API and IP Newsletter

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FDA approvals: 505 (b) (2) approvals in July 2024


We follow ANDA approvals and 505 (b) (2) approvals every month. In last month, ie in July 2024 there are about 8 applicants sought approvals via 505 (b) (2) route. 


More details are in below table. 


Drug Name

Comments

VASOPRESSIN IN SODIUM CHLORIDE 0.9% 


NDA   #217766


Sponsor

LONG GROVE PHARMS

Active ingredient: Vasopressin


This approval is for IV solutions, 20 units/100mL, 40 Units/100mL and 50 Units/50mL.  This NDA would help to address the need of hospital pharmacies for premix vasopressin with a long shelf life.  Thus, Long Grove's new product offering will deliver immediate value to hospital pharmacies and their patients.  


The company will initially enter the market with the following concentrations of Premix Vasopressin:
20 units/100 mL (0.2 units/mL) in 0.9% sodium chloride
40 units/100 mL (0.4 units/mL) in 0.9% sodium chloride

VOQUEZNA                      NDA   #218710


Sponsor

PHATHOM PHARMACEUTICALS INC

Active ingredient: Vonoprazan Fumarate 


This approval is for 10 and 20 MG tablets. This approval of VOQUEZNA (vonoprazan) would provide doctors a new first-in-class therapeutic option that could demonstrate faster healing in the more difficult to treat GERD patients with Erosive Esophagitis. 


In addition, VOQUEZNA (vonoprazan) would provide superior maintenance of healing in all grades of Erosive Esophagitis, compared to lansoprazole, a commonly prescribed PPI. 

ZITUVIMET XR                NDA   #216778


Sponsor

ZYDUS

Active ingredient: Metformin Hydrochloride; Sitagliptin


These are extended release tablets. Zituvimet™ XR (sitagliptin and metformin hydrochloride) extended-release tablets are indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus.


Three strengths are approved.

500MG;50MG: metformin hydrochloride; sitagliptin

1GM;50MG: metformin hydrochloride; sitagliptin

1GM;100MG: metformin hydrochloride; sitagliptin


FEMLYV                              NDA   #218718


Sponsor

MILLICENT PUERTO RICO LLC

Active ingredient : Norethindrone Acetate And Ethinyl Estradiol


This approval is for 1MG/0.02MG Tablet. 

This combination is very old. Ethinyl estradiol and norethindrone acetate in combination as an oral contraceptive tablet was first approved in 1968.

This is the first ODT formulation of a birth control pill.

ERZOFRI                            NDA   #216352


Sponsor

LUYE INNOMIND PHARMA SHIJIAZHUANG CO., LTD.

Active ingredient : Paliperidone Palmitate


These approvals are for six different strengths for treating schizophrenia in adults and for treating schizoaffective disorder in adults as monotherapy and as an adjunct to mood stabilizers or antidepressants. 


ERZOFRI, administered once a month. It is the first patented paliperidone palmitate long-acting injection developed in China to seek USFDA approval. The product is protected by the granted a U.S. patent (US 11,666,573) in 2023, which will expire in 2039. 

POTASSIUM PHOSPHATES IN SODIUM CHLORIDE  NDA   #218343


Sponsor

AMNEAL EU LTD

Active ingredient: Potassium Phosphates In Sodium Chloride


This approval is for injectable intravenous, 15MMOL/250ML / 22MEQ/250ML. New presentation of potassium phosphates in 0.9% sodium chloride injection intravenous (IV) ready-to-use (RTU) bags. 


This sterile presentation reduces the compounding steps for clinicians typically required with administering the product.

ZUNVEYL                          NDA   #218549


Sponsor

ALPHA COGNITION INC

Active Ingredient: Benzgalantamine


This approval is for delayed release tablets of benzgalantamine, 5 MG, 10 MG and 15 MG. The approval of ZUNVEYL is for the treatment of Alzheimer's disease (AD). This is only the second oral AD treatment approved in more than a decade.  


ZUNVEYL was designed to address a critical need for a tolerable and effective treatment that can potentially enhance patients' daily lives with improved long-term outcomes. 

TEZRULY                           NDA   #218139


Sponsor

ANI Pharma

Active Ingredient: Terazosin


The approval is for 1MG/ML solution. Terazosin is currently only available in capsule form and is used to treat high blood pressure (hypertension) and benign prostatic hyperplasia (BPH). 


