API and IP Newsletter
Contents
Analysis of DMF filings in August 2021.
General information.
Online pharmacies can be risky.
Quality issues remain for Indian pharma companies: USFDA.
Intellectual Property.
T 2458/17 (METHOD FOR PRODUCING FLUORINATED COMPOUNDS/HONEYWELL) of 16.9.2021.
Analysis of DMF filings in August 2021
We analyse DMF filings by Indian companies. This month we had looked at DMFs filed in the month of August 2021. About 45 DMFs filed in the month of August. Some of our findings are listed below.
General information
Online pharmacies can be risky
The FDA says more people are turning to online pharmacies for a variety of reasons. Health insurance plans encourage the use of online pharmacy services and home delivery of maintenance medications. Many consumers value the convenience and privacy of buying their medications online and are attracted by cost savings advertised there.
There are 35,000 online pharmacies operating at any given time, but only 3 to 5 percent comply with U.S. pharmacy laws and practice standards. Many appear to be in Canada, which has gained a reputation as a source for buying less expensive drugs, but some of their drugs are manufactured in Russia, China, and other countries on the other side of the globe. That doesn’t necessarily make them bad, but it does make it ever more important that you deal with a legitimate online pharmacy.
News here.
Quality issues remain for Indian pharma companies: USFDA
Indian pharmaceutical companies are among the leading suppliers of generic medicine to the United States. After setting up the most USFDA-approved plants, they have had some quality-related issues in recent years. Ever since USFDA opened its India office, Indian companies are no longer forewarned of the arrival of the inspection team, just like in the US. Recently US has given 7 observations in 6 days audit.
News here.
Intellectual Property
T 2458/17 (METHOD FOR PRODUCING FLUORINATED COMPOUNDS/HONEYWELL) of 16.9.2021
EP 1968922, issued to Honeywell International Inc.
This patent was upheld at the first instance by the opposition division. The opponent Arkema lodged an appeal against this decision of the opposition division. The matter was before Board of Appeals at EPO (European Patent Office).
Though other sections were discussed in this case, for this write-up we are covering only inventive step argument. This case would be interesting for all process chemists.
An independent claim 1 of EP 1968922 is as follows:
A method for producing 2,3,3,3-tetrafluoro-1-propene (HFO-1234yf), comprising.
i) fluorinating a tetrachloropropene of Formula (I)
CX2=CClCX3 (I)
where X is independently selected from H and Cl provided that the total number of Cl atoms is 4, to form CF3CCl=CH2 (HFO-1233xf);
ii) fluorinating HFO-1233xf to form CF3CFClCH3 (HFC-244bb); and
iii) subjecting HFC-244bb to a dehydrohalogenation reaction, to form HFO-1234yf.
Following prior art documents were cited:
(9) Henne, A.L. et al: "Fluorinatedderivatives of propane and propylene. VI",J. Am. Chem. Soc., vol. 68, 1946, pages 496-497,
(11) EP-A-0 939 071,
(17) US-2-787 646,
(20) WO-A-2005/012212,
(21) ACS abstract of the article: G. L. Heard and B. E. Holmes. "1,2-FCl Rearrangement as an Intermediate Step in the Unimolecular 1,3-HCl Elimination from Chlorofluoropropanes", J. Phys. Chem. A 2001, 105, 1622-1625, and
(27) Zhu Li et al. "Rate Constants and Kinetic Isotope Effects for Unimolecular 1,2-HX or DX (X = F or Cl) Elimination from Chemically Activated CF3CFClCH3-d0, -d1, -d2 and -d3" J Phys. Chem. A 2006, 110, 1506-1517.
The board (The Board of Appeals) agreed document (9) as the closest prior art.
The document (9) discloses the preparation of HFO-1234yf starting from 2,3-dichloropropene.
In EP oppositions (at EPO), after identifying the closest prior art, then Board identifies what is the technical problem solved by the invention. Later the Board determines whether the claimed invention, starting from the closest prior art and the objective technical problem, would have been obvious to the skilled person, for doing so the Boards apply the "could-would approach". In short, it is not sufficient that he/she could have made said improvement.
In this case, according to the patentee, Honeywell, the technical problem underlying the patent-in-suit is to provide an improved process for the preparation of HFO-1234yf.
On the other hand, the opponent, Arkema believed the technical problem solved by the invention is just the provision of an alternative process for producing HFO-1234yf.
The Board agreed with the Arkema, that the technical problem solved by the invention is the provision of a further process for producing HFO-1234yf.
Once the objective technical problem was identified, it remains to be decided whether or not it is obvious to the skilled person to modify the process for preparing HFO-1234yf disclosed in document (9) to arrive at the claimed 3-step process starting from tetrachloropropenes of Formula (I)
1. Arkema argued, CF3CF=CH2 (HFO-1234yf) and CF3CH=CHF (HFO-1234ze) are isomers. Thus, the solution proposed by Honeywell in patent was simply to apply the process to produce HFO-1234ze to the production of its isomer HFO-1234yf involving compounds structurally like those used in documents (20) and (13).
2. HFO-1234ze and HFO-1234yf have the same molecular formula, i.e. the same number of atoms of each element. They are thus isomers, but not stereoisomers, since HFO-1234yf have two polar groups (F and CF3) attached to the same carbon atom of the double bond, whereas HFO-1234ze have these polar groups attached to different carbon atoms. There is no evidence that they share similar chemical or physical properties.
3. Therefore, the skilled person seeking an alternative process for preparing HFO-1234yf would not have discarded the entire disclosure of document (9) relating to the synthesis of HFO-1234yf and would not have turned to document (20) or (13) which discloses a process for preparing an isomer thereof, i.e. HFO-1234ze.
4. Even if he had done so, and applied by analogy the process of producing HFO-1234ze by dehydrochlorination of CF3CH2CHFCl (HCFC-244fa) to the production of HFO-1234yf, he would not have arrived at the intermediate CF3CFClCH3 (HCFC-244bb), since HCFC-244bb differs from the intermediate HCFC-244fa disclosed in document (20) or (13) not only in the position of the fluorine atom, but also in the position of the chlorine atom.
Arkema had one more argument of combining (20), (21). The board opined, combine the teaching of document (20) with document (21) to arrive at the claimed subject-matter is based on hindsight.
Therefore, the Board concluded that the subject-matter of claim 1 is inventive and patent was upheld.
Details here.
Disclaimer
Sidvim LifeSciences Private Ltd has taken due care and caution in developing this document. Since the data used for analysis in this document is based on the information available in the public domain, its adequacy or accuracy or completeness cannot be guaranteed. This document is for information only and Sidvim is not responsible for losses that may or may not arise due to any decisions made based on the same. No part of the document shall constitute or be represented as a legal opinion of any kind or nature. No warranties or guarantees, expressed or implied, are included in or intended by the document, except that it has been prepared in accordance with the current generally accepted practices and standards consistent with the level of care and skill exercised under similar circumstances by professional consultants or firms that perform the same or similar services.
