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 .
Status of the Application
Receipt of the Response and Amendment after Non-Final Office Action filed 6 August 2026 is acknowledged. Receipt of the signed Declaration filed on 6 August 2026 is acknowledged.
Applicant has overcome the following by virtue of amendment of the claims: (1) the 35 U.S.C. § 112 second paragraph rejection of claims 10-17 has been withdrawn.
The status of the claims upon entry of the present amendment stands as follows:
Pending claims: 1-19
Withdrawn claims: 1-9 and 18-19
Previously canceled claims: None
Newly canceled claims: None
Amended claims: 10-11
New claims: None
Claims currently under consideration: 10-17
Currently rejected claims: 10-17
Allowed claims: None
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 10-11, 13 and 16 are rejected under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Koerfer et al. (CA 2285820 A1, cited on the IDS filed on 13 December 2023) in view of Gastner et al. (US 2007/0231370 A1, cited on the IDS filed on 13 December 2023).
Regarding claim 10, Koerfer teaches a process which yields shaped, pourable products having a low dust content (p. 2, lines 1-3). The invention provides pourable shaped bodies having a bulk density of from 300 to 850 kg/m3, especially from 600 to 800 kg/m3, and a particle spectrum from 63 µm to 5000 µm, especially from 500 µm to 1500 µm. The shaped bodies contain methionine in a predominant amount, especially from 60 to 98 wt.%, preferably from 85 to 95 wt.% (p. 2, lines 4-11). The shaped bodies may be in the form of extrudates or granulates (i.e., granules) (p. 2, lines 12-14). The method comprises preparing a composition of methionine (p. 2, lines 23-26) and washing the prepared methionine with water (p. 3, lines 10-12) to a residual moisture content in the range of 8 to 40 wt.%, especially from 12 to 25 wt.% (p. 4, lines 7-9). Example 1 provides an embodiment wherein methionine having a residual moisture content of 25 wt.% is extruded and granulated by means of a blade rotating directly at the die (p. 8, lines 4-17). The granules have a particle spectrum from 400 to 1000 µm, a methionine content of 88 wt.%, and a dust content of < 0.5% and high strength (Id.). The shaped bodies of the invention are suitable for feeding animals (p. 5, lines 29-32).
The methionine-containing granules of Koerfer have a methionine content of 60 to 98 wt.%, exemplified by 88 wt.%. This is analogous to the claimed glycocyamine content of 55 to 99.95% by weight of the glycocyamine-containing granules of the claimed invention.
The methionine-containing granules of Koerfer have a bulk density of from 300 to 850 kg/m3, especially from 600 to 800 kg/m3. This is analogous to the claimed bulk density of from 350 to 850 kg/m3 of the glycocyamine-containing granules of the claimed invention.
The methionine-containing granules of Koerfer have a particle spectrum from 63 µm to 5000 µm, especially from 500 µm to 1500 µm. This is analogous to the claimed grain size spectrum of from 32 to 2750 µm of the glycocyamine-containing granules of the claimed invention.
The ranges of the claimed properties of base molecule content, bulk density, and grain size spectrum of the methionine-containing granules of Koerfer lie inside the claimed ranges for those properties in the glycocyamine-containing granules of the claimed invention.
At least because the granules have a low dust content and high strength, it is considered that they are abrasion-resistant in that they do not readily form dust. Where the granules are characterized as “pourable” it is considered that they have free-flowing capacity.
Additionally, Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). Since the granules of Koerfer have the same properties of base molecule content, bulk density, and grain size spectrum, and are produced by the method as claimed, it is presumed that the methionine granules of Koerfer have the properties of being abrasion-resistant and free-flowing.
Koerfer does not discuss that the granules are glycocyamine-containing granules and that the method comprises preparing a composition of glycocyamine and water.
However, Gastner teaches guanidinoacetic acid (i.e., glycocyanime) granules as a feed additive with high bioavailability for breeding and growing livestock (Abstract).
It would have been obvious for one of ordinary skill in the art, at the time the invention was made, to substitute the methionine in the feed additive granules of Koerfer with glycocyamine as disclosed by Gastner. One of ordinary skill in the art would have been motivated to do so in order to produce glycocyamine granules for use as a feed additive. One of ordinary skill in the art would have had a reasonable expectation of success in arriving at the claimed invention because Gastner teaches that it was known to granulate glycocyamine, and Koerfer teaches a method of preparing pourable products having a low dust content from another small molecule (methionine) that results in granules with the claimed properties.