Globally, there are no approved oral liquid forms of an alpha-1 blocker. This creates an opportunity for healthcare professionals in treating patients with dysphagia or in a hospital setting. 



General information


Big Pharma Cuts R&D, Sending Shudders Through Industry


The pandemic led to massive increases in research and development among pharmaceutical companies as they raced to discover vaccines and treatments for Covid-19. But those days are over, and many pharma companies are looking to cut costs as they contend with a slowdown. 

News here



Galera Therapeutics settles lawsuit for $975,000


The legal dispute, which centered on allegations of contract breach and negligence, was resolved with the payment and mutual releases, effectively terminating the existing contracts between the parties. 

News here 



Intellectual Property 


Aragon Vs Generics UK – Apalutamide Form B


European Patent EP 2858985 was issued to Aragon Pharmaceuticals, Inc. and Sloan-Kettering Institute for Cancer Research (Aragon). 

It was opposed by Sagittarius Intellectual Property LLP, Generics (U.K.) Limited and Luigi, Rumi (Patent attorney).

At the first instance, EPO upheld the patent. Two of the opponents at first instance viz Sagittarius Intellectual Property LLP, Generics (U.K.) Limited appealed the decision. 

To the appellate board (Boards of Appeal at EPO), Sagittarius Intellectual Property LLP, Generics (U.K.) Limited  (Generics UK) requested that the decision under appeal be set aside, and that the patent be revoked in its entirety.

The respondent (ie Aragon who is the patentee) requested dismissal of the appeal and maintenance of the patent as granted.


Following prior art documents cited

D1

WO 2007/126765 A2

D2

WO 2008/119015 A2

D3

Experimental report: "Preparation of A52 according to para [0065] and [0066] of WO 2007/126765"

D4

ICH Guidelines 2003 Q1 A(R2), "Stability Testing of new Drug Substances and Products"

D6

S Byrn et al., Pharm. Res. 1995, 12(7), 945-954

D8

Chapter 8 "Preformulation" from "Pharmaceutics: The Science of Drug Design", 2002

D9

Amorphous apalutamide stability study

D10

Clegg et al., Cancer Research, 72(6), 2012, 1494-1503

D18

European Pharmacopoeia 5.0, 5.11. "Characters section in monographs"

D19

"Experimental Information" - Dynamic Moisture Sorption experiment

D27

Chapter 9 of "Drug Stability - Principles and Practices", 3rd Edition Edited by JT Carstensen and CT Rhodes (2000)

D28

Additional stability test results

D33

Decision T 41/17



Claim 1 which was contested reads as follows:

"A crystalline Form B of apalutamide that is characterized as having at least one of:

(a) an X-Ray powder diffraction (XRPD) pattern the same as shown in Figure 2;

(b) an X-ray powder diffraction (XRPD) pattern with characteristic peaks at 12.1 0.1 2-Theta, 16.0 0.1 2- Theta, 16.7 0.1 2-Theta, 20.1 0.1 2-Theta, 20.3 0.1 2-Theta;

(c) unit cell parameters equal to the following at -173 C:

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(d) the same X-ray powder diffraction (XRPD) pattern as (a) or (b) post storage at 40 C and 75% RH for at least a week; or

(e) the same X-ray powder diffraction (XRPD) pattern as (a) or (b) post storage at 25 C and 92% RH for 12 days".

We will discuss inventive step.

Inventive step - Article 100(a) and 56 EPC

  1. The  claim 1 of the main request relates to crystalline Form B of apalutamide.

  2. Both appellants (Sagittarius  and Generic UK) and the respondents (Aragon ) agreed that D1 represented the closest prior art, while appellant II (ie Generic UK) also submitted that claim 1 lacked inventive step over D2 as closest prior art.

Distinguishing features

  1. D1 (WO 2007/126765 A2) discloses the preparation of apalutamide as compound A52 on page 28 (scheme at the top of the page). The physical form of the apalutamide product prepared is not provided (page 28, lines 10-12).

  2. In experimental report D3, Sagittarius reworked the preparation of apalutamide according to D1 and obtained a solid which when analysed by XRPD was revealed as amorphous. Since this conclusion was not disputed by the respondents (Aragon), it is accepted that apalutamide prepared according to D1 is amorphous.

