gtbp_ex42





  Exhibit 4.2











 



CERTIFICATE OF DESIGNATION OF


 



PREFERENCES, RIGHTS AND LIMITATIONS OF


 



SERIES K PREFERRED STOCK OF


 



GT BIOPHARMA, INC.


 


 


GT
BIOPHARMA, INC. (the “Corporation”), a corporation
organized and existing under the General Corporation Law of the
State of Delaware, DOES HEREBY CERTIFY that, pursuant to authority
conferred upon the Board of Directors by the Restated Certificate
of Incorporation of the Corporation, as amended, and pursuant to
the provisions of Section 151 of the General Corporation Law of the
State of Delaware, the Board of Directors, by resolutions adopted
to be effective on February 22, 2021, duly determined that 115,000
of the authorized shares of Preferred Stock, $0.01 par value per
share, of the Corporation shall be designated “Series K
Preferred Stock,” and duly adopted a resolution providing for
the voting powers, designations, preferences and relative,
participating, optional or other rights, and the qualifications,
limitations and restrictions, of the Series K Preferred Stock,
which resolution is as follows:


 


“RESOLVED, that the
Board of Directors, pursuant to the authority vested in it by the
provisions of the Restated Certificate of Incorporation of the
Corporation, as amended, hereby authorizes the issuance of 115,000
shares of Preferred Stock, $.01 par value, of the Corporation (and
fractions thereof in one-one hundredth increments), which shall be
designated as “Series K Preferred Stock” (the
“Series K Preferred Stock”), with each share of Series
K Preferred Stock having a stated value of $1.00 (the “Stated
Value”) and having the following designations, powers,
preferences and relative, participating, optional and other special
rights, and the qualifications, limitations and
restrictions:


 



1.            

Definitions.






 



As used herein, the following terms shall have the following
meanings:


 



(a)            

“Board”
shall mean the Board of Directors of the Corporation






 



(b)            

“Common
Stock” shall mean the Corporation’s common stock, par
value $0.001 per share.








 



(c)            

“Issuance
Date” shall mean the date on which the first share of Series
K Preferred Stock is
issued.






 



(d)            

“Liquidation”
shall mean any voluntary or involuntary liquidation, dissolution
or winding-up of the
Corporation.






 



(e)            

“Preferred
Stock” shall mean the Corporation’s preferred stock,
par value $0.01 per share.






 



(f)            

“Securities
Act” shall mean the Securities Act of 1933, as
amended.






 



2.            

Rank. The Series K Preferred
Stock will rank on parity to any class or series of our capital
stock hereafter created specifically ranking by its terms on parity
with the Series K Preferred Stock.






 






 








 





 






3.            

Dividends. Shares of Series K
Preferred Stock will not be entitled to receive any dividends,
unless and until specifically declared by our board of directors.
The holders of the Series K Preferred Stock will participate, on an
as-if-converted-to-common stock basis (without giving effect to the
“Beneficial Ownership Limitation” set forth in Section
6L), in any dividends to the holders of common stock.






 



4.            

Voting Rights. Shares of Series
K Preferred Stock will have the same voting rights as shares of
common stock with each share of Series K Preferred Stock entitled
to vote on an as-converted basis (after giving effect to the
“Beneficial Ownership Limitation” set forth in Section
6L) at a meeting of the shareholders of the
Corporation.






 



5.            

Liquidation Preference. In the
event of our liquidation, dissolution or winding up, holders of the
Series K Preferred Stock will have a liquidation preference equal
to $0.01 per share of Series K Preferred Stock and thereafter shall
be on parity with the holders of our common stock and will
participate, on an as-if-converted-to-common stock basis (without
giving effect to the “Beneficial Ownership Limitation”
set forth in Section 6L), in any distributions to the holders of
common stock.






 



6.            

Conversion Rights. The holders
of shares of Series K Preferred Stock shall have the following
conversion rights:






 



A.            

Conversion Rate. Each share of the
Series K Preferred Stock is convertible into 100 shares of Common
Stock (the “Conversion Rate”) at any time at the option
of the holder.






 



B.            

