On July 18, 2019, the Company entered into an exchange agreement with Deerfield pursuant to which the Company agreed to, among other things, (i) repay approximately $2.4 million in aggregate principal amount under the 2019 notes held by Deerfield (the “Tranche 4 Notes”) and pay accrued and unpaid interest on the entire principal amount of the Tranche 4 Notes that had been outstanding, and (ii) issue an aggregate of 1,514,423 shares of the Company’s common stock (the “Exchange Shares”) to Deerfield in exchange for approximately $1.6 million in aggregate principal amount of Tranche 4 Notes. The exchange price per Exchange Share was $1.04, which was the closing price of the Company’s common stock on July 17, 2019 as reported on the Nasdaq Stock Market. The principal amount repaid and exchanged under the Tranche 4 Notes represented the principal amount that would have otherwise become due and payable on July 18, 2019 under the Tranche 4 Notes.

On July 18, 2019, the Company repurchased for approximately $433,000 a December warrant to acquire 3,333,334 shares of the Company’s common stock. Following the repurchase of the December warrant, it was cancelled and is no longer issued and outstanding.

On August 2, 2019, the Company and Amphastar amended the Insulin Supply Agreement to extend the term an additional two years (to December 31, 2026) and to restructure the annual purchase commitments as follows:

		As of June 30, 2019			As amended August 2, 2019
2019	€	2.3 million		€		—
2020	€	15.9 million		€	6.6 million
2021	€	15.9 million		€	6.6 million
2022	€	19.8 million		€	8.5 million
2023	€	19.8 million		€	10.9 million
2024	€	8.6 million		€	14.6 million
2025	€		—	€	15.5 million
2026	€		—	€	19.4 million

In connection with this amendment, the Company is obligated to pay amendment fees of $1.5 million by September 15, 2019 and $1.25 million by December 15, 2019.

On August 6, 2019 (the “Closing Date”), MannKind Corporation (“MannKind”) entered into a Credit and Security Agreement (the “MidCap Credit Facility”), by and among MannKind, MannKind LLC, the Company’s wholly owned subsidiary (“MannKind LLC”, and together with MannKind, collectively, the “Company”), the lenders party thereto from time to time and MidCap Financial Trust (“MidCap”), as agent.

The MidCap Credit Facility provides a secured term loan facility in an aggregate principal amount of up to $75.0 million. The Company borrowed the first advance of $40.0 million (“Tranche 1”) on August 6, 2019. Under the terms of the MidCap Credit Facility, the second advance of $10.0 million (“Tranche 2”) will be available to the Company until April 15, 2020, subject to the Company’s satisfaction of certain conditions described in the MidCap Credit Facility, including the Company achieving Afrezza Net Revenue (as defined in the MidCap Credit Facility) of at least $30.0 million on a trailing twelve month basis. Under the terms of the MidCap Credit Facility, the third advance of $25.0 million (“Tranche 3”) will be available to the Company until June 30, 2021, subject to the satisfaction of certain milestone conditions associated with TreT .

Tranche 1 and, if borrowed, Tranche 2 and Tranche 3, each accrue interest at an annual rate equal to LIBOR plus 6.75%, subject to a LIBOR floor of 2.00%. Interest on each term loan advance is due and payable monthly in arrears. Principal on each term loan advance under Tranche 1 and Tranche 2 is payable in 36 equal monthly installments beginning September 1, 2021, until paid in full on August 1, 2024, and principal on each term loan advance under Tranche 3 is payable beginning on the later of (i) September 1, 2021, and (ii) the first day of the first full calendar month immediately following such term loan advance, in an amount equal to the outstanding term loan advance in respect of Tranche 3 divided by the number of full calendar months remaining before August 1, 2024. The Company has the option to prepay the term loans, in whole or in part, subject to early termination fees in an amount equal to 3.00% of principal prepaid if prepayment occurs on or prior to the first anniversary of the Closing Date, 2.00% of principal prepaid if prepayment occurs after the first anniversary of the Closing Date but on or prior to the second anniversary of the Closing Date, and 1.00% of principal prepaid if prepayment occurs after the second anniversary of the Closing Date and prior to or on the third anniversary of the Closing Date. In connection with execution of the MidCap Credit Facility, the Company paid MidCap a $375,000 origination fee.

Upon termination of the MidCap Credit Facility, the Company is required to pay an exit fee equal to 6.00% of the principal amount of all term loans advanced to the Company under the MidCap Credit Facility.

The Company’s obligations under the MidCap Credit Facility are secured by a security interest on substantially all of its assets, including intellectual property. Additionally, the Company’s future subsidiaries, if any, may be required to become co-borrowers or guarantors under the credit facility.