  3. Patent document D2 discloses the preparation of apalutamide and its recrystallisation from DCM/EtOH (paragraph [0091]). There is no information in D2 nor has any evidence been provided by any of the parties as to the specific form of the crystalline material prepared according to D2.

  4. Claim 1 of the main request is therefore distinguished from both D1 and D2 in that a specific crystalline form of apalutamide denoted Form B is provided, while D1 discloses the amorphous form and D2 discloses an undefined crystalline form.

  5. The patent proprietor ie the respondents (Aragon) argued that the advantageous effects of Form B 

  1. less hygroscopic,

  2. highly thermodynamically stable and

  3. highly polymorphically stable.


Obviousness

  1. The appellants' (Sagittarius and Generic UK) arguments on obviousness were not specifically directed to the obviousness of the solution to the objective technical problem as formulated above, namely the provision of a form of apalutamide with a beneficial combination of properties.

  2. Sagittarius submitted that in view of the fact that apalutamide was the subject of an Investigational New Drug (IND) filing before the filing date of the patent as evidenced by D10, the skilled person would have been motivated to perform routine polymorphic analyses or screening. In particular, the skilled person would commence such analyses in the knowledge that apalutamide was at a development stage suitable for stage 2 clinical trials. Such analyses were known to the skilled person from common general knowledge represented by, for example, D4, D6, D8 and D27, and hence would have been carried out by the skilled person on apalutamide. Following such routine guidance, the skilled person would have arrived at the claimed Form B in an obvious manner.

  3. The board disagreed. The board said, the appellants' (Sagittarius and Generic UK) submissions fail to take into account the formulation of the objective technical problem set out above in accordance with the problem-solution approach. 


  1. Specifically, as stated by the patentee Aragon, (the respondents), Form B displays a beneficial combination of properties as set out above which cannot have been expected by the mere provision of a crystalline form per se.


  1. Sagittarius  and Generic UK also relied on the old decision T 41/17 to support the argument that Form B was obvious. Specifically, in T 41/17 the board stated that the skilled person looking for a stable crystalline form of sorafenib tosylate would have screened for thermodynamically most stable form. The appellants Sagittarius  and Generic UK argued on this basis that the same applied in the present case, and the skilled person would inevitably arrive at the claimed subject-matter.

  2. The board disagreed. As stated by Aragon (the patentee), in T 41/17, the claimed crystalline form was alleged to have the advantage that it did not convert to other forms during mechanical stress. 

  3. The technical problem was defined as the provision of a stable form suitable for the preparation of a pharmaceutical tablet, and the solutions was considered obvious because the skilled person would have performed a screening to identify the most thermodynamically stable form, which was also expected not to convert to other forms under mechanical stress. Hence, the provision of thermodynamically most stable form was an obvious solution to that specific problem

  4. In the present case in contrast, thermodynamic stability is only one property from the aforementioned beneficial combination of properties displayed by the claimed Form B of apalutamide. Therefore, even if the effect of thermodynamic stability were to have been considered obvious, the same does not apply to the beneficial combination, since, for example, there is no teaching in the prior art that the effect of lower hygroscopicity could be obtained with the thermodynamically most stable form of apalutamide.


  1. Sagittarius submitted that the skilled person, starting from the amorphous apalutamide of D1, would have been in a "try and see" situation. Specifically, the skilled person would have carried out a routine polymorphic screening as addressed above and arrived at Form B as claimed. Sagittarius cited the Case Law of the Boards of Appeal, where the consideration that the skilled person would have adopted a "try and see" attitude was a reason for denying an inventive step. Hence, Sagittarius argued that this situation applies to the present case.

  2. The board disagreed for the reasons provided by Aragon. Specifically, the "try and see" case law cited by the appellant Sagittarius concerns the situation in which the prior art suggested that a clear way forward would solve the technical problem at hand, i.e. an "approach suggested by the prior art", as mentioned in the text of the case law cited by the appellant Sagittarius. Hence, the try-and-see situation is entirely predicated on the existence of a pointer to the solution in the prior art. In the present case, as established above, no pointer in the prior art leads the skilled person confronted with the above-defined objective technical problem to the solution provided by claim 1. Hence, the "try and see" case law is irrelevant in the present situation.

  3. Given the foregoing, the Board concluded that the subject matter of claim 1 of the main request involves an inventive step starting from each of D1 and D2.


The patent was upheld. 

Decision here












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