API and IP Newsletter

 



Contents


ANDA approvals in August 2024


We follow ANDA approvals on the FDA website. In August 2024, there were about 82 ANDA approvals, 12 tentative. 


Top ANDA approvals were for the following companies. 


ANDA holder

Approvals

SOMERSET THERAPS LLC

6

FRESENIUS KABI USA

4

TEVA PHARMS INC

4

ZYDUS

4

ALEMBIC

3

LUPIN LTD

3

MACLEODS PHARMS LTD

3



Some of our observations are as below:


Active Ingredients

Company

Comments

ETODOLAC

IPCA LABS LTD

Etodolac had annual U.S. sales of approximately $36 million. This is a small product in the US.  There are several other ANDA approved. This approval is for 200 MG and 300 MG capsules. Etodolac is used to relieve pain, tenderness, swelling, and stiffness caused by osteoarthritis (arthritis caused by a breakdown of the lining of the joints) and rheumatoid arthritis.


NELARABINE

ALEMBIC

This approval is for IV, 250MG/50ML (5MG/ML). According to IQVIA, the market size for Nelarabine injection was estimated at $23 million for the 12 months ending March 2024. Nelarabine injection is used in cancer treatment. The approved ANDA is therapeutically equivalent to the reference-listed drug Arranon by Sandoz Inc. There are many other ANDA approvals.


ESTRADIOL

AUROBINDO PHARMA

This approval is for 10 MCG, Vaginal tablets. The approved product had an estimated market size of US$ 268 million in June 2024. There are three other approvals. Estradiol is used for the treatment of atrophic vaginitis due to menopause.

PREDNISOLONE ACETATE

LUPIN LTD

This approval is for 1% suspension/drops, ophthalmic. Prednisolone Acetate Ophthalmic Suspension USP, 1%( RLD Pred Forte®) had estimated annual sales of USD198 million in the U.S. (IQVIA MATJune2024). It is indicated for the treatment of steroid-responsive inflammation of the palpebral and bulbar conjunctiva, cornea, and anterior segment of the globe.


MACITENTAN

TORRENT

This approval is for a 10 MG tablet. The market size for Macitentan tablets, 10 mg, was estimated to be approximately US$800 mio. Four other ANDAs are approved, but there have been no generic launches yet. Generics should wait until December 2025 for the launch. Janssen is defending its IP globally.

Macitentan is used to manage the symptoms of pulmonary arterial hypertension. 





General information



Ozempic Lawsuit Update: New Study Links Semaglutides to Increased Risk of Vision Loss


More plaintiffs are continuing to join the diabetes drug Ozempic lawsuits against Novo Nordisk; and, until a couple of weeks ago, some court watchers were estimating that the total number of federal lawsuits involving Ozempic could reach 10,000 before all is said and done. But, due to a recent development, some are now saying that the final figure could be much higher. 

News here



Laurus Labs Sets Up Rs 250-Cr R&D Centre

The 2 lakh sqft facility at IKP Knowledge Park will support the pharma major’s CDMO biz and provide jobs to over 800 people
News here 




Intellectual Property 


T 2205/21 (PHARMACEUTICAL COMPOSITION CONTAINING CRYSTALLINE MACITENTAN/Sandoz AG) 18-06-2024


European patent No. EP 2 988 733 was granted based on a set of 14 claims.

Independent claim 1, as granted, read as follows:


"1. A pharmaceutical composition, which is an oral solid dosage form, and comprising crystalline macitentan free base characterised by an X-ray powder diffraction pattern showing peak maxima at 2 theta/° values of 11.4±0.2, 13.0±0.2, 16.1±0.2, and 25.4±0.2 when a radiation wavelength of 1.5419 Å is used; and at least one excipient; wherein said pharmaceutical composition is packaged in a packaging material having a moisture vapour transmission rate of at least 0.4 g.m -2 d-1 as measured according to standard DIN 53122-1."


Gill Jennings & Every LLP filed an opposition under Article 100 (a) and (b) EPC on the grounds that the patent's subject matter lacked an inventive step and was not sufficiently disclosed.


In the first instance, the opposition division rejected the opposition. Gill Jennings & Every LLP appealed the decision.


The documents cited during the opposition proceedings included the following:


D6

Bauer, Kurt et al., "Pharmazeutische Technologie" Georg Thieme Verlag Stuttgart, 31 December 1993, pages 102-104 and 402-410

D7

WO 2007/031933 (A2), 22.03.2007

D9

Bolli, Martin et al., "The Discovery of N.[5-(4- Bromophenyl)-6- [2-[(5-bromo-2- pyrimidinyl)oxy]ethoxy]-4- pyrimidinyl]- N'- propylsulfamide (Macitentan), an Orally Active, Potent Dual Endothelin Receptor Antagonist" Journal of Medicinal Chemistry, 31 December 2012, 55, 7849-7861

D9a

Supporting information of D9

D12

Applicant's submission dated August 04, 2017

D13

Applicant's submission dated July 11,2018


According to the decision under appeal, the claimed invention was sufficiently disclosed.

Regarding the inventive step, D7 represented the closest prior art. The subject matter of claim 1 differed in the crystalline form of macitentan and the moisture vapour transmission rate of the packaging material. 


The objective technical problem was providing an oral solid dosage form comprising macitentan with improved storage stability in elevated temperature and high humidity conditions. According to the decision of the first instance at EPO, the claimed solution was not obvious. 


Gill Jennings & Every LLP  filed an appeal against said decision.


With its reply to the statement of grounds of appeal dated 1 July 2022, the patent proprietor Sandoz filed auxiliary requests 1 and 2.


