Prior art — US Patent 11110081

To identify the most relevant prior art for US patent 11110081 and analyze its potential anticipation of claims, a search of the USPTO database was conducted. The USPTO provides tools for searching patents and patent application publications.

Here's an analysis of the prior art cited in US patent 11110081, along with their potential relevance:

1. EP-A-0 184 162

Full Citation: EP-A-0 184 162
Publication/Filing Date: Not explicitly stated, but the patent states that "The preparation of tacrolimus is described in EP-A-0 184 162". Tacrolimus was discovered in 1984.
Brief Description: This patent describes the preparation of tacrolimus (FK-506 or FR-900506). Tacrolimus is a macrolide compound with immunosuppressive activity, used to prevent organ or tissue rejection.
Potential Anticipation: This reference establishes the prior art for the active pharmaceutical ingredient itself, tacrolimus. As such, it could potentially anticipate any claim broadly covering "tacrolimus or a pharmaceutically active analogue thereof" where the novelty does not reside in the specific extended-release formulation or method of treatment. Since US11110081 focuses on a new extended-release oral dosage form and methods of treatment using tacrolimus, EP-A-0 184 162 would not anticipate the novel aspects of the extended-release profile or the specific treatment regimens.

2. EP-A-0 444 659

Full Citation: EP-A-0 444 659
Publication/Filing Date: Not explicitly stated, but the patent notes that "analogues of tacrolimus are disclosed e.g. in EP-A-0 444 659". This patent relates to pharmaceutical solutions comprising derivatives of FK506, which is another name for tacrolimus.
Brief Description: This patent discloses analogues of tacrolimus and pharmaceutical solutions containing them, particularly non-aqueous solutions with long-term storage stability.
Potential Anticipation: Similar to EP-A-0 184 162, this reference establishes prior art for tacrolimus analogues. It would not anticipate the specific extended-release characteristics or methods of treatment claimed in US11110081.

3. U.S. Pat. No. 6,387,918

Full Citation: U.S. Pat. No. 6,387,918
Publication/Filing Date: Not explicitly stated, but the patent notes that "analogues of tacrolimus are disclosed e.g. in... U.S. Pat. No. 6,387,918".
Brief Description: This patent, like EP-A-0 444 659, discloses analogues of tacrolimus.
Potential Anticipation: This reference provides prior art for various tacrolimus analogues. It does not appear to describe an extended-release formulation with the specific characteristics claimed in US11110081, nor the methods of treatment.

4. WO 2005/020993 (PCT/DK2004/000573)

Full Citation: WO 2005/020993 A1 (International Filing Date: 2004-08-30, Publication Date: 2005-03-10)
Publication/Filing Date: International Filing Date: August 30, 2004. Publication Date: March 10, 2005.
Brief Description: This international patent application, by the same inventors as US11110081, relates to modified release compositions comprising tacrolimus. It describes pharmaceutical compositions in particulate form comprising tacrolimus and/or an analogue, where the composition, upon oral administration, releases at least about 50% w/w of the total amount of tacrolimus within about 24 hours. It also discusses enhanced bioavailability, reduced side effects, and formulations where tacrolimus is dissolved or dispersed in a hydrophilic or water-miscible vehicle (e.g., polyethylene glycols, poloxamers). It mentions that the bioavailability of tacrolimus is significantly increased when administered in a modified or controlled release composition that reduces or avoids CYP3A4 metabolism.
Potential Anticipation: This is a highly relevant prior art document as it describes modified release tacrolimus compositions by the same inventors.
- Claim 1: WO 2005/020993 describes modified release compositions and mentions that the active ingredient can be dissolved or dispersed in a hydrophilic or water-miscible vehicle, such as a mixture of PEG6000 and poloxamer 188. It also discusses extending the release of tacrolimus. However, the specific dissolution profile defined in Claim 1 of US11110081 (at most 63.5% release at 12 hours, at least 8% at 4 hours and/or at least 15% at 8 hours using the specified USP II/I method) would need to be directly taught or rendered obvious by WO 2005/020993 for anticipation. The document mentions formulations with T63.6% values ranging from 1.9 to 8.2 hours, which are faster than the "at most 63.5% at 12 hours" in Claim 1 of US11110081. Therefore, it is unlikely to fully anticipate the precise release kinetics of Claim 1.
- Claims 13-17: WO 2005/020993 discusses improved pharmacokinetic parameters like increased bioavailability and reduced side effects related to high peak concentrations. It also notes that improved bioavailability reduces the need for simultaneous food intake and that the difference between peak plasma concentration and 24-hour concentration can be at most 20 ng/mL. While it generally discusses improved PK profiles and reduced side effects, the specific numerical thresholds for Cmax, AUC, MRT, swing, fluctuation, and particularly the conversion ratios and de novo patient treatment outcomes specified in Claims 13-17 of US11110081 would need to be explicitly disclosed or inherently present to anticipate these claims.

