Tier 2 Dependent ILR (Residence period/Interrupted)

Hi

One of my friends is in a similar situation. He is due to apply for ILR in end of May (which he will submit) in the UK. His family (wife and kid) who are currently on Tier 2 General Partner Visa are in India for past 1.5 years due to personal reasons. The query he has is,
1. Can they apply for a fresh (not an extension as we understand that extension is possible only from within the UK) Tier 2 General Partner (dependent visa) from India before expiry of their current visa which is valid till 2nd week of July, 2020? Whilst they are in the process of applying this visa, my friend would have got the ILR. Is that permissible to apply this visa?
2. If point 1 is possible, will the clock reset or they will be able to complete their 5 years as dependent by combining time on both visas?

Thanks

They should apply for entry clearance from India. Their lawful residence can only be maintained if their visa was issued before 11 Jan 2018 and they apply for entry clearance within 14 days of their current visa expiry (or earlier) and be granted new visa.