Item
1.01. Entry into a Material Definitive Agreement.
On
May 5, 2023, Progressive Care Inc. (OTCQB: RXMD) (the “Company” or “Progressive Care”) entered into a Securities
Purchase Agreement (the “SPA”) with NextPlat Corp (NASDAQ: NXPL, NXPLW) (“NextPlat”), pursuant to which NextPlat
agreed to purchase 455,000 newly issued units of securities from Progressive Care (the “Units”) at a price per Unit of $2.20
for an aggregate purchase price of $1 million (the “Unit Purchase”). Each Unit consists of one share of common stock, par
value $0.0001 per share, of Progressive Care (“Common Stock”) and one warrant to purchase a share of Common Stock (the “PIPE
Warrants”). The PIPE Warrants have a three-year term, and will be immediately exercisable. Each PIPE Warrant is exercisable at
$2.20 per share of Common Stock. On May 9, 2023, the Company and NextPlat closed the transactions contemplated in the SPA. The Company
intends to use the net proceeds from the Unit Purchase for its working capital needs. The Company received cash proceeds of $880,000,
net of placement agent commission of $70,000 and legal fees of $50,000.
Simultaneous
with the closing, the Company entered into a Debt Conversion Agreement (the “DCA”) with NextPlat and the other holders (the
“Holders”) of that certain Amended and Restated Secured Convertible Promissory Note, dated as of September 2, 2022, made
by the Company in the original face amount of $2,790,885.63 (the “Note”). Pursuant to the DCA, NextPlat and the other Holders
agreed to convert the total $2,887,228.53 of outstanding principal and accrued and unpaid interest to Common Stock at a conversion price
of $2.20 per share (the “Debt Conversion”). Of the total 1,312,379 shares of Common Stock issued upon conversion of
the Note pursuant to the DCA, NextPlat received 570,599 shares, Charles M. Fernandez, the Company’s Chairman and Chief Executive
Officer, received 228,240 shares, and Rodney Barreto, the Company’s Vice-Chairman of the Board of Directors, received 228,240 shares.
In addition, each of the Holders also received a warrant to purchase one share of Common Stock for each share of Common Stock they received
upon conversion of the Note (the “Conversion Warrants”). The Conversion Warrants have a three-year term, and will be immediately
exercisable. Each Conversion Warrant is exercisable at $2.20 per share of Common Stock.
At
the same time, the Company and NextPlat entered into a First Amendment (the “Amendment”) to that certain Securities Purchase
Agreement dated November 16, 2022 (the “Debenture Purchase Agreement”). Under the Debenture Purchase Agreement, the Company
agreed to issue, and NextPlat agreed to purchase, from time to time during the three-year term of the Debenture Purchase Agreement, up
to an aggregate of $10 million of secured convertible debentures from NextPlat (the “Debentures”). Pursuant to the Amendment,
NextPlat and Progressive Care agreed to amend the Debenture Purchase Agreement and the form of Debenture attached as an exhibit thereto
to have a conversion price of $2.20 per share. At present, no Debentures have been purchased by NextPlat under the Debenture Purchase
Agreement.
Dawson
James Securities, Inc. (the “Placement Agent”) served as placement agent for the Unit Purchase. In consideration for the
Placement Agent’s services, the Company issued to the Placement Agent and its affiliates warrants to purchase 91,000 shares of
Common Stock (the “Placement Agent Warrants”). The Placement Agent Warrants have a five-year term, and will be exercisable
in December 2023. Each Placement Agent Warrant is exercisable at $2.20 per share of Common Stock.
In
addition, the Company issued 330,000 warrants to certain existing Progressive Care investors to induce them to approve the transaction
contemplated by the SPA (the “Inducement Warrants”). Charles M. Fernandez and Rodney Barreto received Inducement Warrants
to purchase 190,000 and 30,000 shares of Common Stock, respectively. The Inducement Warrants have a three-year term and will be immediately
exercisable. Each Inducement Warrant is exercisable at $2.20 per share of Common Stock.
The
foregoing summaries of the SPA, PIPE Warrants, DCA, Conversion Warrants, Amendment, Inducement Warrants, and Placement Agent Warrants
do not purport to be complete and are subject to, and qualified in their entirety, by reference to the SPA, Form of PIPE Warrant,
DCA, Form of Conversion Warrants, Amendment, Form of Inducement Warrants, and Form of Placement Agent Warrants attached hereto
as Exhibits 10.1, 10.2, 10.3, 10.4, 10.5, 10.6 and 10.7 respectively, which are incorporated herein by reference.