API and IP Newsletter

 Contents


Patent applications filed by Hetero Drugs


In Sidvim, we monitor patent applications filed by Indian Pharmaceutical companies and we try to understand strength of the development portfolio. This month, we analysed patent portfolio of Hetero drugs.

Some of our observations about PCT publications filed by Hetero Drugs in last couple of years are as below. 


Publication Number

Sidvim comments

WO2022003585A1

This family relates to composition useful for preparing diclofenac diethylamine transdermal patch for treating short term pain comprising hot melt pressure sensitive adhesives, permeation enhancers, tackifiers, and excipients. Diclofenac DEA patches are not approved in US. Hetero could be trying for 505( b)(2) application with different variant than diclofenac sodium.

WO2020165741A1

This family relates to new triterpene derivatives used to treating viral mediated disease.  The natural compound betulinic acid, isolated from Syzygium clavifolium was found to possess anti-HIV activity. Chemical modifications were undertaken by several research groups in an attempt to identify potent anti-HIV agents by making semi-synthetic analogs of betulinic acid, leading to the discovery of bevirimat as a compound with a novel mechanism of action. Hetero is working on few of such novel compounds.

WO2020165742A1

This family relates to proprietary compounds developed by Hetero. The family claims triterpenone derivatives used to treat viral mediated disease comprising HIV infection, HBV infection, HCV infection, retroviral infection genetically related to AIDS, respiratory disorders and/or inflammatory disease. 

WO2019207517A1

The invention relates to a process for preparation of deutetrabenazine using tetrabenazine as starting material. Teva Pharmaceuticals received approval from the FDA to market deutetrabenazine in early 2017. Hetero had filed DMF and this must be the process in their DMF. Teva is settling the court cases with many Gxs. As per the public domain information the settlement agreement would permit the generic launch by beginning April 2033.


WO2019197939A1

This family relates to taste masked stable mouth dissolving tablet composition used to make taste masked montelukast sodium and levocetirizine hydrochloride mouth dissolving tablet to treat e.g. asthma and nasal allergy, comprises montelukast and levocetirizine.

WO2021028842A1

The present invention relates to method for the preparation of stable ready-to-use injectable infusion container formulation of Gemcitabine which avoids terminal sterilization and filled into the infusion container which does not contain aluminium over-pouch as secondary packaging.


General comments:

  1. Hetero is investing resources in development of proprietary anti-HIV molecules.

  2. Hetero is working with deuterium chemistry and could work towards building a portfolio of deuterium compounds.

  3. Working on formulation platforms for teste masking and ready to use injectable formulations. 

  4. Overall very interesting patent portfolio.

General information


Alcon and AMO reach global settlement over cataract surgery equipment


American-Swiss medical company Alcon and J&J subsidiary AMO have settled a global patent dispute over technology related to ophthalmic surgery for cataract treatment. The UK case settled in mid-2022, but now proceedings are also over in Germany, the US and the Netherlands. According to reports, the settlement is worth almost $200 million. 

News here.


Leading innovators in therapy compliance monitoring systems for the medical devices industry


The medical devices industry continues to be a hotbed of innovation, with activity driven by increased need for homecare, preventative treatments, early diagnosis, reducing patient recovery times and improving outcomes, as well as a growing importance in technologies, such as machine learning, augmented reality, 5G and digitalization. In the last three years alone, there have been over 450,000 patents filed and granted in the medical devices industry.


Innovation in Medical Devices: innovation areas

Sr.

Emerging 

Accelerating 

Maturing 

1

Biopsy tract ablation device

Cardiovascular implant materials

Capillary blood collection devices

2

Interactive nutrition monitoring and management

Sonophoresis

Microfluidic sampling devices

3

Patch type monitors

Cardiothoracic surgery instruments

Bioresorbable stent coating

4

Neurostimulation therapy

Tissue reconstruction implants

Microneedle-based drug delivery

5

Handheld Ultrasound Systems

Surgical Biopsy Tracking and Markers

Cardiovascular prostheses manufacturing

6

Smart physiotherapy devices

Prosthetic cardiac valves

Ultrasonic stimulation devices

7

Ultrasonic atomizers

Inhalation devices

Cryogenic tissue treatment

8

Real-time IR thermographic imaging

Precision radiotherapy

Cardiac defibrillators

9

Medical image analysis automation

Therapy compliance monitoring systems


10

Robotic suction and irrigation

Cardiovascular implant fixation devices


11

Ventilator flow controllers

Cardiovascular implant delivery catheters

12

Orthodontic imaging system

Electric atomisers


13

Programmable ablation devices

Flow cytometry instruments


14

Surgical system safety arrangements

Oculography instruments


15


Customized prostheses 3D Printing


16


Syringe pump controls


17


Intermittent pneumatic compression (IPC) devices

18


Genetic variance analysis


19


Nebulizers and atomisers


20


Vital Signs Measuring Devices


21


Endoscopic biopsy


22


Iontophoresis


23


Bio-active prosthesis coating


24


Endoscopic imaging


25


Optical stimulation sleeping aids


26


Programmed medical infusion system


27


Fluorescence imaging


28


ML-guided microscopy


29


Pressure infusion devices


30


Anaesthesia delivery system




News here.


Intellectual Property 


Enalpril (EPANED): Azurity Pharmaceuticals, Inc. Vs  Alkem Laboratories Ltd.


