Patent 10166190

Prior art

Earlier patents, publications, and products that may anticipate or render the claims unpatentable.

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Prior art

Earlier patents, publications, and products that may anticipate or render the claims unpatentable.

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To identify the most relevant prior art for US Patent 10166190, I will analyze the citations listed within the patent itself. The patent document provides a list of "Prior art documents" and also mentions several publications in the "Background of the Invention" and "Detailed Description of the Invention" sections that could be considered prior art.

Here's an analysis of the prior art cited directly within US10166190B2:

I. Patent Documents Cited:

  • WO2005/020993 A2

    • Full Citation: WO2005/020993 A2 (Veloxis Pharmaceuticals A/S) March 10, 2005.
    • Publication/Filing Date: Publication: March 10, 2005.
    • Brief Description: This patent application discloses tacrolimus formulations with improved bioavailability and reduced peak-to-trough levels, particularly those comprising a solid dispersion of tacrolimus in polyethylene glycol (PEG). It also includes methods of preparation and related pharmaceutical compositions and dosage forms.
    • Potential Anticipation (35 U.S.C. § 102):
      • Claims 1, 10, 11, 12, 16, 17, 18: This reference teaches tacrolimus in a solid dispersion with a vehicle (like PEG), which forms the basis of many claims in US10166190. While US10166190 adds a stabilizing agent and specific pH/degradation limits, the fundamental concept of a solid dispersion of tacrolimus in a vehicle is anticipated. Specifically, the patent states, "WO2005/020993... disclose tacrolimus-containing pharmaceutical compositions with improved bioavailability... in particular tacrolimus compositions comprising a solid dispersion of tacrolimus in polyethylene glycol (PEG)."
      • Claims 15, 19-27: While WO2005/020993 doesn't explicitly teach the stabilizing agent or the specific degradation limits of US10166190, it lays the groundwork for tacrolimus formulations, which the current patent seeks to stabilize. The current patent explicitly states, "WO 2005/020993 discloses tacrolimus formulations which may be useful in combination with the stabilizing agent(s) disclosed herein to yield a stabilized tacrolimus composition." Therefore, if the stabilizing agent or degradation limits were deemed inherent in certain formulations disclosed in WO2005/020993, it could potentially anticipate these claims.

  • WO2005/020994 A2

    • Full Citation: WO2005/020994 A2 (Veloxis Pharmaceuticals A/S) March 10, 2005.
    • Publication/Filing Date: Publication: March 10, 2005.
    • Brief Description: Similar to WO2005/020993, this patent application also describes tacrolimus formulations with improved bioavailability and reduced peak-to-trough levels, focusing on solid dispersions in polyethylene glycol.
    • Potential Anticipation (35 U.S.C. § 102):
      • Claims 1, 10, 11, 12, 16, 17, 18: This reference, like WO2005/020993, broadly teaches tacrolimus in a solid dispersion within a vehicle, anticipating the basic composition described in these claims. The US10166190 patent itself lists "Tacrolimus composition A (tacrolimus tablets) (disclosed in Example 2 of WO2005/020993 and WO 2005/020994)" as a prior art composition for comparison.

  • WO2008/0145143 A1

    • Full Citation: WO2008/0145143 A1 (Veloxis Pharmaceuticals A/S) December 4, 2008.
    • Publication/Filing Date: Publication: December 4, 2008.
    • Brief Description: This patent application further details tacrolimus-containing pharmaceutical compositions with improved bioavailability and reduced peak-to-trough levels, specifically mentioning solid dispersions of tacrolimus in polyethylene glycol.
    • Potential Anticipation (35 U.S.C. § 102):
      • Claims 1, 10, 11, 12, 16, 17, 18: This document, like the other WO references, describes tacrolimus solid dispersions, which could anticipate the foundational elements of these claims. The patent states that WO2008/0145143 "disclose tacrolimus-containing pharmaceutical compositions with improved bioavailability and a reduced peak-to-trough level as compared to the commercially available tacrolimus products, in particular tacrolimus compositions comprising a solid dispersion of tacrolimus in polyethylene glycol (PEG)."

  • WO2010/005980 A1

    • Full Citation: WO2010/005980 A1 (Veloxis Pharmaceuticals A/S) January 21, 2010.
    • Publication/Filing Date: Publication: January 21, 2010.
    • Brief Description: This patent application, similar to the others, covers tacrolimus-containing pharmaceutical compositions with improved bioavailability and reduced peak-to-trough levels, specifically including solid dispersions of tacrolimus in polyethylene glycol.
    • Potential Anticipation (35 U.S.C. § 102):
      • Claims 1, 10, 11, 12, 16, 17, 18: This patent, like the others, contributes to the general knowledge of tacrolimus solid dispersions in PEG, potentially anticipating the basic composition aspects of these claims. The patent mentions WO2010/005980 as disclosing "tacrolimus compositions comprising a solid dispersion of tacrolimus in polyethylene glycol (PEG)."