5. WO 2005/020994 (PCT/DK2004/000574)

Full Citation: WO 2005/020994 (Publication Date: 2005-03-10)
Publication/Filing Date: International Filing Date: August 30, 2004. Publication Date: March 10, 2005.
Brief Description: This international patent application, also by the same inventors, relates to solid dispersions comprising tacrolimus. It describes a pharmaceutical composition comprising tacrolimus dissolved and/or dispersed in a hydrophilic or water-miscible vehicle to form a solid dispersion or solid solution at ambient temperature, aiming for improved bioavailability. It specifically mentions that the solid dispersion exhibits a very fast immediate release, with at least 50% w/w of the active pharmaceutical ingredient released within about 30 minutes.
Potential Anticipation:
- Claim 1: WO 2005/020994 describes "very fast immediate release" formulations, with at least 50% released within 30 minutes. This is in direct contradiction to the extended release profile of Claim 1 of US11110081, which specifies "at the most 63.5% of the content of the active substance at the 12 hours time point." Therefore, WO 2005/020994 would not anticipate Claim 1 as it teaches an opposite release characteristic.
- Claims 13-17: While WO 2005/020994 discusses improved bioavailability generally, its focus on immediate release makes it unlikely to anticipate the specific extended-release pharmacokinetic profiles and conversion/treatment methods of Claims 13-17 of US11110081, which are predicated on a long, sustained release.

6. WO99/49863

Full Citation: WO99/49863 (Fujisawa Pharmaceutical Co.)
Publication/Filing Date: The patent mentions this was referred to in WO2008145143A1, which has a publication date of November 3, 2008. This document is also cited as WO-9949863-A1 in US11419823B2. Tacrolimus was discovered by Fujisawa in 1984.
Brief Description: This patent describes sustained-release tacrolimus formulations, specifically mentioning formulations where the time for dissolving 63.2% (T63.2% value) of tacrolimus is between 0.7 and 15 hours. It is owned by Fujisawa Pharmaceutical Co. (now Astellas) and relates to the originator of Prograf®.
Potential Anticipation:
- Claim 1: WO99/49863 describes sustained-release tacrolimus formulations with T63.2% values between 0.7 and 15 hours. The dissolution criteria of Claim 1 of US11110081 (at most 63.5% at 12 hours) falls within this broader range. The specific minimum release requirements (at least 8% at 4 hours and/or at least 15% at 8 hours) would need to be further analyzed to determine if they are inherently met or made obvious by the teachings of WO99/49863. If WO99/49863's examples or general teachings are sufficiently broad to cover the precise dissolution profile of Claim 1, it could be considered anticipatory.
- Claims 13-17: This reference pertains to sustained-release tacrolimus and could potentially anticipate general concepts of improved PK profiles. However, the specific quantitative improvements in Cmax, swing, fluctuation, AUC, MRT, Tmax, and Cmin, as well as the precise conversion ratios and de novo patient outcomes defined in Claims 13-17, would need to be explicitly disclosed or made obvious by WO99/49863.

7. WO 03/004001

Full Citation: WO 03/004001 A1 (International Filing Date: 2002-07-05, Publication Date: 2003-01-16)
Publication/Filing Date: International Filing Date: July 5, 2002. Publication Date: January 16, 2003.
Brief Description: This international patent application describes a process for the preparation of particulate material by a controlled agglomeration method, which enables controlled growth in particle size. This method is especially suitable for pharmaceutical compositions containing active substances with low aqueous solubility or subject to chemical decomposition. It involves spraying a first composition (e.g., tacrolimus and a meltable carrier) onto a second solid carrier medium.
Potential Anticipation:
- This patent primarily describes a method of preparation for particulate pharmaceutical materials. While US11110081 mentions that its compositions may be prepared by methods like "controlled agglomeration" and references WO 03/004001, this prior art would likely anticipate the method of preparing certain particulate forms of tacrolimus, rather than the specific extended-release dosage form itself (Claim 1) or the methods of treatment (Claims 13-17). If any claims in US11110081 broadly claim a particulate form per se without specific structural or functional limitations not found in WO 03/004001, there could be anticipation. However, the focus of US11110081 is on the release profile and pharmacokinetic advantages, which are not directly claimed by the manufacturing process in WO 03/004001.

Other general points from the patent text that highlight prior art context:

Prograf®: The patent repeatedly references Prograf® as a conventional immediate-release tacrolimus formulation, approved by the FDA in April 1994. It's characterized by rapid absorption (Tmax of 1-2 hours) and low, variable bioavailability (at most about 20%). This serves as a baseline for comparison for the improved features of US11110081.
Advagraf® (MR4): This is mentioned as an extended-release tacrolimus product approved by EMEA on April 23, 2007. The US11110081 patent often compares its invention against Advagraf® in terms of reduced variability and improved PK profiles. Therefore, Advagraf® itself and any patents describing its formulation (such as WO2008145143A1 which mentions Advagraf® is a sustained release formulation allowing once daily dosing) are highly relevant in assessing novelty and non-obviousness for claims related to improvements over existing extended-release products.