The MidCap Credit Facility contains customary affirmative covenants and customary negative covenants limiting the Company’s ability and the ability of the Company’s subsidiaries to, among other things, dispose of assets, undergo a change in control, merge or consolidate, make acquisitions, incur debt, incur liens, pay dividends, repurchase stock and make investments, in each case subject to certain exceptions. The Company must also comply with a financial covenant relating to trailing twelve month minimum Afrezza Net Revenue requirements (as defined in the MidCap Credit Facility), tested on a monthly basis, and a minimum cash covenant of $15.0 million at all times prior to the funding of Tranche 2, and $20.0 million at all times following the funding of Tranche 2 or Tranche 3.

The MidCap Credit Facility also contains customary events of default relating to, among other things, payment defaults, breaches of covenants, a material adverse change, listing of the Company’s common stock, bankruptcy and insolvency, cross defaults with certain material indebtedness and certain material contracts, judgments, and inaccuracies of representations and warranties. Upon an event of default, the agent and the lenders may declare all or a portion of the Company’s outstanding obligations to be immediately due and payable and exercise other rights and remedies provided for under the MidCap Credit Facility. During the existence of an event of default, interest on the term loans could be increased by 2.00%.

The Company also agreed to issue warrants to purchase shares of MannKind’s common stock (the “MidCap Warrants”) upon the drawdown of each term loan advance under the MidCap Credit Facility in an aggregate amount equal to 3.25% of the amount drawn, divided by the exercise price per share for that tranche. The exercise price per share is equal to the volume-weighted average closing price of MannKind’s common stock for the ten business days immediately preceding the second business day before the issue date. As a result of Tranche 1, the Company issued warrants to purchase an aggregate of 1,171,614 shares of the Company’s common stock, at an exercise price equal to $1.11 per share (the “Tranche 1 Warrants”). The MidCap Warrants are immediately exercisable and expire on the earlier to occur of the seventh anniversary of the respective issue date or, in certain circumstances, the closing of a merger, sale or other consolidation transactions in which the consideration is cash, stock of a publicly traded acquirer, or a combination thereof.

Exchange of 2021 Convertible Notes for 2024 Convertible Notes and the Indenture for the 2024 Convertible Notes

On August 6, 2019, MannKind entered into a privately-negotiated exchange agreement (the “2021 Note Exchange Agreement”) with Bruce & Co., Inc., for itself and on behalf of the beneficial owners of the holders of MannKind’s outstanding 2021 notes, pursuant to which MannKind agreed to, among other things, (i) repay $1,470,147 in cash to such holders ($1,500,000 less the amount of interest accruing under the 2021 notes between August 6, 2019 and August 15, 2019), (ii) issue 4,017,857 shares of MannKind’s common stock to such holders (at a conversion price of $1.12 per share), (iii) issue new 5.75% Convertible Senior Subordinated Exchange Notes due 2024 (the “2024 convertible notes”) to such holders pursuant to the provisions of an indenture (the “Indenture”) in an aggregate principal amount of $5,000,000 and (iv) issue two non-interest bearing promissory notes to such holders, each in the amount of $2,630,750, one of which will mature on June 30, 2020 (the “June 2020 note”) and the other of which will mature on December 31, 2020 (the “December 2020 note”, and together with the June 2020 note, the “2020 notes”), in exchange for the cancellation of the $18.7 million in principal amount of the 2021 notes. The 2020 notes may be prepaid at any time on or prior to their respective maturity dates at the option of MannKind. In addition, MannKind may elect to pay the 2020 notes at any time on or prior to their respective maturity dates, if certain conditions are met, in shares of MannKind’s common stock at a price per share equal to the last reported sale price on the trading day immediately prior to the payment date. The exchange pursuant to the 2021 Note Exchange Agreement was effected on August 6, 2019.

The 2024 convertible notes were issued pursuant to an indenture, dated as of August 6, 2019, between MannKind and U.S. Bank National Association, as trustee. The 2024 convertible notes are MannKind’s general, unsecured obligations, and are subordinated in right of payment to the indebtedness incurred pursuant to the MidCap Credit Facility. The 2024 convertible notes rank equally in right of payment with MannKind’s other unsecured senior debt. The 2024 convertible Notes accrue interest at the rate of 5.75% per year on the principal amount, payable semiannually in arrears on February 15 and August 15 of each year, beginning February 15, 2020, with interest accruing from August 6, 2019. Interest on the 2024 convertible notes will be payable in cash or, at the option of MannKind if certain conditions are met, in shares of MannKind’s common stock at a price per share equal to the last reported sale price on the trading day immediately prior to the interest payment date. The 2024 convertible notes will mature on the earlier of (i) November 4, 2024 or (ii) the 91^st day after the payment in full of, and termination and discharge of all obligations (other than contingent indemnity obligations) under the MidCap Credit Facility.

The 2024 convertible notes will be convertible, at the option of the holder, at any time on or prior to the close of business on the business day immediately preceding the stated maturity date, into shares of MannKind’s common stock at a conversion rate of 333.3333 shares per $1,000 principal amount of 2024 convertible notes, which is equal to a conversion price of approximately $3.00 per share. The conversion rate will be subject to adjustment under certain circumstances described in the Indenture.