  • U.S. Pat. No. 4,894,366

    • Full Citation: U.S. Pat. No. 4,894,366 (Fujisawa Pharmaceutical Co., Ltd.) January 16, 1990.
    • Publication/Filing Date: Publication: January 16, 1990.
    • Brief Description: This patent relates to tacrolimus and its derivatives, including their preparation and use. It provides a structural basis and early understanding of tacrolimus.
    • Potential Anticipation (35 U.S.C. § 102):
      • Claims 1, 15, 16, 19, 21, 22, 23, 24, 25, 26, 27, 28, 29: This patent, being an early disclosure of tacrolimus itself, is foundational. It provides the active ingredient ("tacrolimus") for all the claims. While it doesn't disclose the specific formulations or stabilizing agents of US10166190, it establishes the prior art for the core compound. The current patent refers to the "IUPAC-style nomenclature used in U.S. Pat. No. 4,894,366 for the tacrolimus structure".

II. Non-Patent Literature (NPL) Cited:

  • Hone et al., Transplantation Proceedings, Vol XIX, No 5, Suppl 6 (October), 1987: pp 17-22

    • Full Citation: Hone et al., Transplantation Proceedings, Vol XIX, No 5, Suppl 6 (October), 1987: pp 17-22.
    • Publication/Filing Date: October 1987.
    • Brief Description: This article discusses solid dispersions with different formulations of tacrolimus, providing early insights into addressing its poor solubility and low bioavailability.
    • Potential Anticipation (35 U.S.C. § 102):
      • Claims 1, 10, 11, 12, 16, 17, 18: This publication describes attempts to prepare solid solutions, "preferably in the form of solid dispersions," for tacrolimus. This directly anticipates the concept of a "solid dispersion of tacrolimus in a vehicle" as claimed in US10166190.

  • YAMASHITA Kazunari et al., International Journal of Pharmaceutics 2003, vol. 267, no1-2, pp. 79-91

    • Full Citation: YAMASHITA Kazunari et al., "Establishment of new preparation method for solid dispersion formulation of tacrolimus", International Journal of Pharmaceutics 2003, vol. 267, no1-2, pp. 79-91.
    • Publication/Filing Date: 2003.
    • Brief Description: This article discloses an improved solvent method for preparing solid dispersion formulations of tacrolimus, aiming to avoid the use of dichloromethane.
    • Potential Anticipation (35 U.S.C. § 102):
      • Claims 1, 10, 11, 12, 16, 17, 18: Similar to Hone et al., this reference describes methods for preparing solid dispersions of tacrolimus, broadly anticipating the underlying composition claims.

  • Skytte, D. M. et al.: Synthesis and characterization of an epimer of tacrolimus, an immunosuppresive drug in J. Nat. Prod., 2010 Apr. 23; 73(4):776-9

    • Full Citation: Skytte, D. M. et al.: "Synthesis and characterization of an epimer of tacrolimus, an immunosuppresive drug" in J. Nat. Prod., 2010 Apr. 23; 73(4):776-9.
    • Publication/Filing Date: April 23, 2010.
    • Brief Description: This publication details the synthesis and characterization of the 8-epitacrolimus, the major degradation product of tacrolimus. This is significant because US10166190 explicitly addresses preventing or reducing this specific degradation product.
    • Potential Anticipation (35 U.S.C. § 102):
      • Claims 19, 21, 22, 23, 24, 25, 26, 27: This article directly discloses the degradation product (8-epitacrolimus) that US10166190 seeks to control. While it doesn't disclose the method of stabilization, it establishes the prior knowledge of the problem that US10166190 aims to solve. The current patent explicitly cites this work for the structure determination of 8-epitacrolimus.

  • Sierra-Paredes et al., CNS Neurosci. Ther. 2008, vol. 14, p. 36-46

    • Full Citation: Sierra-Paredes et al., "Pharmacological aspects of ascomycin (FK520): a tacrolimus analogue", CNS Neurosci. Ther. 2008, vol. 14, p. 36-46.
    • Publication/Filing Date: 2008.
    • Brief Description: This article discusses ascomycin, an analogue of tacrolimus, and its pharmacological profile, highlighting that minor structural modifications can significantly alter activity.
    • Potential Anticipation (35 U.S.C. § 102):
      • Claims 1, 15: This reference contributes to the general knowledge of tacrolimus analogues and the sensitivity of their pharmacological profiles to structural changes. While not directly anticipating the stabilized composition, it informs the background of the patent regarding the importance of degradation product control.

General Note on Anticipation (35 U.S.C. § 102):
For a prior art reference to anticipate a claim under 35 U.S.C. § 102, it must describe, either expressly or inherently, each and every limitation of the claim. In the context of US10166190, the earlier WO applications and NPL describe the basic tacrolimus compositions and solid dispersions. However, the inventive step of US10166190 lies in the stabilizing agent and its ability to achieve specific pH ranges and degradation product limits. Therefore, the cited prior art generally anticipates the broad concept of tacrolimus formulations and solid dispersions, but the specific combination of a stabilizing agent to achieve the recited stability characteristics is likely the distinguishing feature of US10166190.

It is important to note that the priority date of US10166190 is May 30, 2008. Any publications or patents with a publication date before this priority date would be considered prior art, subject to specific exceptions like those for an inventor's own prior disclosure within a grace period (35 U.S.C. § 102(b)(1)(A)). The family history of US10166190 shows a priority claimed from PCT/DK2008/050130 filed May 30, 2008, which aligns with the prior art dates.

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