Home - EPANED

EPANED is indicated for the treatment of hypertension, to lower blood pressure in adults and children older than one month.


This lawsuit was initiated by  Azurity Pharmaceuticals, Inc. ("Azurity") claiming that an ANDA submitted by Alkem Laboratories Ltd. ("Alkem") infringes U.S. Patent Nos. 10,786,482 (the '482 patent) and 10,918,621 (the '621 patent), both titled "Enalapril formulations." 


Azurity asserted claims 16, 18, 22, 23, and 28 of the '482 patent and claims 4, 7, 17, and 18 of the '621 patent. Alkem denied infringement and alleged that the patents in suit are invalid due to obviousness and insufficient written description.


Let us discuss only obviousness arguments in this write-up:


  1. The parties agreed that all ingredients in the asserted claims, including enalapril itself, were individually known prior to Azurity's invention, and that it was known that enalapril could be mixed with water to make a liquid dosage form. 

  2. Azurity also did not seriously challenged Alkem's evidence that it was known that enalapril liquids could include buffers, preservatives, sweeteners, and flavors including the same choices for these ingredients as used in the asserted claims. 

  3. Azurity itself had marketed the Epaned Kit, before the priority date of the impugned patents, which contained enalapril in the claimed concentration, a citrate buffer, sweeteners, and paraben preservatives. 

  4. It was, however, also undisputed that the prior art did not disclose any liquid formulation of enalapril known to be stable for a year or more at refrigerated temperature. 

  5. The parties disagreed as to whether a POSA would have expected, before Azurity's invention, that enalapril in water could be as stable as the asserted claims require. 

  6. The parties also disagreed as to whether it would have been obvious to use the particular combination of ingredients recited in the claims.

  7. The heart of the parties' obviousness dispute is whether a POSA would have reasonably expected that enalapril in water could be as stable as the claims require that is, at least 95% stable at refrigerated temperature after 12, 18, or 24 months. 

  8. To prove that Azurity's invention was obvious, Alkem must establish that a POSA would have had a reasonable expectation that attempting to make a long-term stable enalapril liquid would succeed.

  9. It is not enough for Alkem to show that it would have been obvious to try making a long-term stable enalapril liquid, but, at the same time, absolute predictability of success is not required.

  10. Azurity argued there was no prior art reference stated either that it was or was not possible to make an enalapril liquid that was 95% stable for 12 to 24 months at refrigerated temperature. 

  11. The longest examples of stability mentioned in the prior art taught that some liquids are 90% stable for 36 weeks (252 days) at an unspecified temperature; and one  prior study reportedly produced enalapril liquids stable for 262 days (at an unspecified per-centage) at room temperature despite using a non-optimal pH. 

  12. On the other hand, no prior art reference included data showing that enalapril in water at refrigerated temperature and a pH near 3 was less than 95% stable for the duration of whatever test was conducted. 

  13. Thus, prior art publications did not conclusively reveal whether enalapril in water at a pH near 3 could be stable for 12 to 24 months.

  14. Azurity interpreted this state of the art as teaching that enalapril was generally unstable in water and that long-term stability was out of reach. Azurity's expert Dr. Little testified that the breadcrumbs in the prior art suggesting how to achieve long-term stability were too thin to create a likelihood of success. 

  15. Dr. Little also considered it significant that prior art studies of enalapril used various pHs, some quite different than prior art’s reported most stable pH of 3

  16. Alkem acknowledged that the prior art did not provide a direct road map for making enalapril stable, but Alkem's expert Dr. Constantinides testified that it would be an easy task to make an enalapril liquid stable for 18 or 24 months based on knowledge in the prior art.

  17. Throughout trial, Azurity pointed to the 60-day shelf life of its Epaned Kit as evidence that the two-year stability of the present invention was a dramatic improvement. 

  18. But the present invention claims stability at refrigerated temperature, not room temperature. No witness testified how long the Kit liquid would be stable if it were kept refrigerated. And Azurity's ready-to-use Epaned product also has a shelf-life of 60 days when not refrigerated, the same as the Kit. 

  19. So according to the Judge, The comparison Azurity attempts to draw between the present invention and the Epaned Kit is therefore uninformative.

  20. The Judge agreed with Alkem that the claimed stability would have been obvious because a POSA would have known how to achieve it through routine application of a well-known problem-solving strategy.

  21. A formulator would have been immediately guided to focus on adjusting a single variable, the pH. The prior-art literature strongly conveys that pH drives the stability of enalapril in water and does not suggest that any other variable should be adjusted. 

  22. In view of these teachings, the Judge accepted Dr. Constantinides's opinion that this optimization would have been easy through routine experimentation.

  23. The variable was known, the target range (about 3) was known, and the method of adjusting and testing was known.


The Judge opined, 

  1. Alkem has proven by clear and convincing evidence that the prior art would have led a POSA to expect success in making a long-term stable enalapril liquid. 

  2. The prior art did not show that enalapril's long-term stability in water was guaranteed, or that it would necessarily be stable for any length of time or meet any threshold. 

  3. But the prior art did confer a reasonable expectation that mixing enalapril with water and adjusting the pH to about 3 could result in a drug that was highly stable for an extended period of time.


Therefore, the Judge concluded that Alkem's ANDA though infringes all asserted claims, those claims are invalid for obviousness.


Decision here









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