Claim 10 is therefore rendered obvious.
Regarding claim 11, Koerfer teaches a process which yields shaped, pourable products having a low dust content (p. 2, lines 1-3). The invention provides pourable shaped bodies having a bulk density of from 300 to 850 kg/m3, especially from 600 to 800 kg/m3, and a particle spectrum from 63 µm to 5000 µm, especially from 500 µm to 1500 µm. The shaped bodies contain methionine in a predominant amount, especially from 60 to 98 wt.%, preferably from 85 to 95 wt.% (p. 2, lines 4-11). The shaped bodies may be in the form of extrudates or granulates (i.e., granules) (p. 2, lines 12-14). The method comprises preparing a composition of methionine (p. 2, lines 23-26) and washing the prepared methionine with water (p. 3, lines 10-12) to a residual moisture content in the range of 8 to 40 wt.%, especially from 12 to 25 wt.% (p. 4, lines 7-9). The shaped bodies are dried (p. 6, line 24 – p. 7, line 5). Example 1 provides an embodiment wherein methionine having a residual moisture content of 25 wt.% is extruded and granulated by means of a blade rotating directly at the die, and the resulting granules are dried (p. 8, lines 4-17). The granules have a particle spectrum from 400 to 1000 µm, a methionine content of 88 wt.%, and a dust content of < 0.5% and high strength (Id.). The shaped bodies of the invention are suitable for feeding animals (p. 5, lines 29-32).
The methionine-containing granules of Koerfer have a methionine content of 60 to 98 wt.%, exemplified by 88 wt.%. This is analogous to the claimed glycocyamine content of 55 to 99.95% by weight of the glycocyamine-containing granules of the claimed invention.
The methionine-containing granules of Koerfer have a bulk density of from 300 to 850 kg/m3, especially from 600 to 800 kg/m3. This is analogous to the claimed bulk density of from 350 to 850 kg/m3 of the glycocyamine-containing granules of the claimed invention.
The methionine-containing granules of Koerfer have a particle spectrum from 63 µm to 5000 µm, especially from 500 µm to 1500 µm. This is analogous to the claimed grain size spectrum of from 32 to 2750 µm of the glycocyamine-containing granules of the claimed invention.
The ranges of the claimed properties of base molecule content, bulk density, and grain size spectrum of the methionine-containing granules of Koerfer lie inside the claimed ranges for those properties in the glycocyamine-containing granules of the claimed invention.
Where Koerfer teaches granulation of methionine and water (i.e., wet granulation) the claimed limitation of mixed granulation is met.
At least because the granules have a low dust content and high strength, it is considered that they are abrasion-resistant in that they do not readily form dust. Where the granules are characterized as “pourable” it is considered that they have free-flowing capacity.
Additionally, Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). Since the granules of Koerfer have the same properties of base molecule content, bulk density, and grain size spectrum, and are produced by the method as claimed, it is presumed that the methionine granules of Koerfer have the properties of being abrasion-resistant and free-flowing.
Koerfer does not discuss that the granules are glycocyamine-containing granules and that the method comprises preparing a composition of glycocyamine and water.
However, Gastner teaches guanidinoacetic acid (i.e., glycocyanime) granules as a feed additive with high bioavailability for breeding and growing livestock (Abstract).
It would have been obvious for one of ordinary skill in the art, at the time the invention was made, to substitute the methionine in the feed additive granules of Koerfer with glycocyamine as disclosed by Gastner. One of ordinary skill in the art would have been motivated to do so in order to produce glycocyamine granules for use as a feed additive. One of ordinary skill in the art would have had a reasonable expectation of success in arriving at the claimed invention because Gastner teaches that it was known to granulate glycocyamine, and Koerfer teaches a method of preparing pourable products having a low dust content from another small molecule (methionine) that results in granules with the claimed properties.
Claim 11 is therefore rendered obvious.
Regarding claim 13, Koerfer and Gastner teach the method of claim 10.
Koerfer also teaches that the method comprises using water-moist methionine separated off from a production process and having a residual moisture of 15 to 25% by weight – The method comprises washing methionine separated from a preparation process with water (p. 3, lines 10-12) to a residual moisture content in the range of 8 to 40 wt.%, especially from 12 to 25 wt.%, such a composition proving advantageous for shaping (p. 4, lines 7-9).