If certain bankruptcy and insolvency-related events of default occur, the principal of, and accrued and unpaid interest on, all of the then outstanding 2024 convertible notes shall automatically become due and payable. If an event of default other than certain bankruptcy and insolvency-related events of defaults occurs and is continuing, the Trustee or the holders of at least 25% in aggregate principal amount of the then-outstanding 2024 convertible notes, by written notice to the Trustee, may declare the 2024 convertible notes due and payable at their principal amount plus any accrued and unpaid interest, and thereupon the Trustee may, at its discretion, proceed to protect and enforce the rights of the holders by the appropriate judicial proceedings. Notwithstanding the foregoing, the Indenture provides that, to the extent the Company elects, the sole remedy for an event of default relating to certain failures by the Company to comply with certain reporting covenants in the Indenture will, for the first 180 days after such event of default, consist exclusively of the right to receive additional interest on the 2024 convertible notes.

If MannKind undergoes certain fundamental changes, except in certain circumstances, each holder of 2024 convertible notes will have the option to require MannKind to repurchase all or any portion of that holder’s 2024 convertible notes. The fundamental change repurchase price will be 100% of the principal amount of the 2024 convertible notes to be repurchased plus accrued and unpaid interest, if any.

MannKind may elect at its option to cause all or any portion of the 2024 convertible notes to be mandatorily converted in whole or in part at any time prior to the close of business on the business day immediately preceding the maturity date, if the last reported sale price of its common stock equals or exceeds 120% of the conversion price then in effect for at least 10 trading days in any 20 trading day period, ending within five business days prior to the date of the mandatory conversion notice.

On August 5, 2019, MannKind entered into a privately-negotiated exchange agreement (the “Mann Group Exchange Agreement”) with The Mann Group, pursuant to which MannKind agreed to, among other things, (i) repay $3,000,000 in cash to the Mann Group, (ii) issue 7,142,857 shares of MannKind’s common stock to the Mann Group (at a conversion price of $1.12 per share), (iii) issue a new convertible promissory note (the “Mann Group Convertible Note”) to the Mann Group in an aggregate principal amount of $35,000,000 and (iv) issue a new non-convertible promissory note (the “Mann Group Non-Convertible Note,” together with the Mann Group Convertible Note, the “New Mann Group Loan Arrangement”) to the Mann Group in an aggregate principal amount of $35,050,750, in exchange for the cancellation of the $70.1 million in principal amount and accrued interest on the amended and restated promissory note dated March 11, 2018 held by the Mann Group.

The Mann Group Convertible Note and Mann Group Non-Convertible Note will each accrue interest at the rate of 7.00% per year on the principal amount, payable quarterly in arrears on the first day of each calendar quarter beginning October 1, 2019.

The Mann Group Convertible Note will mature on November 3, 2024. The principal and any accrued and unpaid interest under the Mann Group Convertible Note may be converted, at the option of the Mann Group, at any time on or prior to the close of business on the business day immediately preceding the stated maturity date, into shares of MannKind’s common stock at a conversion rate of 400 shares per $1,000 of principal and/or accrued and unpaid interest, which is equal to a conversion price of $2.50 per share. The conversion rate will be subject to adjustment under certain circumstances described in the Mann Group Convertible Note. Interest on the Mann Group Convertible Note will be payable in kind by adding the amount thereof to the principal amount; provided that with respect to interest accruing from and after January 1, 2021, MannKind may, at its option, elect to pay any such interest on any interest payment date, if certain conditions are met, in shares of MannKind’s common stock at a price per shall equal to the last reported sale price on the trading day immediately prior to the payment date.

The Mann Group Non-Convertible Note will mature on the earlier of (i) November 3, 2024 or (ii) the 90th day after the repayment in full, and termination and discharge of all obligations (other than contingent indemnity obligations) under the MidCap Credit Facility. Interest on the Mann Group Non-Convertible Note will be payable in kind by adding the amount thereof to the principal amount; provided that MannKind may, at its option, elect to pay any such interest on any interest payment date, if certain conditions are met, in shares of MannKind’s common stock at a price per shall equal to the last reported sale price on the trading day immediately prior to the interest payment date.

On August 6, 2019, the Company entered into an Exchange Agreement (the “Deerfield Exchange Agreement”) with Deerfield pursuant to which the Company agreed to, among other things, (i) repay $2,000,000 of the aggregate principal amount under the 2019 notes held by Deerfield (the “Deerfield Tranche 1 Notes”) and pay all accrued and unpaid interest on the Deerfield Tranche 1 Notes then-outstanding, (ii) issue an aggregate of 2,678,571 shares of MannKind’s common stock to Deerfield in exchange for $3,000,000 aggregate principal amount of Deerfield Tranche 1 Notes and (iii) cancel the Deerfield Tranche 1 Notes. The principal amount being repaid and exchanged under the Deerfield Tranche 1 Notes represents the final outstanding principal amount that would otherwise have become due and payable on August 31, 2019.