Upon Extraordinary Common Stock Event.
Upon the happening of an Extraordinary Common Stock Event, shares
of Series K Preferred Stock shall be impacted in the same way our
shares of common stock were impacted by the Extraordinary Common
Stock Event. An “Extraordinary Common Stock Event”
shall mean: (i) the issuance of additional shares of Common Stock
as a dividend or other distribution on the outstanding shares of
Common Stock, (ii) the subdivision of outstanding shares of Common
Stock into a greater number of shares of Common Stock, or (iii) the
combination of the outstanding shares of Common Stock into a
smaller number of shares of Common Stock, in each case other than
pursuant to a transaction provided for in Section 6C or
6D.






 



C.            

Capital Reorganization or
Reclassification. If the shares of Common Stock issuable
upon conversion of Series K Preferred Stock shall be changed into
the same or a different number of shares of any class or classes of
stock, whether by reorganization, reclassification or otherwise
(other than a subdivision or combination of shares or stock
dividend provided for in Section 6B, or a reorganization, merger,
consolidation or sale of assets provided for in Section 6D), then
and in each such event, the holders of shares of Series K Preferred
Stock shall have the right thereafter to convert such shares into
the kind and amount of shares of stock and other securities and
property receivable upon such reorganization, reclassification or
other change by the holders of the number of shares of Common Stock
into which such shares of Series K Preferred Stock were convertible
immediately prior to such reorganization, reclassification or other
change, all subject to further adjustment as provided
herein.






 



D.            

Reorganization, Merger or
Consolidation. If at any time or from time to time there
shall be a reorganization, reclassification or recapitalization of
the capital stock (other than a subdivision, combination,
reorganization, reclassification or exchange of shares provided for
elsewhere in this Section 6) (a “Reorganization”), then
as a part of such Reorganization, provision shall be made so that
each holder of Series K Preferred Stock shall thereafter be
entitled to receive upon conversion of such shares of Series K
Preferred Stock, the number of shares of stock or other securities
or property to which a holder of the number of shares of Common
Stock into which such holder’s shares of Series K Preferred
Stock were convertible immediately prior to such Reorganization
would have been entitled upon consummation of such Reorganization.
In any such case, appropriate adjustment shall be made in the
application of the provisions of this Section 6 with respect to the
rights of the holders of Series K Preferred Stock after the
Reorganization to the end that the provisions of this Section 6
(including adjustment of the Conversion Value then in effect, and
the number of shares of Common Stock issuable upon conversion of
the Series K Preferred Stock) shall be applicable after that event
in as nearly equivalent a manner as may be
practicable.






 




 








 





 



E.            

Exercise of Conversion Privilege. To
exercise the conversion right set forth in Section 6A, a holder of
shares of Series K Preferred Stock shall surrender the certificates
representing the shares being converted to the Corporation at its
principal office, and shall give written notice to the Corporation
at that office that such holder elects to convert such shares. Such
notice shall also state the name or names (with address or
addresses) in which the certificates for shares of Common Stock
issuable upon such conversion shall be issued. The certificates for
shares of Series K Preferred Stock surrendered for conversion shall
be accompanied by proper assignment thereof to the Corporation or
in blank. The date when such written notice is received by the
Corporation, together with the certificates representing the shares
of Series K Preferred Stock being converted, shall be deemed the
“Conversion Date.” As promptly as practicable after the
Conversion Date, the Corporation shall issue and deliver
certificates to each holder of shares of Series K Preferred Stock
so converted, or on its written order, such certificates as it may
request, for the number of whole shares of Common Stock issuable
upon the conversion of such shares of Series K Preferred Stock in
accordance with the provisions of this Section 6, and cash as
provided in Section 6J, in respect of any fraction of a share of
Common Stock issuable upon such conversion. Such conversion shall
be deemed to have been effected immediately prior to the close of
business on the Conversion Date, and at such time the rights of the
holder as holder of the converted shares of Series K Preferred
Stock shall cease and the person or persons in whose name or names
any certificates for shares of Common Stock shall be issuable upon
such conversion shall be deemed to have become the holder or
holders of record of the shares of Common Stock represented
thereby.






 



F.            

