solution; and (3) recycling the organic mother liquor solution of step (2) to step (1) as the organic solvent; and,
The limitations of instant application claim 9.
Regarding the limitations of instant application claims 1, 8, and 9, Kimbrell teaches the production of 3-chloro-2-hydroxypropyl trimethylammonium chloride by reacting aqueous trimethylamine hydrochloride with epichlorohydrin and 1,3-dichloro-2-propanol as the cosolvent, where after the reaction 3-chloro-2-hydroxypropyltrimethylammonium chloride (CHPTMAC) is separated by distillation as a product, the “overhead vapors are condensed and allowed to separate into 1,3-dichloro-2-propanol and aqueous phases in a reflux tank/phase separator” and “the 1,3-dihalo-2-propanol, preferably with any unreacted epihalohydrin, is recycled” “for use with additional trialkylamine hydrochloride and epichlorohydrin”, see Col. 4, Lns. 45-54; Col. 6, Ln. 45-Col. 7, Ln. 56; Table 1; Claims 1, 2, 10 & 12, meeting:
Reacting (S)-epichlorohydrin with trimethylamine hydrochloride in an organic solvent in instant application claim 1 and in instant application claim 8;
The production and isolation step (2) of L-3-chloro-2-hydroxypropyl trimethylammonium chloride in a cyclic process in instant application claim 8;
The step (3) recycle of the mother liquor as a solvent in instant application claim 8; and,
The specific halogenated alkane solvent 1,3-dichloro-2-propanol in instant application claim 9.
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 the process of the claims of Hu ‘005 to add and to recover and recycle an organic solvent as taught by Kimbrell with a reasonable predictability of success for the purpose of efficiently and economically “producing halohydroxypropyltrialkylammonium halides” with “a simplified purification” and a “reduced production of dihalopropanol, epoxy and diquaternary by-products”, see Kimbrell, Abstract; Col. 2, Lns. 10-29; Col. 4, Lns. 15-54.
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 the process of the claims of Hu ‘005 to add and to recover and recycle an organic solvent as taught by Kimbrell with a reasonable predictability of success for the purpose of efficiently and economically “producing halohydroxypropyltrialkylammonium halides” with “a simplified purification” and a “reduced production of dihalopropanol, epoxy and diquaternary by-products”, see Kimbrell, Abstract; Col. 2, Lns. 10-29; Col. 4, Lns. 15-54; and MPEP 2143 I. B-D.
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 the claims of Hu ‘005 and Kimbrell both teach reacting epichlorohydrin and trimethylamine to produce 3-chloro-2-hydroxypropyl trimethylammonium chloride, a person of ordinary skill in the art has good reason to modify the claims of Hu ‘005 by relying upon Kimbrell before the effective filing date of the claimed invention for knowledge generally available within the 3-chloro-2-hydroxypropyl trimethylammonium chloride production art regarding the process recycle and recovery, see MPEP 2143 B & G and 2141, for the benefit of efficiently and economically “producing halohydroxypropyltrialkylammonium halides” with “a simplified purification” and a “reduced production of dihalopropanol, epoxy and diquaternary by-products”, see Kimbrell, Abstract; Col. 2, Lns. 10-29; Col. 4, Lns. 15-54; and, MPEP 2141 and 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.
In addition, merely discovering and claiming a new benefit of an old process cannot render the process again patentable, for example reversing the order of the prior art process steps, selection of any order of performing process steps, and selection of any order of mixing ingredients are all prima facie obvious in the absence of new or unexpected results, see MPEP 2144.04 IV.C. and In re Woodruff, 919 F.2d 1575, 1578 (Fed. Cir. 1990).
Conclusion
No claims are allowed.
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/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699
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