Koerfer does not discuss that such water-moist compound is glycocyamine.
However, where substitution of the methionine of Koerfer with glycocyamine according to Gastner would have been obvious as described regarding claim 10, such substitution also renders obvious claim 13 for the same reasons and with the same expectation of success.
Regarding claim 16, Koerfer and Gastner teach the method of claim 10.
The method of claim 10, further comprising drying said granules optionally under vacuum at a temperature of from 50 to 130 °C.
Koerfer also teaches that the method comprises drying said granules optionally under vacuum at a temperature of from 50 to 130 °C – Koerfer teaches, “The subsequent step, which optionally takes place in vacuo, of drying off from the shaped bodies the residual moisture that is still present must be carried out mechanically in a very gentle manner at least at the beginning in order to prevent the shaped bodies from being damaged or destroyed.” (p. 6, lines 31-35). “The product temperatures are in the rge of from 50 to 140 °C, preferably from 90 to 110 °C.” (p. 7, lines 1-5). The disclosed range of from 90 to 110 °C lies inside the claimed range of 50 to 130 °C.
Claim 16 is therefore rendered obvious for the same reasons and with the same expectation of success as described regarding claim 10.
Claim 12 is rejected under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Koerfer et al. and Gastner et al. as applied to claim 10 above, and further in view of Binder et al (US 6,287,627 B1, cited on the IDS filed on 13 December 2023).
Regarding claim 12, Koerfer and Gastner teach the method of claim 10.
Example 1 of Koerfer provides an embodiment wherein methionine having a residual moisture content of 25 wt.% is extruded and granulated by means of a blade rotating directly at the die (p. 8, lines 4-17).
The cited prior art does not discuss that the method comprises granulating with an intensive mixer, a vertical granulator, a spray granulator, a ring-layer granulator, or a ploughshare mixer.
However, Binder teaches a process for preparing a free-flowing, easy to handle animal feed supplement based on methionine, in which an aqueous methionine salt solution is converted into a granular material in one or more stages (col. 2, lines 46-52). The granular material has a bulk density of greater than 650 kg/m3 and a particle size distribution of, in particular, 100 to 1400 µm (col. 3, lines 17-21). The shaping processes to prepare the granular material may by extrusion or an extruder combined with an intensive mixer (col. 3, line 64 – col. 4, line 3; see also claim 5).
It would have been obvious for one of ordinary skill in the art, at the time the invention was made, to further modify the method of Koerfer as modified by Gastner with the teachings of Binder to substitute the extruder with a blade rotating directly at the die as taught in Koerfer with an extruder combined with an intensive mixer as taught by Binder by simple substitution of one known element for another to obtain predictable results. See MPEP § 2143(I)(B). The results would have been predictable because both Koerfer and Binder teach methods of producing free-flowing granules that have similar bulk densities and particle size distributions.
Claim 12 is therefore rendered obvious.
Claim 14 is rejected under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Koerfer et al. and Gastner et al. as applied to claim 10 above, and further in view of et al. Ota et al. (JP H07149739 A, see translation provided).
Regarding claim 14, Koerfer and Gastner teach the method of claim 10.
The cited prior art does not discuss that said glycocyamine has a median grain size diameter of <15µm.
However, in the art of particle wet granulation, Ota teaches melamine cyanurate granules having an average particle size of 100 to 2000 µm, in which non-rod-shaped fine particles having an average particle size of 0.1 to 1 µm are aggregated (claim 1). The melamine cyanurate granules have good powder flowability and no powdering ([0001]). An average particle size of 0.1 to 1 µm is considered to be sufficiently small as to also have a median particle (grain) size diameter of <15 µm.
It would have been obvious for one of ordinary skill in the art, at the time the invention was made, to further modify the method of Koerfer as modified by Gastner with the teachings of Ota to use glycocyamine with an average particle size of 0.1 to 1 µm. One of ordinary skill in the art would have been motivated to do so because neither Koerfer nor Gastner provide a size for the glycocyamine particles and Ota teaches that such particles result in granules having an average particle size of 100 to 2000 µm with good powder flowability and no powdering (i.e., dust-free). These properties are in line with the pourable, low-dust granules of from 63 to 5000 µm produced by the method of Koerfer (p. 2, lines 1-11). One of ordinary skill in the art would have had a reasonable expectation of success in arriving at the claimed invention because Gastner teaches that it was known to granulate glycocyamine, Koerfer teaches a method of preparing pourable products having a low dust content from another small molecule (methionine), and Ota teaches granulation of particles having an average particle size of 0.1 to 1 µm that results in granules with the claimed properties.