In comparison to claim 1 of the main request, claim 1 of the new auxiliary request one had been amended by the further feature "wherein the oral solid dosage form comprises at most 5 % by weight of amorphous macitentan free base, and wherein the solid dose form is a tablet".


There is little difference between main and auxiliary requests in discussions of inventive steps. Hence, this write-up will discuss inventive steps related to the main request.


The parties received a communication from the Board dated 29 February 2024. In it, the Board expressed, among other things, its preliminary opinion that D7 or D9 could be considered the closest prior art for assessing inventive steps.


Closest Prior art and problem to be solved by the invention

D7 served as a suitable starting point, and claim 1 differed from D7 in that macitentan was provided in crystalline polymorph Form I and in the claimed packaging material.


Main request - Inventive step

The claimed invention relates to a pharmaceutical composition comprising macitentan that exhibits improved chemical stability upon storage, particularly at conditions typical for tropical countries.


The opposition division considered Document D7 to represent the closest prior art in its decision. The appellant, Gill Jennings & Every LLP, agreed with this choice, even if it added D9 as a possible alternative closest prior-art.


Document D7 discloses stable oral dosage forms of macitentan or any salt, hydrate or morphological form but does not specify which form is used. The solid compositions are stable for at least six or 12 months when kept at 5 to 50°C. 


D7 does not disclose the claimed crystalline polymorph form I and the property of the packaging material.


The opposition division defined the problem as providing an oral solid dosage form comprising macitentan with improved storage stability, i.e., chemical and physical stability, in elevated temperature and high humidity conditions. Sandoz agreed with this definition of the problem.


The appellant, Gill Jennings & Every LLP, disagreed with the opposition division and defined the problem as providing an alternative oral solid dosage form of macitentan.


The Board agreed with Gill Jennings & Every LLP regarding the packaging material's contribution to a possible technical effect on the stability of the claimed oral dosage form. 


D13 clearly shows that the packaging material has only a marginal effect on the stability of tablets comprising the form I of macitentan. 

This also shows that packaging materials with a relatively high water vapour transmission rate, as claimed, can be used for form I-based tablets and that selecting packaging with a low water vapour transmission rate was unnecessary. The Board notes furthermore that the respondent Sandoz provided no other advantage regarding the claimed packaging material.


The Board agreed with the opposition division's decision regarding the absence of quantitative amounts of form I of macitentan in claim 1. 


It is reasonable to consider that any oral dosage form as claimed to comprise any amounts of form I of macitentan will still be more stable than the same dosage form comprising partially another form of macitentan. 


The same conclusion applies to unspecified excipients in the claimed oral dosage form since some excipients might have either a favourable or unfavourable effect on the stability of the dosage form comprising the form I of macitentan. 


However, there is no evidence on file that some excipients have a specific and exclusive effect on the stability of the dosage form comprising form I of macitentan, and this is further contradicted by the experiments shown in D13.


Consequently, the problem is as defined by the opposition division or the respondent Sandoz, namely the provision of an oral solid dosage form comprising macitentan with improved storage stability in conditions of elevated temperature and high humidity.


It remains to determine whether the claimed solution is obvious. On this point, the parties particularly mentioned documents D7, D9, and D6.


The closest prior art D7 indicates that morphological forms of macitentan can be included in the pharmaceutical compositions disclosed therein. The skilled person would consider this information a clear incentive to select a known polymorphic form of macitentan.


The contested patent references D9 in paragraph [0089], which mentions that the crystalline Form I of macitentan of the claimed invention was prepared according to the method given in D9.


D9 discloses the process for preparing macitentan and purifying it, in particular, its obtention by recrystallising compound 17 of D9 from methanol; D9 mentions that "in general, the target compounds could be purified easily by recrystallisation from methanol." 


As Sandoz has accepted, D9a has identified this compound as the polymorphic form I of macitentan. D9a mentions that "a second X-ray structure analysis was performed with crystals obtained from methanol" on compound 17.


As shown in Tables 5 and 6 of D9, several compounds were tested orally. Compound 17 was promising for further studies, particularly interesting for inhibiting ETA with a significant affinity for the ETB receptor.


D9 identifies on page 7856 (Table 7) an oral composition comprising the form I of macitentan in either 7.5% aqueous modified gelatin or a PEG 400 solution and mentions further on page 7856 in the "Conclusions" that compound 17 had completed a phase III clinical trial for pulmonary arterial hypertension. A phase IIIb clinical trial for digital ulcers and a phase I/Ib for recurrent glioblastoma were ongoing.


Given the disclosure of D9, it appears clear that not only was the polymorphic form I of macitentan known at the filing date of the contested patent, but it was also the preferred form selected for clinical trials. Hence, the skilled person would have been encouraged to choose form I of macitentan and incorporate it in an oral dosage form as disclosed in D7. 


Furthermore, at the priority date, the only known crystalline form of macitentan free base was that disclosed in D9/D9a. Thus, starting from D7, the obvious morphological form to use was the one disclosed in D9/D9a alone.


D6 is a standard general knowledge book on pharmaceutical technology. On pages 407 and Table 21.3, a list of all polymers functional as packaging material for pharmaceutical products and their physicochemical properties, including their water vapour transmission rate, is disclosed. 


This disclosure shows that all known polymers have a water vapour transmission rate, as claimed in claim 1 of the main request. Consequently, the claimed packaging material is conventional and commonly used, and its choice, particularly in the absence of any particular effect linked in addition to that, is also obvious.


Consequently, the claimed solution is obvious, given D7 combined with the teachings of D9 and D6. The main request lacks, therefore, an inventive step.


The patent was revoked. 


Decision here







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