Cash in Lieu of Fractional Shares. No
fractional shares of Common Stock or scrip representing fractional
shares shall be issued upon any conversion of shares of Series K
Preferred Stock. Instead of any fractional shares of Common Stock
which would otherwise be issuable upon conversion of shares of
Series K Preferred Stock, the Corporation shall pay to the holder
of shares of Series K Preferred Stock which were converted a cash
adjustment in respect of such fractional shares in an amount equal
to the same fraction of the Market Price per share of the Common
Stock at the close of business on the Conversion Date. The
determination as to whether or not any fractional shares are
issuable shall be based upon the total number of shares of Series K
Preferred Stock so converted at any one time by any holder thereof,
and not upon each share of Series K Preferred Stock so
converted.






 



G.            

Partial Conversion. In the event some
but not all of the shares of Series K Preferred Stock represented
by a certificate surrendered by a holder are converted, the
Corporation shall execute and deliver to or on the order of the
holder, at the expense of the Corporation, a new certificate
representing the number of shares of Series K Preferred Stock which
were not converted.






 



H.            

Reservation of Common Stock. The
Corporation shall at all times reserve and keep available out of
its authorized but unissued shares of Common Stock, solely for the
purpose of effecting the conversion of shares of Series K Preferred
Stock, such number of shares of Common Stock as shall from time to
time be sufficient to effect the conversion of all outstanding
shares of Series K Preferred Stock, and if at any time the number
of authorized but unissued shares of Common Stock shall not be
sufficient to effect the conversion of all then outstanding shares
of Series K Preferred Stock, the Corporation shall take such
corporate action as may be necessary to increase its authorized but
unissued shares of Common Stock to such number of shares as shall
be sufficient for such purpose.






 



I.            

No Reissuance of Series K Preferred
Stock. Shares of Series K Preferred Stock which are
converted into shares of Common Stock as provided herein shall not
be reissued.






 



J.            

Issue Tax. The issuance of certificates
for shares of Common Stock upon conversion of any shares of Series
K Preferred Stock shall be made without charge to the holders
thereof for any issuance tax in respect thereof; provided that the
Corporation shall not be required to pay any tax which may be
payable in respect of any transfer involved in the issuance and
delivery of any certificate in a name other than that of the holder
of the shares of Series K Preferred Stock which are being
converted.






 






 








 





 






K.            

Closing of Books. The Corporation will
at no time close its transfer books against the transfer of any
shares of Series K Preferred Stock or of any shares of Common Stock
issued or issuable upon the conversion of any shares of Series K
Preferred Stock in any manner which interferes with the timely
conversion of such shares of Series K Preferred Stock, except as
may otherwise be required to comply with applicable securities
laws.






 



L.            