Claim 14 is therefore rendered obvious.
Claim 15 is rejected under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Koerfer et al. and Gastner et al. as applied to claim 10 above, and further in view of Yu (Yu, L. (2001). Amorphous pharmaceutical solids: preparation, characterization and stabilization. Advanced drug delivery reviews, 48(1), 27-42. https://doi.org/10.1016/S0169-409X(01)00098-9).
Regarding claim 15, Koerfer and Gastner teach the method of claim 10.
The cited prior art does not discuss that more than 40% by weight of said glycocyamine is in amorphous form.
However, Yu teaches that amorphous solids have higher solubility, higher dissolution rate, and sometimes better compression characteristics than corresponding crystals (p. 28, col. 1, ¶ 2). Yu teaches that amorphous solids can be produced by common pharmaceutical processes, including melt quenching, freeze- and spray-drying, milling, wet granulation, and drying of solvated crystals (Abstract). Therefore, it was known in the art before the time of the invention that converting crystals to amorphous solids increased the solubility and dissolution rate of chemical compounds.
It would have been obvious for one of ordinary skill in the art, at the time the invention was made, to further modify the method of Koerfer as modified by Gastner with the teachings of Yu to provide the glycocyamine in an amorphous form. One of ordinary skill in the art would have been motivated to do so to improve the solubility and/or dissolution rate of the glycocyamine feed additive. One of ordinary skill in the art would have had a reasonable expectation of success in arriving at the claimed invention because Koerfer and Gastner teach the method of claim 10, and Yu teaches that amorphous solids have a higher solubility and higher dissolution rate compared to corresponding crystals.
It is considered that given the teachings of Yu, the percent of glycocyamine that is in amorphous form is a result effective variable; a higher percentage of amorphous glycocyamine results a greater increase in solubility and dissolution rate.
Therefore, it would have been obvious for one of ordinary skill in the art, at the time the invention was made, to determine the optimal value for the weight percent of amorphous glycocyamine used in the process of Koerfer in view of Gastner and Yu, through routine experimentation, to provide an increased solubility and/or dissolution rate, including more than 40% by weight of amorphous glycocyamine as claimed.
Claim 15 is therefore rendered obvious.
Claim 17 is rejected under pre-AIA 35 U.S.C. 103(a) as being unpatentable over Koerfer et al. and Gastner et al. as applied to claim 10 above, and further in view of Vassel et al. (US 2,654,779 A, cited on the IDS filed on 13 December 2023).
Regarding claim 17, Koerfer and Gastner teach the method of claim 10.
The method of Koerfer comprises preparing a composition of methionine (p. 2, line 23 – p. 3, line 9).
The cited prior art does not discuss that said glycocyamine is produced from reaction of glycine and cyanamide in an aqueous solvent, with addition of a base.
However, Vassel teaches “a process for the preparation of glycocyamine which comprises preparing a solution of free cyanamide, adding to the solution glycine and sodium hydroxide in quantities sufficient to cause the pH of the solution before heating to exceed 9.0 and after heating not to exceed 10.3, heating the mixture, and crystallizing the glycocyamine product from the resultant solution mixture” (claim 5). The cyanamide and glycine are suspended in water (see Example 1, col. 4, line 34 – col. 5, line 9).
It would have been obvious for one of ordinary skill in the art, at the time the invention was made, to further modify the method of Koerfer as modified by Gastner with the teachings of Vassel to prepare the glycocyamine by reaction of glycine and cyanamide in an aqueous solvent with addition of a base, as claimed. One of ordinary skill in the art would have been motivated to consult Vassel in order to determine a suitable means to produce the glycocyamine substitute for the methionine of Koerfer. One of ordinary skill in the art would have had a reasonable expectation of success in arriving at the claimed invention because Koerfer and Gastner teach the method of claim 10, and Vassel teaches synthesis of glycocyamine as claimed.
Claim 17 is therefore rendered obvious.
Response to Arguments
Claim Rejections – 35 U.S.C. § 103: Applicant’s arguments filed on 6 August 2026 have been fully considered, but they are not persuasive.
Applicant first asserted that the specific parameters of glycocyamine (GAA) granules recited in the instant claims 10-11 allow for mixing such granules without segregation with animal feed, in particular with poultry feed. Applicant referenced the Rule 132 Declaration of Stephan Winkler of July 29, 2019 as support of unexpected properties of the granules (p. 6, ¶¶ 2-3).
The Declaration under 37 CFR 1.132 filed 6 August 2026 is insufficient to overcome the rejection of claims 10-11 based upon Koerfer et al. and Gastner et al. as set forth in the last Office action. The Declaration does not appear to be relevant to the rejections at hand. The Declaration was originally filed on July 29, 2019 in U.S. Application No. 14/570,633 to demonstrate unexpectedly superior free-flowing properties, abrasion resistance, and bulk density compared to granules produced outside the claimed ranges in view of prior art references “Alt”, “Swain”, “Farber”, and “Ueda”. None of these references are cited in the rejections of the instant claims, and all of the claimed ranges encompass the ranges disclosed in Koerfer. That is Koerfer teaches ranges inside the claimed ranges, and as such, the issue of criticality of the ranges is moot.
Applicant next argued that Koerfer relates to methionine-containing granules, not GAA-containing granules, and methionine and GAA are fundamentally different compounds where process and formulations valid for methionine are not easily transferrable to GAA (p. 6, last ¶, p. 7, table). Applicant argued that the chemical structures and associated properties of methionine and GAA with regard to water absorption, wetting, crystal bridge formation, binder interaction, drying behavior, and granule formation are quite different, and as such, a person having ordinary skill in the art would have expected a hydrophobic methionine system and a polar guanidino-containing GAA system to react quite differently, and it would not have been obvious to transfer parameters or process steps developed for methionine to GAA (p. 7, ¶ 1 – p. 8, ¶ 1).
Applicant’s arguments have been considered, but they are not persuasive. “Arguments presented by the applicant cannot take the place of evidence in the record. In re Schulze, 346 F.2d 600, 602, 145 USPQ 716, 718 (CCPA 1965) and In re De Blauwe, 736 F.2d 699, 705, 222 USPQ 191, 196 (Fed. Cir. 1984). Examples of statements which are not evidence and which must be supported by an appropriate affidavit or declaration include statements regarding unexpected results, commercial success, solution of a long-felt need, inoperability of the prior art, invention before the date of the reference, and allegations that the author(s) of the prior art derived the disclosed subject matter from the inventor or at least one joint inventor.” See MPEP § 716.01(c)(II).
In the present case, Applicant has provided no actual evidence supporting the assertion that processes used in granulating methionine would be incompatible with granulating GAA. Applicant’s arguments regarding the differences in chemical properties leading to incompatibility of the process steps are speculative.
Koerfer granulates the methionine/binder composition by extrusion through a die having 0.8 mm holes and a rotating blade directly at the die (p. 8, Example 1). The particle spectrum can be altered by adjusting the hole size of the die (p. 8, Example 2). Therefore, particle/grain size spectrum is controlled by adjusting parameters of the granulating equipment and not necessarily the chemical make-up of the granulation substrate. Furthermore, reference of record Ota teaches melamine cyanurate granules having an average particle size of 100 to 2000 µm, in which non-rod-shaped fine particles having an average particle size of 0.1 to 1 µm are aggregated (claim 1). The melamine cyanurate granules have good powder flowability and no powdering ([0001]). Melamine cyanurate contains several polar groups and is still able to be granulated to an average particle size that is within the claimed grain size spectrum, and the granules have good flowability and no powdering. Given these teachings, one of ordinary skill in the art would not have been dissuaded from substituting the methionine of Koerfer with polar or hydrophilic molecules, including GAA. Therefore, also for at least these reasons, Applicant’s arguments are not persuasive.
The rejections of claims 10-17 under 35 U.S.C. § 103(a) are therefore maintained. No claims are allowed.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Badawy et al. (Badawy, S. I. F., Lee, T. J., & Menning, M. M. (2000). Effect of drug substance particle size on the characteristics of granulation manufactured in a high-shear mixer. Aaps Pharmscitech, 1(4), 33.) teaches that substance particle size is a result effective variable of high-shear wet granulation; smaller particle size results in larger granules, and increasing particle size decreases the resultant granule size (Table 1). Badawy also teaches particles with a D50 of 5.1 µm (SQ684-001, Table 1).
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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/JAMES P. SHELLHAMMER/Examiner, Art Unit 1793
/EMILY M LE/Supervisory Patent Examiner, Art Unit 1793