Beneficial Ownership Limitation. The
Corporation shall not effect any conversion of the Series K
Preferred Stock, and a Holder shall not have the right to convert
any portion of the Preferred Stock, to the extent that, after
giving effect to the conversion set forth on the applicable Notice
of Conversion, such Holder (together with such Holder’s
Affiliates, and any Persons acting as a group together with such
Holder or any of such Holder’s Affiliates (such Persons,
“Attribution Parties”)) would beneficially own in
excess of the Beneficial Ownership Limitation (as defined below).
For purposes of the foregoing sentence, the number of shares of
Common Stock beneficially owned by such Holder and its Affiliates
and Attribution Parties shall include the number of shares of
Common Stock issuable upon conversion of the Series K Preferred
Stock with respect to which such determination is being made, but
shall exclude the number of shares of Common Stock which are
issuable upon (i) conversion of the remaining, unconverted Stated
Value of Preferred Stock beneficially owned by such Holder or any
of its Affiliates or Attribution Parties and (ii) exercise or
conversion of the unexercised or unconverted portion of any other
securities of the Corporation subject to a limitation on conversion
or exercise analogous to the limitation contained herein
(including, without limitation, the Preferred Stock or the
Warrants) beneficially owned by such Holder or any of its
Affiliates or Attribution Parties. Except as set forth in the
preceding sentence, for purposes of this Section 6L, beneficial
ownership shall be calculated in accordance with Section 13(d) of
the Exchange Act and the rules and regulations promulgated
thereunder. To the extent that the limitation contained in this
Section 6L applies, the determination of whether the Preferred
Stock is convertible (in relation to other securities owned by such
Holder together with any Affiliates and Attribution Parties) and of
how many shares of Preferred Stock are convertible shall be in the
sole discretion of such Holder, and the submission of a Notice of
Conversion shall be deemed to be such Holder’s determination
of whether the shares of Preferred Stock may be converted (in
relation to other securities owned by such Holder together with any
Affiliates and Attribution Parties) and how many shares of the
Preferred Stock are convertible, in each case subject to the
Beneficial Ownership Limitation. To ensure compliance with this
restriction, each Holder wall be deemed to represent to the
Corporation each time it delivers a Notice of Conversion that such
Notice of Conversion has not violated the restrictions set forth in
this paragraph and the Corporation shall have no obligation to
verify or confirm the accuracy of such determination. In addition,
a determination as to any group status as contemplated above shall
be determined in accordance with Section 13(d) of the Exchange Act
and the rules and regulations promulgated thereunder. For purposes
of this Section 6L, in determining the number of outstanding shares
of Common Stock, a Holder may rely on the number of outstanding
shares of Common Stock as stated in the most recent of the
following: (i) the Corporation’s most recent periodic or
annual report filed with the Commission, as the case may be, (ii) a
more recent public announcement by the Corporation or (iii) a more
recent written notice by the Corporation or the Transfer Agent
setting forth the number of shares of Common Stock outstanding.
Upon the written or oral request (which may be via email) of a
Holder, the Corporation shall within two Trading Days confirm
orally and in writing to such Holder the number of shares of Common
Stock then outstanding. In any case, the number of outstanding
shares of Common Stock shall be determined after giving effect to
the conversion or exercise of securities of the Corporation,
including the Preferred Stock, by such Holder or its Affiliates or
Attribution Parties since the date as of which such number of
outstanding shares of Common Stock was reported. The
“Beneficial Ownership Limitation” shall be 9.99% of the
number of shares of the Common Stock outstanding immediately after
giving effect to the issuance of shares of Common Stock issuable
upon conversion of Series K Preferred Stock held by the applicable
Holder. A Holder, upon notice to the Corporation, may increase or
decrease the Beneficial Ownership Limitation provisions of this
Section 6L applicable to its Preferred Stock provided that the
Beneficial Ownership Limitation in no event exceeds 9.99% of the
number of shares of the Common Stock outstanding immediately after
giving effect to the issuance of shares of Common Stock upon
conversion of this Series K Preferred Stock held by the Holder and
the provisions of this Section 6L shall continue to apply. Any such
increase in the Beneficial Ownership Limitation will not be
effective until the 61st day after such notice is delivered to the
Corporation and shall only apply to such Holder and no other
Holder. The provisions of this paragraph shall be construed and
implemented in a manner otherwise than in strict conformity with
the terms of this Section 6L to correct this paragraph (or any
portion hereof) which may be defective or inconsistent with the
intended Beneficial Ownership Limitation contained herein or to
make changes or supplements necessary or desirable to properly give
effect to such limitation. The limitations contained in this
paragraph shall apply to a successor holder of Preferred
Stock.






  





 








 





 






7.            

Miscellaneous.






 



(a)         



The Corporation
covenants that all shares of Common Stock which may be issued upon
conversions of shares of Series K Preferred Stock will upon
issuance be duly and validly issued, fully paid and nonassessable,
free of all liens and charges and not subject to any preemptive
rights.






 



(b)         



No share or shares
of Series K Preferred Stock acquired by the Corporation by reason
of redemption, purchase, conversion or otherwise, shall be
reissued, and all such shares shall be cancelled, retired and
eliminated from the shares which the Corporation shall be
authorized to issue.”






 


The
number of shares of Series K Preferred Stock authorized is 115,000,
none of which have been issued.


 


IN
WITNESS WHEREOF, this Certificate of Designation has been signed by
an authorized officer of the Corporation as of the date first
written above.


 


 



By:            

/s/ Anthony
Cataldo             








Name:
Anthony Cataldo


Title:
Chief Executive Officer